How to plan a group holiday (without ending your friendships!)

Ah, the group holiday. Mentioned by many, attempted by some, succeeded by few. Every so often, there will be a fleeting ‘omg guys, we should go on holiday together this year’ that pops up in the group chat (often by the keenest lil nerd in your chat – AKA me). People agree out of politeness, throw in a couple of suggestions, and then nothing happens. Nobody wants to take on a role less coveted than Brexit secretary: the holiday manager.

That’s where I come in.

Being a total control freak with an alarming dedication to planning things, I take on the position of holiday organiser quite aggressively. I guide the conversations about destinations, accommodation and flights into something meaningful until a holiday begins to take shape. Then I plan the shit out of it.

We’ve had two successful holidays now as a group of 10-15 people (bar a few punches thrown, some noise complaints and one or two stolen phones). I’m now planning the third 🤞🏼 and couldn’t be more excited about it.

Friends in Parc Guell Barcelona

Gather your comrades.

It sounds silly, but you need to actually determine who is genuinely up for a holiday and who is erring on the side of flake. Find your definites and add them to a separate group chat. Entitle it ‘LADS ON TOUR 2020 ✈️🍻☀️’ or something of that kind of stature. This is your base group of confirmed attendees, and the people whose opinions matter the most in the planning stage.

Friends walking towards Magic Fountain in Barcelona

Be upfront and realistic.

If, like me, your group chat is 25-odd people strong, not everyone is going to have every single one of their needs met. Sometimes you just have to realise that you know best – which is why you have taken on the role in the first place, remember. Group holidays are not democracies, so make some of the decisions and tell the others to thank you for making sure there’s a holiday for them to go on in the first place.

Dorada beer Tenerife

Find out the vibe before you make any big decisions

Finding out what people want from their holiday is a crucial part of deciding where to go and what type of accommodation to find. There’s no point going to a quiet seaside town in southern Italy if people want high octane adventures, messy nights out and Irish pubs stretching as far as the eye can see. 

Ask people what they’re looking for and try and reach some kind of consensus. If half of you want to lay by a pool for a week while half of you are looking to hike nature trails and climb mountains, people will have to compromise. 

Once that decision is made, however, you can take the reins and plan to your heart’s desire. If you know that the gang is big on watersports, find somewhere with an action-packed coastline. Looking for a more cultured experience of sightseeing, museums and history? There are plenty of places that fit the bill. 

At this point, your main goal is to create a Venn diagram of people’s general wishes. Find the places that have the most overlap with what you want and then start figuring out specifics. 

Friends dab in Parc Guell Barcelona

Balance the spontaneity

Think about some of the best days, evenings or events in your life. Were they meticulously organised down to the minute? (The day you got married doesn’t count).

It’s no coincidence that sometimes the best experiences we have are things that ‘just happened’. As humans, we love the unknown, as long as it goes right. You go into a situation with no expectations and end up stumbling across something unexpected – it plays into your sense of adventure.

It’s important to plan some things, don’t get me wrong, but leave some room for unplanned adventures too. Or even just some downtime. Your friends will thank you for it, trust me.

Friends smiling at PortAventura waterpark Salou

Share the load

Look, you can’t organise everything. Sure, you can try, but you’ll be too busy organising to actually have a good time or the worst will happen: everyone will blame you when things go wrong and you’ll forever be the one who ruined that holiday.

Learn to delegate and take some of the pressure off yourself. Have someone organise car hire, have someone keep a track of finances (if you all end up splitting food shops or a deposit for your accommodation, this is a really handy person to have), and let everyone decide for themselves if they want to take part in the stuff you’ve planned.

Friends smiling in apartment in Barcelona


This one’s a bit of a cliche, but it’s true. This is your holiday too, and if you get too caught up in making sure your group are enjoying themselves, you’ll miss out yourself. Things will go wrong, people will hurt themselves or get lost or argue, but everything will be fine. 

Have the holiday that you want to have, enjoy the company of the people you like most in the world and be thankful that you’re not at work!

I hope you find these tips helpful if you’re planning any big holidays with your friends in the future. If you’ve had a great or terrible experience on a big group holiday I’d love to hear it, so do comment below!

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