
How can you plan a successful group trip without putting strain on your friendships?
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Matthew
Foreign.
Alison Stewart
You're listening to all of it on wnyc. I'm Alison Stewart. This week we are discussing travel. Yesterday we talked about how to be an ethical tourist. And coming up later this week, we have guests sharing their tips on how to travel on a budget and quick weekend getaways. But today our conversation will follow. Traveling with a Group. Whether you're traveling with friends you've known your entire lives or ones you've just met recently, planning a group trip has its challenges, shall we say? Joining us to discuss the best ways to plan and to execute a group trip, we have Ali Volpe from vox. Hey Allie, thanks for having me, listeners. Time for you to weigh in. Do you have a group trip coming up?
Ali Volpe
Do you need advice?
Alison Stewart
Or maybe you have some sort of tips or tricks from past group trips that went successfully, give us a call or Text us at 2124-3396-9221-2433. WNYC Tips or Tricks from past group trips that went beautifully. Or maybe you have a group trip coming up and you need some advice. 2124-3396-9221-2433. WNYC okay, so as people are getting their questions for you and calling in, what are the three most important pieces of advice you would give to people who are planning a group trip?
Unnamed Expert
Yes, the first one I would say is definitely everyone needs to get on board with the kind of trip that everyone wants to be having because you don't want to get to your destination. And someone's like, I want to relax, I want to be chill. And someone's like, no, I'm trying to pound the pavement. I want to see everything. Those are two kind of opposed viewpoints. So you want to make sure everyone is on the same page with like, are we going to relax? Is this going to be a family trip or a kid friendly trip? You need to sort of be on the same page there. Another thing you need to be on the same page with is budgets. Again, if you want to do a bunch of excursions that might add up and cost a lot of money, we need to talk about those things. If you want to stay at the same hotel, we need to make sure that everybody is on the same page with what they're comfortable spending. And even when it comes down to the restaurants you want to eat at, what is everybody's budget? You really need to be transparent about that, like setting clear, clear terms and not sort of dancing around the conversation. And another big tip is you want to be on the Same page with how you're going to spend your time. And I find this comes up a lot in large group trips where maybe some people want to spend all their time together and some people want to have some more alone time or break off into smaller groups. I think you need to really set clear expectations of, I'd like to do X, Y and Z together. Or, you know, I wake up early and I want to work out. And don't think that I'm ditching you because when you wake up and I'm not in the hotel room because I'm at the gym, you need to set those expectations beforehand so nobody feels like they're being left out or, oh, my gosh, are they mad at me? They don't want to hang out with me this whole time. I think it's totally normal to want some alone time on a group trip.
Ali Volpe
All right, let's break those down. We should dep. You should plan on the type of trip that you want to take. Like you said, some people like to go to the beach. Some people want to travel a new city, see all the sites in three days. What is the best way to have this talk and when should you have it?
Unnamed Expert
Yes, this talk needs to happen as soon as, like, even the idea of the trip is on the table. I would say. One of the experts told me, like, usually trips kind of come about one of two ways is like one person sort of dreams up this idea and then they loop other people in. Or a few people may be at dinner one night. They're like, oh, it would be really great to. To do this trip. And it's sort of like a group decision. Regardless of how the idea originates, you need to talk about the sort of vibe that you're going for. Another expert said a good question to ask is like, what is everyone's intentions for this trip? And so that kind of opens the floor to like, oh, yeah, I'd like to relax, or I'd like to go to an all inclusive or I'd like to see as many sites possible. And it gives people an idea to voice their opinions.
Ali Volpe
Do group texts work in this situation?
Unnamed Expert
You know, that's a really good question. I would say to do this face to face because as you have people voicing their opinions, things can get lost in the shuffle. Though I did talk to somebody who every year they plan a big group trip with their friends and via text, they find it really helpful to list out all the dates that are potentially on. On the table. And people will do like a, like, emoji for the date that they can do. And they found that that is really helpful for sort of just getting everyone's attention for what date might work best. But I think for more nitty gritty logistics, you want to have those conversations.
Ali Volpe
In person, let's take a call. Let's talk to Matthew who's calling in from Harlem. Hey Matthew, thank you for taking the time to call all of it today.
