You’ll Never Want to Check Out of These 12 Magical Hotels in Tuscany

Talk about an entrance: a lane flanked by cypress trees leads guests to this 10th-century castle turned boutique Tuscany hotel, whose setting on 4,200 rolling acres of Tuscany countryside means sweeping views from each of its 42 rooms. Many are housed in separate stone farmhouses, which feature original paintings and beamed ceilings. After a dip in the infinity pool, refresh yourself with a treatment in the wine cellar-turned spa before a hearty dinner of Tuscan classics—potato and Tuscan cabbage ravioli stuffed with aged Stracchino cheese and partridge ragout; fillet of beef Tosca with foie gras and black truffle—and regional wines at restaurant Tosca.

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This sprawling, 2,700-acre estate once owned by the Medici family is like its own village, complete with a clutch of stone farmhouses for rent and a five-star resort with rooms overlooking the valley, a 27-hole golf course (Tuscany's largest), a restaurant so good it could convince you to never want to leave the grounds, and an 11,000-square-foot spa with its own bio sauna, hammam, and salt and ice cave.

In the 15th century, a noble family bought and redecorated this former military fortification into a home of their own, complete with frescoes and expensive art and furniture. Along with the original watchtower, there's also a main loggia (built during the Renaissance) that houses 46 guest rooms—a mixture of old “Castle” suites (vaulted oak-beam ceilings, terracotta tile floors, decorative fireplaces) and newer “Sunset” suites, all of which overlook the Val d’Orcia. The best feature is the hot spring spa, which features two mineral water-fed pools, a Turkish bath and sauna, and treatments that incorporate local grapes and olive oil. Follow it all up with a glass of Brunello di Montalcino, produced at the Tuscany hotel’s own winery.

Overlooking the Adriatic, Borgo Egnazia's 45-acre fig and olive grove estate on the hills of Itria Valley is the definition of romance—so much so that Justin Timberlake and Jessica Biel tied the knot here in 2012. Just picture it: an impressive complex of white buildings (traditional for Puglia) built from local tufa stone, tiered swimming pools, standalone villas, rooms with private terraces, Mediterranean gardens, and even a spa with its own Roman baths. Hungry? None of the restaurants disappoint either, from the buttoned-up La Frasca and Due Camini (both with Michelin stars) to the more laidback Da Frisella.

Itching to live like fashion royalty? Rosewood took over this working Tuscan wine estate owned by the Ferragamo family and turned it into one of the most beautiful hotels in Tuscany. Today, you'll find (among other distractions) 34 lavish rooms and villas decked out with four-poster beds and antiques, an infinity pool, a cooking school where you can learn how to make fresh pasta or pizza using ingredients from the kitchen garden, a Gothic chapel, an 18-hole golf course, and Etruscan ruins dating back to 600 B.C. The price is steep, but the luxury you'll find here is second to none.

Danish owners Claus and Jeanette Thottrup have given this 13th-century country manor a majorly luxe facelift, adding trompe l'oeils and glittering chandeliers everywhere from the restaurant (which holds a Michelin star) to the guest rooms, where oil paintings and clawfoot bathtubs complete the picture. The real stunner, however, is the grounds—we're talking winding paths lined with rose bushes, a vegetable garden for the restaurant, and a new standalone spa that incorporates a line of products launched by Jeanette herself featuring ingredients grown right on the estate.

COMO's first hotel in Italy debuted inside a 12th-century castello in the heart of Chianti wine country. Expect serene, contemporary rooms; a signature COMO Shambhala Retreat on property; and three restaurants including the Michelin-starred La Torre, which sources its ingredients from the estate's own kitchen garden, vineyard, olive groves, and beehives and switches locations—between the former stables and the garden terrace—depending on the season.

The ultimate form of Italian indulgence is perfected at this all-inclusive wellness retreat, which serves up a tantalizing menu of beautiful scenery, stellar food and wine, and a comprehensive spa program that delivers on whatever avenue you hope to pursue. Ayurvedic treatments, thermal water rituals, couples massages—you can have it all paired with wine tastings. After fully blissing out, spend all the time you need (or want) luxuriating in the indoor and outdoor thermal pools and steam bath. Got more time on your hands? Why not take full advantage of your surrounds and arrange day trips to nearby wineries in Chianti or Montepulciano?

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Jackie Onassis is just one of many famous names that have checked into Hotel Il Pellicano, a cliffside hideaway above the Mediterranean Sea that retains its glamour after all these years. Guest rooms, scattered between the main house and freestanding villas, are countryside-chic with their terra cotta floors and beamed ceilings and look down on the hotel's saltwater pool and private beach. The two-Michelin-starred restaurant is pricey but worth the splurge—especially after a day spent on the water and exploring the nearby Spanish fortress.

You have to scale a steep, winding road to reach Monteverdi Tuscany, a stunning Tuscany hotel set in the tiny medieval hamlet of Castiglioncello del Trinoro overlooking the Val d'Orcia, but the trek is worth it. Each of the 11 rooms, which are scattered across the village, is romantically rustic with their four-poster beds, original wood beams, natural linens, and fresh flowers. There's also a wine bar in addition to a farm-to-table restaurant, while the pool and terraced gardens are some of the prettiest in Italy. The biggest news is the spa, set in the village's former granary, which incorporates local ingredients like sage and lemon balm into its treatments, offers yoga in the lavender gardens, and features private stone baths on a terrace with views of the valley.

Talk about a view: the 750 acres that make up Borgo Pignano, a centuries-old villa turned boho-chic country house hotel, are set on a hilltop overlooking the Tuscan hills. The saltwater infinity pool is, as you can see, magnificent—but you'll want to tear yourself away so you can explore everything else, including the gardens and stables (where yoga, bocce, and horseback riding are on offer), and your guest room (just one of 14) done up with Italian period furniture and original frescoes.