Locanda al Colle
Location: Versilia
Minimum stay: 3 nights
Price starts at: €245 in low season, €395 in high season
Individual rooms
Without reception desks or room service, Locanda al Colle feels more like you’re staying at a friend’s elegant villa than a hotel. The views over the Tuscan countryside and Ligurian coastline are rivaled by the interiors, which have been turned into a type of private art gallery by owner Riccardo Barsottelli, who also hosts sculpture exhibitions throughout the year. Wine tastings, beachside aperitivos, shopping in Forte dei Marmi, and insane cycling trails are all well within reach.
Forte San Giorgio
Location: Isola di Capraia
Minimum stay: 1 week
Price starts at: €29,700 in shoulder season, €33,000 in high season
Entire villa, minimum 12 people and maximum 22 people
From the 120-meter-high infinity pool at the renovated Forte San Giorgio on Capraia, you can see seagulls and falcons flying below, with Italy’s mainland just a 2.5-hour ferry ride away. Known as “Il Castello,” the renovated fort features 11 suites, a communal kitchen, a number of balconies with stunning views, activities like sunrise yoga, and plenty of access to explore the wild island as well as dive into the clear, protected waters.
Stella d’Italia
Location: Florence
Minimum stay: 1 night
Price starts at: €220 x night
Individual rooms
Vintage movie posters, restored frescos, clawfoot tubs, and double-headed showers are just some of the Italian-themed antiques, artwork, and furnishings you’ll find in the 24-room Stella d’Italia. Located in a historic 16th-century palazzo on Via de’ Tornabuoni, the hotel also boasts a cozy loggia with views of the Bellosguardo hills and a breakfast room with wrap-around frescoes.
La Guardia
Location: Isola del Giglio
Minimum stay: 3 nights
Price starts at: €200 x night
Individual rooms
La Guardia, a boutique hotel overlooking Giglio’s harbor, is a minimalist dream, designed with a contemporary and sophisticated lens that perfectly compliments the island’s wild, serene essence. After leaving your chic, sea-view room, set out to scuba dive off the coast, indulge in Mediterranean flavors at their two on-site restaurant options, or just lounge around to really live island life. You’re guaranteed to leave feeling sunkissed and restored thanks to what owners Flaminia and Flavio have deemed the “Giglio Effect”.
Casa Howard
Location: Florence
Minimum stay: 1 night
Price starts at: €300 x night
Individual rooms
This boutique hotel in Florence’s city center reflects three generations of the Forneris family’s eye for detail and beauty. Featuring original pieces gathered on trips abroad along with custom-made furniture, each room takes on a new personality much like an actual home. It’s this duality–the warmth of staying in a home with the spirit of a high-end hotel–that we love. Well, that and enjoying daily breakfast in bed–hand delivered on a tray with Ginori crockery and silver cutlery–under the silk-filled duvets.
Le Caviere
Location: Val d’Orcia
Minimum stay: 7 nights
Price starts at: €1,400 x week
Entire villa, maximum 4 people
Conceptualized and run by Kate Middleton (no, not that Kate Middleton) along with her partner Brad, this impeccably decorated guest house might just convince you to buy one of your own nearby. Located on a fully functioning organic farm, you can savor freshly picked fruits, vegetables, and the couple’s own cold-pressed olive oil after strolling through the tranquil estate. The guesthouse offers total privacy and the chance to really settle into the area, but Kate and Brad, who live nearby, are always up to join for a glass of homemade Vin Santo.
Villa San Sanino
Location: Torrita di Siena, Val d’Orcia
Minimum stay: 1 night
Price starts at: €490 x night
Four suites available for individual rent or as entire property
This 1700s-farmhouse was originally renovated by Laura and Ubaldo to be their family home, but, driven by a passion for design, hospitality, and food, they decided to share their so-called “dreamhouse” with others. Each suite is the perfect, cozy country home, and their design–wooden beams, terracotta floors, antique furniture–combines the typical Tuscan farmhouse style with the family’s tastes. Spend the day swimming in the salt water pool and reading books under the strawberry grape pergola or exploring the surrounding towns and villages, returning in the evening to dine on local, seasonal food at the villa’s private restaurant.
