Stay At One of Italy’s Coveted Islands for a Relaxing Getaway

Recover from months of mind-numbing lockdown and isolation by revitalizing your senses in the Tuscan countryside or on one of Italy’s coveted island escapes.

By Sheean Hanlan

Rosewood Castiglion del Bosco
Seventy miles outside Florence, this storied castle is a fairy-tale retreat for modern times.


About: Around 800 years ago, the grounds of Castiglion del Bosco, which means “walled castle in the forest,” were home to a thriving farming village and some of the great Sienese families. In 2003, the 5,000-acre Tuscan wine estate caught the eyes of Chiara and Massimo Ferragamo, and the couple restored and crafted it into something of a medieval fairy tale. The farmhouses and school buildings of the borgo now house the resort, which became a Rosewood property in 2015. Located on the same estate as the hotel, the Castiglion del Bosco vineyard grows Sangiovese exclusively, and the winery is the fifth-largest producer of Brunello di Montalcino.

What’s new: The resort underwent an expansion and reopened in June 2021 with a new complex that includes 19 one-bedroom suites and an infinity pool, all designed by Teresa Bürgisser.

Stay: You’ll find 42 suites and 11 villas spread among the estate’s olive and cypress trees. Ranging from 2,809 to 7,819 square feet, the converted farmhouse villas overlook the vineyard or the stunning circle of Montalcino hills, and each includes a living room, private garden, pool, and kitchen or kitchenette. Groceries are provided upon arrival, and daily breakfast is delivered to your door.

Culinary: Two restaurants are overseen by Michelin-starred Executive Chef Matteo Temperini. Most of the produce comes fresh from the hotel’s organic garden. Private dining experiences can include a personal chef flipping pizza in your villa’s stone oven or grilling bistecca alla Fiorentina in your garden. If you came for the Italian wine, enjoy an alfresco picnic prepared for you by the vineyard, take part in a private wine selection by a sommelier in the cellar, or sip on a glass at the resort’s Campo del Drago bar.

Do: Scour the forest for white and black truffles with hunting dogs, take a forest bath, or learn to make tagliolini pasta in the La Canonica Cooking School. Get a whiff of organic pecorino at a cheese tasting after a horseback ride, or join a guided tour of the Val D’orcia. The hotel can also arrange experiences in other parts of Italy, like racing a Ferrari or Lamborghini on the Autodromo di Modena near Bologna, escaping on a 24-meter yacht to Portofino, or touring the Amalfi Coast in a helicopter adventure. From $4,729;


Borgo Santo Pietro

This boutique oasis is set on a 12th-century compound.


About: Weary pilgrims embarking on the Via Francigena route from Canterbury to Rome and the Holy Land paused on the property’s grounds to rest and recover before continuing the arduous journey to the tombs of St. Peter and St. Paul. Centuries later, Danish couple Jeanette and Claus Thottrup chanced upon the ruins of the former stopover. In 2001, they began a seven-year renovation of the 12th-century villa and surrounding area. The plan was to make the countryside estate a family home, but instead they decided to share it. Thus, it became a hotel with a 300-acre organic farm and 13-acre garden, officially opening its doors in 2008.

What’s new: In May 2021, the hotel debuted an herb house, allowing guests to see how herbs are formulated into oils for the brand’s all-natural skincare line, Seed to Skin. In a new series of soap and cream workshops, herbalists led by Giusdino Mazic will explain the restorative properties of plants. The hotel also added a pop-up garden restaurant, Orto, complete with a fermentation lab of 250 vegetables and herbs. Not only can guests dine on fermented dishes, but they can also learn how to make these dishes themselves in cooking classes. There’s also a new forest gym.

Accommodations: As if inspired by the earth’s irregular beauty, each of the property’s 22 rooms and suites is individually styled. The lodgings embody the timeless quality of 19th-century French palaces, such as expansive garden suites, with subdued beige palettes, jeweled chandeliers, and marbled Roman baths. Their private terraces, perfectly situated for candlelit dinners, look out onto the orange trees of the Mediterranean courtyard. Other rooms are covered in delicate frescoes or else lined with old hardback books.

