Tips | 04.06.2023

How to Stay Sane & Organized on a Group Trip

A group of woman outside consulting a map. They look happy.

By Franki Hanke

Put ten of your friends together on a long train ride, are you having a blast or suffering? With the right planning, group travel can be a lot of fun! These travel tips all center around one main way to plan a group trip: communicate early and often. 

With enough forethought, you can find a solution for most issues that arise on group getaways. 

Pick a Planning Focus

You have to start somewhere with planning. Before anything, decide what’s your first decision:

→ Dates – If you have a set vacation or you’re celebrating a set anniversary or birthday, build your trip around the dates. 

→ Destination – If you know a spot you or many of you want to see, determine your trip around when a destination is less busy, experiencing a seasonal novelty, or more affordable.

Two phones show the interface for the app Troupe which aims to make planning a group trip simple.

The app Troupe was created to make the planning process of a group trip simpler. You can take suggestions for destinations, dates, and other details and then run a vote for all your companions. 

Book a Vacation House

It’s much easier to fit a large group in an Airbnb or VRBO where you’ll have an entire home with multiple rooms. Plus, extra space and a kitchen add more flexibility for activities and mealtime. 

We’ve rounded up our favorite rentals in Napa Valley and Central Texas if you need recommendations. 

Tip: Be mindful of the sleeping arrangements in a rental. Aim to get everyone the same quality of bed, and if someone is on a pull-out couch, they should pay less than someone with a private room. When booking, read through all property details to know the kind/size of each bed listed. 

If someone would need to sleep in a comparably lesser bed, talk it out ahead of time and predetermine who would do that and if they’re comfortable with that. Let them know why you’re considering this house so they know the pros and cons. 

For example: “This house would work, but one person would be in a twin-sized bed. I found another option that has queen-sized beds for everyone, but it’s half an hour further from downtown. Would anyone be okay with the smaller bed?” 

Be Flexible

Your friends may have different budgets or work schedules that conflict with the shared house you’re booking. Communicate your plans early enough to coordinate with each other. 

→ How many people do you need minimum to justify your chosen rental property? Most properties large enough to fit a group get expensive if you’re not splitting the cost between people do the math on how many people would justify the house. 

→ How long are you staying?

Communicate these to people early on and everyone to confirm their own plans. If guests need to stay separately so they can arrive late or leave early, you can plan on that ahead of time. 

Woman laying on her stomach books a flight on her cellphone. Everyone booking their own flights helps when you plan a group trip.

Have Everyone Book Their Own Flight

Unless you all live at the same local airport, coordinating flights can be challenging, and a whole group of people is a large charge for your credit card. Instead, have everyone look at flights from their home airport and compare options in a group chat. 

If flights dictate a lot of different arrival times, a portion of your full group may want to coordinate a second wave of arrivals together so they can share transportation or one night of a hotel room as necessary before joining the full group. 

Communicate Main Details

Be Upfront and Frank About Money

The most complicated aspect of a group trip is the cost. Tell people early on your plans for how to pay for things and coordinate a pay-back method. 

A large group of friends uses their cellphones at a table to Venmo the one person who paid the bill.

Venmo is a simple way to immediately pay back whoever puts down their card for an excursion or meal. Agree ahead of time if you’re splitting by item or evenly dividing a meal. If you know your group has a variety of budgets, based on your time with your friends previously, opt to split by item cost so someone making a price-conscious decision isn’t swept into paying more than their share. 

If this is a bachelorette or birthday trip for one group member, consider pre-making a pool of money from everyone attending besides the guest of honor so you can collectively cover their share. 

Ask Everyone Their Expectation for Activities

When we lack specific information, we make assumptions. When you’re on a group trip, those assumptions can trigger conflict. Instead, check in on some common trip-related decisions.

→ Will we eat out for every meal or cook group meals? 

→ Who’s getting the best/biggest bedroom? 

→ How are we getting around? Is everyone comfortable with public transit or Uber? 

→ Does everyone have and use Venmo?

→ How much walking are people comfortable with? 

