Montestigliano Estate

7 nights

Self Drive Holidays





£ 1090 per week


A unique collection of eleven high-quality apartments and farmhouses, on an exquisite Tuscan estate in the Senese hills, that is perfect for couples, families and group celebrations.

Efficiently run by the Donati family and with regular BBQ’s, pizza evenings and Tuscan dinners.

Tuscan views at their finest - rolling hills, sunflower fields and the towers of Siena appearing in the distance.


11 self-catering apartments and one Villa


from £1090 per apartment


7 nights self catering sharing a one-bedroom apartment

Fully comprehensive car hire arranged at the airport

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Situated on the brow of a hill, with views over woodland and cypress-topped hills, Montestigliano is a classic Tuscan working estate just 12km from Siena.


Yet in between producing prestigious D.O.P olive oil from its 3,000 olive trees and farming wheat, barley and maize, the Donati family have, apparently effortlessly, converted traditional farm buildings into individually-styled apartments and villas and created a rural holiday idyll amidst the olive groves and glorious countryside.


There is also a games room with table tennis, table football and snooker table.


Accommodation is in a collection of amber-hued restored farm buildings, ranging from the pretty little Casa Damiano (sleeps 3) to the fabulous Villa Donati (sleeps 14).


Villa Donati (sleeps 14): Originally the principal house on the estate, the 18th century country house is elegantly furnished and has a large fruit-tree filled garden and glorious woodland views.

Ground floor: large entrance hall, dining-room, lounge, kitchen with open fireplace, bathroom with shower, 2 single bedrooms. Another twin bedroom and bathroom with shower are on a half-landing.

First floor: large living room with working fireplace, 2 double bedrooms (with wash basins), 2 twin bedrooms.

Second floor: Bathroom with bath, plus half bathroom.


Casa Luisa (sleeps 10): A traditional Casa Colonica with beamed ceilings, terracotta floors and antique wooden furniture. The living, dining room and kitchen are open plan and there are 5 bedrooms (3 twins, 2 double) and 4 bathrooms (2 with bath, 2 with shower). Outside space includes a partly covered terrace to the rear with a pergola and barbecue, and a furnished loggia with woodland views.


Casa Marta (sleep 6): A centrally-located apartment, close to the courtyard, with private ground floor access. An internal staircase leads up to the spacious apartment. A back door on the ground floor leads to a secluded garden with a semi-covered furnished pergola.
Living room with wood burning stove, kitchen with table and chairs, 3 bedrooms (2 twins, 1 double), 2 bathrooms (1 with bath, 1 with shower).


Casa Massimo (sleeps 4): Occupying the loft space that was once used for making Vino Santo, access is via an external staircase to the first floor. The apartment overlooks the olive groves and orchard, with a private garden and semi-covered terrace.
Large open plan living room with fireplace, kitchen, 2 bedrooms (1 twin, 1 double), and 2 bathrooms (1 with bath, 1 with shower).


Casa Virgina 1 & 2 (sleeps 4 each): Simple in style, with white washed walls and terracotta floors, the apartments were once used as store rooms, barns and wine cellars. Both apartments have a large living room with open fireplace, kitchen, 2 bedrooms (1 double, 1 twin), and a bathroom with shower. Both apartments have a furnished covered balcony and access to a large garden.


Casa Adriana (sleeps 4): Ground floor poolside apartment with access for special needs guests.
Open plan living room and kitchen, 1 twin bedroom with adapted bathroom, 1 double room with bathroom (shower). Outside, there is a covered dining terrace with countryside views.


Casa Damiano (sleeps 3): An independent house with fabulous views towards Orgia and a large private garden with furnished covered terrace. Open plan living and dining room, with fireplace and kitchenette. 2 bedrooms (1 double, 1 single), 1 bathroom with bath


Casa Ropoli Sopra (sleeps 4) and Sotto (sleeps 6): Situated overlooking the olive groves, these two properties are situated in a farmhouse just 300m below the summit of the hill. Access to the upper apartment (Sopra) is via an external staircase leading to a furnished loggia.

Casa Ropoli Sopra (sleeps 4) has an open plan living and dining room with traditional fireplace, and a kitchenette. 2 bedrooms (1 double, 1 twin), 1 bathroom with bath.

Casa Ropoli Sotto (sleeps 6) has a large living and dining room and a stone staircase to a kitchen (with table). From here, a back door opens on to a semi-covered terrace with wood fired oven. Another staircase leads up to the second floor where there are 3 bedrooms (1 double, 2 twins), 2 bathrooms (1 with bath, 1 with shower), and a half bathroom.