Matthew
Hey there. So my tip is whether you're traveling with 2, 3, 4, however many, and regardless of whoever they are, you need to mandate time where everybody is away from the group and you need to like whether you want to be away from the group or not, everybody needs to get away from the group at least once a day.
Ali Volpe
Do you plan the time you're going to be away, Matthew, or do you just put your hands up and go, I'm away, I'm gone now?
Matthew
No, it needs to be planned like the group is not together at a certain time and some people won't want to do that. But it's like everybody, there will be people who want to be away from the group and won't speak up. And so it's really good to like everybody needs to be away from the group every day for a certain amount of time.
Ali Volpe
Matthew, thanks for the tip. This text says best group travel advice. Pick one major activity for your days, a tour, museum, dinner, plans, whatever for the group and the rest of the day is yours. Part of the fun of travel is both the sights and the spontaneous. It sets the tone of spending time both together and getting giving independence. Those are both great suggestions. Our Phone number is 2124-3396-9221-2433. WNYC it's travel week here on all of it and we want to talk about group trips. If you need advice, if you have a trip coming up or if you have a tip or a trick from past group trips that went perfectly, call us 2124-3396-9221-2433. WNYC my guest is Allie Volpe from Vox. She written all about this. All right, so when planning a group trip, how do you decide who plans?
Unnamed Expert
Yeah, one friend might be the natural planner and I don't think anyone should feel bad about that. I'm definitely one of those people who is the planner. I'm a little bit type A and so I think it's okay if one person wants to really take the reins, but you should also get buy in from the rest of the group because you don't want to be making again, dinner reservations that are out of people's budgets or booking tickets to museums that maybe not everybody wants to go to. For instance, last summer a large group of friends and I, we went to Japan for two weeks. It consisted of two couples, two women, a baby and a nanny. And so a wide variety of tastes and preferences. And my birthday was one of the days that we were on the trip. And so I had just sent out a text of, you know, does anyone want to do this dinner for my birthday? Here's what we're looking like in terms of budget and the folks who wanted to go, I booked the reservation for. And so I think one person might need to take the lead on one of those things. But again, making sure you're getting buy in from everybody else.
Alison Stewart
What kind of system can be put in place so that it allow everyone to get to do at least one thing that they really want to do?
Unnamed Expert
Right. I think having a collaborative Google map is really, really good for that. So anyone can add whatever locations that they want onto the map. It's great for those more spontaneous moments where you're in between that sort of one big thing that you've booked for the day. And so, you know, like, okay, this person added this bar to the map. Like it would be great to go visit that because we're nearby. And if anyone has again, like any sort of like big preference ahead of the trip and they're just like, I really want to do this thing. Cool. And maybe the planner person is the one who books the tickets. But again, they've heard from everybody else about like what it is they want to do. Because again, we all have very limited vacation days. We're all on this trip together. We all want to make sure we're having a really good time. So it involves a lot of communication.
Alison Stewart
Is it a good idea to have a third person, someone outside of the group plan something for you? A travel agent or a tour guide? Are they helpful in these situations?
Unnamed Expert
Oh, yeah. I think there's been a total resurgence in people turning to tour guides and travel agents lately because we're sort of overwhelmed with information. You open up any sort of social media platform and look up travel tips and there's so many posts and it's really easy to get overwhelmed. And so I talked to a couple of travel agents who said like, people are really turning back to these professionals who might have deals with certain locations, deals with certain vendors or activities, and they are in touch with people in the location who have better ideas about what to do something that maybe you won't find on Instagram or TikTok. So I think it's really great to rely on experts who have connections in the areas where you're going to.
Ali Volpe
All right, let's get to some text.
Alison Stewart
This one says, a little structure, a few group dinners, and mostly optional plans.
Ali Volpe
Another text says, in a shared house, the last day of meals should all be leftovers. That's good advice.
Alison Stewart
Another one says, number one rule is.
Ali Volpe
You don't have to do everything together. Sometimes catching up at dinner about what you did is the best part of the day. Let's talk to Meredith from Somerset, New Jersey. Hi, Meredith, you are on the air at all of it.
