10 Tips For Planning a Group Trip Without Losing Your Friends

How did you plan a trip for so many people?

It’s crucial to understand the “art of gathering,” a huge inspiration for both approaching the planning of this trip and the telling of the tale.

If you have a big celebration ahead, these are my top 10 tips for how to plan a group trip. Of course, while the experience was seamless, no trip unfolds without a few surprises. The one consistency among all these tips is flexibility.

Because while planning and prep are both paramount, of-the-moment shifts are inevitable. The key is embracing them.

10 tips for planning a group trip that you’ll remember for years to come:

  • 1: Consider Personality Types.
    • Who do you want to celebrate with? Seems like an easy question, but as you plan your group trip, it’s crucial to think about.
    • Consider who would work well in a space together, who is excited and cool with being around new people, and who can spark a conversation with anyone.
    • Take the time to reflect and consider who you’re bringing together. Do you want to manage egos all throughout the trip or sit back and watch beautiful friendships form?
  • 2: Size Matters.
    • Depending on where you’re traveling, keep in mind that the more people you have, the harder it might be to make reservations, book the same train tickets, or get in anywhere as a big group. Thankfully, in the instance of my Paris trip, we were able to do two separate tables, splitting the couples up to a men’s and a women’s table. Be sure to plan in advance though, as it’s harder to accommodate larger parties.
  • 3: Keep the Itinerary Open.
    • Keeping the itinerary open and loose for everyone to choose their own adventure. You could share a few things you’d like to see in your trip, but knowing who was participating, leaving your options open so everyone could have their own experiences, too. That freedom allowed everyone to have their own solo time and come together as a group.
  • 4: Communication is Key.
    • It’s important to keep everyone informed on updates but to also allow everyone to begin building some familiarity and rapport before the event/trip. It’s amazing how quickly inside jokes can materialize through text and email!
  • 5: Ask for Advanced Needs.
    • Just as you’d approach any kind of gathering, asking your friends if they have any specific needs (dietary restrictions, not drinking, ADA-compliant rooms, etc.) will help set them at ease. What’s more, this advance planning will show your guests how much you care about them when booking any reservations or experiences. This might also serve as an open invite for a friend to share what’s going on in their world so you can be mindful of when they may need rest, space, or anything else that will help them feel supported.
  • 6: Let Your Guests Decide.
    • From where to stay to what they want to do, let your guests structure their experience. Let the trip be a free-game. Remember — we’re all operating on different schedules, with different budgets, and coming from different contexts. We always want to come from a place of gratitude. Keep in mind that your guests chose to spend time with and to celebrate you.
  • 7: Learn What They’re Excited About.
    • What do your guests want to see? What do they want to do? Chances are, the answers to both of these questions are roughly the same — making the task of planning a day all the more simple. Plus, it gives you more opportunities to connect!
    • For example, a majority of your group wanted to see the same museums and first-timers were adamant about catching the Eiffel Tower or stopping at the same great falafel spot. Because of this, we were able to connect for a few serendipitous moments.
  • 8: Discuss Money Up Front.
    • Larger groups likely mean you’ll be splitting meals and will owe people money at some point. Before you dive into these conversations, know this — talking about money doesn’t have to be awkward.
    • Several apps (like Splitswise, or, of course, Venmo) can be used for larger groups. We made the decision to Venmo on the spot after meals when one person grabbed the bill. Just don’t forget to include the exchange rate, ensuring that whoever pays is fully reimbursed.
  • 9: Carve Out On-on-One Time for Everyone.
    • As much as possible, make sure you’re getting to spend intimate moments with everyone who took the time out of their busy lives to celebrate you or to join you for the trip. Change up who you sit by at meals, on trains, or on walks. Ask how they’re doing. Make sure you’re checking in and showing that you care. It’ll make them feel seen, and you’ll quickly learn if you need to make any adjustments to the schedule.
  • 10: Ask Someone To Plan One of the Days.
    • Hosting is fun because you get to bring people together. It’s one of my greatest joys and pleasures. But it can be somewhat exhausting to make sure that everyone is having a good time and that you get to spend intentional time with each person. In hindsight, it would be even better if one day the hosts get to “be the guest” of the party and not have to think about anything. So if you’re going through the steps of how to plan a group trip, consider offering up a day for someone else and ask if you can take a backseat.

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