Hotel Highlights

  • Contemporary, comfortable neutral tones
  • Incredible views of rural Tuscany
  • Enjoy lazy days in the leafy garden and by the pool


A boutique hotel in Tuscany, Villa Sassolini is the perfect marriage of contemporary chic and historic charm. With heart-stopping views over the Tuscan hills, bright and spacious rooms decorated with precision and attention to detail, it is a tranquil hideaway in the heart of Chiantishire.

Smith Extra

Here's what you get for booking Villa Sassolini with us:

A complimentary bottle of champagne


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Villa Sassolini Hotel – Tuscany – Italy

Need To Know




11am. Earliest check-in, 2pm.


Double rooms from $278.81 (€202), excluding tax at 10 per cent.

More details

Rates include breakfast and minibar.

At the hotel

TV, Internet. Guests can use the villa’s mountain bikes for excursions.

Our favourite rooms

The Marrakech room has fantastic views over the pool. The A Caccia suite has its own balcony and is decorated with hunting prints and has views of the wild hills of Chianti.


Outdoor pool with bar, panoramic terrace and formal garden. A light lunch is served by the pool between 12.30pm and 2.30pm.

Packing tips


Cots are free for under-twos; extra beds are €20 in low season, €40 at other times.

Food & Drink

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Hotel Restaurant

The hotel’s seasonal menu presents a modern take on fresh, traditional Tuscan ingredients, such as Chianina beef and wind-cured ham.

Hotel Bar

On the terrace next to the pool.

Room service

The restaurant menu is available from 7.30am to 10pm. An early breakfast can be provided. Both the restaurant and the bar are closed on Sunday evenings.

Smith Insider

Dress code

Chianti chic.

Top table

Alfresco on the terrace by the swimming pool.

Local Guide

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Eat, drink, see, do: local favourites and more…

Local restaurants

Osteria Locanda II Canto del Maggio in Terranuova (+39 0559 705 147) is a family-run restaurant set in a wild garden, famous for its goose pappardelle and home-made desserts. Fontebussi on Borgo di Fontebussi in Cavriglia (+39 055 916 811) serves traditional Tuscan dishes and has great views from the terrace. Osteria di Starda, in Starda Castle in Gaiole (+39 0577 734 100) is set in the vaulted cellars and has a traditional menu.

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Tranquil Chianti

Villa Sassolini

Piazza Ezio Rotondi 17, Moncioni, Tuscany, 52025


The closest airport is Florence, an hour away by car. For more choice, Pisa, Perugia and Bologna airports are only half an hour further. From Pisa airport, you can take a two-hour train (changing in Florence) to the nearby station San Giovanni Valdarno, from which a 20-minute taxi ride will take you to the villa.


San Giovanni Valdarno station is a 20-minute drive from Villa Sassolini. Direct trains from here reach Florence in 50 minutes and Arezzo and Siena in half an hour. For information on trains in Italy, see Trenitalia (


Villa Sassolini is located 20 minutes from the A1, Italy’s main North–South motorway. You’ll need to take the Montevarchi exit and then follow signs for Pestello and San Tomme, continuing through these towns and straight on until you reach Moncioni. Perfectly situated between Florence and Siena (50 minutes by car to either), the hotel's within easy driving distance of several towns on the Tuscan trail; San Gimignano, Montepulciano, Pienza and Arezzo are all 45–90 minutes away.


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Anonymous review

by Casey Gorman , Luxury accessories expert

For the first time in my life, when I get off the plane in Florence, I walk through customs and straight past the baggage-carousel area. For a woman who loves and lives fashion, this is a great accomplishment – I have packed my whole weekend into a carry-on (ladies, take note: gold flip-flops will save you packing endless shoes in...

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Villa Sassolini

Anonymous review by Casey Gorman, Luxury accessories expert

For the first time in my life, when I get off the plane in Florence, I walk through customs and straight past the baggage-carousel area. For a woman who loves and lives fashion, this is a great accomplishment – I have packed my whole weekend into a carry-on (ladies, take note: gold flip-flops will save you packing endless shoes in summer, since you can dress them up or down). I feel like my old, breezy Californian self once again, travelling short-haul for a relaxed weekend away, with few wardrobe rules to worry about.

