How To Plan A Killer Group Vacation Without Stressing Out

I’ve often discussed elaborate plans for trips and fun activities with my friends that never quite pan out. We’re always so excited to do something over the top, then laugh about how it never happened six months later.

Group trips become a lot harder to plan as you grow up because there are many variables that come in to play. Work schedules, finances, and weather, can derail your trip faster than a speeding locomotive. Plus it can be hard to keep up with a group chat that is constantly buzzing.

If your friends are committed and everyone’s itching for getaway, though, here are my suggestions to plan a successful group trip.

Elect A Group Leader

This may sound silly and you may be thinking, “We’re all grown adults who can work together in cooperation to plan a vacation.” Well, I’m here to tell you that assumption is completely false. Someone will always make it extremely difficult or want to do it their way. By electing someone to serve as the group leader, the responsibilities for the overview of the trip fall in one person’s lap. From the itinerary to coordinating arrival/departure, this leader will be the liaison for the whole trip.

Use An Online Calendar

One of the biggest obstacles when planning any trip is locking down a date. By using a service such as Doodle or Survey Monkey, your group has a selection of dates that will help narrow plans down. It also helps everyone see each other’s availability or lack thereof..

Set Expectations Up Front

It’s your responsibility as a grown adult to voice your opinion. If there are certain activities you prefer or places you want to visit, make it your mission to communicate that. Every group is going to plan their trip differently, but prioritizing your wishes can make everyone a lot happier. Setting expectations also means being honest about how much you are willing to spend on the trip. If you’re on a budget, make sure the group knows. On the other hand, if you can afford something high end but everyone else can’t, don’t be an asshole and suggest things you know are out of peoples’ price points. Learn to compromise.

Venmo Is Your Best Friend

Venmo is an app that allows people to transfer funds to others.   For any group trip, try to figure out what needs to be paid in advance and allocate funds for it.  Venmo will help you keep track of who has paid and what the group paid for, which keeps everyone accountable while removing any potential conflict. Venmo has all the receipts!

Set Up Reminders

This should go without saying, but ensure that every person on your trip remembers that they’ve committed to this trip. You don’t want to have your bags packed then have someone say, “Oh damn, I totally forgot about that!” and bail on the trip. Whether you send out email reminders or text alerts, stay on top of your group to prevent last-minute cancellations from happening.

Leave Room For Spontaneity

Your vacation is exactly that: a vacation. It doesn’t need a set structure that feels like you’re in prison. My fondest memories of trips with friends are the completely spontaneous moments. Sometimes unplanned events hold a longer shelf life in your brain than the pre-planned ones.

All in all, group trips should allow you and your friends to escape your day-to-day lives. Whether you all live close to each other or are convening from various places, vacations are a time to reconnect, have fun, and make new memories (with obnoxious Instagram posts). You’ll thank me after your next group trip when you take my advice and see how much better the experience was!

Photo by Shazmyn Ali on Unsplash


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