Culinary: What sets the hotel’s food offerings apart isn’t just the seven-course banquet at its Michelin-starred restaurant, Meo Modo. It’s also the intense devotion to local produce and sustainability. An organic farm, culinary garden, fermentation lab, herb garden, and working animal farm provide raw ingredients like fresh milk and cheese for the hotel’s three restaurants. Guests can visit Trattoria sull’Albero’s gourmet market, handpick their ingredients, and watch chefs prepare their dinner in the open-plan kitchen.

To do: Weekly activities and retreats are both enjoyable and restorative. Rise early to join the sheep-milking process at the dairy farm. Learn about gut health at the food lab, go for a bath in the shaded river of the forest, or try out Tibetan bell therapy. Get your heart pumping on an off-road mountain bike tour or take archery classes. The hotel can also arrange private transfers to the coast, as well as to its private sailing yacht Satori. From $684;


Paradise Found

Lose yourself on one of these idyllic Italian islands.



About: Italians have been escaping to this Mediterranean gem for years. The largest island in the Bay of Naples, Ischia is quieter and more reserved than its famous neighbor, Capri, but that’s the point. People come here for the beautiful sandy beaches and natural hot springs.

Do: Castello Aragonese is a sight to behold. Connected to the main island by a causeway, the medieval castle majestically sits atop Ischia Ponte. Take a mud bath in the town of Lacco Ameno, whose thermal waters are rumored to have healing powers. Don’t leave without trying the island’s iconic rabbit stew, coniglio all’Ischitana, and sampling a Rucolino cocktail made with locally grown arugula. On the south side, visit Spiaggia dei Maronti, the island’s longest beach, and later, catch an outdoor concert in the Greek-style theater of the Giardini la Mortella.

Stay: The 52-room Mezzatorre Hotel and Thermal Spa—formerly a 17th-century watchtower—dangles on the edge of a craggy cliff in a secluded bay. From $865;

Getting there: Take a 75-minute ferry from Naples to Ischia Porto, the main port on the north end of the island.



About: Water that sparkles like champagne. White-washed villas dotting lush hills. Lemon trees leading the way to the town’s designer boutiques. There’s a reason this resort island was once the playground of Roman Emperor Tiberius: Capri exudes tropical elegance.

Do: Spend an afternoon sailing around the Faraglioni rock formations. If the tide permits, row a boat over to the luminous waters of the Blue Grotto sea cave. Relax on a lounge chair at Marina Piccola beach, then enjoy an alfresco lunch at one of the restaurants in La Piazzetta. At night, dance the evening away Italian style at Anema, one of the most popular taverns in town.

Stay: Capri Tiberio Palace is perfectly situated near La Piazzetta. Styled by Milan-based interior designer Giampiero Panepinto, the 54-room boutique hotel overlooks a picturesque hillside of white villas facing the Mediterranean Sea. The property features two on-site restaurants, one of which serves kosher food and wines, a cocktail bar, vegetable garden, spa, and pool. From $550;

Getting there: Most people will take the ferry. The price of sanity? Roughly $1,500 to charter a private boat for the 50-minute ride from Naples.



About: Halfway between Trapani and Tunisia, this rugged island in the Strait of Sicily is so low key that even mainland Sicilians forget it exists. Home to fewer than 8,000 people—although one of them is Giorgio Armani—many residents live in historic rural stone houses called dammusi. Jagged volcanic stone and quiet coves take the place of white sand and crowded beaches.

Do: Embrace the dolce far niente lifestyle: Do nothing. When you want to cool off, float in the cerulean blue bay of Cala Tramontana. Enjoy a mud bath in the naturally hot and color-changing waters of Lake Specchio di Venere on the north coast, then have a picnic at the rocky Balata dei Turchi ocean cliffs. Go wine tasting at Donnafugata winery and vineyards. Pantelleria is one of the few producers of the rare Zibibbo wine, and the methods used to cultivate the white grapes with low vines are on the UNESCO Heritage List.

Stay: The idyllic Tenuta Borgia is set on a farm featuring pinewoods, bougainvillea, Zibibbo grapes, and olive trees. Seven standalone dammusi are spread throughout the property, each housing two to eight guests. The four-bedroom Dammuso Grande has a private patio leading out to an Arabian garden, and ample living space decorated with antiques and contemporary furnishings. From $115 (three-night minimum);

Getting there: Hop a flight from Palermo, Trapani, or Catania into the island’s only airport.

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