The Ultimate Guide to Planning a Group Holiday

Planning a group holiday, either with friends or family, offers a great chance to experience something new and to spend some time with your nearest and dearest.

However, as attractive as a group holiday may sound, planning it can be daunting – especially if you’re trying to organise a large group of people. With dates, destination, budgets, and itineraries to consider, it’s enough to give even the most well-organised of us a headache!

So, if you’re thinking about biting the bullet and organising a group holiday, we’ve put together the ultimate guide, with tips on surviving the planning process and how to ensure everything runs smoothly and successfully.

Start Planning Early

Whilst spontaneous trips can be some of the best, this is not likely the case for a large group holiday. With both travel and accommodation to book, leaving it until the last minute could mean missing out on amazing deals and ultimately end up costing more in the long run.

Planning early also gives everyone the chance to put the dates in their diary, minimising the risk of anything else cropping up and people having to cancel as a result. Don’t forget, if you’re travelling with family, you’ll also need to consider annual leave, school holidays and social engagements, so get planning in plenty of time!

Agree on a Destination

It is wise to agree on a destination as the first priority – this will make it easier to search for deals on flights and accommodation, as well as the cheapest dates to travel. This will also establish the type of holiday it’s going to be – if some of your friends are expecting a relaxing walking holiday, and others, an activity-based break, it may be wiser to plan different trips.

For multi-generational family trips, consider a destination that caters towards everyone’s needs and interests. For families spread across the globe, cost and ease are two factors which come into play: It’s more costly for a family of four to fly across the world, for example, than it is for a couple, yet be mindful that elderly family members might not be able to travel as far.

Assign a Group Leader

Some people love organising, whilst others prefer to go with the flow. When it comes to a group holiday, however, it is crucial that someone takes charge or else inevitably, nothing will get done.

This doesn’t mean the holiday should become a dictatorship though! – it’s important for the group leader to delegate tasks to others and keep everyone in the loop with decisions and options for each part of the trip. Have someone organise the itinerary, while another takes charge of accommodation, and as group leader, collate all the information and ensure everything remains on track.

Plan the Itinerary

You can choose to split up the itinerary by day so that each friend or family member gets to pick one thing they are particularly interested in. This tends to save any arguments and ensures everyone enjoys their time away.

Don’t forget to schedule in some down-time too! As exciting as it may be to have several activities lined up, it’s important not to burn yourselves out. Why not consider accommodation with hots tubs or spa passes for this?

Book Activities and Restaurants in Advance 

As a large group, you lose an element of spontaneity. It’s much harder to wander into a restaurant for an impromptu dinner for example, than if you were travelling as a couple. While you don’t need to book everything beforehand, it’s worth calling a few hours ahead for that extra piece of mind.

The same goes for activities. Whilst many tourist activities do cater to large groups, it might be worth booking ahead, especially if the activity involves being seated or grouped together – you’ll want to ensure your entire group can remain together throughout.

Find the Right Accommodation 

Perhaps one of the most crucial parts of the planning process is the accommodation. Each family or group of friends is different and so it’s important that the style of accommodation you choose caters to everyone’s needs.

One big holiday home or villa might work out cheaper per head and is a great option for families, but for those who prefer a little more privacy, separate hotel rooms or smaller holiday homes might be the better option.

For those travelling with family members, it might be worth considering an apartment or holiday cottage with multi-floor bedrooms. Not only does this ensure everyone gets their own space but can be particularly beneficial to elderly or disabled family members who won’t have to climb stairs.

If children are involved, search for accommodation that is “child friendly”. This could mean having a safe area for them to play outside, giving them plenty of opportunities for fun, and you, peace of mind.

Split the Bills

Ensure you build up a money pot of petty cash that can be used for food, drinks, and other shared costs during your stay. People owing each other money can get confusing and even a little messy at times, so it’s best not to complicate things more than necessary.

There are apps such as Splitwise which are incredibly simple and can split the bill for you, showing who owes what and who’s paid. These tools are perfect for planning group holidays and make life a little bit easier.

Make some Memories

Amongst all the planning and preparing, don’t forget the most important part of the holiday – to make memories with loved ones and to have fun!

Consider a Cotswold Staycation

Travelling abroad for your group holiday has its own challenges – not everyone can afford international travel and with the ever-changing Covid-19 rules and regulations, many might not want to.

A staycation holiday in the heart of the Cotswolds can be a much safer option than jetting off across the globe: you get all the benefits of travelling with your friends and family, without the hassle of organising flights, travel insurance and passports!

The Cotswold countryside has much to offer – you can lounge by the stunning lakes in the sunshine, or for the more active members of the group, hike among the many hills and walking trails available. Visit our around & about page for a list of family friendly activities you can choose from.

Cotswold Holidays for Groups

At Orion Holidays, we have a number of properties available to suit any style of group holiday, from luxury spa breaks and lakeside cottages, to fishing trips and hot tub properties. Many of our properties are also pet friendly, meaning every single member of the family can enjoy a group holiday in the Cotswolds!

If you are planning a group trip, why not take a look at some of the properties we have to offer.

Book online today or call 01285 861839 to find out more.

group of people with backpacks walking in the woods

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