It is 3pm when we arrive at the Villa Sassolini in the hills of Tuscany. The charming hotel manager, Andrea, comes to meet us at the gate of what appears to be a village monastery hiding behind a strong stucco façade. Mr Smith remarks that Andrea has an air of Lex Luther about him. It might be fair to say that his levels of passion are comparable to the comic-book villain but, rather than obsessing about global domination, Andrea’s focus is clearly to ensure the world is a better place – especially for guests at Villa Sassolini.

As we enter the lobby, it feels as though no one is home, and that we’re the only guests here. We tread the slate-coloured wooden floors that run throughout, past a spacious living room with a fireplace, books and oversized lampshades. The low yellow lighting enhances a pervading sense of calm. There is a small reception, but the greeting at the gate counted as check-in.

Andrea shows us to our room on the top floor, helping with Mr Smith’s bulky baggage while I saunter up the stairs with my carry-on. Mr Smith notes that, though we have a lounge and bedroom with beautiful old white-painted beams, what we don’t have is a bathtub. Without so much as a whiff of irritation, Andrea lumbers himself with Mr Smith’s luggage once again and takes us off to another room on yet another floor. Our new abode has a lovely four-poster bed, fresco-painted ceiling, grey walls and a bathroom large enough to house a whole family – with a beautiful, oversized bath in the middle of it.

With the heat absolutely scorching at 30 degrees, the pool beckons. I am reminded of my childhood in the Californian valley, where pools were more important than passports. Having had to adjust to leisure-centre versions in London, it is a joy to swim outdoors again. We’ve come straight from the airport, with no lunch pitstop, so we are starving: Andrea, who is nothing short of a miracle-worker, whips together a plate of cheeses, pears, honey and rolls, while we have a cooling splash about.

It’s such a beautiful night that we decide to eat outside again at sunset. There are two options at Villa Sassolini: inside is a softly lit dining hall near the tower, with a vaulted ceiling and a wine cellar; outside there’s a honeysuckle-framed garden full of overgrown rosemary and lavender bushes. We choose a garden table, where my handbag is even given its own pedestal – how nice to be in a hotel where the staff anticipate the whims of a fashionista. The food is gorgeous, but beware: don’t fill your belly on the tasty traditional Tuscan fare. Make sure you save room for the homemade puddings – namely the chocolate fondant and the cheesecake.

We’re back in the garden once more for breakfast and to plan our day out. Nothing is too far, but nothing is quite on the doorstep either, so a car is crucial; taxis aren’t really an option out here. We begin with a stop at the local Prada outlet. There are lots of charming hilltop mediaeval villages to visit, but shopping is taken just as seriously as heritage around here. (We pull in to a petrol station on the way to check where we’re going and, without prompting, a serviceman approaches us and says, ‘Next light, left and left again.’ Three shopping bags later, I realise my hand-luggage-only approach might not work for the return journey.

Our next foray is to Badia a Coltibuono, an old monastery and vineyard where we enjoy a light lunch with a stunning view of the hills and valleys. It is clearly marked on the tourist map, though, and in high season we feel like dots in the crowd, so we set off on a mission to seek out a rather more intimate wine-tasting experience. At our first stop, Monterotondo, the owner gives us a private tour of the cool cellar and a broken-English explanation of his wines. We’re no connoisseurs and, after several tastings, we have to confess that everything tastes like a glass of Canaletto Primitivo. When Mr Smith points out that a particular vintage tastes a bit like Um Bongo, I take it as a sure sign that it is time to go back to the hotel.

As we say farewell to Sassolini, I realise that the place has caused me to reconsider exactly what accommodation means. This is a small hotel with a relaxed ethos and wonderful service, whose atmosphere serves as a valuable reminder that a holiday in Tuscany is best enjoyed unhurriedly. I see the region as a little like my home of Napa Valley, but quainter and more personal. And I have yet to find a hotel as unique in style and personality as Villa Sassolini in the Californian wine country. Our break doesn’t end with the simple pleasure it began with: at Gatwick, I stand by the carousel waiting for my luggage, smiling in the knowledge that I am returning laden with rewards both sartorial and spiritual.

The Guestbook

Whenever you book a stay at a Smith hotel with us, we'll invite you to review it when you get back. Read what other Smith members had to say in Villa Sassolini's Guestbook below.