Oltrarno Splendid
Location: Florence
Minimum stay: 1 night
Price starts at: €150 x night
Individual rooms
Located in Florence’s Oltrarno neighborhood, this stylish, history- and design-forward hotel is splendid indeed. Designed and decorated by Florentine local Matteo Perduca, the 14 rooms all have a sense of individuality, culture, and style, and each boast different, but equally beautiful views, over the Renaissance City. Enjoy a morning breakfast on the top floor of the 16th century palazzo before heading out to explore the quieter side of the Arno River.
Oltrarno Splendid; Photo by Ilaria Costanzo
Photo by Ilaria Costanzo
Tenuta di Tramonte
Location: Countryside of Lucca
Minimum stay: 1 night for rooms or 1 week (Saturday to Saturday) for entire villas
Price starts at: €160 x night for room; €13,500 x week for villa Volpi; €18,000 x week for villa Trenta
Individual rooms or entire villas (either 7- or 12-rooms)
This idyllic estate is the brainchild of couple Lorenzo and Laurence, who left their fast-paced careers in finance and entrepreneurship to embrace a life connected with nature. To do so, they set about reviving an ancient convent on vast farmland into a thriving sanctuary and opened it up to visitors. From the organic farming practices to the farm-to-table cuisine, the tenuta is committed to sustainability, as well as to providing an experience that allows the natural heritage of their villas and land to shine.
Villa Talamo
Location: Talamone
Minimum stay: 4 nights
Price starts at: €25,000 – €45,000 x week, depending on season
Individual rooms or entire villa, maximum 22 people)
If there is a place that embodies the concept of dolce far niente, this pastel, 18th-century monastery-turned-villa cascading down into emerald waters amidst palm trees is certainly it. A stay here is of utmost Mediterranean luxury: sure, the rooms, amenities, and on-site dining are high-end quality, but it’s the views of the Tyrrhenian sea, bright green foliage, and sounds of waves and birds that are the most luxurious. It’s perfect for a summertime getaway al mare, with you and 21 of your closest friends and family members.
Villa Talamo
Palazzo Guadagni
Location: Florence
Minimum stay: 1 night
Price starts at: €150 – €300, depending on season
Individual rooms
Right off the buzzing Piazza Santo Spirito, Palazzo Guadagni is a quiet, and ultra Florentine, respite. Built in 1505, the palazzo garnered much of its unique character from the personalities who passed through its walls, from artisans to writers to German and Austrian intellectuals who hid here during WWII. When they revived the spot in 2007, Ferdinando and Laura ensured that the rooms retained their historical–and individual–charm, with restored frescos, furniture from vintage markets, and personal touches like fresh flowers and linen sheets. Each room also offers a different view of the Florentine skyline, though the best secret is the loggia–one of the most beautiful terraces in the city, unparalleled for a sunset spritz.
Villa Roma Imperiale
Location: Forte dei Marmi
Minimum stay: Depends on the season, anywhere from 1 to 5 nights
Price starts at: €880
Individual rooms
On the Tuscan coast of Versilia, Villa Roma Imperiale has become our dream casa al mare–a hotel defined by the understated luxury, extraordinary service, and privacy that only a home can provide. Tasteful decor, private terraces and balconies overlooking the manicured gardens, travertine bathrooms, and a collection of books selected by the owners and guests from all over the world adorn the interiors. It’s a great spot to experience the kind of lifestyle that has made Versilia into one of the most glamorous destinations of the Tuscan coast, hosted by a family that really knows what they’re doing when it comes to hospitality.
