How to get your group trip off the ground

From Monzo bill-splitting to the art of a group WhatsApp, here’s how to take all the stress out of your bigger trips

My phone pings. ‘Shall we organise for 2026?’, the WhatsApp notification reads. It’s the girls’ chat. One of us is organising a wedding, another buying a house – a few of us are experiencing the financial pressure of living in one of the most expensive cities in the world. With so much life getting in the way, it’s taken days of back and forth to settle on a date for our next group holiday. Another ping. ‘June?’

There’s no denying bigger trips can be a nightmare to plan, with even more expectations to meet and preferences to please. And when some swear by cabin baggage only, another can’t live without a pool and one of us is prolifically anti-sun, how can we ever meet in the middle?

“There are always learnings when it’s the first time the group goes on holiday,” explains psychotherapist and author Eloise Skinner. “The key is to have fun, remain respectful, prioritise the friendship and cultivate shared experiences.” To get you started, give this guide a read, take the tips you like with you, and have your best group trip yet…

Find your communication style

Before you start planning, figure out (or simply ask) how your group prefers to communicate, whether that’s over email, in-person or over the phone. “Then, reflect on the frequency of communication,” adds Eloise. “Will this be a daily chat, a weekly meeting, or even a one-off planning session? Consider people’s different styles of planning and commitment. And if you have a friend that is unlikely to commit until the last minute, make sure the trip doesn’t hinge on that person.”

Share your calendar

We might be busier than ever before, but securing a date that everyone is free has been made easier thanks to free social calendar apps like Howbout. Simply add in your availability, share the link with your friends and Howbout will instantly output when works best for your group. If there’s a couple of dates available, there are polls so you and your friends can vote.

Delegate roles

“Instead of feeling like you need to wait for someone to do something that isn’t natural for them, try a divide and conquer approach for tasks,” suggests Eloise. “Someone highly organised will enjoy booking flights, while someone else might enjoy researching restaurants or holiday packing prompts.”

Plan with TripMapper

With TripMapper you can create holiday itineraries with a card and list view. Add the country you want to visit (or use the Discovery library for inspiration) and TripMapper will rattle up suggestions with an explanation and star rating. All you need to do next is add in your dates and budget.

Remove the hassle

Book a great-value package with British Airways Holidays – all hotels are vetted and holiday packages are ATOL protected, with 23kg baggage included per person. Choose from thousands of carefully selected hotels, car hire and even sightseeing experiences to make up the perfect trip – and collect one bonus Avios for every £1 spent (plus double Tier Points until 31 December 2024).

Split your bills

Keep track and split the expenses of the trip through Splitwise or Monzo. Split bills individually or add multiple bills to a shared tab so you can keep track of who owes what and settle after the trip. Easy.

Let AI do the work

“I get everyone to pitch into the WhatsApp group with ideas of the kind of activities they prefer to do on holiday (e.g. pool days, beach trips, sightseeing, boat trips, fancy restaurants vs cooking),” says freelance PR and journalist Giselle Wainwright. “Then I feed it into ChatGPT with all my info and the destination of where we’re going and staying and for how long, and it provides me with a full itinerary for each day. It saves so much hassle and provides a bespoke itinerary that we get to follow.”

Stay safe together

There’s nothing worse than getting separated from your group on holiday and struggling to find your way back. Before you fly, download what3words, a global system for communicating location. What3words has divided the globe into a grid of 3m x 3m squares and given each one a unique combination of three words, so you always know the precise location.