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)

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)

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.

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.