The paella was a breaking point. I was in the middle of the most complicated group trip I’d ever planned—13 people, flying in from six different cities, all gathering in a seven-bedroom villa in Andalucia. We were there, ostensibly, on a joint 30th-birthday trip, a group vacation we’d been planning for years. As high school classmates, some of us had known each other for decades, and the group had grown to include significant others and even a not-yet-announced pregnancy.
It would have been an ambitious trip no matter how many people were attending. We had chosen Spain as a middle ground between North America and East Asia, where my friends and I had scattered after college graduation. We were basing ourselves in Ronda, but rented several cars and planned day trips to see the bigger cities—Seville, Granada, Cordoba. But, inevitably, the dreamy idea of bringing us together for a milestone trip took on a life of its own: destination suggestions ranged from Croatia to Marrakech, and a total of 26 people were invited at some point. And I was wrangling it all—finding a villa, planning activities, making restaurant reservations, confirming the rental cars, and generally making sure it all went smoothly. Thankfully, I had some help: a villa specialist, plus a subset of friends I could count on for strong opinions and quick decisions. I took on this role naturally—and my friends were great about checking in to see if I needed any organizational help whatsoever. But generally, it was up to me to shape the flow of the trip while accommodating every travel personality, from super-planner to totally blasé.
Like every group vacation I’ve ever been on, our Spain trip had its ups and downs. On the first night, my head spinning while trying to keep track of a group text chain that had lost all sense of reason, I found myself struggling to keep my eyes open. Even though I was seeing my friends for the first time in a while, enjoying a home-cooked, multi-course meal as we shared exciting news (A new job! An international move! That pregnancy!), all I wanted to do was lie down after a very long travel day of planes, trains, and cars. On day two, I came downstairs to a breakfast spread of eggs, cheese, meats, and bread (there’s nothing like traveling with someone who likes to wake up early and prepare breakfast), and proceeded to try and block out the morning noise—questions about what to wear, what to bring, where the chargers were—way too much before I’d had my morning caffeine.
I hung back a bit that day during the group tour, scanning the crowd to make sure all my friends were having fun. Did they like the tour guide we had booked? Were they tired and jet lagged? Was the lunch reservation at an appropriate time? That night at dinner, a random spot we found within walking distance of our villa, I was happy to let someone else take the lead in ordering for the group, since the menu was only printed in Spanish. And then, the next night, we were so excited when our paella was delivered. It was in a massive pan the size of my wingspan, and took two people to carry. The saffron-infused aroma was coming through the aluminum sheets, and we were all crowded around the stove, awaiting the big reveal—until we uncovered the aluminum and realized they hadn’t seen my note about dietary restrictions, and my friends with shellfish sensitivities would be eating leftovers instead.
At its best, travel has a way of making every daily anxiety feel absolutely insignificant. And at its worst, even the tiniest mishaps, like the wrong ingredients in the paella, feel like the end of the world. This is even more the case on group trips, when you’re dealing with people of different ages, needs, and activity levels, or traveling with a group of friends of friends, where you’re close with some and not quite as comfortable with others. When you’re trying to accommodate everyone’s travel wishes, but somehow end up pleasing nobody. And of course, that moment when you realize you’re going to need a vacation to recover from this vacation.
That’s not to say that I didn’t have a great time in Spain. When I look back, I think about the one night we picked to be our joint birthday dinner. We were all gathered around restaurant table, 13 of us trying to blow the candles out together, each dissolving into giggles at different times. And of the one day we smartly split up into smaller groups—one group exploring the town, the other hanging by the pool—and then gathered together at night to share the highlights of our day. And how our long car rides led to long conversations, which was a way for me to really get to know my friend’s significant other—something that would have been nearly impossible otherwise, as they live in Toronto and we only see them a few times a year.
It always takes a few days for me to settle into vacation mode, but this time around, I had the added stress of worrying about everything that could go wrong, when a group of people who became friends at 18 meet again to travel together a dozen years later. I needed those moments of joy, of spontaneous laughter, of lounging around in silence, to be reminded of why we were all together in the first place—and why a few years earlier, we had known that we needed to prioritize setting aside time in our schedules to find a week that worked for all of us.
I think about how, during the vacation, we fantasized about what the next reunion would look like. Would we alternate continents? Would we take a cruise? Would we bring partners and kids along for our 40th birthday trip? At one point, someone brought up making it an annual trip—but the panicked look on my face might have nipped that suggestion in the bud immediately.
Group travel requires a herculean amount of coordination and compromise. But there’s something about having a group of people in the same place at the same time that can give every trip that once-in-a-lifetime feeling—an adrenaline rush that I only get when I’m traveling. I got to see a new side of my friends, who I haven’t lived in the same city as since I was 18—how some woke up early to check in at the office, how others were unflappable through hours of traffic and confusing driving directions, and how the parents-to-be soaked up the last few months before they became a family of three. That’s the magic of a group trip—you get to see your travel companions out of their daily element, in their vacation selves. And, if you can manage to stay calm throughout the planning process, the truth is, that’s often our best selves.
Why we built this guide
Group trips don’t all have to be stressful before they get good. If you’re reading this, it’s likely because you’ve been tasked to be the planner, at least in some part, for an upcoming trip. Here at Condé Nast Traveler, we embrace group travel in all forms, from big family vacations to a core group of friends that always travels together to traveling alone in a larger group. And we put this package together to help you take care of the big things—from where to stay and how to save money with points and miles—to the little ones, like how one app can change the group travel game.
We’re also letting you in on our best-kept secret, for when it’s time to throw your hands up and let the travel gods take over: Book a cruise. It’s what I did for my recent bachelorette party, where we paid just over $300 per person for 3 nights in the Caribbean, unlimited food and drinks, and endless entertainment. Okay, there was still a little planning, but it was limited to where we’d eat lunch on port day and whether we had brought enough sunscreen for our kayaking trip. As the de facto planner, I never had to think about signing a bill, or making sure everybody was entertained. I simply soaked it all in as my friends congregated in various combinations and got to know each other in vacation mode. It was the best gift I could have given myself—second to this guide, of course.
Four golden rules for every group trip
If you’re dealing with noncommittal guests, make everyone pay a deposit.
Don’t overschedule: plan the days as loosely as possible.
Come together for at least one meal a day.
Yes, everyone must download Splitwise.
Friend trips that won’t ruin friendships
Getting comfortable traveling with (near) strangers
It’s all about the money
And everything else you need to know
Group Travel: A Complete Guide to Traveling With Family, Friends, and Near-Strangers – Condé Nast Traveler