Meredith
Hi, Alison. Thanks for taking my call. So as soon as I heard the segment, I knew I had to call in. Back in 2018, I went to Germany with my now husband, best friend and her boyfriend and friends of friends. And we did go to Oktoberfest. And one of the big things I remember is one of the friends had said, oh, I speak German. It'll be okay. It really wasn't okay because at one point the waitress who was taking care of our table in Oktoberfest said, I'll just speak English to you. It's not a problem. So my suggestion would be to make sure that if you're going away to a foreign country, if you say you're fluent, make sure you're fluent. My husband and I like to just pick up easy phrases. Hello, how are you? Thank you. Anything like that. Good morning, good night. Just to show that we are thankful for being there and being able to travel to wherever we're going. But if you have someone who purports to be the language translator for that country, please make sure they are, because otherwise you just look like the dumb Americans that can't speak the language.
Ali Volpe
Thanks for the tip. We appreciate it. We're discussing the best way to plan and execute a group trip with VOX writer Ali Volpe.
Alison Stewart
This text says says separate checks, which.
Ali Volpe
Brings me to budget. This is a very sensitive subject for many people. Money in general is a sensitive subject. How can you go about talking about budgeting without offending anyone?
Unnamed Expert
Yeah, it is really tough, especially if you're going with a group of people who have very different salaries or comfort ability on what they want to spend. A financial therapist I talked to said that people, you know, tend to dance around the conversation about, like, oh, I'd like to say somewhere nice, but not too fancy, when you really need to say, like, my budget is $100 a night, $200 a night. Like that's much more clear. And people shouldn't feel too hurt if someone has a larger budget and they might want to stay somewhere else. Yes, it can, it can really sting and you should be prepared for those sort of things. But I think if, if something is just out of the price limit for you, you should never, ever spend beyond what you're willing to pay for. And it's okay if you don't end up staying in the same hotel as, as someone else. So maybe you found an Airbnb that's a little cheaper. As long as you're all making an effort to see each other during the day. I don't think it really matters where you stay as far as, you know, splitting the checks or, you know, getting separate bills. I know in, you know, some countries, it is a little difficult to even commun. So I think it's okay if one person, you know, picks up the bill. Like, I'm going to get every dinner, or even one person who wants to get all the credit card points, they're like, I will pay for everything and I'm going to put it in split wise, I'm going to put it in tab and we will calculate it later. Again, like that is another responsibility for somebody. But I think it could be a lot easier that way if, you know, like, this is the person who's going to handle all of this. Or again, you can split it up by activity. One person is going to pay for all the dinners. One person is going to do all the museums. Of course, like everyone's, you know, individual shopping, they can handle themselves. But I think it's really important to have a plan about how you're going to pay for things, how you're going to split it up, and how you're going to pay people back afterwards. Maybe you are like, oh, I, this is really going to add up. Can I pay you back in installments? And usually friends are okay with that, but make sure you talk about it first. They might not be okay with it. They're like, you know, listen, my credit card bill's coming up, I might need it all, and that might change your plans. So again, talk about it beforehand.
Alison Stewart
Can you think of an activity that will fit almost anybody's budget?
Unnamed Expert
Oh, that's a really good one. I mean, a lot of times there are, in any city, there are museums that are free or very low cost. I think those are always really good activities to do. And they're good for different ages, too. If you go to a tourism board for whatever city or town you're going to. They oftentimes will have a list of those low or no cost museums or activities. Or sometimes it's, you know, a park or and they have events in a park. I think those are all really great for for any type of budget.
Alison Stewart
This text is good on the subject. A group of nine friends all spent two weeks at a home we all shared in Tuscany. Most of these folks had not met or spent any significant time together. In order for everyone to feel that we were sharing our expenses equitably, we pooled the same amount of money together for shared expenses until we used it up, then pooled it again and at the end we simply split.
Ali Volpe
Split what was left over.
Unnamed Expert
Oh, that's very interesting. I've never heard of that before, but I guess yeah, if everybody's comfortable doing that by by all means.
Alison Stewart
This says non drinkers should never go on a group trip with all drinkers speaking from experience. Which brings me to Craig who's calling from Morganville, New Jersey. Hey Craig, thanks for calling all of it.
Matthew
How are you doing? Two things real fast. One is just because everyone's such great friends doesn't mean they're great traveling companions. I've seen friendships break up over that. The other thing is I remember in traveling in France when before you go to a country, learn some catchphrases and always try to speak their language, even if you butcher it. Especially in France, when they see that you're making an effort to learn their language, they will bend over backwards and they will not be the snooty Parisians everybody thinks.
