A Historic Tuscan Retreat: The Former Convent of San Francesco

In Tuscany’s Maremma, perched on the edge of the breathtaking hill town of Pitigliano, lies the former Convent of San Francesco part of a 16th-century compound designed by Antonio da Sangallo the Younger for the noble Orsini family. Just a 10-minute walk from Pitigliano’s medieval center—one of the most ancient and picturesque borgos in Tuscany—this estate offers a truly magical escape.

The Estate & Grounds

Lovingly restored, the convent is now a luxurious home for family and friends, blending modern comforts with timeless architectural beauty. Set on 26 dramatic acres, it overlooks a wooded ravine with views of vineyards and grazing sheep. The surrounding land includes Parco Orsini, with Etruscan throne seats and sculptural garden remains, and Poggio Strozzoni, rich in history and natural wonder.

The house features 7 bedrooms (6 doubles, 1 single) and 7 bathrooms, including one with an 800 lb ceramic soaking tub. Guests enjoy fine linen sheets, down pillows, and cozy sitting areas. The upstairs library and lounge open onto a terrace with views of the lavender parterre and ancient fig garden, stunning at sunset. Private nooks throughout the property invite reading, relaxing, and quiet conversation.

Living Spaces & Amenities

Original features shine in vaulted stone rooms, one still housing giant chestnut wine barrels. Below, a hand-carved tufa cantina (wine cellar) has become a second sitting room with a wood-burning hearth, dining for 20 or 6, and an auxiliary kitchen. The main chef’s kitchen is fully equipped with a six-burner gas stove, dishwasher, toaster oven, refrigerator, blender, and food processor—ideal for serious cooks.

Outside, a 60-foot flowering arbor offers shaded dining, while the 18-meter saltwater infinity pool overlooks the ravine and Monte Amiata. The estate is naturally air-conditioned thanks to **three-foot-thick stone walls and a perfect north-south window axis that channels cool breezes. The cantina maintains a constant temperature ideal for wine and summer comfort.

Included in your stay are high-speed internet, a laundry room, and 12 hours of weekly maid service. Additional cleaning, laundry, in-house massage, and private chef services are available upon request.

For Lovers & Weddings

This may be one of the most romantic places on earth. Weddings are warmly welcomed, with ceremony locations including the enclosed courtyard and the fig and lavender garden. The architecture invites romance—sunset terraces, secret passageways, candlelit baths, and velvet sofas perfect for lounging. Whether celebrating new love or honoring a lifelong bond, this is the perfect setting.

The estate can host family and close friends, and we’re happy to arrange nearby accommodations for additional guests. Before and after the ceremony, guests can enjoy a variety of activities: stroll through Pitigliano with gelato in hand, soak in the Saturnia hot springs, hike ancient Etruscan trails, sunbathe by the pool, or enjoy yoga and painting in the garden.

Film & Photo Shoots

With its rich architectural heritage and stunning natural surroundings, the convent is ideal for historical film productions, luxury brand shoots, and fashion photography. The dramatic landscape and timeless interiors offer endless creative possibilities.

The Neighborhood

Pitigliano, often called “Little Jerusalem” due to its historic Jewish community, offers a wealth of cultural experiences. Visit the ancient synagogue, explore Etruscan museums, and wander cobbled streets steeped in history. Nearby activities include cycling, horseback riding, golf (just 20 minutes away), and excursions to the Mediterranean coast and Argentario peninsula, about an hour’s drive.

Whether you’re planning a family reunion, a romantic getaway, a wedding, or a creative retreat, the Convent of San Francesco offers a once-in-a-lifetime experience in one of Italy’s most enchanting settings.