Where to Stay in Tuscany

To explore the true Tuscany that only insiders know about, and away from the crowds, stay at Villa Ardore – a newly renovated 16th century Tuscan stone farmhouse that sleeps up to 18 guests, in the heart of Chianti’s iconic wine region. It’s the passion-project of California-based attorney Christian Scali and screenwriter Stephen Lewis who were determined to find their dream vacation home and open it up for guests to enjoy. The owners enlisted leading Florentine architect Massimo Pieratelli to bring the project to fruition, transforming the ancient farmhouse into a luxurious home-from-home complete with modern comforts and amenities, while keeping the building’s authentic character intact. Available for a group of friends or families to book in its entirety for exclusive use, the villa comes with a private chef preparing farm-fresh breakfasts and meals every day. There’s also a luxe private spa with a whirlpool looking out onto the vineyards, as well as an infinity-edge pool with panoramic views, vast manicured gardens and one-of-a-kind experiences, from countryside driving tours in vintage Fiat 500s, to cooking classes and pizza parties at the villa. Themed itineraries from culinary, to culture and relaxation are available to book year-round, in addition to newly launched experiences such as the “Italian Land and Sea Experience”. In partnership with world-class yacht specialists, Worth Avenue Yachts, this itinerary combines the best of your Villa Ardore stay, with the ultimate Bond-style yacht getaway, exploring the Italian coast and the Med beyond.

After a period of restoration, Forte San Giorgio – a listed national monument – reopened in 2021 as a singularly individual property for private hire. Its British-Italian owners invited in designer Sue Timney (whose CV includes designer Paul Smith and theatre and film director Sam Mendes) to reimagine the interiors of this wonderfully sprawling building, bringing a light, natural style to the historic architecture. The fort is now a characterful island retreat, with 11 bedrooms (10 ensuite) set around the stronghold, with a variety of drawing rooms, terraces for sunbathing and dining, two infinity pools, a games room for billiards and table tennis and a contemporary kitchen for entertaining. It is available in July and August for exclusive buy-out hire for holidays, and Capraia – the wildest and remotest of all the Tuscan Islands – serves as the perfect destination for a group escape away from the crowds to reconnect with nature and community.

Italian design aficionados will love the 1960s furniture inside this luxurious, little-known Florentine ancestral family mansion, where framed Pucci scarves and original prints hang on the walls. Strolling through the lush, surrounding gardens, you might forget you’re in the centre of Florence, but the bustling Piazza Santo Spirito is only a short walk away. If you’re looking for an original souvenir, drop by silversmith Giuliano Ricchi’s hidden jewellery atelier at number 12, whose clients include president Bill Clinton and perfumier Nina Ricci.

There’s more to Tuscany than tourist-trailed Florence: in fact, Siena has churches and cathedrals in the same style as the famous Florentine Duomo – but in Siena they come minus the crowds. This elegant palazzo sits right by Siena’s gothic Baptistery of St John. Rooms include original-tile floors and exposed wooden ceilings. Be sure to stop by the wine shop on the ground floor to pick up some of Tuscany’s prized liquid produce, or have a glass of red in the hotel’s cellar, home to a medieval aqueduct and a secret passageway once used by Pope Alexander VII. Ask nicely and local owners, Giovanni and Cinzia, will give you the scoop on all things Sienese.

Located on a hillside beyond Florence’s historical centre, this aristocratic residence created for Baron Oppenheim overlooks the cypress-filled Boboli Gardens and has been receiving important international guests, such as yourself, since the 1960s. It also boasts a top-notch restaurant, pool bar and roof terrace. But if you want something more local, descend the hill into Firenze’s Oltrarno quarter – the lesser-known “other side of the Arno” – to browse hole-in-the-wall ateliers and meet the craftsmen who ply their wares there. Finally, toast the day’s exploits with an aperitivo in the Piazza Santo Spirito, then leave take dinner amid the tranquillity of restaurant Gurdulù’s courtyard, where the chatter of Italian voices sets the soundtrack.

