How to have the perfect group holiday: choose a leader, allow for different interests, and plan, plan, plan

When Ashley Yue packed her suitcase for a trip to Taiwan with a group of 14 friends, she wasn’t sure what to expect. With so many different personalities, interests and expectations among the group, the possibility of conflict and fall-outs loomed.

“I’d never travelled with such a big group before,” says the 25-year-old, who runs the Hong Kong Food Crawlers tour group. “But I found it surprisingly easy, even though there were so many of us.”

Key to the group holiday’s success was pre-planning, ground rules and flexibility.

“I love solo travelling,” she says. “But going on holiday with a group of friends means you have someone to share that experience with – and you get to try a lot more dishes at restaurants.”

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Differing budgets, eating habits and interests are a common cause for disagreement during group holidays, but these can easily be avoided by discussing preferences before departure.

“These misunderstandings sometimes come about because of the lack of communication during trip planning,” says Janice Lee Fang, Asia-Pacific communications director at TripAdvisor.

“A trip with your family or closest friends can create the most wonderful and lasting memories, but it is the planning that can often be stressful since everyone in the group may have different preferences and priorities for travel.”

Here are some of the best ways to make group holidays run smoothly.

Appoint a leader

“Every person has a different idea of what they want to do on a trip,” says Zaky Prabowo, co-founder of WeTravel, an online payment platform for group trips. “If this isn’t handled well, it can create conflict and make for awkward or tense group dynamics instead of making the trip a bonding experience.”

To overcome this, Prabowo suggests a person is appointed to coordinate both the holiday preparation and the group when it is at the destination.

“Too many cooks spoil the broth,” he says. “You need a leader – or two, if there are many tasks – to make a successful group trip. In an ideal world, you could organise a group trip as, well, a group. But realistically, it’s best to appoint someone, even just to be the go-to person, who knows how the planning is progressing and what needs to be done next.”

Plan, plan, plan

Agreeing on a plan in advance can lessen the potential for disputes ruining the holiday, Yue says.

“There are bound to be small arguments or disagreements in the group about where to go, what to do and where to eat,” she says. “The best way to overcome this is to discuss these small details before the trip.”

Prabowo recommends the leader compiles a simple questionnaire asking for people’s preferences regarding budget, tastes and activities. A basic mandatory itinerary can be created based on the survey. Two or three additional suggested itineraries can be added to cater to different preferences.

Getting people to commit to the trip is also important to avoid drop-outs after the booking has been made – or indecisive holidaymakers signing up a few days ahead of take-off. “I’ve seen group leaders get scrambled because of this too many times,” Prabowo says.

For larger groups it is worth collecting a deposit and setting a deadline for its payment, as well as for the full balance.

“You'll know exactly how many people are interested in joining the trip and can make the booking for accommodation, meals, tours and transport accordingly,” Prabowo says, adding that it is important to clarify details such as whether the deposit is refundable if people pull out.

Putting together a spreadsheet to track payments, and using free online forms to collect information such as passport details and dietary requirements, also saves time in the long run. A range of free website builders available online, such as Wordpress, Wix, Weebly and Squarespace, can be used to create a one-stop hub detailing the itinerary, prices and other information to share.

“A group trip is fun, but organising it is hard,” Prabowo says. “Trip leaders spend a copious amount of time chasing participants to pay for the trip, sending email reminders and calling people, because often the leaders use their own money to book for the group in advance.”

On the ground

Working out an itinerary that caters to everyone’s tastes can be tricky, which is why identifying common interests is useful.

“What does everyone’s ideal trip look like?” Yue says. “Is it more history- or culture-focused? Do you want to cover the major touristy sites, or prefer a more local experience instead?”

Yue, who often leads large groups of friends on her food tours of Hong Kong, says this can be where a local tour guide comes in handy.

“They can customise a tour that fits everyone’s tastes and you also get to experience the place through the eyes of a local,” she says. “Within a big a group, there will be people who have different personalities. Some are more outgoing, and some take time to warm up to talk, so a tour guide is great to get everyone engaged – if you pick the right one.”

 Another option is to join an Airbnb Experience, which include a range of activities designed and led by locals to offer insight into the place they call home. Yue herself runs a Hidden Bar Crawl Airbnb Experience in Hong Kong available for groups of up to eight people.

Finding the right place to stay is of utmost importance. Renting a house or flat is more convenient than multiple hotel rooms for large groups. It makes it easier to hang out together, cook group meals and enjoy a relaxed evening at “home” over a few bottles of wine. Websites such as Airbnb, HouseTrip and HomeAway offer plenty of options.

“Make sure you have enough bathrooms in the house or flat for the whole group because you’ll have the same schedule,” Prabowo says.

He adds that if the group prefers a hotel, they should contact the property directly rather than book online. This way group discounts, room upgrades or additional services thrown in for free can be requested.

Split up

“Create alternative options for the group to split up,” Prabowo advises. “Just because you travel in a group does not mean you have to be glued together all the time.”

When Yue travelled to Taiwan two years ago, the group enjoyed meals together and split up for daytime activities.

“Sometimes my friends and I would go off to do our own things while their parents and family friends did the more touristy stuff or shopping,” she says. “I’m not that into shopping so I try to avoid malls. It is important to break into small groups so everyone can make sure they get to do what they really want to.”

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While planning can help a trip run smoothly, it is also vital to remain flexible, says TripAdvisor’s Lee Fang. “Changes in weather or even mood can easily derail plans. Leave a few mornings free during a trip to explore and you may just stumble upon a local gem.”

With these elements locked in, an enjoyable group holiday full of memories awaits.