Here’s where to stay on your next trip to Tuscany

Nothing says luxury quite like Tuscany. 

Whether you’re an art historian or lover of good food and wine, Tuscany hits all the high notes when it comes to an immersive haute experience. High-net-worth travelers seeking a city experience can make a stop in Florence, while others can travel outside the city walls to find beautiful, family-run boutique hotels and wine resorts.

Here’s a roundup of our favorite properties to have on your radar for your next trip.

Villa Cora

Consider Villa Cora an oasis outside the hustle and bustle of the busy streets of Florence. This five-star resort, which was once a private estate, makes guests feel like bona fide Florentine aristocrats.

What makes the property so special are the small touches — everything from the exquisite fine dining in the Moorish Room or at Le Bistrot; to the Bellevue rooftop terrace, a perfect place to take in a sunset. The property also boasts a year-round heated pool, the Bene Spa, a full-service gym and a complimentary shuttle that brings guests directly into the main parts of Florence. 

Castello di Fonterutoli Wine Resort

This wine and hospitality group, owned and operated by the Mazzei family, has two resorts in the heart of Tuscany and one in Sicily.

The Castello di Fonterutoli Wine Resort is one worth a visit, located in the heart of Chianti Classico. The hotel is spread throughout a small, medieval village owned by the family and offers a variety of housing options—everything from luxe rooms to larger apartments and villas for groups and families. Guests can truly embrace living like a local by stopping for a coffee or aperitivo in the village bar or for a tasting from the family’s portfolio of wines. The property showcases Osteria di Fonterutoli, which highlights Tuscan cuisine at its finest by using local produce and wild game.

Borgo San Felice

Borgo San Felice, in the Chianti countryside, is just outside Castelnuovo Berardenga and Siena. The expansive property, which includes 15,000 olive trees, encompasses 685 hectares of land, with 188 of those being vineyards. The hotel property has 28 rooms and 31 suites, with a swimming pool, gym, tennis courts and full-service Botanic Spa. The vineyard villas offer a more secluded stay, complete with a private pool, and offer tailor-made experiences for guests.

A highlight of this property are the culinary options, including restaurants run by Executive Chef Juan Quintero in collaboration with multi-starred chef Enrico Bartolini. They include Poggio Rosso, which boasts one Michelin star, and Osteria il Grigio for a more rustic dining experience.

While guests are drawn to the fine touches of the hotel accommodations, they also visit for on-site wine tasting experiences, where they can learn about the birthplace of the very first Super Tuscan wine in Chianti Classico.

Castel Monastero

One of the most spectacular properties in Tuscany is Castel Monastero, a Leading Hotel of the World property housed in a restored monastery just outside Siena.

While driving up to the property, guests are greeted with cornfields, chestnut forests and long rows of cypress trees. Once inside, guests are wowed by how the property has transformed from its humble roots as a monastery into a beautiful Tuscan culinary and wellness retreat. The property has 74 rooms and suites and one villa on-site.

They also have two restaurants and a wine bar, perfect for the late-afternoon aperitivo. The casual dining concept is La Cantina, built into the property’s medieval wine cellar. Contrada, in comparison, is connected to La Cantina through a secret passageway and is the fine-dining concept, run by Executive Chef Enrico Marmo.