Our Favorite Summer Travel Tips (SB1686)

Summary

The Stacking Benjamins Show – Episode: "Our Favorite Summer Travel Tips" (SB1686)
Release Date: May 23, 2025
Hosts: Joe Saul-Sehy and OG
Guests: Jesse Kramer and Crystal Hammond (Co-hosts of Stacking Adventures)

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1. Introduction to Summer Travel Tips

Kicking off the episode, Joe Saul-Sehy welcomes listeners to a special Memorial Day weekend edition, setting the stage for an engaging discussion on making summer vacations both affordable and memorable. The hosts emphasize that the insights shared come from regular, money-savvy individuals rather than travel experts, ensuring relatability for the audience.

2. Choosing Travel Partners

Crystal Hammond underscores the importance of selecting compatible travel companions to enhance the vacation experience.

"Think about the people you hang around with anyway. Then decide, okay, who would I get along with?"
(04:27)

Doug, one of the hosts, shares his positive experience traveling with OG, highlighting the synergy of shared interests and travel styles.

"My oldest son and I are just, we just travel the same way. We're like the perfect adventure buddies."
(20:31)

3. Planning and Budgeting for Travel

The conversation delves into effective travel planning strategies to avoid breaking the bank. Crystal recommends creating a list of desired destinations and capitalizing on sales and deals to make trips financially feasible.

"I have a list of places that I want to go. When they go on sale, that's when I start planning."
(12:21)

OG emphasizes prioritizing the destination over the budget, suggesting that knowing where you want to go first makes budgeting easier.

"In the hierarchy of budget or location, we would pick location first."
(13:03)

4. Resources for Travel Planning

The hosts discuss various resources for researching and booking trips. Jesse Kramer relies on Google, listicles, and user reviews, while Crystal complements this with detailed guidebooks like Lonely Planet and Fodor’s.

"I have to admit, I don't do a lot of that myself. I'll do some Googling and listicles."
(25:23)

They also highlight platforms like TripAdvisor and Viator for booking tours and activities, stressing the importance of reliable reviews.

"Check them for their reviews because they have the most dependable and reliable."
(28:49)

5. Credit Card Points and Travel Insurance

A significant portion of the discussion centers on managing credit card points and the benefits versus the complexities involved.

Jesse Kramer adopts a balanced approach, using one generic rewards card and another specific to certain expenditures, avoiding the pitfalls of overcomplication.

"We have essentially two cards. One that is very generic but has a pretty decent reward on anything you can buy, and then one that's specific."
(37:55)

Crystal Hammond advocates for simplicity, emphasizing paying off credit cards monthly to avoid debt while strategically using points for travel rewards.

"I do follow a couple people that post every month... but I have not done it yet."
(40:06)

Doug prefers cashback rewards over travel points, citing concerns about point devaluation and the hassle of maximizing their value.

"The value of the points goes down so often that I just don't think I would be getting the most value out of whatever the percent back is."
(39:40)

When discussing travel insurance, Crystal and Jesse agree on its necessity for longer or international trips to mitigate potential high costs from unforeseen events.

Crystal: "I usually get it like when you're booking for the flight cancellations."
(52:34)
Jesse: "For the big trips... we will [get travel insurance]."
(53:54)

6. Timing Your Travel: Shoulder Season vs Peak Season

The hosts advocate for traveling during shoulder seasons to avoid crowds and secure better deals. Crystal advises researching local holidays and weather patterns to ensure a smooth trip.

"I want to get great service. I don't want to be trampled. I don't want to have to wait too long to experience things."
(45:32)

Jesse echoes this sentiment, highlighting the benefits of avoiding peak tourist seasons to enjoy a more authentic and relaxed experience.

"Definitely shoulder season. I'm not a big crowds person anyway."
(47:20)

Joe shares a personal anecdote about traveling to Chile during their Independence Day, leading to an unexpectedly solitary and challenging experience, yet finding joy in local festivities.

"We ended up being, as far as I could tell, the only obviously non-Chilean people at the Chilean Independence Festival."
(46:27)

7. Accommodations: Hotels vs. Airbnb vs. Staying with Friends

The discussion shifts to choosing accommodations based on the size of the traveling group and personal preferences.

Crystal prefers hotels for solo trips due to cleanliness and security but opts for Airbnbs or staying with friends for larger groups to provide ample space and flexibility.

"For big groups, definitely Airbnb, but smaller trips, definitely prefer a hotel."
(49:50)

OG shares his positive experience with renting a condo for a family ski trip, enjoying the freedom of cooking and having more space compared to hotels.

"We rented a condo a little farther up the slope from where the hotel was. Everybody had way, you know, 50 times the room."
(50:14)

8. Airport Tips and Experiences

The hosts exchange tips and anecdotes about navigating airports efficiently. Joe emphasizes the benefits of programs like TSA PreCheck and CLEAR, while OG shares a humorous story about almost missing a flight but managing to board by switching terminals.

"TSA PreCheck is well worth it."
(57:54)

Doug recounts his frustrations with credit card travel insurance requirements, highlighting the practical challenges travelers face.

"They required some proof from the company that organized the whole thing...and I spent so much time trying to deal with that, I just gave up."
(56:17)

9. Fun Segments: Toothbrush Bristle Competition

Adding a playful element, the hosts engage in a competition to guess the number of bristles in an average toothbrush. Jesse Kramer emerges as the winner with an accurate guess of 2,500 bristles, earning accolades for his precision.

"The correct answer is 2,500 in the average toothbrush, making Jesse our winner."
(36:15)

10. Upcoming Projects and Conclusion

Wrapping up the episode, Crystal Hammond teases upcoming trips to Belize and Greece on the Stacking Adventures podcast, while Jesse Kramer mentions a deep dive into the Ready for Retirement Study on his own podcast, Personal Finance for Long Term Investors. The hosts encourage listeners to share their travel tips and experiences through social media and their Facebook group to foster a community of informed and savvy travelers.

"What are we going to talk about today?... Let's help each other travel better this summer."
(62:18)

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Key Takeaways:

1. Choose Compatible Travel Partners: Ensuring your companions share similar travel preferences can significantly enhance the vacation experience.

2. Plan Ahead and Be Budget-Conscious: Start with a list of desired destinations, monitor for deals, and prioritize spending to make trips affordable without sacrificing quality.

3. Utilize Reliable Resources: Leverage platforms like TripAdvisor, Viator, and trusted guidebooks to plan and book trips effectively.

4. Manage Credit Card Points Wisely: Opt for a balanced approach with credit card rewards, avoiding overcomplication to prevent debt and maximize benefits.

5. Travel During Shoulder Seasons: Avoid peak tourist times to enjoy better prices, fewer crowds, and a more authentic experience.

6. Choose Accommodations Based on Group Size: Hotels work well for solo travelers, while Airbnbs or staying with friends are ideal for larger groups seeking more space and flexibility.

7. Streamline Airport Experiences: Programs like TSA PreCheck and CLEAR can save time and reduce stress during travel.

8. Stay Prepared with Travel Insurance: Especially for long or international trips, having insurance can mitigate unexpected expenses from cancellations or emergencies.

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Notable Quotes:

• Crystal Hammond [12:21]: "I have a list of places that I want to go. When they go on sale, that's when I start planning."

• OG [13:03]: "In the hierarchy of budget or location, we would pick location first."

• Jesse Kramer [37:55]: "We have essentially two cards. One that is very generic but has a pretty decent reward on anything you can buy, and then one that's specific."

• Joe Saul-Sehy [45:32]: "I want to get great service. I don't want to be trampled. I don't want to have to wait too long to experience things."

• Doug [56:17]: "They required some proof from the company that organized the whole thing...and I spent so much time trying to deal with that, I just gave up."

---

For more insights and personal stories, tune into The Stacking Benjamins Show on StackingBenjamins.com and follow their guest podcasts, Stacking Adventures and Personal Finance for Long Term Investors.

Transcript

[Joe Saul-Sehy]

This message is brought to you by Navy Federal Credit Union. May is Military Appreciation Month and we're celebrating the military community that goes above and beyond every day along with Navy Federal Credit Union. For over 90 years, Navy Federal's mission has been to support and uplift all active duty veterans and members of military families. And this May is no different. It's a special time to recognize the profound contributions they make. Learn more@navy federal.org Navy Federal Credit Union Our members are the mission. Navy Federal is insured by NCUA and now word from our sponsors at Betterment when investing your money starts to feel like a second job, Betterment steps in with a little work life balance. We're the automated investing and savings app that handles the work so you don't have to. Your money's diversified and optimized day after day, again and again. Because your money doesn't need a work life balance, you do. Plus, new investing customers can get up to $1,000 with a qualifying deposit. Terms apply. Make your money hustle with Betterment. Get [e-mail] Investing involves risk. Performance not guaranteed.

[Doug]

Can you fly this plane and land it?

[OG]

Surely you can't be serious.

[Crystal Hammond]

I am serious.

[Doug]

And don't call me Shirley. Live from the basement of the YouTube headquarters, it's the Stacking Benjamin Show. I'm Joe's mom's neighbor, Doug. And you may not realize it, but I'm the Punxsutawney Phil of Memorial Day. Because I get to say this is the unofficial start of summer. Memorial Day weekend, baby. And so you don't break the bank this summer. And so you make the most memories while on the road. Today we're chatting with our roundtable about what makes an affordable and memorable vacation. And now a guy who always reminds OG that camping can actually be fun. It's Jo Sal. Sia.

