Planning a group trip can be exciting or paralyzing, depending on who you ask. There’s a pressure to make everyone happy, both in the decision-making process, and during the vacation itself—but whether you’re organizing for 3 or 13, trying to please a range of personalities is always going to be its own challenge.
That’s why, when a group trip goes really well, it feels kind of miraculous. You want to tell everyone about that massive Airbnb you found that every single person in the group raved about; you want to mass email the city-hopping itinerary that gave both the extroverts in the family enough to do, and the quieter folks enough time to escape everybody else. Group travel usually involves a bit of compromise, but, ultimately, every guest wants to come home pleased with (most of) the experience. So we asked our editors: Which group trips did you get right this year? Which would you do all over again, and recommend to others? (We’ll save the recap on the ones we wouldn’t repeat for another time…)
Below, our destinations editor Shannon McMahon shares fond memories of a music-lover’s road trip to Louisville that brought her family together; senior features editor Rebecca Misner reflects on a leave-the-family-at-home getaway in Mexico that gave her uninterrupted time with friends. All that and more below.
Here’s to a 2025 in which group trips continue to hit just the right note.
A music-centric road trip from Nashville to Louisville Pride
An impromptu roadtrip for a Pride festival this past June was the best trip my family and I have taken to date (and we’ve taken many). After realizing through the Nashville grapevine that Chappell Roan was playing a $5-ticketed outdoor concert at Kentuckiana Pride (no doubt scheduled before this year’s Coachella thrust her into the spotlight), my sister and I hopped a plane for our cousin’s Nashville abode to spend a few days listening to live music (Tootsie’s Orchid Lounge, anyone?) before driving three hours to a weekend of rainbow-hued delights in Louisville. The highlights were a massive pride parade, tons of Kentucky barbecue and bourbon, and a stylish, dog-friendly stay at the lovely Hotel Genevieve (by Bunkhouse Hotels) that made me fully realize how truly cool, colorful, and inclusive the Southern city is. Not to mention, the Chappell show itself was well worth the five dollars—plus a plane ticket and group lodging. —Shannon McMahon, senior destinations editor
A reunion in Indonesia with my oldest friends
A trip that started as a WhatsApp message way back when COVID forced us to stay apart in 2020 was extremely worth the four years of planning, deciding, debating, and painfully waiting for it to happen. In September, six of my closest girlfriends and I met up in Indonesia, publicly calling it (and justifying the expense) a 40th birthday celebration—but mostly, we just realized two decades had passed since we’d all been in the same place together. The trip was split between Bali, where we sipped margaritas, got massages, and swam in the hot Indonesian sun at the spectacular Bamboo House, an airy rental just outside of Ubud. We then took a boat across to Gili Meno, a car-free isle of low shrubs where donkeys roam and beaches are lined with shack-style bars and restaurants. We rented a villa where seven standalone cottages had been transformed into guest suites with large terraces and outdoor showers, and an open-air lounge and kitchen surrounded a palm tree-studded courtyard. We’re talking a pool, hammocks, loungers, and bean bags. The gates opened right onto the beach, meaning we could tip-toe down for morning snorkels to spot turtles in the waves before breakfast. There was no TV and limited connectivity, which suited us just fine. We moved slowly during the days, from pool to loungers to couches, falling into conversation and fits of laughter with whomever was close by, our glasses always full (and a fully stocked fridge of our duty-free purchases nearby, should we need a top-up). By day one we were already started discussing the absurdity that it took us so long to get back together, though in fairness we live across four continents, with competing schedules, families, and jobs. We decided to make this a bi-annual reunion going forward and, already, our WhatsApp group pings day and night with thoughts on Morocco, Mexico, or wherever else we decide on for 2026. —Erin Florio, executive editor
A summer rental in Fire Island Pines, New York
For the last decade, I have participated in a summer pilgrimage to Fire Island Pines, a small island community off the coast of Long Island, about halfway between New York City and the Hamptons. A well-known destination for the LGBTQ community for over half a century, this spot is dotted with rental homes and a small commercial district (currently under construction and scheduled to debut in time for the 2025 summer season). Houses in this small enclave rent by a quarter of the season, which means you and your closest friends get a rental one week per month from May through September. The best part about the Pines is there is no pressure to do much, and there is anything and everything at your fingertips. Drinks at Low Tea in the late afternoon morph into clubbing at High Tea into the wee hours of the night. Cooking dinner with friends at the house can be followed by singing show tunes video karaoke style at the Pavilion. Sit by the pool or beach all day or head to a drag brunch. Fire Island is a make-your-own adventure getaway perfect for a group of friends with diverse interests. —Eugene Shevertalov, associate entertainment director
A destination wedding in Mexico City
Group trips are all about stepping into something new. Earlier this year, I tagged along (as a plus one) with my partner to a destination wedding in Mexico City. From the lush streets of Condesa to incredible food and art, everything felt alive and vibrant. The wedding at General Prim was next-level—fun and chic design, nonstop dancing, and of course, a dancer dressed in disco-inspired mirrors head-to-toe on the floor. Trying and seeing new things with new people—it’s trips like these that keep life feeling fresh and inspired. —Jessica Chapel, commerce writer
A bachelorette party in Miami
