Getting the whole family away together, kids, parents, grandparents and everyone in between, always sounds like a brilliant idea. And it is. But it also tends to involve at least one spreadsheet, a few too many WhatsApp messages that often never really get resolved, and at least one disagreement about the destination.
There is usually a moment in the planning where you realise you are trying to combine about five different holidays into one as everyone has different ideas. But somehow it still works out, just not without a bit of back and forth first and many discussions.
Here are your reminders and sense-checks to get your planning down to a tee.
Agree on budget first and holiday expectations
This is the bit nobody is ever excited to talk about, but it really does make everything much easier if you can agree on the budget.
With bigger groups, expectations can drift quickly. One family is thinking simple apartment and chilled meals in, another is thinking swanky hotel already planning the restaurants for most nights, and nobody quite realises.
Before you get too far into scrolling accommodation and destinations, it’s a good idea to discuss and try to agree:
- what each household is comfortable spending for the whole trip including meals
- how you are splitting the bigger shared costs like accommodation if one family has more members than others
- whether meals and activities are mostly together or more flexible
Some families like a shared pot for group costs, where everyone contributes upfront towards things like accommodation, food shops or shared activities, and expenses are paid from one fund during the trip. Others prefer to keep things separate and split shared costs individually as they arise, whether that’s dinners, taxis or excursions. Neither approach is better but agreeing how you’ll handle money early on helps avoid awkward conversations later in the planning process.
If you do need to travel during peak school holiday periods, it is worth booking as early as possible. Larger family groups often need specific room setups, adjoining hotel rooms for teenagers, accessible rooms for grandparents, or bigger villas that get booked up quickly. Booking early can also help secure better prices and take advantage of early-booking discounts before availability becomes more limited.
Trying to keep everyone happy? Start here
This is usually where things get interesting as there are so many things to consider.
It is very easy for one strong opinion to quietly shape the whole trip, and before you know it, you have booked something that only really suits part of the group and everyone else is just hoping for the best.
Big families end up needing a bit of everything. Enough going on for the teenagers so they do not get bored. If there’s young kids entertainment and the right facilities. Enough calm for grandparents so they are not exhausted. And enough downtime for parents so it actually feels like a holiday.
Before booking anything, it helps to properly talk it through:
- do people want proper rest, activities, or a mix of both
- how much independence teenagers are realistically going to want
- what type of destination works best for everyone (beach, city, countryside, resort, etc.)
- do you want to be near bars and restaurants or somewhere quiet
- how far people are happy to travel to (short-haul vs long-haul)
- how long the trip should be so it feels worth it but not exhausting
- whether a hotel, villa or apartment setup works best for the group
- self-catering vs all-inclusive vs eating out most days
- accessibility and suitability for younger children or older family members
- what “comfortable” actually looks like for older family members in practice
The best multigenerational trips are usually the ones where not everything is done as a group. Giving people the flexibility to split off during the day and come back together later helps everyone enjoy the holiday at their own pace, without the pressure of trying to agree on every single activity.
A bit of independence alongside quality time together tends to make the whole trip feel more relaxed and enjoyable for everyone.
And realistically, there will probably still be at least one debate about what to do by day three, but that’s all part of the family holiday experience.
Consider what makes the perfect family hub
Where you stay ends up shaping the whole holiday more than most people expect.
For bigger families, villas or holiday homes usually make things easier. There is space to spread out, a shared area where everyone naturally gathers, and somewhere to disappear to when you need a bit of quiet. Which, in a big group, is important.
The kitchen often becomes its own little hub, even if nobody planned it that way. It’s a good idea to discuss how you’d use the accommodation and weather cooking meals will play a big part of the holiday or whether you’re likely to eat out most days.
What is everyone’s ideal type of holiday – do they like being amongst lots of people in a hotel or is a private villa with a pool more suitable.
If a hotel works better, it is worth checking:
- family rooms or connecting options
- lifts, step-free access and general ease of getting around
- whether the layout actually works for a group, not just couples
Accessibility is not just about mobility needs. It is about whether the whole group can relax without constantly thinking about logistics.
Avoid airport stress – get the paperwork sorted
This is always the bit that gets pushed to the last minute and then suddenly becomes the most stressful part of the trip.
Start with passports. Check expiry dates early because some destinations require months left on them beyond your return date, and this can often catch people out.
Then check entry requirements. If children are travelling with adults who do not share their surname, some countries may ask for extra paperwork so it’s good to check this out in advance as it can catch you out.
If the country you’re visiting requires the group to have vaccinations these also need a bit of forward planning, especially if there are multiple GP appointments involved.
And then there is travel insurance, which becomes even more important with a mixed-age group. The main thing is making sure everyone is properly covered for what they are actually doing, especially if there are different ages, medical needs or activity levels in the group.
Specialist insurance providers like Staysure offer cover tailored to older travellers and those with pre-existing medical conditions. They also offer group insurance, which is often the best way to insure the trip, particularly when you are combining different generations in one booking. The key thing is to check the cover limits properly. Ensure each person has enough cancellation cover for their portion of the cost of the holiday rather than assuming a standard policy will automatically suit. If one of you becomes ill before departure and you need to cancel the trip it can all be dealt with under one policy rather than each person having to put in separate claims to different insurers.
Getting all this discussed, researched and agreed early removes a surprising amount of last-minute panic.
When in doubt, book a cruise
Cruises are one of those things people either love or assume are not for them until they actually try one. But for multigenerational holidays, they often work surprisingly well. Once you are on board, everything is in one place, so there is no constant decision-making about where to eat, what to do, or how to get there. Which, in a big family group, is half the battle.
Grandparents can take things at their own pace and still access support if needed. Children have structured clubs and activities. Teenagers get a bit of independence without disappearing completely. And adults finally get a chance to properly switch off.
Cruise expert Mark Barton, working with Avanti, says: “Family cruises are a great way to get everyone involved. Their all-inclusive nature takes much of the stress out of planning and budgeting, allowing families to focus on spending quality time together. Unlike traditional cruises, they also offer a wide range of activities for children and teenagers as well. In fact, the Royal Caribbean have family decks on a lot of their ships with interconnecting cabins.”
For this type of holiday, you need a specific cruise travel insurance policy. He adds that if you are planning to take part in onboard activities or excursions, just to make sure everything is covered.
Multigenerational holidays do take a bit more planning than a typical break. There are more opinions, more logistics, and usually at least one moment where you wonder how it is all going to come together.
But when they work, they really do.
It is not just the destination. It’s everything in between. The family discussions that never stop. The shared meals where everyone actually gets time to sit together. The small moments you would not get on separate trips and the long-lasting memories.
It takes a bit more effort, but that extra planning is what makes the trip run smoothly and ensures everyone gets a holiday they’ll genuinely enjoy and remember for a long time.
Find the right travel insurance for you
Travelling with a pre-existing medical condition doesn’t mean you have to compromise on your holiday. With the right cover in place, you can relax knowing you’re protected if anything flares up while you’re away.
Dr Asimah Hanif, medical expert at Staysure, says: “It’s always good to have medical travel insurance in case you suffer from severe symptoms abroad and need urgent medical care. Declaring your pre-existing medical conditions is also important to ensure you’re fully covered abroad.
“This should be a key part of your holiday-prep, so you can travel with reassurance knowing you’ll be looked after should anything go wrong on your trip.”