Alison Stewart
Craig, thanks so much. Good tips by the way. My guest is writer Alex Volpe. She writes for Vox and we are discussing the best ways to plan and execute a group trip. If you need advice or you have some tips of your own, give us a call. 2022-1243-3969-2212, 433. WNYC in there. I heard you mention a few apps along the way which I want to tell people about. You mentioned Jeti. What does it do?
Unnamed Expert
Yes, there is an app called let's Jetty. Three friends who, you know, travel together started this app and it's a group travel planning app where everybody can go in and sort of like pick the things that they want to do add to the itinerary. A similar app that I personally really love and use is called wanderlog. My boyfriend and I use this for every trip we go on. It breaks down day by Day of your trip, it automatically populates your flights, your hotel, lodging, any sort of transportation, and you can put in, like, all of your little events and activities into the app. And so it's great. Like, you wake up that day, you pull up the app, and you're like, oh, great, this is what we have planned for the day. And again, it's really great for seeing big picture. Like, oh, we don't have anything booked on day five of the trip. Like, maybe let's get a dinner reservation. Or what is the one big hallmark event we're going to do on that day?
Alison Stewart
You also mentioned tab or splitwise.
Ali Volpe
What do they do?
Unnamed Expert
Yes, those are for splitting up the checks. Very important. And split wise is great because even if you know you have a group of 10 people but only three people did a certain activity, you can pick and choose which of those folks contributed to that activity, and it only splits the cost up among those people.
Ali Volpe
This text says, when I plan my trips, I state my all in budget, and then I break it down into travel and transportation, lodging, activities, activities and food and beverage.
Alison Stewart
I share that to start and ask.
Ali Volpe
How that aligns with my companions. That's great.
Unnamed Expert
I love that. I love that.
Ali Volpe
This is another good one. This is funny. Never, ever go camping. Traditional tents, no real bathrooms, et cetera, with a group. Unless you go glamping. Which brings us to the kind of vacation you want. Do you want to, like, rough it or do you want to be at the Four Seasons? Right.
Unnamed Expert
Oh, exactly. And, like, I'm definitely the latter. So I don't think any of my friends would ever invite me camping, and that is fine.
Ali Volpe
Well, let's talk about accommodations. What are good group accommodations?
Unnamed Expert
Yeah, I think if people really want to stay together, they really are valuing that. Like, we want to sleep in the same place. Airbnb, vrbo. Those are good for, you know, large home accommodations, especially if, you know, you're doing a sort of, like, lake activity. It's really good to find those, like, sort of larger accommodations if you want everyone to stay together again, for more, like, city kind of trips. Again, for. For our big friend trip to Japan last year, we all stayed in different hotels that we all chose based on, you know, each person or each couple's budget. So, you know, some folks may have stayed in a little more expensive and, you know, someone else stays in a slightly cheaper hotel, but we all generally agreed on staying within the same area. So we could sort of wake up in the day, meet at a central loc. Um, again, if someone wants to pick first class seats. You know, you should be prepared that people might have a certain way about it. But if that is what you know you value on your trip, to have that sort of comfort in first class, you need to decide whether it's worth a little bit of hurt feelings over.
Alison Stewart
That's important to bring up arguments they can come up on trips. How can these arguments be controlled and not get out of hands?
Unnamed Expert
Yeah, to hearken back to what that one caller said, that some people are might be great friends but you just should not travel with them. I think it's kind of important to keep that in mind. You know, how much time have you spent with this person? Are you comfortable spending that much time with that person? I think, you know, it is a little bit risky to sort of like go on a multi day trip with a bunch of people you don't even really know. Again, like that can't be in everyone's control of the time. I'm thinking of like bachelor bachelorette parties. It could be a little nerve wracking. And especially in those sort of situations where, you know, you might not have a lot of control, arguments are bound to come up. And I think it's important to remember, you know, who you are outside of this travel scenario because sometimes it can feel like when we're on vacation that we're, you know, a different version of ourselves. And you need to remember that, you know, whatever happens here will follow you home. So to keep in mind all of this sort of good conversation habits that you maybe think of at home, you know, I statements, don't blame somebody. Especially you know, after you've had a couple glasses of wine and saying, what's your problem? That will follow you home. I think it's important to give people space because again, they could just be hangry. Maybe they had a really bad night of sleep. I know again, to bring it back to my trip from Japan last year. Towards the end of our trip we were in September, it was really hot in Osaka and I was just sort of having a meltdown. And again, it was nothing personal against anybody I was with and I sort of snapped and then I had to quickly apologize. Like, listen, it's the heat, I'm really tired. This is nothing that has to do with anybody else. And I hope my friends understood.