Casa Newton
Location: Pienza
Minimum stay: 2 nights
Price starts at: €700 x night in high season
Individual rooms or entire villa available for rent
Originally built in 1846 by Isaac Newton’s nephew, this large, brick red country house is an agriturismo designed to welcome you no matter the season. Named after the children of the former estate owners, each of the 11 rooms and suites offers a different vibe. Antonie Bertherat-Kioes, the architect and interior designer, filled the casa with specific mid-century vintage furniture, purpose-woven fabric signature walls, and unconventional ceramics. The current owners, who live on the other side of the hill, treat this as their second home, one that they’ve filled with art from the likes of Alighiero Boetti, Lucio Fontana, Carla Accardi, and Giosetta Fioroni. Designed by Luciano Giubbilei and overflowing with rosemary, the manicured garden is especially noteworthy, and the tiled pool particularly invigorating in the heat of the summer. In typical Tuscan fashion, the casa sits at the top of the family’s vineyard, with an on-site cellar you can visit for olive oil and wine tastings.
La Chiocciola
Location: Cellai
Minimum stay: 3 or 4 nights, depending on apartment
Price starts at: €1,100 or €1,300 x night, depending on apartment
Two individual apartments
This massive 16th-century villa in the countryside has been in the same family for over a century, and they still use one of the three apartments as a countryside vacation destination. Rustic details like terracotta flooring, wooden-beamed ceilings, and antique kitchen items compliment the eclectic, modern room decor, embodying the spirit of the Tuscan countryside with the family’s contemporary tastes. Florence is only 25 minutes away, but you’d be hard pressed to leave the surrounding gardens–once a private hunting ground–with a stone pool, cypress and olive trees, vine-clad pergola, and vast terrace.
Fattoria and Villa Rignana
Location: Rignana
Minimum stay: 1 night for rooms
Price starts at: €185 x night for rooms
Individual rooms and apartments, or entire villa option at Villa dè Ricci
Here, laze away the days in an infinity pool overlooking the Chianti hills, sip on the fattoria’s wine, or stroll through the gardens before returning to your charming room, whether in the fattoria–a classic, rustic Tuscan farmhouse–or within the 18th-century Villa dè Ricci. In the latter, which features particularly stunning original frescoes, you can book independent apartments or the whole villa, which hosts 19. Refreshingly relaxed and cozy, Rignana is a perfect destination for independent traveler types who like to explore–or lounge around–as they please. The renowned restaurant Cantinetta di Rignana is just two minutes by foot down the road, but be sure that your stay includes a Tuesday evening, when Sebastiano, the owner’s son, offers special farm-to-table dinners (April through October only).
AdAstra
Location: Florence
Minimum stay: 1 night
Price starts at: €150 x night
Individual rooms
AdAstra spans the first and second floors of a 19th-century mansion in Florence’s hidden Torrigiani garden, Europe’s largest privately owned garden within city walls. The hotel’s name–“to the stars”–comes from the neo-gothic tower with an astronomical observatory located within the gardens and visible from nearly every window. Inside, the rooms blend classic and contemporary design, and each has a clawfoot tub, original frescoes, modern upcycled furniture, and a sprinkling of knick knacks from the 50s, 60s, and 70s. The terrace, with comfy green benches and a stunning view of the garden, is perfect for whiling away an afternoon, book and Negroni in hand.
Terre di Sacra
Location: Capalbio
Minimum stay: 1 night
Price starts at: €100 x night
Individual lodges
This is the chicest way to camp (or perhaps better, glamp) on the wild side of the Tuscan coast. Terre di Sacra’s elegantly furnished tents have all the amenities you might need, including AC and a fully stocked kitchen, and are set right in the sand dunes or on the beachfront–unsurprisingly, the sunsets are unparalleled. This is a stay that won’t break the bank, where you can go from aperitivo on your private porch to a swim in the sea in a matter of minutes. They also have a fantastic beach club and restaurant, La Dogana. We recommend booking the newer sea-lodges, with doors.
