8 Heritage Hotels and Resorts to Transport You Back to Medieval Tuscany

Castelfalfi Hero Image - Destination Deluxe
Photo: Courtesy of Castelfalfi
Experience medieval Tuscany with the comforts of modern amenities

Travel back to a time when knights roamed the land at a lovingly restored medieval castle or relive the medieval days at a village ancient house in the countryside of Italy with these heritage hotels in Tuscany. 

Discover old-world Tuscan charm at a medieval hilltop village in the Val d’Orcia region, a former hunting lodge in Lucca, a luxurious farm stay on the hills of Siena, or a former monastery and castle immersed in nature. These deserted villages, neglected properties, farmhouses, and estates have been carefully restored and given a new lease of life. Steeped in history, these unique locations also provide a magical experience for exclusive parties and milestone anniversaries. Here are eight heritage hotels and luxury resorts in Tuscany that offer a Tuscan fairy tale and medieval experience.

1 Castelfalfi - Heritage hotels Tuscany - Destination Deluxe
Photo: Courtesy of Castelfalfi


The story of Castelfalfi stretches back centuries. Il Borgo, Castelfalfi’s well-preserved medieval village, first appeared on a map in 754 A.D. It changed hands several times over the years and the village was restored and revived in the last century. The gourmet restaurant La Rocca located in the ancient castle, offers magnificent views at the big terrace. RAKxa Wellness Spa at Castelfalfi, the first groundbreaking establishment in Europe, combines the ancient oriental culture of wellness with the modern technologies, with the inclusion of local products such as essential oils and indigenous herbs. Castelfalfi’s variety of venues, 5-star services, cutting-edge technology and activities for meetings or parties; the sun-kissed hills of Tuscany are the perfect setting for a private and romantic dinner.

2 Borgo Bernardini - Heritage hotels Tuscany - Destination Deluxe
Photo: Courtesy of Borgo Bernardini

Borgo Bernardini

Borgo Bernardini was once the hunting lodge retreat of Count Cosimo Bernardini of Lucca centuries ago and the Borgo was extended to become a small village for the workers of the estate which included an olive press, bakers and chapel. Today Borgo Bernardini is an elegant and exclusive Tuscan retreat with original features and picturesque views over hills and olive groves. Explore time-forgotten courtyards and lemon scented Italian gardens or discover a private collection of Tuscan wines at the wine library. 12 individually styled bedrooms feature the typical Tuscan hamlet style of wood beamed ceilings and terracotta floors. Other facilities include a card and billiard room, a domed music room with log fireplace, grand banquet room, a large Tuscan kitchen, several comfortable lounges and a workout room.

See also: 16 Best Wellness Retreats In Italy

3 Castel Monastero - heritage wellness hotel - destination deluxe
Photo: Courtesy of Castel Monastero

Castel Monastero

Cradled in lush greens overlooking fields and century-old forests lies Castel Monastero, a beautifully restored medieval monastery and its hamlet. Almost ten centuries of history await you at the luxury resort, which went through an accurate restoration process to restore its ancient splendor. Each of the 70 rooms and suites located around the piazza have their own identity and the exclusive two-level resort villa offers secluded privacy and a private jacuzzi with a view. Wellbeing activities at Castel Monastero include purifying spa treatments, yoga, meditation, and trekking, and relaxed poolside reading nestled in lush greens. Spa Monasterii offers a nourishing, calming experience merging the ancient wisdom of monastic herbal remedies and modern therapies that draw upon the botanicals and other natural ingredients.

4 Borgo San Felice Resort - heritage hotels tuscany - destination deluxe
Photo: Courtesy of Borgo San Felice

Borgo San Felice Resort

Set amidst 685 acres of pristine woods and Chianti hills, the 5-star Borgo San Felice is acclaimed for its discreet luxury. Accommodation is spread throughout the medieval hamlet of Borgo San Felice in Tuscany’s beautiful Chianti, the 30 suites and 29 rooms are made from the ancient houses of the village. Enjoy personalized wellness experiences and vinotherapy rituals at the Botanical Spa, which also has a sauna and a steam room. There’s also a heated pool, fully equipped gym and tennis courts. Fresh ingredients from the resort’s own vegetable garden and herb garden are used in gourmet creations at the Michelin-starred Poggio Rosso and traditional rustic dishes at Osteria Il Grigio.

See also: 10 Of The Most Stylish Hotels In Europe For A Luxurious Getaway

5 Monteverdi Tuscany - heritage hotels tuscany - destination deluxe
Photo: Courtesy of Monteverdi Tuscany

Monteverdi Tuscany

Explore the beauty and heritage of Val d’Orcia atop a luxury hilltop hotel. Neglected properties of the medieval village of Castiglioncello del Trinoro have been exquisitely restored. Take your pick from a selection of rooms, suites, and private village houses. Bask in the sunrise from your balcony at the Monte Cetona Suite or take in the serenity of the landscape at a Tuscan View suite. Restore and rejuvenate at the new Monteverdi Spa and Wellness Center where ancient beauty rituals are fused with time-tested luxury beauty products and modern treatments. Guests can also taste seasonal Tuscan produce at the fine-dining restaurant, relax at the Library bar or enjoy a glass of wine at the lounge.

6 Laticastelli-Villa Limonaia - destination deluxe
Photo: Courtesy of Latiscastelli


Discover the old charm and beauty of a genuine historic village with the comfort and services  of a 4 Star Country Hotel. The lovely small medieval Tuscany village has been transformed into a beautiful Country Relais and rooms are all individually decorated with Tuscany style furniture. Guests can enjoy the amazing views of the countryside, the Crete Senesi and the Tuscan hills at the Infinity Outdoor Pool; or savor traditional old recipes and good wine at the restaurant La Taverna Toscana, built in the cellars of the old winery. The mystical and historical atmosphere, and ample spaces, also makes Laticastelli a magical venue for  wedding ceremonies.

See also: 9 Best Wellness Getaways In Eastern Europe

7 Montestigliano1 - heritage hotels - destination deluxe
Photo: Courtesy of Montestigliano


Enjoy a luxurious and relaxing farm holiday stay in Montestigliano, surrounded by nature among the hills of Siena. This heritage hotel in Tuscany is a Tuscan hilltop hamlet of beautiful burnt orange farm houses, located among the rolling hills of olive groves and lush vineyards in the Siena countryside, dates back to 1783. Here you can find a wonderful balance between new and old, tradition and innovation. Montestigliano is a sustainable farm that believes in organic and bio-active practices such as solar panels for energy, a water purifying system and a biogas plant for renewable energy. The restaurant serves traditional Italian cuisine and fresh, organic produce picked directly from Montestigliano’s own vegetable garden.

8 Casali di Casole - heritage hotels tuscany - destination deluxe
Photo: Courtesy of Casali di Casole

Casali di Casole

Stay in a remarkable authentic farmhouse at Casali di Casole and live among the sweeping hills, vineyards and olive groves of an historic estate which dates back to the end of the 10th century. From its early beginnings in 998 to its 21st century transformation, Casali di Casole seamlessly blends Old World Tuscan charm with modern luxuries on a restored Italian estate.

 Situated throughout the 4,200-acre estate are fully restored farmhouses that showcase stunning views of the countryside. The very first restored farm home on the estate Gabbro features furniture that are an ode to Tuscan history. Modern conveniences and amenities such as gourmet Italian kitchens and bocce courts to outdoor wood-burning ovens, fire pits, hot tubs and heated glass-tiled infinity pools ensure a comfortable stay.