[Joe Saul-Sehy]

It can be og. It can be fun. Hey everybody. Welcome to Friday and Memorial Day weekend. You made it here. Even if you got to work today, I mean, it's pretty darn close to a holiday.

[Doug]

So I'm sure you haven't worked since Tuesday.

[OG]

This week, nobody has.

[Joe Saul-Sehy]

Which week? Tuesday of which week? Yeah. Well, we've got a great show. We got a fantastic crew today. Let's meet them. Let's begin with the guy across the card table from me. Mr. OG is here. How are you, brother?

[OG]

I'm just happy to be here.

[Joe Saul-Sehy]

Where are you traveling to this summer? Since we're going to be talking traveling, let's see.

[OG]

I'm going to Nashville.

[Joe Saul-Sehy]

Awesome.

[OG]

I'm going to Tony Paco's in Toledo, Ohio.

[Joe Saul-Sehy]

Toledo, Ohio.

[Doug]

Tony Paco?

[OG]

What's wrong with Tony Paco?

[Doug]

There's nothing wrong with it, but the fact that that's your destination, that's a little bit.

[OG]

I'm going to see family and I will also eat a hot dog. Then we're going to go to stomping grounds up north, Houghton, Lake, Michigan. We got orientation in College Station, a work trip to Chicago, Illinois, and probably some after school activities and other places across the great United States.

[Joe Saul-Sehy]

A lot of Midwest and College Station.

[OG]

Is what I heard, which is basically the same.

[Joe Saul-Sehy]

That's it. And speaking of hot dog, Jesse Kramer's here. How are you, man?

[Jesse Kramer]

Hey, I'm good. I'm more of a hamburger guy, but I'll take a hot dog.

[OG]

Choking down a hot dog.

[Joe Saul-Sehy]

Hey, what's the.

[Doug]

What is, what's that now?

[Joe Saul-Sehy]

The. Moving on. What is, what's your travel schedule look like this summer, Jesse?

[Jesse Kramer]

I think we have a wedding in D.C. we got some local trips to the Finger Lakes. I'm going on a big hike up in the Adirondacks. And there's a slim chance before summer is out, I might go to Portland for fincon. But that's still up in the air.

[Joe Saul-Sehy]

Oh, you got to come to Fort, to Portland, to portcon. I'm just going to combine Portland and fincon. Why wouldn't you go to fincon? You gotta go.

[Jesse Kramer]

I know. It's just a matter of, you know, we got the baby at home. We're trying to figure out schedules. Trying to figure out. Got a lot of moving pieces. That's all. That's all. Want to go. It's just about getting the pieces lined up.

[Joe Saul-Sehy]

Isn't it wild how the baby changes.

[Jesse Kramer]

Everything just a little bit? Right?

[Joe Saul-Sehy]

It does.

[Jesse Kramer]

Just. Just a few things.

[Joe Saul-Sehy]

It does. And the woman who changes everything on our sister podcast, you like, like where we. How that smooth transition wasn't at all from the Stacking Adventure show. Crystal Hammond's here. How are you?

[Crystal Hammond]

Welcome, welcome. I'm welcoming myself. Good.

[Jesse Kramer]

How are you guys?

[Joe Saul-Sehy]

We are good. We're better. Now that you're with us, you and I host a show that some people might not know about, which is about travel, which is why you're here with us today. So tell everybody about the Stacking Adventures podcast.

[Crystal Hammond]

Well, we talk about adventuring. Every adventure, every traveler has a story, so we share our stories. But my most fun part is sharing your stories, too. So we have an episode after. We'll cover someplace that we've Been with our budget friendly tips and all the other tips and the things you wouldn't expect and the things you would expect. We hear from our lovely listeners and they tell us, hey, you got it all wrong. This is when you should go or this is what you should do. So it's really fun.

[Doug]

So budget friendly. So OG has never been on the show.

[Joe Saul-Sehy]

Clearly not yet.

[Crystal Hammond]

We opened it with Doug. That was like our best show. We sure did.

[Joe Saul-Sehy]

Jesse told us his story about Thailand and a trip to a doctor's office.

[Jesse Kramer]

Yes.

[Joe Saul-Sehy]

Wow.

[Jesse Kramer]

On the Phi Phi islands.

[Joe Saul-Sehy]

You haven't lived until you've been to a doctor in the PP Islands.

[Jesse Kramer]

It's true.

[Joe Saul-Sehy]

Yeah. Which is true. Crystal, you think Texarkana is not a real place. PP island though is fine.

[Crystal Hammond]

I believe that one. But Texarkana, what is it? The Turducken of the Midwest or wherever it is.

[Joe Saul-Sehy]

That's very interesting. Of the South? Maybe. I don't know. Well, we're going to have a lot of fun, as you can hear already.

[Jesse Kramer]

Can I tell a teaser, Joe, to get people to go listen to that episode of Stacking Adventures?

[Joe Saul-Sehy]

Yes.

[Jesse Kramer]

Just from my story. All I'll say is that when the Thai doctor on the Phi Phi Islands looked inside my ear, he recoiled instantly and said, there's so much blood. That's the only part of the story I'll tell. You'll have to go listen to the episode for the rest of it.

[Joe Saul-Sehy]

The drama, teaser, suspense. He should be on every episode with this Crystal. The way he can tease stuff.

[Crystal Hammond]

I liked it. The adventures of true crime.

[Jesse Kramer]

Part of being a hot dog man, you got to be a bit of a teaser, you know.

[Joe Saul-Sehy]

All right, we're going to talk travel today. What are your best travel tips? How do you plan effectively for travel so you don't break the bank? You end up making travel worth the money. And I'm super excited for us to dive into this. But one, one last thing before we get rolling today. Just none of our contributors are travel experts. These are regular people sharing their thoughts around travel. Certainly we've got three money savvy individuals here today. But I always think it's really neat to look at not just what the people that love to travel hack are doing, but to what extent is average money conscious people. What are they doing to think more about whether they should use points or their budget. So just a little fair warning there. This is not going to be travel expert show. This is going to be regular people struggling with the same stuff you are every day. So with that in Mind, we've got a couple sponsors that make sure this is free and you don't have to pay for any of this. Goodness. Today we're going to hear from them. And then we are rolling with Jesse, Crystal, and OG on your summer travel plans. Today's show is sponsored by Strawberry Me Stackers. All right, everybody, let's talk careers. You know, you work hard, you bring in a paycheck, maybe even contribute to your 401k. Like a responsible adult gold star for you. But here's the thing. Making money is great, but making the right moves to actually grow your career and earn more, are you doing that because, let's be honest, hoping your boss finally notices you and hands you a raise. That is not a plan. That is a gamble. Humble. And unless you're the type of person who gets excited about betting their retirement on meme stocks, you probably want a better strategy. I certainly do. I have a coach, Mary Lou, that I meet with every Monday morning. And Mary Lou and I lay out my week. We talk about doing the things that are important to my family, that are important for my health, and the things that are important for financial literacy and stacking Benjamins and the intersection of all those things. And that's where Strawberry Me career coaching can help you. They'll match you with a certified career coach. Somebody knows how to help you get ahead. Like, my coach helps me negotiate better pay and actually make smart money moves. So you're not leaving money on the table. You've heard me talk about this before. The key is to have people around you, smart people around you who hold you accountable to getting those things you say that you want for yourself. If you're anything like me, you've been meaning to, quote, update your resume for like, the last five years. I remember what Mary Lou said. Are we going to keep talking about this book? Are you finally going to write it? And I'm very proud of Stacked. But without Marie Lu, I would have never had Stacked. Your career is your biggest financial asset. It's time to start treating in that way. When I started treating it that way, things change. It can be the same for you. So here's the deal. Go to Strawberry Me. It's Strawberry Me stacking, and you'll claim your 50 credit. That strawberry Me Stacking. Because maximizing your earnings is just as important as maximizing your investments. Strawberry Me does not facilitate or provide health care services. Please consult with a health care professional. But, guys, let's get smart people around us, shall we? This message is brought to you by Navy Federal Credit Union May is Military Appreciation Month and we're celebrating the military community that goes above and beyond every day with Navy Federal Credit Union. Navy Federal was created for the military community. It is dedicated to ensuring that its members feel celebrated and honored every single day. For over 90 years, Navy Federal's mission has been to support and uplift the military community. And this May is no different. It's not just a credit union, it's also a partner dedicated to helping its members achieve their financial goals. All active duty veterans and members of the military families are eligible to join. Navy Federal is excited to celebrate Military Appreciation Month as a special time to recognize our troops and the profound contributions that they make. Learn more@navy federal.org Celebrate Navy Federal Credit Union Our members are the mission Navy Federal is insured by NCUA all right, we're going to kind of riff off of a piece I found from Next vacay.com Doug calls it vacay all the time. I'm sure. Don't you vacay?

[Doug]

That's all the cool kids say.

[Joe Saul-Sehy]

Yeah, vacay. Because the word vacation is so long. But next vacate.com how to plan a vacation 12 tips for planning the Perfect Trip Krystal, let's start with you. When you're planning that perfect trip, what's first on the list? Is it I want to go to X place or I have Y amount of money? Let's see how far that'll take me?

