The Ultimate Guide to Planning a Group Holiday

Ed Maughan
Ed Maughan

Going on a group holiday, either with friends or family, is always a good idea. It’s important to spend some quality time with your nearest and dearest, however, planning a holiday can be daunting – especially when you are trying to organise 10+ people. If you’re thinking about heading off on a group holiday, then you’ve come to the right place.

Choose your group wisely

It may sound obvious but choosing the right people to go away with is crucial. In a perfect world, you’d only travel with people who have similar interests, personalities and budgets, but if that’s not the case then you need to be able to compromise.

Life is short and the world is wide

Once you have your group sorted, you then need to decide on when and where you’re going. This is where things can get complicated. One way to choose the holiday destination is for everyone to write down where they’d like to, put the choices into a hat and pull out the winner.  This is one area that will likely need a little negotiation – so you might need to have a few rounds and see which one gets picked the most! Although, with hundreds of places to see, the world really is your oyster. Then you’ll need to tackle dates. Try picking a selection of dates and whicher gets the most votes, wins.

As Northern Lauren says, “If you’re flexible-ish on dates, it’s probably best to get your location down first and then search for the cheapest flights. Figure out your location and take it from there. I recommend using Skyscanner’s ‘Anywhere’ search function for this stage, as it’ll help you figure out the cheapest destinations too.”

Spread the duties

It’s likely that everyone will want to have some involvement when it comes to booking a holiday, and things can often get out of hand when 10+ adults are trying to book transport. Hand Luggage Only advises, “Let everyone have a role. Someone sorts out flights, someone sorts out hotels, someone sorts out that vineyard trip, …etc. This way, everyone feels like they’ve contributed and no one is left feeling overworked or stressed out.”

Get booking

As with everything, the sooner you book it, the better your chances are at getting a good deal. This is even more important when planning a group holiday. Villas, apartments and houses also tend to be much cheaper for groups in comparison to hotels, and it means you can stock the fridge with your favourite food and drink – this also helps to keep costs down as local shops and supermarkets often have great deals. If you’re looking for the ideal group accommodation, have a look on our website for some inspiration.

Jessica Aitken, from STA Travel says, “Flights go on sale 10-11 months before you’re planning to travel, they are almost always cheapest when they first come on sale. So, the sooner you start planning, the more money you will have to spend on fun activities later.”

Create a ‘kitty’

Many groups prefer to have a shared money pot (or kitty), once they’re on holiday. It makes paying for dining out, activities and food shopping much easier. Why not start the kitty before you go away? When booking anything holiday-related, it’s often better if one person pays for it rather than trying to book separately. Starting your holiday ‘kitty’ in advance will help towards alleviating any pre-holiday stress.

Hold meetings and create messaging groups

Not only will this build the excitement for the upcoming trip, but it’s a chance to get everyone involved, including the kids. A group text message or chat will also allow for easy communication. For example, a Facebook group allows you to share photos and funny memories when you’re back home.

Plan the itinerary

Even if you’re going on holiday to simply relax and do nothing, you still need an itinerary. When planning a group holiday, you should to remember that it’s everyone’s holiday as much as it is yours. Some will want to party, some will want to go off on active adventures. It’s healthy for the group to split up and go their separate ways for the odd day or two, but make sure that it’s in the plan, or gets added to it if things change. Another idea is to create more than one itinerary in case of bad weather, if people have a change of heart or just to have other options. When kids are involved, it makes a huge difference to have things planned out, and it’s always a good idea to have a few extra tricks and trips planned to prevent boredom from setting in!

And, finally… Enjoy yourselves! You’re on holiday!

We have an extensive portfolio of properties at, including homes specifically suited to multiple family groups.

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