The Thinking Traveller have some of the finest villas in the Mediterranean on their books for multi-generational holidays. Here are just a few of the highlights.
Every New Year brings with it new opportunities and potential for success, but as we head out of the starting gates for 2025, it’s worth remembering that another twelve months can go by in the blink of an eye. And making time to get away and properly reconnect with loved ones throughout the year is hugely important; these holidays are the chance to make memories you’ll treasure for decades to come.
When it comes to summer getaways, there is nowhere better on Earth than the Mediterranean, and nobody knows the region better than The Thinking Traveller. Over the years they have developed an outstanding reputation amongst the cognoscenti for their carefully curated collection of exceptional villas across Puglia, Sicily, Tuscany, Greece and Corsica.
At The Thinking Traveller every villa on their books is hand-selected for its unique story, magnificent location and excellent amenities – providing a home from home which guests can enjoy without having to lift a finger. Their properties come in all shapes and sizes, ranging from romantic beachfront retreats to Tuscan Agritorismos in the countryside or large private estates with multiple swimming pools, private chefs, tennis courts, private beaches and gardens peppered with olive and lemon groves.
For 2025, multigenerational holidays – where two, three or even four generations holiday together – are expected to continue grow in popularity and for these clients The Thinking Traveller offers a selection of substantial properties which are perfect for family and friends who want to holiday together but also require their own space when they need it.
When time is precious families don’t want to worry about organising trips and booking tables, and The Thinking Traveller has expert local teams on the ground in every location who act as a concierge service, taking care of everything from recommendations for the best beaches and local markets, to organising yacht charters and restaurant bookings.
Below we have rounded up some of the finest The Thinking Traveller villas in the Mediterranean for different kinds of multigenerational groups, from those with young children to families looking to host a milestone occasion in style; but if you can’t find exactly what you’re looking for, the experts in their villa matchmaking service will talk through your requirements to provide a shortlist, and then help you to handpick the perfect retreat for your family this summer.
The Best Mediterranean Villa for families with small children: Trulli Andrea in Puglia, Italy
Comprising two traditional Trulli buildings, Trulli Andrea is large enough to guarantee everyone their own space; with six bedrooms the property sleeps 12 comfortably. Outside, the expansive lawn is fantastic for lots of running around, and there are plenty of shaded areas plus two swimming pools – one for grown-ups and one for the children. Find out more about Trulli Andrea
The best Mediterranean villa for a special celebration or milestone birthday: Don Arcangelo all’Olmo, Sicily, Italy
Unquestionably one of the finest properties in Sicily, Don Arcangelo all’Olmo is an incredible place to host a milestone birthday or celebration. Inside, the interior design is beautiful, with elegant reception rooms and twelve generous bedrooms. Outside are mature gardens including olive and lemon groves, sea views, and a luxurious pool area complete with shady terrace. Guests enjoy evenings dining under the stars in the gazebo, receiving five-star service from the villa’s in-house team including their marvellous private cook. Find out more about Don Arcangelo all’Olmo.
The best Mediterranean villa for relaxing with older teenagers: Treis Villas in Paros, Greece
Set up as three neighbouring houses, each with its own pool and sea views, the communal spaces at Treis Villas provide plenty of places to eat, drink and relax together – but it’s also easy to escape to your own space when you need it. Just a short walk from the beach, the property comes with an on-site basketball court, table tennis and a barbecue. Find out more about Treis Villas.
The best Mediterranean villa with an in-house chef: Azalea in Skiathos, Greece
Set directly on a stunning beach, the in-house team at Azalea offers a family style service, and prepares a refreshing daily breakfast, a light lunch and dinner every night so you don’t need to lift a finger all holiday. Find out more about Azalea.
The best Mediterranean villa for activity lovers: Crossing Together, Sicily, Italy
Sicily is an all-year-round paradise for lovers of adventure and culture alike, whether you’re looking to explore ancient Etruscan sites, climb Mount Etna, or escape to the beach or the golf course, Crossing Together is the perfect seafront villa from which to explore the island’s east coast. With eight large bedrooms the villa features a refreshing natural water pool, expansive terraces and the option to set up an outdoor cinema after a long day exploring. Find out more about Crossing Together.
These villas are just a taste of what The Thinking Traveller has to offer – their hand-picked properties across the Mediterranean are all exceptional places in which to relax, unwind and enjoy some precious family time. Discover more at www.thethinkingtraveller.com and get in touch with their teams directly to find your perfect Mediterranean escape.