[Crystal Hammond]

Well, it's both. I have a list of places that I want to go. That's what sucks about having the Stacking Adventure show because after every single call, I am ready to immediately go to every place we just talked about. So that makes it hard. But I do, I do have a list of places that are on my list. And then when they go on sale, that's when I start planning.

[Joe Saul-Sehy]

We'll talk about where you look for the sales later. But what's kind of top of your list right now of those dream bucket list places?

[Crystal Hammond]

The top of the list? Paris. I need a Paris do over. I also want to see if I can do it for cheaper and do different activities.

[Joe Saul-Sehy]

Oh, you didn't have a good time in Paris last time?

[Crystal Hammond]

No, I did not. Well, I did. I went by myself too, but now I know I learned a lot about going by myself and I I I could have used this show. Of all the stuff we're about to talk about on the planning front, you.

[Joe Saul-Sehy]

Kind of did it wrong.

[Crystal Hammond]

I did it completely backwards.

[Joe Saul-Sehy]

Paris is one of my favorite cities Me too.

[Crystal Hammond]

I can't wait to go back.

[Joe Saul-Sehy]

Fantastic. Oh, gee. Where do you start at? Or does Mrs. OG go? Here's where we're going next.

[OG]

In the hierarchy of budget or location, we would pick location first.

[Joe Saul-Sehy]

Okay.

[OG]

Yeah. We would say, this is what's on the list. This is where we want to go. As a matter of fact, I just started a list of places where I would think about where I'd see, you know, read an article about something that seemed pretty cool. And, you know, you just. That stuff goes in. In one ear and out the other. So I actually just started keeping a list of vacation ideas. So we kind of tend to go to the same things over and over again. Generically speaking. We go to the beach, go to the mountains. That's funny. That might change, like which mountain we go to or which beach we go to. But generally speaking, it's kind of the same.

[Joe Saul-Sehy]

And that I think is different person to person because my spouse is allergic to going back to the same place. I would love to go back to some of these places. I'm like, let's do this. And she's like, there's so many other places.

[Crystal Hammond]

I like that.

[Joe Saul-Sehy]

And I like. But once I've been once, now I can just go and be comfortable and have some fun knowing some, you know, revisit some of the cool places I went to. Jesse, where do you start? Do you start with budget or with destination?

[Jesse Kramer]

I think we start with itinerary. We definitely start with itinerary, which is. Right. Destination. Once we know that though, then some budget conscious thoughts kick in. But I always envy those people. Like, I know a couple people who, they start with very much budget first and they'll be like, yeah, found a super cheap flight to, to Denver this weekend. I've never been to Denver. And so on a whim, on Thursday night I decided I'm taking a Friday noon flight to Denver and just going to go spend the weekend there. And I'm like, that's kind of cool. That's a cool way to live.

[Joe Saul-Sehy]

It's hard to do that with a baby, though.

[Jesse Kramer]

Oh, correct, correct. Yeah, it'll, it'll be a while until we can do that, but I think that's a really cool way if, especially, you know, if you're the kind of person where either, maybe you're a points maximizer. You just, you, you like the idea of going to the airport, getting on a plane, just saying, like, I don't really care where I go. I'm just going to go somewhere new and do it cheaply. And that goes back to what OG said. We're definitely new place people, especially if it's like a big trip, if it's just a weekend. Like I mentioned earlier, you know, we've got our weekend destinations here in upstate New York of the Finger Lakes and Adirondacks, whatever, Toronto. But for the big trips, we usually try to do something new every time.

[Joe Saul-Sehy]

Yeah, Finger Lakes, pretty easy for you. Just hop, skip and jump away.

[Jesse Kramer]

Yeah, really nice.

[Joe Saul-Sehy]

It's interesting. When we were younger, I think we. We started with budget. I mean, we always started with we've got X amount of money. And so what's inside the sphere of that money? The older I get, it's more, how can I afford to do this big thing that I'd like to do next? So Scandinavia is on my list. But because my spouse's list supersedes mine, that is three years away, we've determined that Joe can get to the next thing if he lives three more years. We can go to Scandinavia, second on their list. So they start off on this piece. The reason I want to start there was they say, choose your destination is first. And once you do that, then it's easy to do the budget. I want to highlight something, Jesse, that you talked about, which was, have you guys ever done that? The spontaneous, Hey, I found a cheap flight. Oh, gee, have you ever done that? You know, you get the last minute online deal on a Tuesday, so on Thursday you're packing up and going to X place. I've never done that.

[OG]

I tend to do the exact opposite of that, which is the. Oh, crap, I thought we were supposed to leave on Thursday. Who bought tickets? Nobody yet. Oh, great.

[Joe Saul-Sehy]

I did that first strategic coach meeting once.

[OG]

Yeah, I mean, I would say our spontaneous stuff is more around something that is time sensitive. And I'm just thinking of one. When we were in spring break this year, both Michigan and Texas A and M played basketball in Denver for the basketball NCAA championships. We were in Colorado, skiing. It was an hour and a half drive. We're like, let's go. You don't get the best deal on tickets we had. We got. We drove, we didn't fly, of course, but you know what I mean? Like, that would be more of our spontaneous type of trip. A lot less. Let me just play the roll the dice thing. Although I will say when my son was interested at tcu, they have. Their freshman orientation is called Frog Camp. Makes sense. But they have different places that you can go to Frog Camp at some local, some, you know, regional, but Then they have one choose your own adventure type of thing, where you, like, literally show up at the airport with your passport and your bag. They tell you, we're going someplace warm, pack warm clothes, we're going someplace called Pack Hill, and you just show up and it's all TCU freshmen. I thought for somebody who never would do that in a million years, I thought that would be kind of fun.

[Joe Saul-Sehy]

That does sound fun.

[OG]

But it's already organized. It's not like I had to. Like, it's Tuesday. Oh, my God, we're going to Portland on Thursday.

[Joe Saul-Sehy]

Yeah.

[OG]

Somebody else is organizing it.

[Crystal Hammond]

But that's my other way to plan a trip, is let someone else do it and just show up. Sign me up for that every single time.

[OG]

Yeah.

[Joe Saul-Sehy]

I gotta tell you, the older I get, the more those organized tours, the ones I've done through Disney, have been just phenomenal. I mean, we're getting ready to go to Greece. I'm practicing a few Greek words that don't ask me for any because I'm not good enough to say any of them yet.

[OG]

More beer, please.

[Joe Saul-Sehy]

Yes. That's going to be the key phrase. Encore. Right? That was my favorite phrase. First time I went to Paris, I realized the encore was just a French word. Who knew?

[OG]

I didn't know a lot of people, but it was.

[Joe Saul-Sehy]

It was pretty amazing. The dude looks at me and goes, encore. I'm like, oh, there's my word.

[OG]

You stand up and you just start clapping.

[Joe Saul-Sehy]

Second on the list here is pick your travel partners. And it's interesting, Crystal, because you talked about going to Paris alone, and I don't know, you. And I have told some stories where it seems like you've had some great travel partners and some horrible travel partners. What are you looking for in the perfect person to go travel with?

[Crystal Hammond]

Well, I am my favorite travel partner, I must say. I live alone, and it's so hard. It is so hard to give up that independence, because if someone else is late, oh, my goodness, I hate being late. I hate waiting for people. Or it's just, oh, man, my foot hurts. What do you mean your foot hurts? Can you. Who told you to come on this trip if your foot hurt? You know, so there's all these different things you have to deal with, but then you have other extremes, because I went to Hawaii with the spreadsheet of activities friend, and it's like, okay, that's an over planner. You're going to be exhausted the whole way. But then there's the other, like, the lazy, you know, I don't want to do anything. I just, I could sit on the beach and read my book all day. It's like. But don't you want to get steps? So think about the people you hang around with anyway. And then that's when you decide, okay, who would I get along with? Because even one time we. There were four of us in one hotel room. That did not go well. Big surprise. But hey, we learned something from that.

[Joe Saul-Sehy]

Experience to never do it again.

[Doug]

Joe, have we talked much about my trip with OG to skiing this winter?

[OG]

Speaking of that, it was awesome.

[Joe Saul-Sehy]

I think we did talk about that slightly.

[Doug]

I'm not sure. I can't put my finger on it, but something Crystal just said made me think of that trip.

[Joe Saul-Sehy]

So, Doug, who is your perfect travel.

[OG]

Partner besides OG in a sleeping bag?

[Doug]

Actually, OG was a blast to travel with.

[OG]

Thank you.

[Doug]

Because, you know, he just, he'll, he'll do anything. He just, you know. Yeah. You want to go eat there? Fine, let's go eat there. What? You know, no, that was all good. But my preferred travel partner. You find people to your point, Crystal, you find people that you're just sort of in sync with, whether it's the pace of how you know, what time you like to leave in the morning and get out of bed and get rolling or the types of activities you want to do. My oldest son and I are just, we just travel the same way. And it's just like, we're like the perfect adventure buddies.

[Joe Saul-Sehy]

That's a big one for me. We were traveling to the Lake District in England with a family we knew who lived in Manchester. And so the next day we're going to the Lake District. I know it's going to be about a two and a half hour ride. There's from Manchester, I believe it was about two and a half hours. Cheryl and the kids, we are ready at like 7:00am thinking that, you know, that gives us. Then it's 9:30 and we can start hiking around the beautiful Lake District and see Beatrix Potter's house. And who else is there? Wordsworth's house? I. I think just some beautiful and.

