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Where to Stay in Tuscany, Italy

Enjoy the view from a luxury Tuscan castle
Enjoy the view from a luxury Tuscan castle | Courtesy of Castello di Vicarello / Expedia
Photo of Liza Karsemeijer
Liza Karsemeijer
20 December 2020

Take off on truffle hunts, sip wine in style and master the art of fresh pasta-making at these historic hotels in Tuscany.

Sure, Tuscany may be one of Italy’s most touristed corners, but for good reason. And even here, you can blend in like a true Tuscan at the region’s storied stays, set in age-old castles, artfully restored palaces and family-run farms, where they’ll teach to eat, drink and live like a local. Get ready to enthuse about your love of the land (they do that a lot here) and follow our insider’s guide to uncover a few tucked-away ateliers and unpretentious trattorias along the way.

AdAstra, Florence

Boutique Hotel
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AdAstra
Courtesy of AdAstra / Expedia
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.
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Il Battistero, Siena

Boutique Hotel, Budget Hotel, Independent Hotel
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Il Battistero
Courtesy of Il Battistero / Expedia
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.
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Villa Cora, Florence

Hotel, Villa
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Villa Cora
Courtesy of Villa Cora / Expedia
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.
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Borgo Scopeto, Chianti

Hotel, Villa
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Borgo Scopeto
Courtesy of Borgo Scopeto / Expedia
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.
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Antica Residenza Cigogna, Siena

Budget Hotel, Independent Hotel, Boutique Hotel, Bed and Breakfast
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Antica Residenza Cicogna | Stuart Green
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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.
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76 Via delle Terme, Siena, Toscana, 53100, Italy
+390577285613
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Borgo Santo Pietro, near Siena

Boutique Hotel, Spa Hotel, Hotel, Luxury
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Borgo Santo Pietro
Courtesy of Borgo Santo Pietro / Expedia
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.
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    • Lupaia, Montepulciano

    Boutique Hotel, Hotel, Luxury
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    Lupaia
    Courtesy of Lupaia / Expedia
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    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).
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    74 Località Lupaia, Toscana, 53049, Italy
    +3905771917066
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    Il Borro, near Arezzo

    Boutique Hotel, Hotel, Luxury
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    Il Borro
    Courtesy of Il Borro / Expedia
    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.
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    Borgo Pignano, near Volterra

    Hotel
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    Borgo Pignano
    Courtesy of Borgo Pignano / Expedia
    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.
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    Castello di Vicarello, Cinigiano

    Hotel
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    Castello di Vicarello
    Courtesy of Castello di Vicarello / Expedia
    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.
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    Belmond Castello di Casole, near Siena

    Hotel, Villa
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    Belmond Castello di Casole
    Courtesy of Belmond Castello di Casole / Expedia
    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.
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    Località Querceto, Casole d'Elsa, Toscana, 53031, Italy
    +390577961501
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    These recommendations were updated on December 20, 2020 to keep your travel plans fresh.
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