Casa Emilio (sleeps 4): Still retaining the charm and character of an old farmhouse, and offering complete privacy, the house stands independently on the edge of the hill.

Ground floor: The open plan kitchen/living room has floor to ceiling glass doors out to a private garden. Laundry room and half bathroom; double bedroom with en suite bathroom.
First floor: 1 double bedroom with shower.


Regular BBQ’s, pizza evenings and Tuscan dinners are organised regularly as well as Olive oil and wine tasting classes.


The atmosphere is convivial and you'll sahre the long table with the other guests.




two swimming pools with diving board free internet wi-fi connection sun loungers and umbrellas game room with TV area pool table, table football and table tennis walking and mountain biking trails


10 apartments and 1 villa central heating wi-fi internet connection fully equipped kitchen

julie frenchman
julie frenchman
09:16 09 Jul 19
This is the third occasion that Antonio has organised an Italian holiday for me. As it was a Birthday celebration involving a party of 10, the arrangements were complex, involving a villa, guides and attendance at the Palio on July 2nd. Without exception everything went exactly as planned. The recommended villa on the Montestigliano Estate, south west of Siena, was wonderful. Our guide made sure we had a full understanding of the history and culture of the Palio which meant that, with a spectacular view over the Campo from the apartment booked by Antonio, we were able to appreciate the event that much more. We shall certainly be going back to Italy with more
Kay James
Kay James
12:08 03 May 19
We had an amazing trip organised by Antonio, we visited Naples for a few days then stayed in Sant’ Agata. Both hotels had fabulous amenities and restaurants. The trip was effortless and everything was meticulously arranged. Antonio was also on had for anything we needed during the trip. I would definitely recommend Expert to Italy and we will definitely use this company again in the futureread more
Grant Stupart
Grant Stupart
18:31 16 Aug 18
Antonio with his meticulous planning and caring service has been solely responsible for the best Italian holidays we have had. His ability to offer excellent hotel accommodation which provides for every need and requirement is second to none . Hotels that are not main stream , that provide high quality of service in excellent locations are one of Antonio’s strength. It’s great to have a provider that know and understands his market. Grant B Stupartread more
Jonathan May
Jonathan May
18:06 01 Aug 18
July 2018 _________________________________ Have just completed another 10 day holiday arranged by Antonio at Expert to Italy. We went with Antonio's suggestion and spent 2 days at Matera and then the remainder in Pisciotta in the Cilento. Matera was amazing and felt completely different to anywhere else we have been in Italy. We loved Pisciotta and the hotel was wonderful with lovely owners who were great at suggesting things to do. We visited a buffalo farm, a vinyard and tooks boats to isolated coves with lovely clear water. All arrangements were absolutely faultless. We would never have found such lovely places without Antonio! 2016 _________________________________ We have just returned from a fantastic holiday suggested no arranged by ExpertTo Italy. Once again the organisation by Antonio was flawless and everything worked perfectly. We spent 5 nights by lake Maggiore and 3 in Cogne in the Italian Alps. Both hotels and locations were fantastic - particularly the Bellvue in Cogne. Please see trip advisor if interested in the hotels as I will give a more specific review there - I'm not a fanatic reviewer but both really deserve it. We have used this company for the past 5 years and Antonio seems to have a real gift for finding fantastic hotels and matching locations to his clients. I would not usually put the level of trust in anyone to arrange holidays for me that I have with Antonio but he has delivered every time and I can unreservedly recommend his services. Italy is a beautiful country with huge variety - if you describe what you like to Antonio and let him make suggestions then you will not be disappointed. Very definitely 5 stars from me. So - Antonio and team, please keep it up! Jonread more
Amanda Chapman
Amanda Chapman
22:28 25 Aug 17
Antonio delivered more than expected! Our family of four stayed at two beautiful villa's on the Amalfi Coast. Both of the locations were top class. Antonio provided excellent service and was always available if we had questions about the details of our trip. He was easy to work with and we would recommend his services to others traveling to more
Susan Davidson
Susan Davidson
09:04 19 Jun 17
This was our second holiday with ExpertoItaly, and it was just as good as the first! Antonio provided us with fast, efficient and personal attention. His choice of hotels was first class. Real attention to detail means that you get a holiday that really suits your personal requirements. Brilliant!read more
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