[Doug]

Beautiful Abraham Lincoln, I think.

[Joe Saul-Sehy]

Do you know what time he had a summer house?

[Crystal Hammond]

Oh my goodness.

[Joe Saul-Sehy]

True story.

[OG]

Yeah.

[Joe Saul-Sehy]

I think right next to Grant Cardone's house. Right. But the people we were traveling with didn't get ready to go till almost 11am oh God.

[Doug]

Good.

[Joe Saul-Sehy]

It was horrible. I was like, what are we leaving? Oh, we just got to do a couple more things. We just got to do a couple more things. And then we Got there and we literally made a beeline for Beatrix Potter's place. And Cheryl's like, so you want to do hiking? Oh, I think we need to get back. I think it's time to get back. We spent as much time on the road as we spent in the Lake District. I can't wait to go back to the Lake District because we didn't hardly see any.

[Crystal Hammond]

So frustrating about them. Yeah.

[Joe Saul-Sehy]

Yeah. Jesse, are you sitting on the beach? Well, no, I don't think you are. Sit on the beach person.

[Jesse Kramer]

No. But I loved that Krystal brought this up because it's something I thought about independently. But it totally makes sense that it occurs for most travelers. My wife, she's a huge activity person. If we're going to go fly to X Country, we are going to jam pack our schedule with lots of activities. And I totally get that mindset that I'm just like one or two steps removed from that. You know, I don't mind having a day filled with 10 hours of activities as long as, you know, the end of the day, we're going to kind of relax for a couple hours and chill out. I need a little bit of chill time where she's more of like, no, no. We still have four things to do. Like, I know we've been going all day, but we gotta go. And that's where we get some friction in our travel. Because I'm just. I'm not quite all the way at that end of the spectrum. But wouldn't it be nice if it's like, just hearing your stories and seeing some of the comments come in from YouTube about picking your traveling partner is a huge part of the experience if you're going to travel with people. Because those misaligned expectations are just a recipe for disaster.

[Joe Saul-Sehy]

Yeah, that's. Andrea mentioned that in the chat. Pick your travel partner. Not at all. Should be first on the list. What's interesting about choosing your travel partner, too, is that, you know, I've been researching what the happiest retirees know. The happiest retirees actually travel once a year with people they're not related to, people that aren't immediate family with some friends.

[Crystal Hammond]

Yeah.

[Joe Saul-Sehy]

Throughout my life, I've been allergic to that kind of. For the reasons that we talked about. We have different expectations of what we're going to do. We have one friend who is that spreadsheet person, Crystal, that you talked about. And Jesse sounds like your spouse kind of is to some degree. And we used to be that. We used to be that. And we Kind of have traveled enough now where we're like, you know what? We're going to plan two big things a day and then the rest of it is serendipity. Like whatever happens, we're just going to go to an area and maybe we do nothing. Maybe we something, we're just going to leave it up to how we feel spur the moment. What I also found though was important was having even we travel people who aren't immediate family members. Having me time, you know, where it's okay that we're traveling together, but you know what? Cheryl and I are going to go do dinner by herself tonight. We're just going to go do the thing. Og do you travel with people outside the immediate family?

[OG]

I mean, other than Doug? Let me just think.

[Joe Saul-Sehy]

Doug's family. I mean, come on, he almost certainly bickered like brother.

[OG]

Family. Yeah. You didn't tell me where you were going, young man. Let's see. I don't think that I can, I can place a trip other than an after school activity thing. I know nothing that well. I do my annual golf thing with all my mastermind group. That's all. None of that is family. That's seven other guys. And you know, we play golf and do some work and some kind of coaching type thing.

[Joe Saul-Sehy]

But is it structured enough that everybody has the same expectation or do you run into some of the problems of different expectations with these people?

[OG]

That's kind of loaded. We play a lot of golf. I think that's the only thing, you know, because tee times are tee times. Right. So it's like, hey, the tee times at 8, the car's leaving at 7. I could think of one trip where half the group did something and half the group did something different, you know, because travel schedules upcoming or something. It was like, well, you know, I've got an early flight, I need to do this instead of that type of thing. Yeah, other than that. No, it's all family or extended family, which is a whole nother world.

[Joe Saul-Sehy]

Let's talk about resources. Crystal, you brought up finding deals before. Jesse, it sounds like your wife is a planner. Let's start with you. What resources do you use when you're researching a new place that you go to?

[Jesse Kramer]

That's a great question. Uh, I, I have to admit I, I don't do a lot of that myself. I mean, I'll do some Googling, I guess Google and, and Listicles and those kind of things are a lot of my top resources and reviews that other people have written. But I mean, my wife goes really deep. Whether it's like guidebooks.

[Joe Saul-Sehy]

Yeah. She. She buys a. That's Cheryl. Cheryl's a guidebook addict.

[Jesse Kramer]

Exactly.

[Joe Saul-Sehy]

She tends to prefer the Lonely Planet guidebooks.

[Jesse Kramer]

Okay.

[Joe Saul-Sehy]

Likes those. Rick Steve's guidebooks are pretty good. Fodders, I would say is third. Is that who pronounce that word? Fodders. Fodders. Fodor. Anybody know F O D R?

[Doug]

I've always said fodors.

[Joe Saul-Sehy]

Fodors photo.

[Jesse Kramer]

What are your guys on between three and five fodors. What are your guys thoughts on, like when you guys travel, do you do the things that are kind of like the must dos? If you're gonna be in Dublin, you must see temple bar. Or are you like off the beaten path? You're looking for things that.

[Doug]

Out of my way to avoid the temple bars or any of those things.

[Jesse Kramer]

Exactly. Yeah, yeah, yeah.

[Doug]

Hate it.

[Joe Saul-Sehy]

Is that you too, Jesse? You avoid that?

[Jesse Kramer]

That's my preference. That's my preference. I would much rather go to like Hole in the Wall. Like a place that has good local culture, but that is not the tourist destination. That's what I want to find.

[Joe Saul-Sehy]

Crystal, how about for you?

[Crystal Hammond]

Well, it depends. Going back to even looking for the deals, I have been on a few Groupon trips where the itinerary was already planned, so I already knew what I was getting into. But I also loved having that tour guide where we hit the classic touristy thing. Yeah, the big leaning Buddha in Japan and Thailand. They knew what time we needed to go to see it without all the other people being there. And then they also knew to tell us, hey, this is where we eat. You know, like this is what the locals do. This is where there is. So that's what I liked about that Groupon, those two. And they were through the tour group. So Gate one is a popular one. Affordable Asia. I think they might have a different name now, but they were the tour group that ran the trip just to see their itineraries and then try to recreate theirs. That's what I end up doing.

[Joe Saul-Sehy]

Also Affordable Asia. Now, I believe from our story about that a few weeks ago on Stacking Adventures as part of just Affordable world.

[Crystal Hammond]

Right, that's what it was.

[Joe Saul-Sehy]

Ochi, how about for you on the.

[OG]

Doing the stuff versus off the beaten path? I don't think we've done anything adventurous enough to have an opinion about this. I would like to think that if I was going somewhere that is some special. Like if you're going to Paris as an example, I want to see the Eiffel Tower. I don't necessarily need to go in it and go up it and whatever. It's like, okay, I don't care about that. But if you were like, oh, everybody sees the Eiffel Tower, we don't need to go see it. I'd be like, well I'm here, I should probably at least see it, you know, or it's like everybody, everybody wants to see the Mona Lisa. It's like, I know. Well, there's a reason for that I suspect. Right. So let's, Can I at least just check that box off? I don't have to hang out there forever. So I think I'd probably lean toward wanting to do more of the known knowns at least on the first kind of go around. And then on travel deals, that's that. I'm not the guy to ask on that.

[Joe Saul-Sehy]

We use TripAdvisor a lot. Viator. Viator. I think Crystal, we still can't pronounce that word.

[Crystal Hammond]

I don't know. Say it both ways.

[OG]

Never heard of any of these places.

[Crystal Hammond]

Well, they're the booking people. But I did hear that early on when I was in my travel planning. Is that TripAdvisor. You're going to get good sound advice from TripAdvisors. So it's like check them for their reviews because they have the most dependable and reliable.

[Joe Saul-Sehy]

Yeah, we've had, we've had great luck there and we're trying to book a cheap but good tour of the, like a walking tour of the downtown area to see kind of what to look at. We've had great luck with Vater Fighter, Viator, don't know, whatever, both, whichever it is.

[Crystal Hammond]

Tomato and tomato.

[Joe Saul-Sehy]

Yes. We're going to talk about the budget, the spreadsheet, we're going to talk about points programs. We get all that in the second half of today's show. But at the halfway point we put on the brakes for a moment because we have a year long competition between og, Jesse and Paula. And today Crystal, you're team Paula. And that means I've got some good news for you Hammond and some bad news. Which one would you like?

[Crystal Hammond]

The news.

[Joe Saul-Sehy]

All right. Well the, the good news is Paula, who's normally in last place is not in last place. That Honor goes to Mr. Jesse Kramer. Right now he is three and a half, Paula has four and a half points and OG pulled a little bit further ahead last time with six after Jesse and Paula were reeling him in. So today you've got an opportunity to put some heat on OG which is what we're all looking for Crystal.

[Crystal Hammond]

This is difficult.

[Joe Saul-Sehy]

Jesse will guess last. Crystal, you'll guess in the middle. OG goes first. So for all that, we need a question to kick off this holiday weekend. Doug, what are we going to talk about today?

