Last Updated on September 1, 2026
We’ve all been on one of those friend trips. You know the ones: the person responsibly or the accommodation didn’t read properly and now the group is a bed short (guess you’re taking the couch, Susan!), no one double checked the dietary requirements and now at least two people can’t eat what you planned for dinner (“Is there a Cheesecake Factory anywhere near here?” suddenly becomes an incredibly relevant question), and someone (probably me, honestly) didn’t fill the tank before you headed out so now you’re in the middle of nowhere, sweating in the summer heat and waiting for one unlucky individual to return from their hour-long hike looking for help. Fun and relaxing, no, but memorable…maybe memorable, maybe infamous.
Planning a group getaway gives me every kind of anxiety you could possibly imagine, because a group of people is relying entirely on me for their enjoyment, comfort, and safety, and OH BOY that is a lot. As a result, I’ve formed a foolproof planning checklist (this works for planning any kinds of trip but particularly well for one that includes a large number of people and all of their priorities, preferences and plans) that gets me and the group through the planning stage without the group chat erupting into World War 3 and the actual trip without forgetting anything or missing out on one magical moment.
Pick Your Date and Destination
First things first: where are you going and when? It’s the simplest part of the process in terms of planning, but do choose carefully because where you are sets the tone for the entire experience.
Choose The Group Carefully
Next, make the Sophie’s Choice that is crafting the invite list. If your friend group all has exactly the same interests and preferences…well, lucky you. Most groups are composed of people who like different seasons, destinations, and activities, so it’s usually simplest to invite those who are excited about the destination and what it has to offer (beware: this is more of a challenge than it sounds!).
Travel Well
Now, as an experienced traveller both locally and further afield and an adult who is not fond of backaches, catching other people’s colds and arriving at your destination late and in a foul mood, I have this to say about the travel position of the trip: do it right. Unless the journey is part of the experience (think road or rail trip), do yourselves a favour and arrange for private jet hire. The benefits are numerous: You all get to sit together in a space that’s just for you: no switching seats and shuffling up and down the aisles, and no sharing private information in what amounts to a public space. Your schedule is yours to command: you set the takeoff time and this, the landing time too. All of your bags will arrive together and in one piece; you can select a menu that is far more customizable to everyone’s preferences and needs, and you’ll arrive refreshed and relaxed rather than hanging onto your sanity by a thread. It’s a no-brainer, really.
Keep it Democratic
When you’re planning everything and anything for the trip, do it democratically. Put forward everyone’s options, take a vote, and go with the restaurant, experience, club, activity, or whatever else is chosen by the majority. No one can complain when it’s majority rules, and this keeps the peace when things get tense. When it comes to accommodations, take a similar approach: if you’re all staying in a house together, just draw straws to pick rooms (except for the person who did the planning who automatically nuggets a good room for that trouble…and that’s you, you lucky thing), ask for volunteers for meals and ask everyone who didn’t cook to clean and make it everyone’s job to tidy up after themselves in common areas.
Budgeting: Divide and Conquer
When it comes to the budget, be sure to have the discussion early. Any communal expenses like accommodation (if you’re sharing a house), home-cooked meals, travel transfers, the plane, etc should be split evenly without question. If someone wants to treat the group to dinner or cover a friend, of course that’s a kind and lovely thing to do. Outside of that, ensure that everyone knows how much each expense amounts to and how much each person owes (couples will of course pay a 2-person portion). Money conversations can be uncomfortable even if everyone is very close and ok with people knowing, to a degree, about their finances, so double-check and re-state everything for maximum clarity.
Plan But Dont Over Plan
Once you’ve gotten everyone’s suggestions for activities and chosen the winners, remember that you’re going on vacation. Vacation doesn’t mean cramming things into every waking hour of the day; it doesn’t mean rushing around like lunatics trying to see every single sight and landmark. Vacations are there for enjoyment, experience, and, crucially, relaxation too. Plan so that everyone, from the most enthusiastic to the most chilled in the group, is able to enjoy activities and day trips but also has time to rest, so that they can live to fight another day. Leave some recreation time unplanned to leave the door open for serendipity and spontaneity. Leave room for sunset watching, coffee savouring, sleeping in, fireside conversations, and making memories that are the real treasure of experiences like these.
Trust Me, I’m An (Armchair) Expert
You’ll be lauded as a planning genius who crafted a vacation so smooth and seamless that it’ll be talked about in hushed tones for decades and enter the hallowed Friend Trip Hall of Fame that sets the standards for all other trips.
