How to plan a memorable multi-gen family holiday

Planning a multi-generational family holiday can be daunting, but so worthwhile. Here are our top tips and ideas for organising a (relatively) stress-free trip all ages will enjoy.

In the mad rush of everyday life, it can be difficult to carve out quality time with family. Maybe you live away from your parents, children or in-laws. Maybe you see each other all the time, but never all at once – or not long enough. Getting all the generations together in one special place can be a wonderful way to make lasting memories you’ll talk about around the dinner table for years to come.

But planning this kind of trip can be a challenge. With a range of ages and personalities, you’ll have different needs to accommodate. You might want twin rooms or baby cots, accessible ensuites or large kitchens – or all of the above. There may be small children to entertain, older children to tempt off their screens, or tired adults desperate for free childcare (cue the grandparents). So if you want a holiday that goes off without a hitch, it’s all about the planning.

Choosing your destination

1 Keep travel simple

One of the most important things to consider with a trip like this is the schlep. For groups travelling with older, newer or less mobile members of the family, we recommend choosing a destination that is just a short flight away, and preferably as close to the airport as possible.

2 Pick your priorities

With the youngest and oldest members of the family chiming in, there are bound to be differing opinions on where to go. It’s almost impossible to make everybody happy, but you can certainly find a destination that checks at least most boxes.

If you’re a family of outdoor adventurers or beach-goers, there are destinations made for you. But usually, some want to lounge by the pool, others want to explore cultural sites, the kids want watersports, and it seems impossible to please them all. We find that countries like Italy, Greece and Portugal are great for having a little bit of everything: culture, food, coast and countryside, and inexpensive rentals for large groups are easy to find.

3 Break up the winter

Long haul isn’t an option for all families, but a sunny escape can be the best way to break up a dreary British winter. Some of our favourite winter-sun destinations for families include Sri Lanka and Costa Rica. South Africa is a fairly easy journey from the UK with no jet lag and has everything from city to safari. If you need a shorter flight, there are winter sun destinations in Europe or Morocco is a great option – especially around February half-term.

4 Consider a staycation

Going abroad can be lovely, but sometimes all you need is to get everyone together and away from their daily routines. A staycation is an especially good idea for those with elderly family members who aren’t up for a flight, however short. There are plenty of beautiful UK rentals perfect for a family getaway closer to home.

Choosing your accomodation

Spread out in a villa

One way to simplify things for large groups is booking one super-sized villa with everything you could need including a pool, lots of space to lounge, and a large kitchen and dining area. Being all together in one place as opposed to scattered across multiple rentals can make it easier to gather, make plans and organise day trips.

If you want a more catered experience, splash out on a daily cleaning service, a private chef or even a fully staffed villa. Cooking together can be fun, but let’s be honest, it usually falls to the same people night after night, and they deserve a holiday too.

What to look for in a family villa

A large kitchen: Even if you don’t plan on cooking much, the kitchen is the natural gathering place for most families.

A separate lounge for kids: Having a room for the youngsters to hang out in isn’t essential, but we highly recommend it if the adults want a chance to sip wine and chat uninterrupted.. at least for a moment or two.

A pool: This isn’t a must, but it can be a great activity for all age ranges and is another space for the family to gather and relax.

Bed and room types: Don’t just look at the number of bedrooms. You might want a twin room for children to share or a bedroom with space for a baby cot. You may also need a bedroom on the ground floor for family members with mobility issues.

Bathrooms: Ensuites are best when sharing with family, but it’s also good to have a common WC close to the common areas.

What to look for in a family resort:

The perfect size: You want all the facilities of a large hotel, but if it’s too gargantuan, the service won’t be as personal and the communal areas will be crowded.

Rooms/houses close together: Having some space can be nice (sometimes necessary) but you want to be able to gather easily too.

Kids club: Not all kids clubs are alike! Do some research ahead of time to find out what activities they have on offer and what their facilities are like.

Restaurant/Bar: If you’re looking for the easiest possible family holiday experience, having a restaurant and bar onsite makes all the difference. If you’re hoping to spend lots of time at the hotel, having at least a couple of options is even better.

What to look for in a rental/hotel hybrid:

A space for everyone to gather: If you’re spread across multiple rooms/rentals, make sure there’s at least one communal space large enough for the whole family to gather for meals.

Villas/houses close together: Having some space can be nice (sometimes necessary) but if the rooms or villas are too far apart, you’ll spend the whole holiday walking back and forth between them.

A large pool: If you’re relying on a communal pool, make sure it’s large enough for your family and then some. Some retreats offer rentals or suites with private pools, which is a great option if you want a little more privacy.