Under One Roof: The Art of the Grand Celebration with The Thinking Traveller

There comes a point in most families’ lives when a restaurant table simply will not do. A sixtieth birthday, a fortieth wedding anniversary, three generations who have not been in the same place since Christmas: such occasions ask for somewhere with room to breathe. Not a hotel, with its corridors and its checkout times, but a house, ideally a rather magnificent one, with the sun on its stone and long tables set beneath the trees.

For nearly 25 years, The Thinking Traveller has been quietly finding such houses. Founded in 2002 and, this year, once again named Best Villa Rental Company in the World for the eleventh time, the company has built its reputation on a simple principle: it only offers what it has seen for itself. Every villa has been visited, and many stayed in, by its own team. When they tell you a house will suit twelve friends, two toddlers and a formidable grandmother, they know because they have checked the bedrooms, tested the sightlines and counted the sofas.

That experience underpins the company’s new Celebration Collection, ten of its largest villas, chosen specifically for gatherings that matter.

The best of both worlds

What distinguishes these houses is that each is fully serviced. For anyone who has hesitated over renting a villa, fearing the shopping, the cooking and the general organising of other people, this is the bridge between hotel and home. Staff are on hand, meals are taken care of and the practicalities quietly disappear, while the great advantages of a villa remain: complete privacy, days that run to your own schedule rather than the dining room’s, and gardens where grandchildren may roam without disturbing a soul. There are rooms in which to gather and, just as importantly, rooms in which to escape.

Where to go

Sicily claims two of the finest. Rocca delle Tre Contrade, with fifteen bedrooms, is the sort of house around which one could organise a special reunion or a very long lunch. Don Arcangelo all’Olmo, with twelve, offers the island’s particular blend of palatial grandeur and warm hospitality.

In Tuscany, Villa Talamo sleeps ten, and needs little introduction as to why: direct access to the waters of the Talamone Gulf, and views incorporating the gentle theatre of the Italian countryside.

Further south, in Puglia, Casina Cinquepozzi, also with ten bedrooms, sits within a landscape of olive groves and whitewashed light that seems made for unhurried celebration. And for those drawn to the Aegean, Villa Aetos in Greece has nine bedrooms and the kind of views that silence a room.

Those five — all pictured on this page — are only the beginning. All ten villas in the collection can be explored online, each with its own guide to the occasions it suits best.

A portfolio of rare breadth

The Celebration Collection is, in truth, one corner of a far larger map. The Thinking Traveller’s portfolio runs from centuries-old farmhouses and restored palazzi to strikingly contemporary architecture, and from intimate hideaways for two to the grandest of family houses.

Its destinations include Sicily, Puglia, Tuscany, Corsica, Sardinia and Greece, where more than twenty islands are on offer, each with its own character. Whether you picture a stone masseria among almond trees or a modern house above a quiet Cycladic bay, there is a good chance it has already been found.

Why now is the time to book

Anyone who has attempted to book a large house at short notice will know the difficulty. Properties of this size are few, and those worth having are secured early, particularly for the summer months. With 2027 marking the company’s 25th anniversary, demand looks set to be strong. Booking now offers the pick of the homes and, no less valuable, time: time for the team to help shape the occasion, from the arrangement of the bedrooms to the menus, the excursions and the small touches that turn a good week into one that is spoken of for years.

It is rarely the grandest gesture that people remember. More often it is the long evening when everyone was finally in one place, the youngest asleep on a sofa and the eldest holding court by the pool. The right house makes that possible, and those who plan early will have the best chance of finding it.

To explore the Celebration Collection and enquire about 2027, visit thethinkingtraveller.com/celebration-villas.