10 Tips for Planning a Group Trip—Without Losing Your Friends

It’s possible!

By Kelly Krause

A few months ago, I celebrated my 40th birthday in Paris. Upon my return, while I did get a few restaurant recommendation requests, what most people really wanted to know was, “How did you plan a trip for so many people?!” Because y’all, I threw a Parisian party with my 11 closest friends. So, if you’re wondering how to plan a group trip, boy—do I have answers.

To be clear, that’s not hyperbole. I hold these people close to my heart, and there’s no one I’d rather celebrate such a milestone birthday with. And while I do have a knack for both planning and bringing the right group of people together, I was a little surprised by how well this trip went.

Featured image by Michelle Nash.

Image by Michelle Nash

If you’ve been following Priya Parker for as long as I have, then you know how crucial it is to understand what she calls the “art of gathering.” Priya was a huge inspiration for both approaching the planning of this trip and the telling of the tale that I’m reflecting upon here.

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, and one that I’ll never forget, no trip unfolds without a few surprises. I’ll preface it here: 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.

Image by Melissa Gidney for Jenni Kayne

10 Tips for Planning a Group Trip That You’ll Remember for Years To Come

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. For this one, I wanted it to feel easygoing, fun, accommodating, spontaneous, silly, and full of energy-givers (a long list, I know).

I had to 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. When I tell you this group clicked so well immediately and had the best time, I mean it. Literally: There were exactly zero moments of frustration, annoyance, or attitude. In fact, it was quite the opposite.

There was more laughter than I thought possible. (The name of our group text thread has changed no less than 25 times—the inside jokes just keep rolling in.) 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?

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.

Image by Michelle Nash

Keep the Itinerary Open

With the exception of a one-day trip to Reims (located in France’s Champagne region for champagne tasting) and my 40th birthday dinner, I kept the itinerary open and loose for everyone to choose their own adventure. I shared a few things I’d like to see in Paris, but knowing that I had five couples joining the trip who may not have traveled or spent time away from their kids in recent years, I wanted to leave it open so they could have their own Paris experience, too. That freedom allowed everyone to have their own solo time and come together as a group.

Alison Wu springtime brunch_how to plan a group trip
Image by Mikola Accuardi

Communication Is Key

I was quick to get the group on an email and text thread not only to keep everyone informed on updates but to also allow everyone to begin building some familiarity and rapport before we met in Paris. It’s amazing how quickly inside jokes can materialize through text and email!

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. 

Let Your Guests Decide

From where to stay to what they want to do, let your guests structure their experience. The one event I wanted everyone to attend was my birthday dinner. Beyond that, the whole trip was free-game. Some of my guests came for different parts of the week and others stayed the entire time. Remember: We’re all operating on different schedules, with different budgets, and coming from different contexts. I always want to come from a place of gratitude. Keep in mind that your guests chose to spend time with and to celebrate you.

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. (Bonus: It gives you more opportunities to connect!)

Lots of folks in our 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 (Hint: this was the clear winner!). Because of this, we were able to connect for a few serendipitous moments.

Image by Michelle Nash

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. 

Carve Out One-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.

Ask Someone To Plan One of the Days

I love hosting and bringing 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 I get to spend intentional time with each person. In hindsight, I would have loved one day 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. 

If You’re Planning a Paris-Specific Trip

Camile’s Paris Guide served as an *amazing* starting point. But, of course, I wandered off and found a few favorites during my trip that I can’t help but recommend.

  • Day-trip to Reims for a champagne tasting. Our favorite house was Taittinger.
  • Shop at Le Bon Marché, one of the most iconic indoor malls à la Barney’s (RIP) in the US
  • Eat at Frenchie on Rue de Nil. They don’t take reservations so get their early! 
  • Grab oysters at Regis Huiterie
  • Late night drinks at Le Comptoir. Don’t miss this famous spot where they bring you a full plate of butter and bread as you sip an incredible selection of wines.
  • If you love jam, you must visit La Chambre aux Confitures. My favorite thing to do is grab a jar, a baguette, some fromage and charcuterie (plus a good wine!) and sit on the Seine to people watch.
  • Last but not least: It’s not a trip to Paris without dinner at La Fontaine de Mars.