How to Plan a Group Trip Successfully

So you don’t, you know, murder anyone before you even get there

Think about what a group holiday with your best friends would look like for a moment. If you’re anything like me, you’re picturing sandy beaches, ice-cold cocktails, and tapas-fuelled 30 Seconds tournaments as the sun sets. What you’re likely not picturing, is exchanging passive-aggressive messages over the WhatsApp group chat about who’s putting the least effort into planning the actual trip, or threatening to call off the whole holiday entirely a week before your flight – prompting an influx of DMs.

The thing is though, that you can’t get to the first, idyllic picture without battling your way through the second. Because travel agents aren’t exactly a millennials go-to, it behooves you to know how to plan a group trip successfully.

Here are four steps on how to plan a group trip like a boss (so you don’t, you know, murder anyone before you even get there).

1 Pick your Monica

Identify the Monica Geller of your group. For those of you who have not yet watched Friends (WTF are you even doing? But anyway), Monica Geller is a compulsive planner. She is painfully organised, has a label maker for every occasion, and while she drives you fucking nuts, there’s no denying she gets the job done. Simply put, you’ll need someone to be in charge. Maybe two someones. This ‘captain’ had better want the job though because believe me, as a Monica myself, it’s far from easy to plan a big dinner party, let alone an actual holiday.


2 Pick your budget

This applies whether it’s you and one bestie, or a group of 10. You need to know what your budget is for flights and accommodation up front. The conversation around a daily spending limit then also needs to happen. This doesn’t mean you can’t spend your hard-earned rands raiding the local market for cute jewellery, but it does mean that the whole group has a better understanding of what kind of activities will be done as a group.

3 Pick your sanity

Listen up, as an introvert, I can tell you for free that you NEED to prioritise being upfront about your solo expectations for the holiday. If you know you’ll need an hour a day to yourself to read or that you despise anyone trying to nap next to you, tell your friends that. Often we assume that people want and need the same things we do. That’s bladdy well not the case. Tell your squad about your little sanity-saving quirks up front – it gives them permission to do the same with you.


In fact, it’s important to ask your friends what they’re hoping to get out of the trip in general. Is your one friend planning on spending a solid four hours a day trawling Grindr? Are you planning on drinking four pina coladas before 11am? None of these things are wrong – it’s just that you’ll want your one annoying friend who likes to hike to manage her expectations from day one.

4 Pick a few fun things to do beforehand

Whether it’s a museum or water sport, decide as a group on a few cools things you’d like to do at your destination, and book it beforehand. This will take the pressure off you to make tough decisions when you’re finally on holiday, and lets the group know, as a whole, where to carve out their alone time/couple time.

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