How to successfully plan a large group holiday

Going on holiday together with a group of friends can truly take a friendship to the next level – but it can also break it if the trip isn’t properly planned. Creating lifelong memories while experiencing new places and having endless fun outside your usual haunts are some of the best things about travelling with friends and family, but squabbles over everything from money and group bookings to itineraries can mean at best things never make it out of the group chat, and at worst, fisticuffs in faraway climes.

So fire up a new spreadsheet, submit annual leave dates and pay those deposits without hesitation: here’s how to gear up for group travel like a boss.

Do: talk about money

Nothing makes a trip awkward like arguing over bills, so make things as transparent as possible from the start. Annie Lo, founder and CEO of group trip planning app MiTravel , says, “Start with an open and honest chat to align on budgets and travel preferences.”

Keep a record of the group’s transactions – especially if someone’s putting a group dinner or activity on their credit card – to avoid any bad blood. (Snapping a quick photograph of the bill goes a long way.) Create a shared expenses spreadsheet or use an app like Splitwise to log payments and calculate how much everyone owes.

Do: Designate a leader

Having a group leader who coordinates major things like hotels, activities, transport and more will give your trip structure and keep things from slipping through the cracks. 

Christelle Davis, an Australian academic, has found herself an unofficial expert in group trip planning after organising countless holidays of varying length, group size and complexity – from party weekends in Macao to an upcoming 18-person trip to Thailand with kids, encompassing everything from music festival passes to renting a villa with room for all.

Davis likes to take the reins, but isn’t afraid to delegate. “I’ll pull together a few options for accommodation and put them all in a shared spreadsheet that shows the link, price per person, location, pros and cons, then I ask people to add their own comments or highlight their favourites.”

Allocating responsibilities based on people's interests also helps move things along the pipeline. Davis adds, “Split up the jobs and it makes it much easier. One person for accommodation, one for transport, one for tickets.”

Don’t: Do too much

Resist the temptation to overstuff your itinerary. Scheduling down time is crucial, as is making it clear that members can break away and do their own thing before later reconvening. Keep tabs on everybody’s energy levels and be flexible with your plans – and morning starts, as not everyone is an early bird.

“Don’t feel that you have to do every little thing together on a group trip. Everyone should be free to do their own thing then meet up for a cocktail at the end of the day,” says Davis.

Don’t: Assume everyone’s on the same page

Miscommunication can make or break a group holiday, which is why designating a messenger is important. Lo says, “Have someone take on the role of a ‘communication czar’. This person will be in charge of keeping everyone in the loop, so no one feels stranded on their own island of confusion.”

Talking to one another keeps things drama-free. Everyone has their “own travel quirks”, says Lo, adding: “Understanding group dynamics and discussing overall expectations helps avoid conflicts during the trip, as does having open and honest conversation.”

Tips for smarter group travel

Better rates: “A lot of villas are spread across multiple booking sites. You can sometimes get a cheaper rate by booking directly with the owner or through their own website,” says Christelle Davis.

Split sleepers: “Cities can be trickier because accommodation tends to be smaller. If you can't all stay together, pick a neighbourhood and get rooms in the same hotel or district.”

Pay up: “In places where cash is king, which is most of Southeast Asia, it helps to have a communal kitty that you all contribute towards then use to pay for shared expenses.”

An ideal group holiday planning timeline

Planning a group getaway is like conducting an orchestra: it requires harmony and precision, says Annie Ho.

6-12 months out: Begin the symphony with a discussion about where to go, setting the budget, and nailing down dates. 

4-6 months out: As the planning crescendos, research and book accommodation, transport and those must-do activities. 

2-4 months out: When you’re in the groove, create a detailed itinerary, solidify the budget and assign responsibilities like a conductor would.

3-5 weeks out: Harmonise by confirming all reservations and ensure everyone has their visas and passports in date. 

1-2 weeks out: Fine-tune and reconfirm your plans, pack like a minimalist, and distribute a trip checklist. Then take a bow!