[Doug]

Well, hey there, Stackers. I'm Joe's mom's neighbor, Doug, and I've been so excited for today's celebration. That's because on today's date, way back in 1896, the father of. Wait for it, nylon was born. Wallace Carruthers was working for DuPont when he realized that women's dresses were entirely too long. And what if he thought, what if he could invent something that would make them want to raise those hemlines? So he created nylon stockings?

[Joe Saul-Sehy]

I'm sure no.

[Doug]

You don't think that's. I don't think that's how it happened. Well, consider this fan fiction then, because I'm a huge fan and. And I'm wearing nylons right now. I mean, you know, because they improve your circulation. Speaking of nylon and being a fan, I'm also a fan of brushing your teeth. Hold on. Edit that. I'm a fan of brushing my teeth. I'm not brushing your teeth. And dupont actually began making nylon to use in toothbrushes beginning in 1938. The stockings not on sale until 1939. So here's a nylon inspired question to celebrate old Wallace's big B day. How many? I know you see this coming a mile away, but I just gotta say it out loud. How many bristles are in the average toothbrush? I'll be back right after I finish counting. One, two, three. Oh, crap, I lost count. One, two.

[Joe Saul-Sehy]

He's gonna be here all day counting the bristles of the toothbrush. Nylon and toothbrushes. You're going first, Og how many bristles in the average toothbrush?

[OG]

I brush my teeth no less than twice a week, 12 times a year. So I should have a pretty good sense of this. See, I'm just trying to picture it's about yay big. And you're talking about each strand of nylon is a bristle, correct? Yes, as it were. I'm just gonna pick a nice round number and say a thousand.

[Joe Saul-Sehy]

A thousand bristles. What do you think of that, Crystal?

[Crystal Hammond]

I'm gonna say. I'm gonna say 1500.

[Joe Saul-Sehy]

1500 thinks there's even more than a thousand bristles. Jesse, you got 1000. 1500 to the uprights.

[Jesse Kramer]

I wrote down on my notepad here 40 pods and then 50 bristles per pod. My guess in the blind was going to be 2000. So I'm going to go 1501. Ah, sorry, Crystal.

[Joe Saul-Sehy]

One for Jesse.

[Crystal Hammond]

What do you have to do with pantyhose again? Nylon bristles. Pantyhose.

[OG]

Everything in Doug's world revolves around pantyhose.

[Joe Saul-Sehy]

Everything.

[Jesse Kramer]

Yes.

[Joe Saul-Sehy]

Doug loves pantyhose. Well, he heard about nylon being created on today's date in history. So we got 10001500 and it was going to be 2000. It's 1501. Who's right? We'll be right back.

[Doug]

This episode is brought to you by Progressive Insurance.

[Joe Saul-Sehy]

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[Doug]

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[Joe Saul-Sehy]

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[Doug]

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[Joe Saul-Sehy]

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[Doug]

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[Joe Saul-Sehy]

And it could mean hundreds more in your pocket.

[Doug]

Visit progressive.com after this episode to see if you could save. Progressive Casualty Insurance Company and affiliates. Potential savings will vary. Not available in all states.

[Joe Saul-Sehy]

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[Doug]

You know that feeling when someone shows up for you just when you need it most?

[Joe Saul-Sehy]

That's what Uber is all about. Not just a ride or dinner at your door.

[Jesse Kramer]

It's how Uber helps you show up.

[Joe Saul-Sehy]

For the moments that matter.

[Jesse Kramer]

Because showing up can turn a tough day around or make a good one even better.

[Doug]

Whatever it is, big or small, Uber.

[Jesse Kramer]

Is on the way.

[Joe Saul-Sehy]

So you can be on yours. Uber on our way. Oh, gee. You open this up by saying a thousand bristles and both Crystal and Jesse thought that's not enough bristles. What do you think?

[OG]

Yeah, I honestly haven't studied it enough. I should brush more.

[Jesse Kramer]

Crystal.

[Joe Saul-Sehy]

Crystal, you've got from 1,251 to 1500. So you feeling good now that Jesse capped you?

[Crystal Hammond]

Wait, Yeah, I think he's going to be over by one bristle.

[Joe Saul-Sehy]

There's some confidence. Jesse, how you feeling? You like your 2000 number still?

[Jesse Kramer]

Yeah, I'm feeling okay. I'm feeling okay. There's a lot of little press. They're really small, you know, they're really small.

[Joe Saul-Sehy]

Doug, I believe you made it up to seven in your count. So we know it's more than seven.

[Doug]

Yeah. And Joe, I just wanna. I just listening to you play it back. I wrote down different answers than I just heard you say out loud. So I've got OG at a thousand. And I thought I just heard you say 1250 because I said Crystal has.

[Joe Saul-Sehy]

From 1251 up to 1500. She'll be the winner.

[Doug]

Got it. Okay. And then Jesse didn't guess 2000.Jesse guessed at 15.

[Joe Saul-Sehy]

1501.

[Doug]

Yeah.

[Joe Saul-Sehy]

Even though his thought be guested, I think is the way we say that.

[Doug]

Okay.

[Crystal Hammond]

Were you listening with your eyes closed again, Doug? Maybe that's what it was.

[Joe Saul-Sehy]

All right, who's going to win this thing? Oh, gee. Pulling further ahead, Crystal getting Paula closer to og. Or is Jesse going to move into second? Doug, who's the winner?

[Doug]

Hey there, Stackers. I'm Doug. Guy who loves popcorn and flossing. Joe's mom's neighbor, Doug. Ah, the toothbrush. Apparently, this device wasn't well received at first because if it were, wouldn't they have called it a teeth brush? It's like people only have like one tooth. Luckily they got to it before that last one was gone, though. Just saved by the day. So today's question, how many nylon bristles are there in the average toothbrush? I'm not going to tell you the answer. I'm going to do OG's favorite part. I will tell you the answer is 1,500 more bristles than OG Guest. 1,000 more bristles than Paula slash Crystal Guest. 999 more than Jesse Guest. Because the correct answer is 2,500 in the average toothbrush, making Jesse our winner.

[Joe Saul-Sehy]

Congratulations, Mr. Kramer.

[Jesse Kramer]

Thank you, guys. Thank you.

[Crystal Hammond]

Well, you would have been the closest with your 2k answer.

[Joe Saul-Sehy]

He would have. Yeah. Get it either way, very, very close.

[Jesse Kramer]

It's a lot of bristles.

[Joe Saul-Sehy]

That's a ton of bristles. You look at that little. It just doesn't. I don't know how they put 2500 on that.

[Crystal Hammond]

Also, congrats, whoever guessed right. You still lose because who. Who knows that?

[Joe Saul-Sehy]

Well, now you got something to tell your friends all weekend, Crystal. Guess what. I know.

[Crystal Hammond]

Yeah, right.

[Joe Saul-Sehy]

All right, let's talk about the credit card points game. Because, Jesse, this can be a minefield for people, right? They hear people successfully doing it, next thing you know, they got a bunch of credit card debt and these points that are probably not worth the 30% interest they're paying on the credit card. Do you pay? Do you play the points game?

[Jesse Kramer]

So we do play the game, but. But I guess maybe we don't. We have essentially two cards. One that is like very generic but has a pretty decent. It's like a pretty decent reward on anything you can buy. And then one that's specific. And I heard from a couple people I respect who play the points game really hard. And the two responses I've heard the most are either you get one credit card that's just generically good no matter what you spend on, or you get one thing that's like great on groceries and gas, and then a second thing that's just generically good. That's our approach. And I know it's not maximized, but this is just one aspect of my financial life that I'm happy, I'm okay not being maximized.

[Joe Saul-Sehy]

Why is that? Do you fear that you would get into credit card debt or it's just too much management for too little squeeze?

[Jesse Kramer]

Yeah, it's the same reason why I don't clip coupons, Joe. I mean, I think at the end of the day, it's juice for the squeeze. I don't know, at some point for the credit card game, I think people are probably squeezing really hard and not getting that much juice left. And it's just. It's where you choose to draw that line personally. Or it's like portfolios, you know, like, you know, you've been talking, you've been doing some really cool stuff recently, Joe. On what? The Merryman, like the 10 fund, Merriman portfolio. Yeah, I think that's really cool. I think other people, though, in this world are like, just give me one stock fund and one bond fund and I'll leave the excess return for the birds. It's just different strokes for different folks.

[Joe Saul-Sehy]

Shoot me now. Shoot me. And those people be wrong. Jesse.

[Jesse Kramer]

I know, I know.

[Joe Saul-Sehy]

Nick Clements, who's in the credit card industry, used to advise this before he retired. And Nick said, if you've got a cash back credit card that pays you 2% or better, that's a great place to be. So, Jesse, if yours is a cash back card and gives you 2%, I think you're right. Doug, you use Cashback Rewards.

[Doug]

It's all I use. Yeah, I don't do any travel stuff because I don't travel to all the cool places you guys do. So traveling isn't as much of a priority for me. I wouldn't use them fast enough. And the inflation or deflation. What's the right word on how the Value of the points goes down so often that I just don't think I would be getting the most value out of whatever the percent back is.

[Joe Saul-Sehy]

Crystal, you play the points game to some degree.

