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Young and old can have fun in the sun. Photo: Michael Brooks/Alamy

Multigeneration holidays – the villa break where nobody is left behind

By Sean Caulfield

Multigeneration holidays – the villa break where nobody is left behind

Mum, dad, grandma, grandad – and don’t forget the kids… multigeneration holidays are all the rage. At To Tuscany, we’ve noticed more and more of you booking these convivial get-togethers during the past five years. In fact, we’re boosting our offering of villas with five bedrooms or more to meet demand.

The fact that more of us are holidaying together as extended families seems to be largely down to the generosity of grandparents, who are putting their hard-earned cash to good use creating memory-making experiences for the whole brood. Don’t just take it from us: a recent passenger survey by Virgin Holidays revealed that seven out of 10 families who travelled with the tour operator chose to take a multigeneration holiday. It seems we just love spending quality time together.

A stress-free, unhurried environment is what’s needed for happy co-existence of family who normally live in different homes, towns, cities, even parts of the world. Choice of space is crucial, with large terraces for communal dining and quieter corners for a bit of me time, as well as the comfort of facilities such as en-suite bathrooms. We asked Sean Caulfield, owner of To Tuscany, to give his top tips for planning a multigeneration trip.

Sentimental journey: create special memories on a villa break with the whole family. Photo: Shutterstock

Configuration is crucial

Don’t choose a property just for its size – give serious consideration to its internal arrangement. No matter how well they get along, big groups need space and independence. Look out for large villas divided into apartments, which can be opened up to interconnect, ensuring everyone gets some privacy. Grandparents, especially, might even appreciate their own annexe. At the very least, ensure there is a suitable mix of en-suite bedrooms and extra bathrooms.

Pools, gardens and on-site facilities

For most mixed-age groups private pools are essential and a pleasant diversion for everyone, a place to relax together. Many larger properties benefit from their own pools, fenced to keep small children safe. Large gardens are also a bonus, with different areas to enjoy a spot of tranquillity. Some villas have playgrounds, ping-pong tables or even tennis courts on site, while others have saunas and gyms for wellness.

Table for… 12, or 20

Although large groups enjoy holidaying together, different generations will often split up during the day to do their own thing. But they generally want to come together for the evening meal. A property with a large terrace and excellent views can be a place to relax, from aperitivo time until after midnight. A barbecue or outdoor pizza oven is also a bonus for fun al-fresco meals. Plus, for special occasions, guests can book a recommended private chef to cook up a treat.

Location, location

Think about the make-up of your party and choose a base with a spread of attractions to meet the needs of young and old alike. Being within walking distance to a local village or town is handy for elderly people and small children. While a villa near a train station can give teenagers a bit of independence and the opportunity to visit a larger town, or offer a taste of cultural treasures for adults. Plus if the beach vibe is important to your group, choose a property with easy access to the coast.

Extra services and activities

Depending on budget, your group might want to book extra services – a regular housemaid or chef is very common, helping to avoid stress around cleaning and cooking. Most of our villas have local activities to choose from. We can recommend more gentle pastimes, from vineyard wine-tasting sessions to cookery lessons, as well as more active pursuits such as horse-riding and hiking.

Three properties for the whole family

Ideal for a multigeneration party of up to 16, Villa Querciola 16 has an annexe with en-suite double bedroom – a good choice for grandparents or a younger couple. There’s also a private pool, mini golf green, Jacuzzi and sauna, and the villa is just 15 minutes from the medieval walled town of Volterra, for a great day out.

Casa Ceperano 14 offers the ultimate in flexible accommodation – sleeping 14, it is, in fact, made up of four apartments that can interconnect. There’s almost a bathroom for each bedroom, plus there are three living rooms and three kitchens to cater for everyone. And, it’s within walking distance of the Chianti town of Radda, with a handful of great cities to explore nearby.

A contemporary, stylish property, Villa Capalbio is set in huge landscaped grounds with private pool. It’s just a stone’s throw from the beach, and there is also a renowned bird sanctuary to explore nearby. The villa has several comfortable and well-equipped outdoor rooms for lounging and dining, as well as lots of indoor spaces to retreat to for a bit of peace. Most rooms are on the ground floor, so it’s perfect for guests with limited mobility.

To Tuscany has a range of villas with five bedrooms or more across the region.


Over 20 years ago, I moved to Tuscany with my Italian wife and founded To Tuscany as a villa rental company. Our first rentals were in a country residence in Chianti and we offered guests a tailored vacation using our local knowledge and personal service. Today, you can experience the same at over 600 superb villas.

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