Guilt trip: Signs your group holiday is doomed

Lots can go wrong after a vacay makes it out of the group chat. Look for these red flags before you start booking

We’ve all mourned the Goa plan that died in the group chat. But sometimes, that’s divine intervention. Not every trip ends with a Zindagi Na Milegi Dobara–style bonding montage. Some conclude with sulks, slammed doors, and passive-aggressive silence that echoes all the way to baggage claim.

One bestie wants to party until sunrise, and the other wants to hike at dawn? Cancel those tickets. (SHUTTERSTOCK)

Everyone’s idea of “holiday” is different. Your bestie might want to party until sunrise, the other BFF might want to greet the sunrise on a hike. Some are spa-day people, some are souvenir-hunting types, and some insist on a 12-point sightseeing itinerary. Put them all in one Airbnb and you’re basically signing up for a reality show. Here are six red flags that scream, Abort Mission, before you even book the tickets.

You don’t like the same food. One person wants to taste every local delicacy. Another insists on a safe menu. A third is chasing that viral Banh Mi for Instagram. Cue: Hangry wars. Travel influencer Flexcia D’souza (@Flexcia_Dsouza) once begged her friends to try local Kannada food in Chikmagalur. They revolted. “After a point, they were like, ‘Can we just have normal food?’” she recalls.

Rishul Bangar (@explorishh) says he’s “seen vegetarians get offended because non-vegetarians eat their portions too.” Meanwhile, meat-eaters sulk if the group only stops at vegetarian places. D’souza’s Vietnam group refused to eat pork, which put three-fourths of the cuisine off limits. By day two, they stopped eating local food altogether. She ended up dining solo.

Vegetarians and meat-eaters can make the worst travel combo. (SHUTTERSTOCK)

You don’t enjoy the same things. A beach bum, a party animal, a sightseeing nerd, a foodie and a shopaholic walk into a hotel. That’s it. That’s the joke. Because it ends in disaster. On a recent trip to Istanbul with seven girlfriends, travel influencer Smitha Menon (@Smitha.Men) said they each wanted to do different things. Torn between coffee, shopping, spa or workouts, the ladies broke off into small groups. “We reunited for the big meals and larger bookings.”

It only works when you’re willing to pay extra for separate taxis, and sometimes even separate hotels. D’souza loves remote hostels and homestays. Her friends, not so much. “We were staying at a coffee estate in Coorg. It was quite remote. My friends couldn’t handle the silence and left for town.”

It’s important to make room for everyone’s interests, like the guys did in ZNMD.

You don’t share energy levels. Some travellers love walking across Brussels to admire the architecture. Others prefer a city whooshing by from the Uber window. Broker a compromise, says Bangar. “If the group is big enough, adjust by sharing cabs. Or sometimes the group splits. Some take a cab, some walk, and then we meet again at a designated point.” Choose your battles. Or blisters.

You’ve got different budgets. “It’s better to talk upfront about how much everyone is comfortable spending,” says Menon. It’s possible to rough it out in an expensive destination, or upgrade all the way at a cheaper one, so long as everyone’s on board with the idea. On a trip, allow every person to veto one activity. Bangar recalls skipping a $150 opera in the US. “I wasn’t interested, so I did something else that evening. My friends enjoyed it, and it didn’t ruin the trip.”

In Thailand, D’souza’s group stayed in a budget hostel in Bangkok and splurged on better rooms in the resort town of Chiang Mai. “We book accommodation in advance so everyone knows what to expect. The idea is to save when you’ll hardly be in the room, and spend more where the hotel is part of the experience.”

Some of your friends will inevitably have to work. Try to plan your activities around their work calls. (SHUTTERSTOCK)

Your body clocks tick differently. During his recent trip, Bangar wanted to catch Yellowstone’s wildlife at dawn. But his group refused to leave the Airbnb before 11 am. “I didn’t have a US driving license, so I had no choice but to wait for them. When we reached, all the animals were gone, and so was the mood.”

Journalist Jaideep Deo Bhanj and teacher Natasha Raheja, both 36, are avid travellers. Their hack for people who don’t match their freak: “Leave the rest behind. Like lost luggage, they will eventually show up.” They also have a rigorous screening process for friends they plan holidays with. “We start with a staycation, and if that goes smoothly, we build them up slowly to a week-long vacation, before planning anything serious.”

A remote worker is coming along. Nothing kills the vibe faster than someone yelling, “just one quick email!” while you’re sipping cocktails at sunset. D’souza urges groups to be flexible. On a Kerala trip, one of her friends had to log in to work on weekdays. “We planned the schedule around this. We travelled at night so she could be ready for work in the morning. We kept weekdays relaxed, and saved the hikes and water sports for the weekend, so she didn’t have to panic about Wi-Fi.”

From HT Brunch, September 20, 2025

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