[Crystal Hammond]

I do, but it is a simple. I play the simple game. I have the one card that I pay off every month and that's what people get. And they, that's where people get into trouble. They're trying to do something that they don't understand or chase points that they don't understand. And like you said earlier, Joe, they end up paying that 30% interest on something where, just like with Doug mentioned that the points get devalued. I do follow a couple people that post every month. Hey, if you transfer your points here, it's a 30%, you know, sale for this airline for this month. I've gotten into a habit of checking those, but I have not done it yet. I always book through my portal, which you definitely give up a little bit of edge when you book on your, your credit card company's portal. But I went to Thailand on all points, so I hoard my points, I pay off my cards, and then I'm slowly venturing out thanks to, you know, listening to the people we've had on the show to say, hey, you can just transfer your points here and you'll get 30% more for if you're going to this place and you book this way or you travel, because I think it's either hotel or flight is where you can transfer your points and you get to save. So I'll, I'll look and see as long as it doesn't take too much time.

[Joe Saul-Sehy]

Oh, gee, how complicated do you play the points game?

[OG]

I do not pay any lick of attention in any way, shape or form to anything that is optimized. We use credit cards like it's cotton candy and I have so many points and so many buckets, I can't keep track of it all.

[Joe Saul-Sehy]

When's the last time you ate cotton candy?

[Crystal Hammond]

Yeah, my kids have.

[OG]

They bring it home on occasion. I will on occasion if I know there's going to be a large purchase, right? Like, if I know I'm going to, you know, I've got something due that's going to be a big number. I might glance and see, like, is there an offer somewhere? Or, you know, is it better to use the American Airlines card because I've got a flight that I could book right on the heels of this to get the points or, you know, is this going to put me in another tier or is it better to be on the Amex or something. So I will glance at it. But generally speaking, it's honestly whatever, whatever pops up on my phone when I go to pay is what I use.

[Joe Saul-Sehy]

Because I've been spending so much time at like campfi and with people that do this really well, we've started transferring our cards toward the programs that are more flexible. So the Chase Sapphire card, which is very flexible point program, Capital One has a very flexible program. And I had a Capital One card, didn't use it hardly at all. Now I've switched over to using that Capital One venture more. And because of the flexibility.

[Doug]

Yeah, Doug, when you say you transfer, does that mean you transfer the balances onto the card that is better travel.

[Joe Saul-Sehy]

Card or you just use it more? Yeah, I used it more.

[Doug]

Okay.

[Joe Saul-Sehy]

And as an example, hotel points stopped using Marriott, which was, I was all Marriott all the time. Started using now Hyatt. If there's a Hyatt, I'll go to Hyatt first. And I found that I can score. If there is a Hyatt, I will score much, much more quickly free rooms at a Hyatt than I was through Marriott. But to your point, I don't obsess about it a ton. I was talking to our friend, I think we're all friends with Chris Hutchins. Talking to Chris and talk about spreadsheets. Holy cow. Like the amount of work he does. But he travels for free all the time. Goes first class travel for free. So I don't know. Have you ever thought about that, Jesse, about getting more into it to be able to just go for free whenever you want?

[Jesse Kramer]

Thought about it? Thought about. Yeah, no, I've talked to Chris about it.

[OG]

He's got a baby. He can't think about what's for dinner.

[Joe Saul-Sehy]

Yeah, yeah, well, oh gee, if you.

[OG]

Thought about it, then no, no, I mean this isn't a weird flex of any kind. It's just there's so many in so many places. Like I could just look and go like, oh, got a capital, some capital one points. I'll just use those to fly mom down here for vacation, you know, or whatever. It's like booking something on the AMEX website because that's the one I happen to click on. Oh, I got points there. I'll just use those points. I don't, I've, I again, very rarely pay attention to the, you know, oh my gosh, you got 1.7 points, cents per point. You should get 2.1. You're leaving money on the. I don't care. It's, you know, I turned in a bunch of points and got $2,000 worth of Amazon gift cards not too long ago.

[Doug]

Yeah. Trying to play that whole game is almost as complicated as playing one of Joe's board games. Oh, yeah, it is like, it's like a second.

[OG]

Well, and then halfway through the game, you get different set of rules. Like, oh, no, no. You know, that character can't move those spaces. They can only move these space. You're like, since when? Well, since I'm losing and I want to make the rules different.

[Joe Saul-Sehy]

Next on our list is decide when you'll go. Crystal, you prefer to go during shoulder seasons when it's not so busy. Or do you go for the. You know, there's a picture here. Japan. Do you go when the cherry blossoms are out?

[Crystal Hammond]

Yeah, I would avoid the touristy seasons. Like, I don't want to do carnival anywhere. Don't want to go cherry blossom season because I want to get great service. I don't want to be trampled. I don't want to have to wait too long to experience things. I'm going when there's no one else there. So shoulder season, that is, I guess, when the kids are in school. Just be careful of when you're going because you don't want to go. When, like, certain countries they go on holiday for the whole month and you're there wondering, why is everything closed? It's because the country takes a holiday or bad weather. Don't go to places during hurricane season. So it helps to, you know, reach out to people to know when you want to go places.

[Joe Saul-Sehy]

And we found that out after we had our trip to Chile scheduled that that country does nothing on their Independence Day. And we didn't realize when we booked everything that we were going to be there on Independence Day. So we ended up with being, like, the only people at this hotel we were staying at. Everything was closed around town. We actually booked a tour with a guy and this was a horrible tour. The tube was like, I can't take you anything because nothing's closed. I'm like, well, give us your money back. Oh, he wanted to make the money. So we went around and saw a bunch of closed places. It was a horrible, horrible. Now, the thing that was cool was he introduced us to this idea called a fonda, which is the celebrations around town that locals go to. And we ended up being, as far as I could tell, the only obviously non Chilean people at the Chilean Independence Festival. And it was a blast. It was cool seeing what people do during that. But it's kind of like a carnival, though. You don't want to go to carnival.

[Crystal Hammond]

No way, Jose.

[Joe Saul-Sehy]

Too many people, Jesse. Shoulder season or go during the time that the good stuff's happening?

[Jesse Kramer]

Definitely shoulder season. I'm not a big crowds person anyway. I'd rather. Yeah, definitely rather avoid the crowds of other tourists especially. Tourism's a double edged sword for a lot of these localities where it's like, on the one hand it's the lifeblood or it's one of the main drivers of their economy, but then they're kind of losing their local culture because they're overrun by tourists. And so, you know, I'd rather not just be just another tourist during the biggest tourist season, but then also just for all these other reasons we're talking about today. It's like, you know, oh, so you're looking to save money on travel? Like that's a big thing we've been talking about today. Well, are you going to save money just so that you can go and be really inefficient on your trip because it's the busiest time of the year there? Like. No, I'd rather be efficient on my trip and kind of save money implicitly that way too.

[Joe Saul-Sehy]

So that's also about. But there's the other side of that too though, Jesse, which is, you know, you can go to the beach in the winter and it's going to be, you know, you're not gonna be able to sit out on the beach or you go in the summer when it's packed, but you get that beach experience that everybody wants.

[Jesse Kramer]

Yeah. You know, obviously there's definitely an on season and an off season. I'm not saying that, but I just think there are some things where they're just no matter where you go, there's going to be an example of.

[Joe Saul-Sehy]

Right.

[Jesse Kramer]

Carnival is a great one. Cherry blossoms is a great one.

[Joe Saul-Sehy]

Yeah.

[Jesse Kramer]

If the sole reason you're going cherry blossoms, then like you gotta go during cherry.

[Joe Saul-Sehy]

Gotta go then. Well, that's what I was gonna ask OG some of the big events. Indy 500, let's say, do you go to Indianapolis for the Indy 500 or do you skip it because there's a crowd of people? Do you go to Pamplona for the running of the bulls or do you skip it because you don't want to get trampled by all the people? Not necessarily the bulls.

[OG]

Well, like Jesse said, if you're going to the Indy 500 because you want tickets to the Indy 500, you are going.

[Crystal Hammond]

Yeah.

[OG]

During the Indy 500. We went to the Rose bowl and the College Football National Championship a couple of years ago, and it was the absolute worst time to drive to Houston from Dallas. It was the worst weather imaginable, and pouring rain, and just everything about it was awful. That was the ticket, is that. Or stay at home and watch the game. So you travel when you're doing it. I was just talking to. I said something to my wife yesterday. I said, oh, when the kids are gone, we can finally do this trip. And there was a trip that I saw revolved around a bunch of airplane pilots that had a kind of a. It's like a guided tour of flying from Seattle up through Alaska and, oh, beautiful fjords and stuff like that. And I was like, that would be cool. It's in late August, which is a great time to be in Alaska, apparently, but a really bad time to be doing anything if you have children because you're in school, and so we don't have the luxury. I was talking to a client one time, and I said something about. I said, oh, don't you guys usually go to Europe? You go in the summer. He goes, you'll go to Europe in the summer. I said, oh, I thought you guys always go to Europe. So we go in September when all you idiots, you know are in school. You. You guys go in September or you guys go in the summertime? Not us. We're. We're past summer travel, you know, so.

[Crystal Hammond]

Nice.

[OG]

I would do that if I could. I want to do Little Monsters.

[Joe Saul-Sehy]

Yeah. I want to do two more things here. One is, where do you stay? Do you prefer Airbnb? Trying to find friends in the area, if possible, or is that, you know, cramping their style? And you go for the hotel Airbnb Friends or the Hotel Crystal? How about you?