→ Does anyone have specific activities they consider a “must-do?”

→ What’s the vibe at the house going to be: rowdy or chill? How late will people generally want to stay up and active? 

Any spot where you’re tempted to say, “Oh we’ll just…” Don’t “just,” check in with the group of people you’ll be with! 

If there are a lot of disagreements on these points, consider grouping people up based on shared responses. If one trio is especially active into the night, consider asking them to share one wing of the vacation home so everyone else can get to bed, for example. 

By talking about these things ahead of time, you can adjust and find solutions leisurely and without pressure. 

Include Everyone in the Planning Process

On some trips, you’ll play hostess and act as a full-service planner for your friends, but more often, group trips are a shared experience. Getting everyone’s input on the activities can take some pressure off you, and let everyone enjoy the trip. 

Depending on your budget, you could hire a travel agent to do much of this planning for you. They can coordinate many of the nitty-gritty details, but it comes at a cost. To save money, focus on an unofficial group leader to play the role of organizer, which if you’re here reading, I think that’s you. 

Start brainstorming early. 

If you have a month before you’re actually booking reservations, let everyone brainstorm together. Create a shared spot to put ideas. If you’re bringing together a diverse friend group, this is a great way to make some initial connections, too. 

I recommend the app Wanderlog as a one-stop-shop for brainstorming and creating a shared itinerary in on app, but you could also make a shared Instagram Collection, Pinterest Board, or just a specific group chat. 

Tip: Group tours may have a group discount or group rate if you’re booking with a large enough party! Ask your tour operator ahead of time for this. 

Clean up your ideas and share. 

Once everyone’s passed some ideas along, pick through them and organize (if needed) so you can easily browse. 

→ Delete ideas that won’t work. Sometimes places are closed for the season or events don’t align with your timeline, so just chop those off the list. 

→ Identify what would require pre-booking or a high expense. 

→ Share that focused list with the group and ask for input. If you have limited days or budget, have everyone pick their top two or three.

Build your itinerary around the main events. 

Once you know those big ticket items, start your itinerary around those. Fill in other ideas that are physically nearby to those big ticket items to create clusters of activities that fit together. For example, a theater showing nearby to one of the cool dinner spots someone found on Instagram fit together like puzzle pieces! 

Check-in with everyone.

Before booking anything, check in with the group. Allow people to opt-in or out of any activities before you make any group bookings. If group members have a range of interests, see if there are some natural splits where one part of the group can attend one activity while another does something else at the same time. 

Share Relevant Details

Once anything is booked with a reservation or ticket, double (and triple) check that everyone has those details saved. 

Allow for Separation

Especially for longer trips, leave some free time in your itinerary for people to choose their own activity or to enjoy some alone time to refill their social battery. 

You could leave some blank gaps in your itinerary for this, but if you’re a big planner, I know you want to know what’s happening. So, consider denoting some items as open-invite for people to join your plans, but make it clear they are safe to skip. Items that don’t require reservations or advanced tickets work best for this. 

With this bit of flexibility, everyone can find the travel experiences they enjoy while on the same trip. 

Book Reservations

The larger your group, the harder it will be to seat that many people. For any restaurants that allow reservations, make them ahead of time to ensure your party will fit. 

If there’s a spot that doesn’t take reservations, pre-determine if you’re comfortable splitting into one or more smaller parties to eat there, how long you’re all willing to wait, and choose a nearby backup destination. 

Share Numbers

Make sure everyone has everyone else’s phone number. If you’re splitting up for different group activities, you want as many ways to reconnect in an emergency as possible. 

Group vacations can be wonderful experiences with all your favorite people, but with poor communication or planning, they’ll become a nightmare fast! Use these tips so your next group trip is an enjoyable getaway! The above content may contain affiliate links. When you click and shop, we receive a small commission to support our writers.

Want a Free Guide?

You will receive our free 19-page guide and access to our exclusive content, private invitations, and tips you’ll love.

"*" indicates required fields

This field is for validation purposes and should be left unchanged.

What do you think?COMMENTS 0