Why The Trip Should Stay In Your Group Chat: Travelers Share Disastrous Friend Vacations

We’ve all been there: endless WhatsApp threads about “doing something big this year” with friends… and then nothing. Busy schedules, mismatched budgets, and the classic “let me check with work” reply mean group trips often die before they’re even born.

And once you hit your late twenties, everyone’s life is on a completely different channel. Some friends are locked down and only vacation with their boyfriend’s annoying family. Others are busy repopulating the planet and can’t exactly swing a hot-girl summer. One friend only has PTO in August, while another would rather attempt a Benson Boone backflip than travel during those sweaty, crowded months.

Basically, no one is in sync anymore. This is why, in 2025, an increasing number of people are opting for solo group travel instead of navigating the chaos. Think curated adventures with strangers who (shocker) turn into actual friends, deeper connections, and zero passive-aggressive Venmo requests.

So, I talked to an expert (and a few traumatized group trip survivors) to get the truth. Could traveling with friends actually ruin your friendships? And could traveling with strangers… save them? It’s time to leave the trip in the group chat and try solo travel instead.

Can Group Trips Be Bad For Your Friendships?

Image Credit: HBO

“Traveling with friends is a bit like choosing to share an apartment with friends,” says Lee Thompson, co-founder and CMO of Flash Pack, when asked why so many people are saying “thanks, but no thanks” to friend trips.

“It doesn’t always work out the way you imagine, and when things go wrong, it can make or break a friendship. On top of that, friends tend to develop different priorities when they reach their 30s and beyond; either in life, travel, or both. Some will be settling down, others will be drawn toward a beach break on a budget, and still more will crave high-octane adventure. It’s hard to find a compromise, especially when you factor in the difficulties of finding dates that suit everyone.”

(Literally, who among us hasn’t been personally victimized by a Doodle poll?)

“For all these reasons, it can feel really liberating to opt out of friend vacations altogether,” Thompson continues. “We’ve seen a spike in solo travelers choosing group trips (AKA strangers) over friend holidays (AKA the people you love), because it means freedom. You pick the destination, the budget, and the activities you actually want — no compromise, no drama.”

Just like we learned the hard way not to date inside our friend group (DON’T DO IT, BABE), we’re learning the same rule applies to travel. You can love your friends, but maybe 72 straight hours together is too much. Sometimes a two-hour bottomless brunch is plenty.

Never Again: Travel Edition

I know you’re here for the tea, so let’s talk about what happens when the trip does leave the group chat — because those stories live forever. Whether it’s pre-wedding shenanigans gone wrong, discovering your bestie sleeps with a white-noise machine that sounds like an industrial fan, or finding out your friend is just… feral, here’s what can go down. (Names changed because I don’t need anyone’s group chat blowing up on my account.)

Michaela, 27, Miami

Michaela* and Jenny* had been friends for two years before deciding to do a Fourth of July trip together. “She wanted to go clubbing every night and then sleep all day, not even getting brunch or sightseeing. Then she brought a guy home one night while I was already asleep in the bed we were sharing. I heard them hooking up in the living room. The next morning, when I made a joke about it, she denied it with a straight face.”

That was their first and last trip together. Their friendship fizzled soon after. RIP.

Laura, 32, New York City

Laura* had already done three bachelorette trips that year and was over it. “It’s like Love Island without the confessional — everyone is bitching, but never to the actual person. The bride was crying by night two, the Airbnb host fined us because they didn’t know it was a bachelorette, and half the group got food poisoning. I’m done. Never again.”

Jake, 33, London

To prove this isn’t just a girl problem, Jake* shared his own nightmare. “In our early twenties, group trips were fine. But in our thirties? Not so much. Four of us went to Portugal — one was even expecting a baby — and suddenly Dave* is hitting on girls barely out of college. Next thing we know, he’s making out with one and inviting her and her friend back to our Airbnb. He’s engaged, by the way. We’re supposed to be at that wedding. Arguments followed, and yeah, never again.”

Emily, 24, Berkeley

“In the group chat, everyone’s obsessed with the idea, but then no one actually wants to plan it. I always end up organizing everything, and then people complain about the budget, the itinerary, the dates… I’m out. I travel solo now, or max with one friend.”