[Crystal Hammond]

Again, it depends. Because Switzerland, we stayed with friends. But then when there was a group of us back in the ski con days, there were 35 of us, and we stayed in this huge Airbnb that was amazing. But then solo trips. I'm definitely staying at a hotel where there's eyes on me, you know, and cameras everywhere. And I like the people to clean up everywhere.

[Joe Saul-Sehy]

Oh, I've heard at Airbnbs they have cameras everywhere.

[OG]

You're not looking close enough.

[Crystal Hammond]

Ouch. But it does depend, though. Like, with the big, big group, I would. Usually someone else has the account, but big group, definitely Airbnb, but, like, smaller. Definitely prefer a hotel.

[Jesse Kramer]

Yeah, Jesse, it depends on the place. When we were in Chiang Mai, Thailand, it's like you could stay at one of the nicer hotels there for, for $50 a day or you could go get, you know, an okay Airbnb for $30 a day. There's some places where it's like, well, the difference between the nicest place and the mediocre place might be hundreds of dollars a night. And maybe that's the place where we'll settle on the more mediocre place to save some money.

[Joe Saul-Sehy]

Oh, gee, how about you?

[OG]

Yeah, we've done all of the things. Our ski trip recently where we went spring break with the kids. We've always stayed in a hotel and gotten to adjoining hotel rooms and, you know, that's plenty of space for everybody. But you're kind of beholden to the hotel. Here's when food is, here's what the restaurant's open, here's you got to make reservations. This year we rented a condo a little farther up the slope from where the hotel was. And I don't think anybody would do that. I don't think we'd ever go back to the hotel. Never with, with the family because we went to the grocery store, we got to eat when we wanted. Everybody had way, you know, 50 times the room, you know, versus the little hotel rooms. We had a, you know, nice condo. So that's helpful. I, I've also done, you know, we've done the big giant houses like Crystal was talking about with all the friends. And again, as long as you're kind of all on the same schedule or there's enough space where if you're not, you can be like, you know, oh, gee's going to bed, it's 10 o' clock, so I'll see y' all tomorrow. Like, you can go do your thing, you know, that's okay. But if you try to mix those things, right, like, yeah, I think, I think we've all done this where you go, it would be a great idea if we all slept in the same hotel room. And then you realize about halfway through night one that, nope, it was a terrible idea. You would pay any amount of money to not do that again.

[Crystal Hammond]

Oh, yes, been there.

[OG]

So you gotta choose your own adventure there carefully.

[Joe Saul-Sehy]

But yeah, I think they're definitely for that big group. I do like the Airbnb and that communal activity, the fact that we have our own, our own space. We did that for my nephew's graduation recently. We did for my son's graduation where we had a seven bedroom house in Austin, which really made it nice. But to your point, OG you just got to have enough room.

[OG]

It's better. That's right.

[Joe Saul-Sehy]

Yeah. I want to ask about travel insurance. Krista, where do you draw the line on travel insurance?

[Crystal Hammond]

I usually get it like when you're booking for the flight cancellations. Just because. I've had flights cancel a couple times and it's become more common. There was a time where I would never even think about it, but now I do second guess it just because. And I don't want to be stuck anywhere and I want my money. I want my freaking money back. Health wise, my. My insurance is pretty much covered everywhere and I've had to go to a hospital. Well, I was sick. They didn't believe me that I was sick, but my friend was pretending like he was sick and he. They gave him IV and everything. So I thought that was hilarious. But.

[Joe Saul-Sehy]

Well, you were actually sick and he was.

[Crystal Hammond]

Yeah, I was and he was not. It was pretty funny.

[Joe Saul-Sehy]

Why was he pretending to be.

[Doug]

I was gonna say why? Did I miss something?

[Crystal Hammond]

Extra vacation. Extra vacation days from. I don't know where he worked, but it was extra vacation time from work.

[Doug]

Oh, I thought you were gonna say he was looking for a free night stay at the hospital.

[Crystal Hammond]

Oh, that's funny. No, I hope no one's a traveling. Yeah, but then also your credit card too, because the chase, the shop fire reserve, they have very good protections because one time, well, both times I went to Vegas, my luggage didn't arrive after I did. So I did end up getting money for. To buy new stuff. And that was pretty cool.

[Joe Saul-Sehy]

That's cool. That's great. Know what your credit card offers and what it doesn't. Jesse, what do you do about travel insurance? Do it, don't do it.

[Jesse Kramer]

I think on the big trips we've usually done it and on smaller trips we won't. If it's like a long weekend domestically, we won't. We won't get it. But for the big like week long, 10 day, 2 week trips internationally, we will for the same reasons Crystal said is like at some point you're just like the risk of something going wrong and we're going to be thousands and thousands of dollars out of pocket. Here is just pony up for the hundred dollars of travel insurance knowing that it probably won't pay off but you're covered just in case it matters.

[Joe Saul-Sehy]

That's funny. It's like any other insurance decision. It's a magnitude and probability. And while probability might not be high, that magnitude gets high enough. When I travel international, I get it. So of course I only buy it when it's really expensive, when it's really cheap, I don't. I don't worry about it. Oh, gee. How about you?

[OG]

No, but what we do, we don't buy it individually, but what we do is we have a contract, an annual contract with Allianz. It covers everything. It's just a once a year premium. And I have to look up how much it is.

[Doug]

But specifically for travel, though.

[OG]

Yeah, it's for travel. You know how, like, when you book your trip on the flight or the hotel or whatever, it always gives you. It's like, what state are you in? And you can. It's all covered, but then you also. It's kind of double dipping, I should say. We've done it in the past. I don't have it actively right now, but I've done the. Done the annual thing before. And then you also have to know, like, how your credit card works. Like Crystal was saying, there's a lot of benefits on your travel cards.

[Doug]

Now, Doug, I'll say that I've only tried to take advantage of the insurance provided by the credit card one time, and we ended up not being able to use it or get the benefit of it, not because of the credit card, but because they required some proof of some things. And my son had gone on a packaged, you know, vacation, it was a spring break thing in college, down to Mexico. And they needed us to get that the credit card, needed us to get proof from the company that organized the whole thing. And that company wouldn't give us what we needed. And I spent so much time trying to deal with that, I just gave up. Eventually, we just ate the cost, so that sucks. Yeah. So it's. It's not. I mean, every time I book anything now, I think I'm not paying for the extra insurance. I've got it. But it might not be the credit card company that throws the hurdles up in front of you. It might be the requirements you have to satisfy the people have to provide that to you. The Airbnb host or something like that.

[Crystal Hammond]

That's why I do. Yeah. I don't like booking through Expedia and those others for that reason, too is I like to have my flight booked through the airline and I like to have my hotel booked with my card for my own safeguarding.

[OG]

Yep. I prefer that as well, for that exact reason, because it is such a pain to unravel something via the travel agent, whether the travel agent is the Capital One portal or the Amex travel portal or whatever. It's just.

[Joe Saul-Sehy]

And they'll send you there in a hurry. They'll go, oh, look, not my problem.

[OG]

Not my problem. Contact your travel agent immediately.

[Joe Saul-Sehy]

Yeah. Last thing when you're flying. Pre check. Clear. Jesse, do you do pre check? Do you do. Clear? You're nodding.

[Jesse Kramer]

We have TSA PreCheck, which in some airports, it's funny, in our local airport, it's so small that it probably doesn't save us that much time, but there's some places where, man, it saves you an hour. It just makes things so much smoother, so much easier. You get to keep your clothes on or whatever. And again, naked.

[Doug]

Why would you do that?

[Crystal Hammond]

Well, yeah, you guys don't put your pants back on.

[Jesse Kramer]

You guys don't get randomly selected every time you go to the airport.

[Crystal Hammond]

Must be a to take your clothes off, apparently.

[OG]

I'm not hiding what you're hiding, Jesse.

[Jesse Kramer]

Go back to the hot dog joke.

[Joe Saul-Sehy]

Jesse finds out the hard way that you don't have to take off your.

[Doug]

Pants when they tell you to take off your belt and your shoes. I can see where this is going.

[OG]

Skip to the end.

[Doug]

Saving everybody some time.

[Jesse Kramer]

But, yes, TSA PreCheck is well worth it.

[Joe Saul-Sehy]

Well, that's funny. Your report, Jesse's a lot like ours in Texarkana. I feel like I'm paying that fee just to make sure I don't take off my shoes.

[Jesse Kramer]

Like, thanks.

[Joe Saul-Sehy]

That's why. Because there's never more than three people in front of me in the line. And Dallas is pretty good, too. OG I mean, the Dallas airport has so many portals that those lines. I think I've been in line one time. Oh, gee, that was a little long.

[OG]

I could think of one time where I was. You know, we always play the game of, like, how close can we make it?

[Joe Saul-Sehy]

Yeah.

[OG]

You know, and they tell you, be to the airport. Three hours.

[Crystal Hammond]

Not fun.

[OG]

Yeah, no, more like six minutes before boarding. But I remember one time I pulled in, parked, walked into the terminal and saw the line and walked all the way down to where the line was and kind of did the mental math of like, okay, yeah, this ain't happening. Went back outside, got in my car, drove to a different terminal, walked in, went through security, got on the train, all the way back to C, got off the train, and they were boarding, and I was like, oh, so that worked out perfectly, but I would have never made it.