Alison Stewart
Yeah, sometimes when somebody has a bad time on a trip, it just happened because of that trip. You shouldn't necessarily bring that home with you.
Unnamed Expert
Exactly. Yeah, sometimes you just need a little sugar, you need a little nap, you need some air conditioning.
Alison Stewart
Let's talk to Steven in Tenafly. Hi, Steven.
Matthew
Hi, there. Listen, I have Parkinson's, and I have friends who do, and I'm looking for trips that would be walker or wheelchair accessible.
Alison Stewart
I don't know. Allie, can you answer that? Or. It brings us up to another question of we have to make sure that everybody can do everything right.
Unnamed Expert
Yeah, I think that's a really, really good point. And, yeah, you just want to be really mindful of the group that you're traveling with. Like, you wouldn't want to plan something that requires a lot of walking with folks who, you know, might not, you know, be able to do that. I think it's first and foremost being mindful of your friends and the group that you're traveling with and making sure that you're doing something that is accessible to everybody.
Alison Stewart
And if anybody has any suggestions for Stephen and Tenify, you can DM us, and we'll make sure he finds out. I think we have time for one more question. Juanita, real quick.
Unnamed Expert
Yeah. Am I on?
Alison Stewart
Yeah, go.
Matthew
Okay. I recently went on a retreat, and I absolutely refused. It's a cardinal rule of mine to never share a room, and some people were offended by that. But it's to me, it can make or break a trip, especially if something happens like the person has sleep apnea.
Alison Stewart
Oh, imagine I'm gonna cut you off there because we're gonna run out of time. What do you think about that rule of never share a room?
Unnamed Expert
Yeah. Again, as long as you vocalize that to your friends. And again, there might be some hurt feelings, but hopefully they will realize this is about maintaining the peace, not about having too much space and not wanting to be with each other.
Alison Stewart
Our text, our final text says our group had breakfast together each morning to chat about the day's plans, went to our activities, had a big lunch together, bought snacks and Dr. For evening gatherings, had a big siesta, and regrouped in the hotel lobby for a cheap, fun evening. That sounds like a good group, Allie.
Unnamed Expert
Oh, perfect. I want to go on vacation with them.
Alison Stewart
Allie Volbe is a writer for Vox. She was helping us discuss the best way to plan and execute a group trip. Thanks to all our callers and texters.
Ali Volpe
And thanks to Allie.
Alison Stewart
By the way, the transcript from this.
Ali Volpe
Conversation will be up on our website.
Unnamed Expert
In the very near future.
Alison Stewart
Thanks, Allie.
Unnamed Expert
Thanks so much for having me.
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Podcast Summary: "How to Plan a Successful Group Trip with Friends"
All Of It is WNYC's vibrant exploration of culture and its myriad consumers, hosted by Alison Stewart. In the episode titled "How to Plan a Successful Group Trip with Friends" released on August 5, 2025, Alison delves into the intricacies of organizing group travel. Joined by Ali Volpe from Vox, the conversation is enriched with insights from callers and text submissions, providing a comprehensive guide for listeners aiming to navigate the complexities of group trips.
Alison Stewart opens the episode by setting the stage for the week's focus on travel, highlighting previous discussions on ethical tourism and upcoming segments on budget travel and weekend getaways. The central theme revolves around the challenges and strategies of planning group trips, whether with long-time friends or newly acquainted companions.
Alison Stewart (00:09):
"Today our conversation will follow. Traveling with a Group. Whether you're traveling with friends you've known your entire lives or ones you've just met recently, planning a group trip has its challenges, shall we say?"
