How to Plan A Stress-Free Summer Group Trip

A group of smiling men and women sit on a rocky ledge with sand and palm trees in the background.

Group travel is one of those things that will turn out to be either an incredible experience you’ll remember for the rest of your life or a nightmare scenario that’ll make you want to tear your hair out from start to finish.

Trip planning is stressful enough when you’ve just got yourself to worry about—adding a handful of friends to the mix, each with their own preferences and ideas, can result in a major headache if you don’t approach things the right way! Luckily, there are steps you can take to make sure your trip goes off without a hitch.

We’ve outlined our best tips below, so round up the gang and read on to find out how to plan the perfect group trip this summer (without losing your mind in the process):


When you’re traveling solo, it’s easy to fly by the seat of your pants—snagging last-minute flights, hopping from town to town on a whim, waking up when you feel like it, and eating at whatever restaurant happens to catch your eye.

With a group trip, a lot of that spontaneity goes out the window. If you want to keep everyone happy and your trip on track, you’re gonna have to plan for it! Discuss everything as a group—what kind of accommodations everyone is okay with, which attractions or areas they’d like to visit, whether or not they’re cool with long layovers and multiple connections. Ask about food allergies and health concerns that might affect the trip (is one of your friends allergic to shellfish? Is someone unable to handle long bouts of walking or adventure-style tours?) and talk about how you’re going to get around once you’re at your destination.

When it comes to group travel, the fewer surprises the better. Creating a solid itinerary that everyone is excited about right from the start will make for smooth sailing later on and head off any mid-trip issues that might have otherwise popped up.


2. Set up a trip HQ online

Remember five seconds ago when I told you planning was key? Well, great planning hinges on organization. Keeping everyone on the same page means having all of your trip documents—booking confirmations, itineraries, sightseeing suggestions, etc.—in a single, easily-accessible spot online.

Sites like TripIt, Evernote, and Trello are great for this sort of thing. They act like virtual binders, keeping all of your plans neatly sorted and guaranteeing that no one will be texting the group the day before your trip asking, “So, where are we going again?” (We all have that one scatterbrained friend. 🙄) Even booking giant Kayak is getting on board with their Trip Huddle tool, which allows groups to add preferred dates, destinations, and accommodations to a shared list where members can then vote for their favorites.

Having a hub for crucial documents and receipts also lays out your trip finances nice and neatly, which means everyone will know exactly who owes what to whom. No one likes having to chase a friend down for cash—being able to see the cost breakdown and everyone’s contributions in the same place keeps things simple and clear.


3. Make a budget and stick to it

Speaking of cash, a big part of the planning process is establishing a trip budget that everyone is happy with. Your #DoItForTheGram friends might want to splurge on a glamorous hotel or fancy meals while your budget backpacker buddies might push instead for cheap hostel bunks and $2 street noodles—as a group, you’ve got to take everyone’s wants and financial needs into account and come up with a number that sits nicely in the middle.

Once your group has a max budget in place, make sure you stick to it! There’s nothing that kills good vibes quicker than someone being forced to pay for something they don’t want to or can’t afford.

One idea is to set up a shared “pot” of money for trip expenses that everyone pays into at the start. This works especially well if you’re staying in the kind of accommodations that allow you to cook food and buy drinks together, eliminating the hassle of splitting bills or swapping IOUs while you’re on the move.


4. Know when you need to split up

Even after all of your meticulous planning and budgeting, sometimes peoples’ wishes just don’t line up. And that’s okay! One of the benefits of group travel is the fact that there will almost always be another person who wants to do the same thing as you on any given day, even if the group as a whole doesn’t.

If half of the group wants to spend time at an elephant sanctuary and the other half wants to check out a boat cruise, no worries—people can pick one or the other and the group will divide up accordingly.

And if you’re the only one who wants to wander around an art gallery or chill by the pool, that’s cool too. Ultimately, it’s your trip as much as anybody else’s, so make sure you do what you want to do and head home with no regrets! Sometimes, a day alone in the middle of a trip jam-packed with friend time is the breather you need to recharge those social batteries and appreciate the remainder of your vacation even more.



BONUS: Awesome apps to help you plan your group trip!


A handy little iOS app that makes splitting group expenses quick and easy! Simply add expenses as they rack up and the app will keep track of how much money each person owes and who they need to pay. Splittr works offline, doesn’t require registration from your friends, and supports all currencies, making it the perfect app for tracking your travel spending!


Similar to Splittr,  Splitwise keeps a running total of shared expenses so the whole group can see at a glance who owes (and who is owed) money. Available for free on iPhone, Android, and the web, Splitwise is a solid addition to your travel app repertoire.


You’ve probably heard of Venmo at this point, but just in case you haven’t: it’s a nifty little app that makes paying back your friends simple by linking to your credit and debit cards, as well as allowing you to store money right in your Venmo account. Best of all, it won’t cost you a cent when you pay someone using your Venmo balance, debit card, or a prepaid card! (Receiving money is always free too, of course.)


HappyCow isn’t explicitly a travel app, but it’s definitely a lifesaver when one of your group trip members happens to be vegan or vegetarian. HappyCow scans your area to locate the closest plant-based food options, keeping your veggie/vegan friend happy and well-fed. (Going hungry on vacation is never fun!)


Travefy is a useful online and mobile group travel planner that works as a sort of one-stop shop, allowing you to discover, share, and discuss trip ideas, track expenses, and create mobile-friendly itineraries that everyone can access. It’s a great organizational tool that’s worth a look if you’ve got a group trip coming up!

So, there you have it! Sticking with these key rules will banish any bad trip demons (tension, indecisiveness, and poor planning) and guarantee that your group getaway is one for the books! Get started DIY-ing your trip with confidence here.

(And if all of that coordinating sounds like a lot of work, you know where to reach us—we’re happy to handle the planning so you and your friends can enjoy a truly stress-free vacay. 😉)