For five centuries, this country-side estate in the middle of the wine-loving Chianti region, minutes away from Siena, was the residence of the Sozzini family, a famous dynasty of the Italian Renaissance. It now houses 58 classically decorated rooms, a wellness centre with grape-based vinotherapy treatments and a restaurant where you can reap the region’s rich bounty. To sample more of Chianti’s flavour, head to the hotel’s winery, or visit Poggio dell’Oliviera, a vineyard and olive grove, that’s been perfecting their craft since 1932. Vespa tours, organised through the hotel, are the last word in living like a local.

This not-so classic bed and breakfast, set within a palazzo in the centre of Siena, is lavished with frescoed ceilings and antique furnishings. Its modest rates enable budget travellers to explore the city and still have some change left for dinner at a local trattoria or an aperitif at one of the talked-about Tuscan wine bars. For a unique view of Siena’s skyline, be sure to visit Fortezza Medicea just outside the centre. Commissioned by Cosimo de’ Medici, locals love a stroll here just before sundown.

This five-star boutique hotel features luxury suites, three different Michelin-starred restaurants, an organic farm and a holistic spa. But despite all that grandeur, the estate lies in a tiny village, housing only 100 inhabitants – so you’ll feel like one of the locals. Be sure to explore the impressive ruins of San Galgano’s abbey and, if you’d like to try a simple Tuscan meal (on top of the fine-dining experiences at the hotel), go to local-favourite Ristorante Antico Tempio for cheeses, classic cold cuts and typical Tuscan pasta with truffle.

Tuscany’s Val d’Orcia is famous for its great wines, characterful towns and picturesque landscape of rolling hills. This romantic country hideaway used to be a goat farm, before being abandoned for 40 years then completely renovated by an enthusiastic Austrian couple. Today, it holds a centrepiece Italian kitchen, where guests gather each evening a for four-course meal made with produce from the garden and the best Tuscan markets. The residence is only 10 minutes away from Montepulciano, where you can sample the best Tuscan red at one of the town’s ancient wineries (hint: try the vino nobile at Cantucci wine cellar).

This luxury estate near the hilltop city of Arezzo boasts suites and apartments spread out over the ancient houses of an old village. Florentine businessman, Ferruccio Ferragamo – grandson of the legendary shoe designer, Salvatore Ferragamo – stumbled upon the abandoned town in the 1990s and decided to buy it, taking 15 years to lovingly restore the medieval buildings. The old streets now house small shops run by Tuscan craftsmen: you can pick up a pair of custom-made shoes or design your own jewellery with the local smith. If you’re visiting Florence, swing by the associated Il Borro bistro to sample more produce from the estate.

Carved into a cliffside, this haute hilltop hotel boasts an impressive infinity pool that takes in Tuscany’s sloping hills. The far-reaching grounds also house an organic farm, herb gardens and bee hives, with ingredients grown on the estate used in everything from cocktails to food and spa treatments. You can opt for a refined dinner al fresco at the restaurant, or a low-key night in the nearby town Volterra, where aperitivi and cheese platters are served at local wine bars, such as Enoteca Scali.

Situated 350m (1,150ft) above sea level, this luxury castle flaunts striking views over the wild Maremma countryside, an area unique for its diversity and untrodden Tuscan coastline. Do as the locals do and take a dip in the natural thermal baths of Saturnia or Petriolo. When you get back, the chef will treat you to a home-made dinner with organic vegetables, meats and cheeses. The 900-year-old castle is now presided over by the Baccheschi-Berti family, who take great pride in serving up their award-winning wines and estate-grown produce. They’ll even teach you how to cook traditional Tuscan recipes to impress friends with back home.

Visit local farms, go on a truffle hunt, make your own pasta or simply unwind at the pool or spa of this no-luxuries-spared Belmond hotel which lets you experience the Italian countryside like a true Tuscan. If you get hungry, choose from two refined restaurants. Foodies who long for a local experience also can’t miss Ristorante La Speranza, a five-minute drive away in Colle di Val d’Elsa, with its informal atmosphere and great value for money.