[Joe Saul-Sehy]

Is this o' Hare?

[OG]

No, it was Dallas.

[Joe Saul-Sehy]

Oh. Oh, at Dallas.

[Crystal Hammond]

Yeah.

[OG]

Yeah. And we have all of the things clear. Pre check, global entry, $50 bill. Like, whatever it takes.

[Crystal Hammond]

Oh, I Didn't know that.

[Joe Saul-Sehy]

Wait, a $50 bill? I almost missed that one. $50 bill to the dude to just let you through.

[OG]

Just slide. Let's like, you know, there's a stack of them, so you just go, can I cut in front of you for 50? Can I cut in front of you for 50? You just like handing out money just to get to the front of the line.

[Joe Saul-Sehy]

Nothing better than getting caught bribing a tsa.

[OG]

All the people in the universe to bribe. Just tsa. Guys like you realize this is like Jesse would say, the juice isn't worth the squeeze here.

[Crystal Hammond]

Thanks.

[Joe Saul-Sehy]

A guy OG that you and I know by BMWs, and he picked one up in Germany, which you can do, and then drive it to the Netherlands. And the price discount you get almost pays for the trip. So he's tooling around Europe and he's in the Czech Republic when he goes speeding through this little village. And this cop pulls him over. And the cop walks up to his window. And this. This guy that we know says. He goes, you know, I'm just wondering how much to make this just go away. And the. The police officer said, are you trying to bribe me? Because. Because that's a stay in jail. And he throws his hands up right away and said, no, no, no, no. I just. I don't know how it works. I'm American. I got no idea. No, no. No way am I trying to bribe you? Not at all.

[OG]

But if I was. Exactly how many pesos does it take?

[Joe Saul-Sehy]

The cop goes back to the car and then comes back up to the window and goes, €120. And it goes away. It was amazing. Goodness, how fast he made.

[OG]

Reminds me of that scene from We Are the Millers.

[Crystal Hammond]

Turned him into a criminal.

[Joe Saul-Sehy]

He did. He did. And then the cop. The cop's life then took a whole different trajectory. Yeah. O.G. you were saying?

[OG]

Oh, no, I just said it sounds like that scene from we are the Millers.

[Joe Saul-Sehy]

I don't even remember the scene.

[Jesse Kramer]

Oh.

[OG]

Where they're leaving the drug compound and they get pulled over by the cop who needs the bribe to keep going.

[Joe Saul-Sehy]

Gotta have the bribe. That movie Crystal Precheck.

[Crystal Hammond]

Oh, yeah. I have global entry, which comes with pre check. And that was a credit card benefit.

[Joe Saul-Sehy]

Yeah. Check your credit card.

[Crystal Hammond]

And I have clear too, thanks to Atlanta Airport. I have clear.

[OG]

Yeah. Oh, yeah. Use clear one time and you go. I can see why this needs to be in my back pocket.

[Crystal Hammond]

Yep.

[Joe Saul-Sehy]

Are there airports that worry you more than others? The two that I always worry about is Orlando is horrible.

[OG]

Mco. Yep.

[Joe Saul-Sehy]

Heathrow is horrible.

[Crystal Hammond]

I've heard that.

[OG]

Lax.

[Joe Saul-Sehy]

Lax. Luckily, I arrived for my flight a couple weeks ago, like at 4am So I was good.

[OG]

Oh, perfect time for all the rush hour traffic.

[Joe Saul-Sehy]

Yeah.

[OG]

Any so much construction going on right now with the Olympic stuff? It's very. Well, the last time I was there anyway was just a ton of construction, so the traffic's all jacked up. And yeah, LAX scares me. MCO is bad. I think Chicago, Dallas, JFK, LaGuardia is great now.

[Joe Saul-Sehy]

I think LaGuardia went from horrible to fantastic.

[Crystal Hammond]

Different.

[OG]

Yeah, DCA was good last time. Detroit's fine.

[Crystal Hammond]

Yeah, they're good.

[OG]

Yeah, I think.

[Joe Saul-Sehy]

Not bad. Jesse, any airports you're afraid of besides those?

[OG]

Rochester.

[Jesse Kramer]

Rochester. I've had some issues transferring through. Chicago has been rough a couple times. Denver's got all those conspiracy theories about it. Still a good airport, but a lot of conspiracy theories there.

[OG]

You're right. Denver sucks.

[Jesse Kramer]

Toronto. The traffic around Toronto is rough. Say that if you've ever flown in or out of Toronto, that's a tough one to get to.

[Joe Saul-Sehy]

I have not. Never have.

[Jesse Kramer]

Yeah. Yeah.

[Joe Saul-Sehy]

All right, well, you know what? Stackers, Give us yours. What airports were you. What are your best travel tips? Either put those online on social media, hit us up, or in our basement Facebook group. We'd love to bring you in on this conversation. Let's help each other travel better this summer. All right, that's going to wrap it for today. Let's find out what all of you are working on. Crystal, thanks a ton for coming over and helping us out. What's coming up on Stacking Adventures?

[Crystal Hammond]

We've got some really, really cool trips coming up that you will hear about. We got Belize on the map. We've got. Well, I can't wait to hear Joe's side of Greece when he gets back. That's also going to be fun. We've got theme parks. What else do we have? We have a lot of fun stuff coming up.

[Joe Saul-Sehy]

So we're going to talk a little bit about Route 66.

[Crystal Hammond]

Yes.

[Joe Saul-Sehy]

Next year's the 100th anniversary. Route 66.

[Crystal Hammond]

Not Route. It's Route 66.

[Joe Saul-Sehy]

We can't pronounce any of the other words, but we get that one right, Crystal. And that's it. The Stacking Adventures where find your podcast are. Jesse, what's happening on the Personal Finance for Long Term Investors podcast.

[Jesse Kramer]

What is happening? We released an episode recently where I took a deep dive on. I think it's called the Ready for Retirement Study from Fritz Gilbert, which is A cool study about kind of retiree and pre retiree expectations. And the way I think of this study is, you know, a lot of people before retirement are worried about X, but then once they retire, they realize they should have been worrying about Y. And I think there are a lot of really cool lessons that we can all take away from that kind of no matter where we are on our financial journey. But so I took a deep dive into that in a recent episode. It was came out pretty well.

[Joe Saul-Sehy]

We're going to also dive into that. But I'd love to hear that episode. And that's it. Personal Finance for Long Term Investors where finer podcast are. Oh gee, what you got going on this Memorial Day weekend besides, you know, watching the Indy 500?

[OG]

No, I don't even know that we'll get that in. Honestly. This is graduation weekend, so everybody is here. It is a packed house. Although it's not because we made everybody stay at hotels, but graduation tomorrow and Caroline's birthday on Sunday.

[Crystal Hammond]

Wonderful.

[Joe Saul-Sehy]

Yes, fantastic. Holiday weekend at the OG residence.

[OG]

Yeah, come on over. We're at barbecue and pool party and whatever. It's basically a non stop party from four days ago till next Tuesday.

[Joe Saul-Sehy]

Sounds fabulous. Let's do it, Doug.

[Crystal Hammond]

We're all invited.

[Joe Saul-Sehy]

I know. Let's get out of here so we can go over to OG's house. What are our big takeaways today?

[Doug]

Well, Joe, here's what stacked up on our to do list today. First, take some advice from the co host of Stacking Adventures, Crystal Hammond. Crystal says choose your travel partners wisely. Hint. It's definitely probably not your spouse. Is that right, Crystal? Is that pretty much what you said?

[Crystal Hammond]

What spouse?

[Doug]

Okay. Second, Jesse told us the best way to get the most out of your trip planning is to plan. Play the credit card point game. Let's pretty much summarize it, Jesse.

[Jesse Kramer]

I think we should pick a couple cards and not chase after the rest of them because sometimes the juice is not worth the squeeze.

[Doug]

There's the phrase I was looking for. But the big lesson. It always makes sense to take a day hike with someone you haven't traveled with before you go on vacation with them. Because if you don't, OG will yell @ you. This is how fast I walk. What's your damn rush?

[OG]

Not. Not true.

[Joe Saul-Sehy]

That's spoken like you might have experienced that before.

[Doug]

Yeah, ask me how I know. Thanks to Jesse Kramer for joining us. You'll find his podcast Personal Finance for Long Term Investors wherever you're listening to us now. We'll also include links in our show [e-mail] it's not not true. Thanks to to Crystal Hammond for hanging out with us as well. You'll find her fabulous podcast Stacking Adventures. Oh, it's hers now. Wherever you listen to Finer, everybody knows it's hers. Pushing you out, Joe. Thanks also to OG for joining us today. Be sure to listen to his podcast Stacking Benjamin's. You can also get on his financial planning calendar at Stacking Benjamin. This show is the property of SB Podcasts, LLC, Copyright 2025 and is created by Joe Saul Sehive. Joe gets help from a few of our neighborhood friends. You'll find out about our awesome [e-mail] along with the show notes and how you can find us on YouTube and all the usual social media spots. Come say hello.

[Joe Saul-Sehy]

Oh. Oh yeah.

[Doug]

And before I go, not only should you not take advice from these nerds, don't take advice from people you don't know. This show is for entertainment purposes only. Before making any financial decisions, speak with a real financial advisor. I'm Joe's mom's neighbor, Doug. And we'll see you next time back here at the Stacking Benjamin Show. What are you still doing here? The show is over. Go home.