Adam, 29, Maidenhead

Planning a trip to Albania with two friends seemed like a great idea to Adam — until one friend Sam* started slowly withdrawing from the group. What began as a minor disagreement spiraled into a full-on meltdown: without warning, Sam booked himself new accommodation and ghosted Adam completely. Three days that were supposed to be beers and cultural sights turned into the end of a budding friendship.

On the plus side, Adam and his other friend Lewis* had a blast together (trauma bonding is still bonding). Adam wonders if it all could’ve been avoided with “mutual respect and communication” on Sam’s side.

“It made me realize that compatibility isn’t just about shared interests; it’s about shared values,” Adam reflects. “And when someone consistently takes but won’t communicate, it’s not a friendship — it’s a transaction.”

Ron, 25, Glasgow

What started as a harmless guys’ trip spiraled fast when two of the group got drunk, and one lost a piece of jewelry with major sentimental value. Instead of admitting it was gone, he accused the others of stealing it — and then held their passports hostage as the clock ticked down to their flight.

“He eventually admitted he was just too embarrassed to say he’d lost it,” Ron explains. “But the passport drama and accusations of theft completely ruined the friendship.”

Ron says that he views vacations differently since that trip, and doesn’t take the decision to travel with someone as lightly anymore.

Georgia, 25, San Francisco

Sabrina Carpenter sings about bed chem, but what about travel chem?

Georgia* and her best friend Wendy* don’t take trips together. “I love her, but I just don’t think we want the same things on holidays,” she says. “She’s a packed-itinerary city girl, and I’m a sit-on-the-beach-with-a-book girl. She loves hostels, I love hotels. She wants to country-hop, I want to settle into one spot. We realized we’re just not travel-compatible, and that’s okay. She does organized trips or solo travel, I travel with people who want the same vibe as me. We’re still best friends, just not travel buddies.”

Non-Friend Trip Options

So, if the group trip is staying in the group chat (where it belongs), what’s left? Georgia already mentioned the two main options: solo travel or organized group trips.

Solo travel

Rebecca Crowe, 30, Manchester, was sick of waiting for her friends’ endless “maybe” replies. “I thought, why am I waiting around when I can just do it?” she says.

Now, she solo-travels so often that she even made it her job — writing about budget solo trips for Wandering and Wine. Sometimes she even leaves her partner behind.

Her biggest tips:

1. Pick the right hostel vibe – If you love sleep, avoid party hostels. If you want to socialize, skip the quiet guesthouses. Check reviews for free events.
2. Choose transport-friendly destinations – Cities with good public transport save you money and stress when you’re not splitting taxi or car hire costs.
3. Start somewhere familiar – Revisit a city you’ve already been to with friends or family. You’ll feel more confident exploring solo, and there’s always more to see.

Organized trips

According to Thompson, group trips with strangers (like the ones Flash Pack runs) have three big perks:

1. You maximize your precious PTO instead of wasting it in a group chat stalemate.
2. You avoid passive-aggressive drama that can nuke your friendships.
3. You meet and bond with people you’d never cross paths with otherwise.

Manuela, who lives in London, took a solo group trip to Bali and Japan and swears by it. “When I’m with friends, family, or even at work, I automatically slip into a certain version of myself,” she explains. “But traveling with strangers? I leave all that behind. I get to tap into parts of my personality that don’t usually surface at home. That journey of discovery feels exciting — it’s liberating.”

Erin, from Indianapolis, has already hit four different countries on organized trips. “Most of my friends back home are married or have kids — and of course I love them and their babies — but they’re in a totally different phase of life. I can’t always relate. So when I was traveling in Vietnam and Cambodia, it felt amazing to connect with people who’d made choices more like mine.”

At the end of the day, the “dream group trip” might just stay a dream — and that’s fine. Sometimes the healthiest thing you can do for your friendships is leave the trip in the chat… and take a trip on your own. Stop waiting for the one magical week everyone’s free. Book the flight. Go to the places you keep saving on TikTok. Like, literally — what are you waiting for? Then, when you get home, you can tell the group chat all about it over brunch!