Ali Volpe emphasizes the importance of aligning the group's expectations to ensure a harmonious trip. Differing desires, such as relaxation versus active sightseeing, can lead to conflicts if not addressed early.
Unnamed Expert (01:40):
"You want to make sure everyone is on the same page with like, are we going to relax? Is this going to be a family trip or a kid-friendly trip?"
Ali Volpe (03:24):
"You should plan on the type of trip that you want to take. Like you said, some people like to go to the beach. Some people want to travel a new city, see all the sites in three days."
Advice: Initiate discussions about the trip's vibe and objectives as soon as the idea is proposed to ensure everyone's intentions are clear and accommodated.
Financial discussions are often sensitive but crucial. The episode highlights methods to handle budgeting without alienating group members.
Unnamed Expert (12:09):
"People, you know, tend to dance around the conversation about, like, oh, I'd like to say somewhere nice, but not too fancy, when you really need to say, like, my budget is $100 a night, $200 a night."
Advice: Encourage honest conversations about individual budgets. Tools like Splitwise can aid in managing shared expenses efficiently, ensuring transparency and fairness.
Deciding who takes charge of planning certain aspects can streamline the process and cater to individual preferences.
Unnamed Expert (07:04):
"One person might be the natural planner and I don't think anyone should feel bad about that."
Advice: Designate planners for different parts of the trip, such as accommodations, dining, and activities, while ensuring that all group members consent to the decisions to maintain harmony.
Balancing group activities with personal time is essential to prevent burnout and maintain relationships.
Caller Matthew (05:26):
"You need to like everybody needs to be away from the group every day for a certain amount of time."
Unnamed Expert (23:12):
"Give people space because again, they could just be hangry. Maybe they had a really bad night of sleep."
Advice: Schedule designated times for group activities and personal downtime, acknowledging that individual needs for solitude or smaller group interactions are normal and healthy.
Conflicts may arise during group trips, but with proper strategies, they can be managed effectively.
Unnamed Expert (20:13):
"It's important to remember who you are outside of this travel scenario because sometimes it can feel like when we're on vacation that we're a different version of ourselves."
Advice: Encourage open communication, use "I" statements to express feelings without blame, and address issues promptly to prevent them from escalating and affecting post-trip relationships.
Ensuring that the trip is accessible to all members, including those with disabilities, is paramount for an inclusive experience.
Caller Steven (22:14):
"I have Parkinson's, and I have friends who do, and I'm looking for trips that would be walker or wheelchair accessible."
Unnamed Expert (22:36):
"You just want to be really mindful of the group that you're traveling with. Like, you wouldn't want to plan something that requires a lot of walking with folks who, you know, might not be able to do that."
Advice: Select destinations and activities that accommodate all group members' physical needs, ensuring everyone can participate fully and comfortably.
Modern apps can simplify the planning process and enhance the travel experience.
Unnamed Expert (16:45):
"There is an app called Let’s Jetty. A group travel planning app where everybody can go in and sort of like pick the things that they want to do add to the itinerary."
Unnamed Expert (17:44):
"Splitwise is great because even if you know you have a group of 10 people but only three people did a certain activity, you can pick and choose which of those folks contributed to that activity."
Advice: Utilize planning and expense-sharing apps like Let’s Jetty, Wanderlog, and Splitwise to coordinate itineraries, manage schedules, and handle finances seamlessly.
Allowing each member to include at least one activity they desire ensures personal satisfaction and diversity in the trip experience.
Unnamed Expert (08:12):
"Having a collaborative Google map is really, really good for that. So anyone can add whatever locations that they want onto the map."
Advice: Create shared platforms where everyone can contribute their preferred activities, fostering a sense of ownership and ensuring a well-rounded itinerary.
Alison Stewart and Ali Volpe wrap up the episode by reiterating the importance of communication, planning, and flexibility in organizing successful group trips. The combined wisdom from experts and listeners provides a robust framework for anyone looking to embark on group travel, ensuring memorable and harmonious experiences.
Alison Stewart (24:30):
"Conversation will be up on our website. Thanks, Allie."
Final Thoughts: Planning a group trip requires careful consideration of diverse preferences, transparent budgeting, effective communication, and the use of supportive tools. By addressing these aspects thoughtfully, groups can enjoy enriching and conflict-free travel experiences.