Villa Castrum

Tuscany, Italy

  • 14
  • 7
  • 5
  • Magnificent 7-bedroom villa
  • Part of a beautifully restored historic hamlet
  • In the heart of Chianti
  • Spacious and comfortable
  • Enchanting walled garden
  • Private pool
  • Simpson family extras available

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This imposing villa stands on the hilltop site of the 1,000-year-old Castle of Cortine, deep in the heart of Tuscan Chianti. Part of the sprawling Canonica di Cortine estate, Villa Castrum is set in its own gated grounds with private gardens and secluded swimming pool reserved exclusively for villa guests. The entire region is dotted with ruined castles and fortifications that bear witness to its turbulent medieval history, but visitors today will find an eminently more civilised landscape of rolling hills, olive groves and, of course, the vineyards that produce some of Italy’s best-known wines.

With its solid stone walls and lofty beamed ceilings, Villa Castrum has been tastefully restored to create comfortable accommodation for up to 14 guests. The main villa sleeps ten with an additional double and twin room in the adjoining self-contained apartment, Il Palagetto. It creates a flexible space for two families or a multi-generational get together and meals are made easy with the option to enjoy breakfasts, light lunches and dinners in the estate dining room (payable locally with advance booking advisable).

Your hosts, Lucia and Stefano, are on hand to provide any day-to-day assistance, and can help you organise a range of holiday-enhancing experiences, from a private chef and beauty treatments to wine tastings or an unforgettable vintage Fiat 500 tour of the Chianti countryside.

The local area

For a meal with celebrity cachet, your nearest restaurant is less than 1.6km away and once hosted George Clooney. It’s easily walkable, but the road isn’t paved or lit at night, so a long lunch rather than dinner is the better bet.

Otherwise, the nearest village is San Donato in Poggio, 2.5km away, where you’ll find basic shops and a handful of small restaurants. More extensive facilities are on offer at Barberino Val d'Elsa just a 15-minute drive from the villa. This medieval gem overlooks the Elsa River valley and is typical of the many authentically unspoilt smaller towns in this area. The big names are not far away, however, with no less than seven UNESCO World Heritage Sites within convenient driving distance. Florence, Siena, San Gimignano and Greve are all under an hour’s drive, while Pisa, Lucca, Volterra and the seaside resort of Versilia can be reached in 60 to 90 minutes by car.

Stay longer… Why not extend your stay in Tuscany with 3-nights or more at the incomparable Hotel Panzano in the heart of Chianti. With so much to enjoy in this charming region, you’ll want to make the moment last. For further details and prices please call 020 8392 5858.


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  • 7-bedroom villa (sleeps 2-14)

Ground floor

  • Large sitting room with piano and fireplace
  • Dining room
  • TV room
  • Kitchen includes hob, electric oven, filter coffee machine, fridge-freezer, dishwasher
  • Double bedroom with en-suite shower room
  • Shower room
  • Separate WC

First floor

  • Master bedroom with en-suite bathroom
  • Double bedroom with en-suite shower room
  • Twin bedroom
  • Twin bedroom (can be configured into a double if required) open to small balcony with garden view
  • Bathroom

Il Palagetto

  • Open plan dining/kitchen area; French doors open to outdoor dining area under olive trees
  • Kitchen includes hob, electric oven, filter coffee machine, fire place (decorative), fridge-freezer, dishwasher, washing machine
  • Double bedroom
  • Twin bedroom
  • Shower room
  • Separate WC


  • Complimentary WiFi
  • Satellite TV
  • Air-conditioning in all bedrooms
  • Barbecue
  • Outdoor dining area
  • Private swimming pool 15m x 8m (depth 1.50m throughout)
  • The door adjoining the main villa and Il Palegetto can be locked when not in use.
  • In Italy, a daily tourist tax applies for the first week of your stay only, which means that an average of €1.50 per person (12+ years) may be charged. This should be paid in cash to your villa or hotel owner during your stay.
  • Due to the cooler temperatures, the swimming pool will be closed from 30 September until the end of the season
  • Security deposit (£750) required 3 weeks prior to departure.

Simpson family extras

  • Complimentary cot and highchair available
  • Car seats and booster seats can be provided at a supplement, subject to availability
  • To pre-book any of our family extras please call 020 8392 5747


  • All properties with WiFi are able to support basic functionality such as web browsing and checking emails*

* We aim to offer an uninterrupted service but sometimes due to factors beyond our control reliability can be affected.

