Torre Della Guardia

Back when Florence and Siena were warring city-states, Torre della Guardia was a lookout post in the front-line defenses between the two rivals. Though only fragments of the 14th century “watch tower” remain, the vistas across the Chianti countryside are as remarkable as ever. In the distance, admire the towers of Siena and San Gimignano, while nearby, discover the renowned wine villages of Chianti. Florence, Volterra and Arezzo are possible day trips (Lucca and Pisa are just too far in my opinion when staying one week in that area).

While the villa’s historic character and fine décor will charm, you’ll also appreciate the many hotel-quality details: comfortable beds, fine linens, and sparkling white bathrooms. A convivial, modern kitchen adjoins the high-ceilinged dining room while the elegant main living room opens out to broad terraces. The estate has a working vineyard and olive groves, a large swimming pool and, best of all, breathtaking views – perfect excuses to just stay close to your Tuscany home-away-from-home.

Note: Multiple configurations of the property are available – please contact us for more details on both smaller and larger groups. 

Our Favorite Things About this Villa

  • The large pool, jacuzzi, outdoor terrace
  • The onsite facilities available for conferences, reunions or weddings
  • The countless local festivals, wine tours, and olive press tours



About Your Hosted Villas Tuscany Vacation

After helping you decide which of our luxury Tuscany villas will fit your needs best, your Experience Manager will begin the planning process. By talking to you to get an understanding of your interests, priorities and expectations for your Tuscany trip, your Experience manager will craft a completely custom itinerary. Whatever you desire in your Tuscany villa vacation, our team will arrange it: airport and rail greeters, child care, cooking classes, language lessons, private tours – the list goes on and on.

Once you arrive in Tuscany, your Local Host takes over—Hosted Villas staff members who live, work and have a wealth of insider knowledge about the region. Upon arrival at your luxurious Italian villa, you are greeted with a buffet of local treats and delicacies—the perfect way to relax after a long journey and kick off your vacation.

Our Local Hosts are what truly set us apart from the rest. They aren’t just the typical on-site concierges. They don’t just serve as tour guides. We think of our Local Hosts as so much more. Using the Tuscany vacation itineraries you created with your Experience Manager, our Local Hosts get to really know and build relationships with our guests so they can serve as more of a friend in the area. They are in essence your Tuscany guide, concierge, translator, trouble-shooter and guarantee that your Hosted Villas stay will be nothing short of brilliant, every time. Why just visit Tuscany, when you can truly experience it?






Kids Allowed?


Max Occupancy


Location Information

The local villages with services in Castellina-in-Chianti are just 15 minutes from your villa and Siena is only 30. Florence and San Gimignano are about 45 minutes to an hour while Chianti wine makers are near by. Lucca is just over an hour from your villa, Pisa and the coast are about two and Rome is just a three-hour trip.