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How to plan a group holiday (without the stress)

Whether you’re planning a wild stag do or rounding up the family for a multi-generational trip, we have tips and advice on how to plan, book, and get the very best out of a group holiday – you super-organised travel wizard, you. 

Groups of friends

Photo credit: Duy Pham

Reunions, post-exam parties, ski trips – a group holiday with your best mates can lead to a trip you’ll never forget. Here’s how to make it memorable for all the right reasons…


  • Choose your friends wisely. Tommy’s here to hit the strip and party all night, while Sarah wants to sample the best museums and wine bars. Save yourself upset and arguments down the line by making sure you’re all on the same page right from the start. Ask yourselves, what kind of trip is this? If half of you want a cultural city break and the other half want a fly-and-flop beach holiday, then it’s better to plan different trips. 
  • Elect a leader. Some people love organising, while others are happy to sit back and go with the flow. When it comes to group trips, too many cooks, or, in this case, self-appointed travel agents, means nothing gets decided. Often, it’s easier if one person takes charge. That doesn’t mean it’s a dictatorship, though! The leader can research and send a list of possible options for the group to choose between.
  • Keep in touch. While group chats might have you reaching for the ‘mute conversation’ button when everything kicks off, they’re are a great way to keep everyone in the loop, discuss ideas and share links while you’re researching destinations and hotels. Once you’ve booked, set up a shared online document (like a Google doc), where you can add trip information and keep tabs on who’s paid who.
  • Share packing lists. If you’re trying to save on luggage space, or just like travelling light, sharing your packing plans in advance can be really useful. Lots of items can be communal if you’re all staying at the same accommodation, so you only have to bring one set of hair straighteners or a travel iron between you. Need some guidance? We’ve already compiled the ultimate packing list for you.

On the ground

  • Don’t split the bill. We’ve all been there. You’re in a restaurant, half the group are throwing cash in a pile and negotiating change, while the other half toss cards toward the frazzled waiter clutching a card machine. After all that, there’s still 40 euros mysteriously missing. Avoid these stressful situations altogether, by setting up a ‘kitty’ and giving it to the most responsible person in your group. Everyone puts in a certain amount of spending money at the start of the trip, and then this money is used for group meals and travel.
  • Book in advance. As a large group, you can’t be as spontaneous as a couple. It’s harder to wander into a restaurant for an impromptu dinner or just jump in a cab. While you don’t need to book everything beforehand, simply calling ahead a few hours before you plan to eat/travel will save a lot of aimless wandering trying to find somewhere that can cater to a large group last minute. 
  • Split up. Can’t agree on what to do? Don’t feel bad about dividing up into smaller groups. If some of you want to go shopping but others want to lounge by the pool, there’s no need to force everyone to do one or the other. You can all meet up for lunch afterwards to catch up – and you’ll have plenty to chat about!

Multi-generational family trips

Photo credit: Konstantin Tronin

Getting away with the extended family has never been more popular, but planning a trip for a range of ages from babies and teens to grandparents can be a tricky one to negotiate. Luckily, we’ve got some great tips to keep everyone happy…


  • Choose the right time and destination. Family spread around the world? If you live apart and use a holiday as an excuse to meet up, try to find somewhere that’s roughly in the middle. If you’re flying to each other, you have a couple of things to think about: cost and ease. It’s more expensive for a family of four to fly long haul, and much cheaper to fly out two grandparents. But elderly grandparents may not be able to travel as far, and so it may be easier for the rest of the family to come to them. Just choose what works for your family and sort the destination (and the dates) out as soon as possible. You’re dealing with multiple ages and stages of life so you’ll have to consider annual leave, school holidays and social engagements.  
  • Find the right accommodation for you. Each family is different, so think about your own family’s dynamic when booking a place to stay. One big house or villa may work out cheaper per head, but if you need your space to have a good time, then a hotel with separate rooms will give you more privacy. If members of your family have totally different budgets and aren’t willing to compromise, look for two separate hotels that are close together. Simply search for hotels in the destination you want and then click on the map search tool in top left-hand corner.
  • Be up front about money. Money can be a tricky issue, even among family. Trips like these are often framed as gifts, with one family footing the bill for everyone. It’s important to be clear upfront what’s included, so find out if you’ll need spending money for drinks, food or activities. It can feel awkward to ask when someone is already being so generous, but trust us, it’ll be even more awkward not to. Just frame your questions politely and explain that you’ll need to budget for the trip. 

On the ground

  • Be sensitive around childcare. Bringing the kids? With plenty of family around, you’ll have lots of extra hands to help with childcare. But don’t just assume that you have a free babysitter every evening. While multi-age holidays are the perfect opportunity for grandparents to bond with their grandkids, remember it’s their holiday too. Instead, book a hotel with a kids’ club or babysitting service, so everyone gets a break.
  • Set up a shared photo album. An iPhone album, WhatsApp thread or file-sharing cloud will all to the job. You may need to explain to the less digitally savvy family members how they work, but it’ll be worth it. There’s nothing worse than posing for every group photo multiple times, while family members hand the helpful stranger five different cameras. Smiles soon turn into grimaces. If you can all share photos, one snap will do the job, the smiles stay genuine and you won’t miss a memory!

Hen and stag dos

Photo credit: Nick Abrams

L-plates, fancy dress and questionable straws can only mean one thing. Hen and stag season is in full swing. While a lot of the friend group travel tips above apply to pre-wedding jaunts too, there are a few extra things to consider…


  • Travel together where possible. It’ll be easier for you all to come on the same flight. Not only does the fun start from the moment you meet at the airport, it’s also easier to transport everyone together (not to mention it’s cheaper to split the cost of a mini bus or transfer in large groups). You’ll also all be subject to the same delays or changes to travel plans, rather than trying to negotiate multiple flights and landing times.
  • Embrace the list. If you’re the organiser, firstly, well done, you brave soul. Secondly, it’ll save you a lot of stress if you send the group a packing checklist and a rough itinerary ahead of time. The checklist should include anything they’ll need for the activities, including any fancy-dress requirements, sportswear, or swimwear.
  • Plan something for everyone. While the trip is all about the stag/hen, make sure there’s an appropriate activity everyone can get involved with. For example, if the Mother of the Bride or younger siblings are coming, consider an afternoon tea or spa day, in addition to any booze-filled, ‘adult’ activities you might have scheduled later on…
  • Limit the guest-list. If you’re the hen or stag, approach your invites the same way you would for your wedding. Your close friends won’t mind spending money on a group trip, but more general acquaintances will. Plus, smaller groups are easier to organise, so you may find you have a better time with fewer people. 

On the ground

  • Break the ice. Unlike other group trips, some people may be total strangers on hen and stag dos. Factor in some time for a few non-cringe ice breakers on the journey, so work mates can meet school friends, and it doesn’t end up with everyone splitting up into their cliques. Think Mr & Mrs quizzes, or maybe presenting small gifts for the bride / groom based on a shared memory.
  • Leave enough time. Plan in contingency time between every activity. Traffic is unpredictable and someone will always oversleep or need to stop for the loo. Plus, it goes without saying, don’t plan activities too early in the morning if you’ve been out the night before. It’s unlikely anyone who got in at 4am will be ready and raring to go paintballing at 9am…

Ready to start planning your group’s great escape? Round up the gang and start searching for flights and hotels below.


All flight and prices mentioned in this article are estimates of the cheapest prices based on Skyscanner’s flight search tools. These are subject to change and were correct at time of writing on 18 June 2019.