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Villa Cipresso is a very beautiful 13th century villa located in the Chianti area, approximately 7 miles from Siena. This villa is composed of two separate structures: the main house (3,500 sqft) and the annex (1,500 sqft). The main house is characterized by a watch-tower to which two lateral structures were added over time. This particular layout, with the annex separate from the main villa, make Il Cipresso the ideal property for large groups who will enjoy gathering together yet having their own privacy when needed. The 27-hectare estate where the villa resides produces its own wine which can be served at the villa upon request.

  • Mountain View
  • Dedicated Parking Space
  • Child Friendly
  • Air Conditioned
  • Central Heating
  • En-suite x 7
  • Air Conditioning
  • Double x 8
  • Shower x 8
  • Hair Dryer
  • Dishwasher
  • Fully Equipped
  • Barbecue
  • Al fresco dining
  • TV
  • Playstation
  • Stereo
  • Wi-Fi
  • Fireplace
  • Washer
  • Swimming Pool
  • Horseback Riding
  • Mountain Climbing
  • Walking
  • Restaurants
  • Shops
  • Nature

Main house
First Floor: 1 double bedroom with en-suite bathroom with shower. 2 double bedrooms sharing one bathroom with shower.
Third Floor: 1 double bedroom with private bathroom with shower.

A/C in uppermost floor bedrooms; the bathrooms are provided with hair dryers.

Ground Floor: 2 double bedrooms, each with its own private bathroom with shower.
First Floor: 1 double bedroom with private bathroom with shower. 1 double bedroom, with shared bathroom with shower. 1 twin bed, with shared bathroom with shower.

Main house
Ground Floor: Much attention has been dedicated to the interiors of the villa during the restoration to maintain the structure as original as possible. This is visible in the wood beamed ceilings throughout, the stone walls, and especially on the ground floor where big arches frame the different areas of the spacious living room (more than 1,000 sqft): the dining area with the large table, the sitting room with comfortable sofas, the sunk-in reading corner with its inviting leather armchairs. Spacious, well appointed fully equipped kitchen and guest bathroom complete this floor.
First floor: in the tower, the main villa features a sitting area with flat screen TV, a cozy space to relax, playing cards among friends, or, in the colder months, where to enjoy the warmth of a lively fireplace.
Third floor: in the tower, a small art gallery with large windows overlooking the beautiful Chianti landscape.

Ground Floor: The annex features, beside a small kitchenette, a large living room with fireplace and dining table, and a TV area with sofa.
First Floor: This floor includes an additional living room.

The villa patio features a large outdoor dining table, perfect for shady relaxing and informal dining, and there is also a BBQ grill and outdoor cooking area to prepare delicious local food feasts. The private large swimming pool is reachable through a paved path and there are sun beds around the pool to enjoy hours of sunbathing. The pool has a ladder on one side. Manicured gardens surround the property for complete privacy.

Due to its traditional stone construction and hilltop position, Cipresso remains cool also during the summer months. The expansive grassy lawns of the estate are perfect for families with children. The location is ideal for wine lovers as it is a great starting point for trips to Chianti Classico and its charming villages of Gaiole, Castellina, and the Castle of Brolio, which are to be found within 10 miles from the villa.

Write a Review

A fantastic week.

Reviewed on 08/02/2018

Michael C.


The villa and the owner and staff exceeded all of our expectations. We had a wonderful time, and Pino (the owner) was a most gracious host. We found the villa to be perfect for gatherings of our large group, but also provided many areas for more private gatherings. The pool was large and refreshing. The concierge (Daria) arranged for a breakfast each morning for the group, which was provided by the staff at the villa – a great way to start the day. We also had a dinner cooked for us at the villa one night, which was a lot of fun. A special treat was the two cases of fantastic Chianti Classico made by our host, which we purchased for a very low price. Pino and his son always greeted us with a smile. A fantastic week.

Nearest Airport: Florence Peretola  1 h 22 min
Nearest serviced town: 10 min
Nearest major city: Siena 36 min
Driving time estimated by Google Maps

The medieval town of Siena is built across several hills and valleys; that's why you will find yourself walking up and down through its historical center. The lack of car traffic makes Siena a wonderful place to stroll, especially with kids! Despite sometimes being packed with tourists, the city always has a quiet and easygoing feel. A must-see is the shell-shaped square called Il Campo. This is the focal point of the city and the perfect setting to snap your Instagram photos while enjoying an over-sized gelato. This is also the venue of the internationally renowned horse race, The Palio, which takes place on July 2nd and again on August 16th each year.
Visit San Gimignano, famous for its skyline, and Volterra, renown for alabaster artifacts. The small fortress cities within easy driving distance of one another, each offer their own special appeal. The medieval walled city of Monteriggioni – for example – was built in the 13th century and it is known to be one of the most well preserved ancient fortifications in Italy, which is why it is a preferred destination for plenty of tourists, scholars, architects and archeologists from all over Europe.

Osteria Le Logge - Excellent Tuscan cuisine at elegant old-world restaurant. The best tables are on the ground floor, but there is also outdoor seating. Delicious handmade fresh pastas (small portions). Don't miss the desserts! Watch out for the small step down as you walk in!
Via del Porrione 33, Siena - +39 0577 480 13
Enoteca I Terzi - casual atmosphere under a vaulted ceiling, market to table seasonal ingredients divinely cooked, extensive selection of wine.
Via dei Termini, Siena - +39 0577 44329
Il colombaio - Michelin starred restaurant (in 2016!) in a very traditional sophisticated atmosphere. Outdoor seating also available.
Localita Colombaio, Casole d'Elsa - +39 0577 949002
Villa Dievole great restaurant with excellent food, set in a wine and extra virgin olive estate. Not only you can buy wine and olive oil produced on the estate, they can even ship it internationally.
Località Dievole, 6 (fraz. Vagliagli) Castelnuovo Berardenga - +39 0577 322613
Officina della Cucina Popolare This restaurant sits right inside the ancient medieval city walls of Colle di Val d'Elsa. Just a two minute walk from the free parking areas nearby the city gate called Porta Nuova. The menus are seasonal and utilize fresh local ingredients grown by nearby farmers. Enjoy true Tuscan food.
Via Gracco del Secco 86, Colle di Val d'Elsa - +39 0577 921 796

Handmade Crystal: Collevilca – besides purchasing their products, take a factory tour available from Monday to Friday and watch the artisans hand-blowing their creations.
Loc. San Marziale, 24, Colle di Val D’Elsa – +39 0577 927 204
Alabaster Houseware: Alab’Arte, an artisanal bottega where one-of-a-kind pieces are created.
Via degli Orti di San Agostino, Volterra - +39 0588 879 68
The best gelato: Gelateria di Piazza in San Gimignano it’s one of the most famous ice cream shops in all of Italy. Award-winning master ice cream maker Sergio Dondoli uses seasonal ingredients to create some unusual flavors.
Piazza Della Cisterna 4, San Gimignano - +39 0577 942244
Specialty Food shop: Pizzicheria de Miccoli - Located in Siena historic center, it is very well known for its special selection of Tuscan cured meats.
Via di Citta 95, Siena - +39 0577 246948




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