Access times

  • Check in time – 4:00pm - 8:00pm
  • Check out time – 10:00am


  • Restaurant 20min walk
  • San Donato in Poggio 5min drive
  • Radda in Chianti 30min drive
  • Greve in Chianti 30min drive
  • San Gimignano 35min drive
  • Gaiole in Chianti 40min drive
  • Siena 50min drive
  • Florence 1hr 10min drive
  • Pisa airport 1hr 30mins drive


Although this property is booked on an accommodation-only basis, we can arrange your flights for an extra charge of £25 per person, plus the cost of the flights themselves.

Below are the flight options available, including the most convenient airports in Italy to help you reach your destination as quickly and easily as possible.


Departure airport Airline Flight days Seasonality
London Heathrow British Airways Saturday All season
London Gatwick easyJet Saturday All season
London Stansted Ryanair Saturday All season
Luton Airport easyJet Saturday All season
Manchester Jet2 Saturday All season
Manchester easyJet Saturday All season
Bristol easyJet Saturday All season
Birmingham Jet2 Saturday All season
East Midlands Jet2 Saturday June - September
Edinburgh Ryanair Saturday All season


Departure airport Airline Flight days Seasonality
London Gatwick Vueling Saturday All season
London City British Airways Saturday All season
London Stansted British Airways Saturday All season
Luton Airport Vueling Saturday All season
Manchester British Airways Saturday June - September
Edinburgh British Airways Saturday June - October

Car hire

Although this property is booked on an accommodation-only basis, we can arrange car hire for you.

Based on the number of people travelling, the following hire car(s) are available:

  • 2 guests – 1 group B, Fiat 500 or similar*
  • 3 guests – 1 group C, VW Polo or similar*
  • 4 guests – 1 group D, Peugeot 308 or similar*
  • 5 guests – 1 group F, Fiat Tipo SW or similar*
  • 6 guests – 2 group C, VW Polo or similar*
  • 7 guests – 1 group C, VW Polo or similar, and 1 group D, Peugeot 308 or similar*
  • 8 guests – 2 group D, Peugeot 308 or similar*
  • 9 guests – 1 group D, Peugeot 308 and 1 group F, Fiat Tipo SW or similar*
  • 10 guests – 2 group F, Fiat Tipo SW or similar*
  • 11-12 guests – 1 group C, VW Polo and 2 group F, Fiat Tipo SW or similar*
  • 13-14 guests – 1 group D, Peugeot 308 and 2 group F, Fiat Tipo SW or similar*

* All our cars include comprehensive insurance with zero excess. For this particular destination, the undercarriage is not included in the cover.

Car specifications

Group B – 1.2 litre engine, 2 medium suitcases*

Group C – 1.6 litre engine, 2 medium and 1 large suitcases*

Group D – 1.6 litre engine, 3 large suitcases*

Group F – 1.6 litre engine, 3 large and 2 small suitcases*

The following cars are available as alternatives. Please call our travel specialists for details.

Group H – Alfa Romeo Giulietta AUT or similar, 1.6 litre engine, 3 large suitcases*

* Suitcase sizes are based on a large suitcase being approximately 75cm x 41cm x 31cm, a medium suitcase of approximately 65cm x 46cm x 29cm and a small suitcase of 55cm x 40cm x 20cm.


Customer feedback

Nice hosts. Large, interesting villa with nice atmosphere.
Simpson Traveller – July 2019

Our choice of Italian properties is diverse, ranging from simple charm to genuine luxury and style. Much of our portfolio is privately owned, and price alone is therefore not a universal guide. We contract all our accommodation in person, and each property has its individual appeal.

To help you make the right choice based on your own priorities, we have devised a simple grading guide to be considered in conjunction with each individual property description, awarding up to a maximum of five stars for the below categories.

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From the moment you arrive in Tuscany, you are invited to share in its grand passions and indulgent pleasures – world-famous wine, mouth-watering food and epic histories. Each of Tuscany’s ten provinces has its own unique personality, but wherever you stay, you’ll find yourself surrounded by a verdant patchwork of olive groves, cypress trees and vineyards. From the birthplace of the Renaissance, Florence, to the narrow streets of hilltop San Gimignano, Tuscany makes for a stunning escape. 

To complete the picture, explore our collection of handpicked villas, boutique Simpson Hotels and charming apartments.

Explore our pre-bookable experiences in Tuscany


Read more on our Tuscany region page

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