I’ve been to several bachelorette parties over the last few years, and if there’s one thing I’ve learned, it’s that group size and location are the biggest factors to a successful trip. This one was a great size (nine of us, not so many that dinner reservations were impossible to come by), and in a prime destination. Our Design District Airbnb meant we were close to the beach and Little Havana, where we had a great dinner with live music at Cafe La Trova. Other highlights: a boat day, drinks at Dante’s HiFi, and as any Floridian will understand, Pub subs. —Madison Flager, senior commerce editor
A weekend in Mexico without spouses or kids
For the past several years, my husband and our two kids and my two closest friends and their families have taken ski trips together. Last December, between waiting for the mountain to open (it was so cold that the resort couldn’t safely open at the usual time) and calling restaurants trying to score New Year’s Eve reservations for a party of 12, the three of us decided that for our next trip, we’d ditch our families and go somewhere hot and beachy. This past October we spent three nights at the One&Only Mandarina. We were all flying from different cities and we wanted somewhere that we could reach via direct flights. Somehow, Puerto Vallarta was three hours from all of us and with enough incoming flights that we landed within 15 minutes of each other. Mandarina is about 45 minutes from the airport and once we reached the property, we didn’t leave. I never travel like that, and am always sniffing out the best local restaurants and trying to do all the shopping, but we didn’t have a ton of time together and the resort is so stunning (and ok, pricey), that it felt like a shame to leave it. We swam in the ocean for hours, had sunset cocktails at the pool overlooking the Pacific, and we laughed and talked nonstop the entire weekend. We were warm. No one needed anything from us. It was heaven. —Rebecca Misner, senior features editor
A Vermont ski trip
Group ski trips are hard, especially if people in your crew are at different skill levels, which is most of the time. They can also require a lot of planning (and map reading) if you try too hard to keep a large group together on the mountain. But when they work out, there’s no better feeling than synchronously carving down a groomer with some of your best friends. One weekend a few of my pals just happened to be in Vermont at the same time so we met up at Killington last minute. The sun was out, the snow was good, and the après was even better. The spontaneity of it was the highlight—proving that group trips can be low-stress with the right people! —Hannah Towey, associate editor
A birthday party in Tulum
There’s nothing better than gathering your girls to celebrate. While my birthday is in April, I’m always looking for a hot weather destination and Tulum was a nice choice for a long weekend getaway. We rented an Airbnb that felt like one big party house with a hot tub and a pool. Through an eco-center tour, we got to go bike riding around the area and snorkeled at a few cenotes. The tour was just us so it felt very private, and we had each cenote completely to ourselves—plus they made us snacks and fed us lunch before we left. It felt like our own little oasis. But the best days were walking the beach and soaking in the sun with my best girls who always take the time to celebrate me and join in on my shenanigans. —Kayla Brock, associate social media manager
A cycling trip through the Hudson Valley and Catskills
The best trip that I went on this year just so happened to be a group trip—in fact, the only group trip—that I went on this year. As a Christmas present to my father, my mother had booked him, my brother, and I a weeklong cycling trip through the Catskills and Hudson Valley organized by Backroads, which is a bit of an extravagant endeavor—why would you pay so much to do something you could conceivably arrange yourself for far less? The answer is convenience—the guides are supremely helpful and kind, you don’t have to think of a single thing yourself, which is especially important when you’re part of a family that likes to play a vicious blame game when something goes wrong (which it won’t at Backroads because they’ve done their homework and then some—they were also supremely helpful when I wiped out on a pothole on the second day, shredding my jersey and opening wounds on my elbow, back, and knee). The reason we booked something so athletic, despite none of us having really road biked. is because my dad is hyperactive and has generally proven himself incapable of/disinterested in relaxing while on vacation. He’s also a beast on the Peloton, never having made a PR that he didn’t beat on the next round. We figured that if cycling 30 to 60 miles a day in the blazing heat couldn’t tucker him out for an afternoon siesta, nothing could, and we were quite right! With Backroads there’s often a long and a short option for both morning and afternoon, so his sons would do the latter while he pushed himself on the former and we’d rendezvous for lunch, dinner, and plenty of drinking. We ate so well—especially at Woodstock’s Silvia—that we actually gained weight despite our massive daily burns, and the hotels we checked into (the Woodstock Way and Troutbeck) were fabulous. —Charlie Hobbs, associate editor
A long weekend at a beach house in Sayulita
The most obnoxious answer here is that my favorite group trip of the year was when I dragged dozens of friends to Peru for a week before my wedding in Cusco. But the less Bridezilla truth is that my heart also lingers on a weekend spent in Sayulita, Mexico, to celebrate my friend Taylor ahead of her wedding. We splurged on a gorgeous home right on the beach, where we tilted back mezcal margaritas by the pool all weekend, bobbed in the sea, and gabbed on the outdoor chaise lounges. It was the quintessential girls’ trip, in a place I’d always wanted to visit; and the house became that perfect kind of world-of-its-own for three days in which we all just got to hang out. I’m still thinking about the outdoor shower in my bedroom—and the shrimp tacos in town at Tacos Gaby—and walking on the beach with old friends, just catching up for hours, grateful to have the time together. —Megan Spurrell, associate articles director