Stayed on 4 Aug 2013

We loved

I liked the total relaxation. The food is excellent at the hotel and the service of the staff is first class. George was the best waiter, manager, driver and advisor we've ever had on a holiday! The location was excellent for the Chianti region. I would firmly recommend the Mall for shopping. The interior design of the hotel was nothing short of exceptional – well thought-out and perfect for the chilled-out vibe of the hotel. Well done; we'll be back.

Don’t expect

For what we wanted, nothing could be better. We wanted chilled-out fun and it delivers everyday!

Rating: 10/10 stars


Stayed on 5 Jun 2013

We loved

The hotel was absolutely magical; Andrea and the team were so attentive, and the rooms gorgeous. While it is a bit of a trek to find, it was well worth it. Nestled away from any disruption and very peaceful our party had two pool-facing rooms with sweeping views of the Tuscan countryside. If you are seeking R 'n' R in a tranquil setting, this is for you. A dream! Note: Parking was not a problem as there is a parking area just outside the hotel gate.

Don’t expect

Venturing out to dinner in the evening was not an easy option. Driving through unfamiliar winding roads in the dark is difficult, and means the driver can not enjoy the local wine. Taxi quotes for a 10-minute drive came in at €60–80, which meant we stayed put in the evening. However, on the second night Andrea and his team brought in special items requested by our party and prepared them well, so we did not feel like we had missed out on variety.

Rating: 10/10 stars


Stayed on 23 May 2013

We loved

Service was faultless – even though we arrived very late the manager was able to conjure up some food.

Don’t expect

Very difficult to say!

Rating: 9/10 stars


Stayed on 3 May 2013 Not a place suited for children, but for couples going for a romantic retreat.

We loved

The professionalism, the hospitality, the good food and the beautiful panoramic views!

Don’t expect

We missed a bit the local touch: the music playing in the restaurant and outside at the pool is Buddha bar CD music and the pictures in the rooms were Greek landscapes with white island houses.

Rating: 8/10 stars


Stayed on 29 Sep 2012

We loved

There is something rather special about Villa Sassolini. We pulled up at the gates at dusk in our ridiculous (though highly economical!) Smart car, having almost missed the turning for Moncioni, and I felt like we'd stepped back in time. A few friendly local children were playing outside the local (and only) shop selling salamis, cheeses and bread, next to the iron gates of the hotel. We were greeted by George, who swept down the steps without prompting and carried our bags up the steps to our room. Room 5 is stunning, with a huge four-poster bed, chaise longue, massive bathroom, and two windows – one with a view of the pool and the other across the rolling Tuscan hills. Here we stayed for four blissful nights, waking up to Italian buffet breakfasts and lunches by the pool, followed by traditional four-course dinners in the hotel's uber-romantic restaurant. They even had wheat-free pasta. Andrea, the hotel manager, is simply lovely and booked us a wine-tasting session with with wonderful Roberto at Manucci Droandi nearby, whose wine features on the hotel's wine list, as well as a table at the nearby Osteria di Starda, which serves brilliantly rustic fare if you don't mind driving on unpaved roads (fortunately our car hire company didn't notice!) Nothing was too much trouble. I really can't recommend Villa Sassolini highly enough.

Rating: 10/10 stars


Stayed on 9 Sep 2012

We loved

Beautiful, relaxing hotel with lovely meals. The rooms are gorgeous and finished to a high standard.

Don’t expect

Showers would be better in rooms rather than hand-held option. Not many other options for restaurants and the hotel likes to get closed. Definitely a place to relax at, not party. Maybe a little bar open late would be nice, as nothing else to do after dinner.

Rating: 8/10 stars


Stayed on 16 May 2012

The other reviews really do ring true about our stay at Villa Sassolini. The service was wonderful and Andrea the manager was an absolute gem when our hire car broke down. He dealt with the firm over the phone for us and lent a hand when roadside assistance showed up. In relation to the car, I would strongly recommend Sat Nav; or a detailed map of the Tuscany roads, as we did find ourselves making a few wrong turns – and it is an absolute must if you plan to explore. We went to Florence, Siena and Greve in Chianti, which were all worthwhile trips. The one night we didn't dine at the hotel we drove to Inn – Fattoria Castello Di Starda (, the nearest place to the hotel. The menu was basic, and handwritten in biro, but absolutely delicious; and all were truly homemade delights – including the wine and olive oil. I would definitely recommend the restaurant as a nice break from the fine dining at the Villa.

Rating: 8/10 stars