Montestigliano Estate

7 nights

Holiday villas for large families or group of friends




Cultural, Family, Food & Wine, Hiking

£ 1090 per week - one bedroom apartment


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

Travel planning

We can help you with

International flights

Tickets for the Palio in Siena


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.



✓ 2 swimming pools with diving board

✓ Sun loungers and umbrellas

✓ Game room with TV area pool table, table football and table tennis

✓ Walking and mountain biking trails

✓ Bike Hire


✓ 10 apartments and 1 villa

✓ Central heating

✓ Wi-Fi

✓ Fully equipped kitchen


Montestigliano is immersed in a spectacular nature, among olive trees and woods, the nearest town is Sovicille on the road linking Siena to Massa Marittima and Follonica. Besides visiting the surrounding medieval hamlets and towns, Montestigliano is also a great base to enjoy the coastal towns of the Maremma Toscana.


Only a few minutes away, there is the 18-hole Golf Club La Bagnaia where guests of Montestigliano receive a 15% discount.

Sleeps16/03 - 20/04
28/09 - 30/11
20/04 - 22/06
31/08 - 28/09
22/06 - 31/08
Villa Donati 14£ 2400£ 3250£ 4200
Casa Luisa10£ 1890£ 2450£ 3400
Casa Marta6£ 1200£ 1500£ 1980
Casa Massimo4£ 1150£ 1300£ 1700
Casa Virginia 14£ 1000£ 1150£ 1550
Casa Virginia 24£ 800£ 850£ 1000
Casa Adriana4£ 1000£ 1180£ 1500
Casa Damiano3£ 800£ 900£ 1000
Casa Ropoli Sopra4£ 890£ 1000£ 1200
Casa Ropoli Sotto6£ 1000£ 1280£ 1750
Casa Emilio4£ 1150£ 1500£ 1850

Prices include linen and towels and swimming towels (one per person) during the swimming season - with a weekly change of laundry for stays of more than 7 days and final cleaning.

Energy for lighting and cooking is included but NOT that for gas for central heating ( normally required low and part of mid season) this is metered and charged separately at Euro 0,75 a unit and payable directly to owner at checkout.

Use of all facilities is included: wifi in all apartments and communal areas (password and username available from reception on request); swimming pools (one adult and one family pool) and swimming towels; Italian bowls; table tennis. Note: Pools are open 1/6-31/9 depending on weather conditions.

    Blake D
    Blake D
    15:43 21 Sep 21
    We loved our week in Villa Lighea booked through Expertoitaly. If you are... looking for a romantic, water-front cottage, this is it. We swam in the sea every day.It’s a bit remote from the major cities of Sicily but we hadn’t planned a lot of sightseeing. We ate at a few great restaurants but mostly cooked at the villa. Great weather and warm water in September.Antonio was easy to work with and flexible when we had to reschedule due to COVID. We would book with him more
    Simon Liddle
    Simon Liddle
    18:07 25 Oct 20
    Antonio arranged a great two weeks in Campania for us this year. It was... excellent to get to places that were quiet, smart and friendly. Everything worked just right, even this crazy year. Previously he has sorted us out a car tour of Sicily, two return visits to that lovely island, and breaks in the bay of Naples. We had done quite a lot of Italy under our own steam, but ExpertoItaly really are experts with a fantastic set of choices , and you get a great personal service. We will be back again next more
    William Jackson
    William Jackson
    15:37 13 Aug 20
    Outstanding service, advice and organisation of our holiday combined with an... intimate understanding and knowledge of places to stay and see.go no more
    andrew Smith
    andrew Smith
    16:49 02 Aug 20
    Expertoitaly (and Antonio) first came to our attention in 2014 when we were... planning a celebratory trip to Italy for 2015. Although we approached a number of household names about our plans and itinerary by e-mail Antonio immediately stood out. He phoned back almost straight away to get to know something about us and what we liked to do.On the back of that discussion he quickly put together a trip and budget. Given his obvious knowledge of the country and his quick grasp of what we were looking for together with the attention to detail it was a 'no brainer' to put our trust in this company. As a consequence we duly enjoyed a 3 week multi-stop trip in July 2015 tailored to suit us perfectly!On return we almost immediately booked to return in October for a short break to 2 of the locations in Tuscany we particularly enjoyed - Lucca and Montepulciano both of which are delightful.We fell in love with Italy and have returned several times since then all courtesy of Antonio:2016 - A short break to attend the Opera in Verona.2017 - 2 weeks in Sicily2018 - the same - we love Sicily and would urge anyone to go. (where we finally got to meet Antonio in Ragusa which was great)We were due to return to Italy this year for a 3 week road trip - albeit with private transfers rather than actual driving - from Verona to just south of Naples - all immaculately put together by Antonio of course. Alas Covid-19 had different ideas.We can only say that Expertoitaly have dealt with this professionally and as speedily as circumstances allowed and have refunded all the monies. We have no reservations about using them again in the future. In fact Antonio is already on standby to reprise the 'lost' trip as soon as this madness ends and unhindered travel becomes possible again - just extended an improved.Andrew & Susan SmithTadworthSurreyread more
    Vittorio S.
    Vittorio S.
    11:22 19 Nov 19
    Very comfy!
    Jane Domb
    Jane Domb
    17:12 28 Aug 19
    If you are looking to go to Italy for a holiday, Antonio at Experto Italy is... amazing. We have just come back from our fourth holiday he has arranged for us. He sent us to places that days of googling would never have found.He also has a knack of keeping to budget even with my numerous demands!Fabulous fabulous!!read more
    Debbie Law
    Debbie Law
    11:10 27 Aug 19
    Just returned from a fab trip to Italy - all organised by Antonio. His time... and effort to get what was just right for us was amazing.. he had a lot to put up with! We have used Expertoitaly before and will do again.We visited Ischia and Naples. Both very different and wonderful. Ischia is perfect for a good rest (visits to the Giardini La Mortella and the Ravino Gardens are a must). The Gardens & Villas Resort is a beautiful setting, very private, calm with amazing staff. Also the little town of Lacco Ameno has some really nice restaurants. Naples was very HOT! but we still managed to spend 7 hours walking about just soaking up the atmosphere and visiting some of the fantastic historic sights. Visit to the underground roman town is well worth it - it is mind boggling to think it was built thousands of years more
    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
    Andrew Rogers
    Andrew Rogers
    09:36 09 Jul 16
    We have just made an amazing journey by train, taxi, boat and bus through... France, a night in Paris, then a night on a mountain in Switzerland, train across the alps on the Bernina Express, 5 days on Lake Como and 6 days on Lake Maggiore. We stayed in the most glorious quality hotels. We made visits to local towns and attractions using buses and boats. Every connection on the journey was planned and executed wonderfully.This is 5 star planning, 5 star service, 5 star experience all personally organised by Antonio at ExpertoItaly. We must never forget the James Bond moment of being whisked across Como by Luca in his luxury Taxiboat from Varenna to the Hotel Filario in Lezzeno with Pavarotti as our musical accompaniment then met on the jetty by a lovely suited receptionist. A dream. Thanks Antonio.See views from our rooms Como then more
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