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How to Plan an Unforgettable Group Trip in 11 Easy Steps

This is going to be the best vacation ever.

Group trips have the ability to make or break a friendship, and sometimes it’s a fine line between lifelong memories with the people you love or a totally boring disaster. Getting a group of people with different interests and schedules to go on a trip together can feel nearly impossible, but when you can pull it off, it’s so, so good. Here’s our step-by-step guide to planning the perfect friend vacation.

INSIDER TIPI’m assuming since you’re reading this that you’re the one planning your trip. If not, please forward this story to the HBIC of your vacation.


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Pick the Right Destination

This is the first and maybe the most important part of the trip: deciding where to go. First of all, keep it simple and stick to Europe, the Caribbean, Central America, or a domestic destination. Unless you’re a group of die-hard travel junkies, getting everybody all the way to Asia, South America, Australia, or Africa will be tough (not to mention incredibly expensive). The key to finding the right place is having a built-in activity for people to do at any time of the day that doesn’t involve planning: beaches, lakes, islands, or mountains are all good candidates. With so many different interests, visiting a city with a group can be a nightmare. If the trip is short enough, maybe two nights, the accommodation could be a destination on its own: a ranch in Idaho, a hacienda in Mexico, or a private island in Cartagena.

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Go for the Right Amount of Time

The right amount of time for a group vacation is five days, max. Do not plan a trip that’s longer than this unless you’ve traveled together before and you have the same travel style. After five days, the introverts will begin to hate everyone and the hyperactive folks will get bored. Somebody will get into a drunken fight and you’ll be left to pick up the pieces. Just say no.

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Pick a Rental With a Great Location

Here’s the key to traveling with more than one other person: people need to have their own agency. For a trip longer than two nights, you need to make sure your rental is within walking distance of the following: coffee, food, alcohol, and other people. Sometimes a remote location seems like a good idea, but you will inevitably be on different schedules and you don’t want to be held accountable for somebody else’s caffeine addiction. Driving gets annoying, especially in rental cars. Access to nearby rivers, lakes, oceans, and pools is a plus. Swimming is an automatic activity, and cutting down on heat rage is a good way to make sure you’ll all stay friends after the trip.

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Ask for Deposits

To plan a great trip, you need two people in charge: one who loves spreadsheets and planning, and one who has a large credit card limit. Sometimes this is the same person, which is ideal. Sometimes it’s not, so find your most fiscally responsible friend and have them pony up the initial charges. Once you’ve booked the rental, which will be your biggest group expense, ask for deposits. The flakier the friend, the more you’re going to need up front. Just to be safe, book a rental with a generous cancellation policy. (Hint: this is a filter you can use on Airbnb).

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Book the Tickets

The way this usually goes is that one person finds the cheapest/most convenient flight and then everyone else follows suit. Use Google Flights to track prices, airlines, travel time, and layovers and choose what’s best for the group at large, taking into account work schedules and check in/check out times. Send your confirmation around so the busy friends can buy the flight without doing the research.

INSIDER TIPIf you have mileage status on the airline you’re flying, don’t book your tickets with a friend. Being on a separate reservation means you can use your status to get upgraded, but if you’re booked on the same reservation with somebody who does not have status, they’ll drag you down with them. There’s no rhyme or reason to this—it’s just one of those unfair things about airlines.


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Set Up a Splitwise Account

If you’ve never used Splitwise, your life is about to change. Splitwise is an app where people input expenses and decide who to share them with. You don’t have to download the app to use it (one person can be in charge) and you can even input your charges in the local currency. Splitwise takes all the stress out of group meals because it means that one person can pick up the tab and have everyone else pay them back later. No need to split the bill 12 ways and make the waiters annoyed. There are options through the app to pay with Venmo or in cash, and the whole thing is super user-friendly—you don’t have to be a tech whiz to figure it out.

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Plan at Least One Group Dinner

Traveling is a special occasion and it’s the best way to celebrate anniversaries, birthdays, or just the simple fact of being alive. But traveling together doesn’t mean that you have to eat every meal together. However, as President of this trip, you should plan one special dinner, whether it’s at a cool restaurant, a picnic, or maybe even a cooking demonstration with a private chef at the house. With one group dinner planned, you can wing it for the rest of the trip. People can split into smaller groups or play it by ear.

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Plan at Least One Group Activity

Hopefully you’ve chosen a destination that’s entertaining on its own—maybe a cute beachfront town with lots of culture or a mountain town with tons of activities. But even so, it’s a good idea to plan one excursion. Ideas include renting a boat, hiking to a cenote/waterfall/mountain lake, or visiting a local theme park. Just make sure to keep it lightly active. Not everybody wants to go to a cooking class or get a guided tour of the museum.

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Do a Big Grocery Shop

As the planner of this trip, you should be one of the first to arrive, mostly so you can claim the best room in the house. You deserve it. On arrival, one of the first things on your to-do list is provisions. Visit the grocery store to pick up some essentials: eggs, bread, salad and sandwich ingredients for light lunches, coffee, milk, paper towels (those rentals never have enough!), butter, olive oil, cheese and crackers, and most importantly, booze. Depending on where you are, a couple of giant bottles of water are important to have on hand as well, and don’t forget the ice. For any big meals cooked at home, you can do another grocery shop. Check to see if the rental has basics like coffee filters, salt, sugar, and pepper; and if not, remember to get those too.

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Designate a Cook

“Let’s make dinner together” is a fun thought, but what it really means is “one of us should cook dinner while everyone else chops vegetables and drinks wine.” The saying “too many cooks spoil the broth” is true, and a skirmish in the kitchen can lead people to hold grudges for the rest of the trip. One person and only one person should be responsible for each meal. If there are multiple chefs in your group, awesome! They can all take turns, and you can even work out a schedule for who’s cooking which meals. Under no circumstances should you let people collaborate in the kitchen because it inevitably leads to compromise, and hence, mediocrity. Sous chefing is encouraged, but only by those who are willing servants.

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Let People Do Their Thing

Don’t force anybody to do anything they don’t want to do. Some people like to go on vacation with their work computer and try to catch up. Some people are training for a marathon and have to schedule a 10-mile run every day. Some people are lazy. Others are more spirited. It’s not your job to make sure that people are discovering the destination or that they’re vacationing the “right” way—as long as everyone’s happy, you should be happy too. If you’re the only who did research or knows the destination, it’s fine to act as the camp counselor, but don’t be a drill sergeant. The best way to go about your vacation is to announce, “Today I’m going to [insert activity here]. Anyone is welcome to join me and I’ll be leaving in about an hour. You can also stay here/walk to town/hang by the pool/do your own thing.” The key to a successful group trip is flexibility.

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