San Gusme

San Gusmè, a walled hilltop hamlet, is a charming Sienese backwater. Set 5 km north of Castelnuovo Berardenga, this tranquil spot has always been in Siena’s orbit. The medieval village only joined the Grand Duchy of Tuscany in the 16th century, after Siena’s definitive defeat. The Sienese gateway still bears Siena’s coat of arms, the Balzana. Stretches of the defensive walls remain, with parts incorporated into gateways. The hamlet is a place for picturesque views, including of the Sienese skyline, the Torre del Mangia and Siena Cathedral. This sleepy hamlet is more about mood than specific sites. Admire the church of Saint Cosmus and Damian, the local patron saints, and the church of Santissima Annunziata, with its quaint bell tower. Wander along concentric alleys, lapping up the timeless mood before retreating to a gourmet inn for creative cuisine or a homely café for wine and a plate of cured meats.

Are you inspired to visit Tuscany and explore a region rich in culture, beauty and history? Explore our collection of villas near San Gusme to start planning your Tuscan holiday today. 

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San Gusmè lies in the southern Chianti and, as such, is well-placed for cultural outings to Siena, Castelnuovo Berardenga and Montepulciano. San Gimignano and Florence are further away but still a tempting day trip for culture-lovers. Closer to home, it’s all about visiting major wine estates occupying lovely villas and castles and indulging in wine-tasting tours, fine dining and rustic inns, including in castles. Work off the calories by horse-riding or cycling along special trails. That’s not forgetting bathing in hot waters in the spa town of Rapolano Terme.

This is just a taster to the Chianti. See our specific guides to top Chianti outposts, all accessed through our Destinations listings.

The Chianti is a place for pottering, cycling and chance encounters, one of which is tiny Campi di San Gusmè, just north of Brolio. A short climb leads to a small tower, Romanesque church and views of tumbledown castles, villas and vineyards. The San Gusmè area is a popular destination for hiking, horse-riding or cycling. The cycle rides can be as easy or tough as you like, with a choice between e-bikes, hybrid bikers and mountain bikes.

Based in Castelnuovo Berardenga, just south of San Gusmè, Chianti Bicycles offer both straightforward independent cycle hire and proper bike tours. The company supplies hybrid or electric bikes and can organise good-value guided tours on request. Alternatively, you can rent their GPS system and go it alone, at your own pace. Their Castelnuovo Berardenga guided cycling tour heads north of town into the countryside around San Gusmè, Villa a Sesta and San Felice. This is a six-hour, 25km-route covering a mixture of asphalted roads and gravel paths, the famous Tuscan strade bianche.

You can also do a so-called sunset tour from Castelnuovo, an easy, early evening 15 km-guided cycle ride ending in dinner in at La Taverna della Berardenga in town. En route, the group can watch the sun set over the ridge and Chianti hills. The company will drive you back to your villa after dinner. To visit Siena by bike from Castelnuovo Berardenga, this leisurely, six-hour 50km guided bike tour is long but easy, taking you along quiet roads en route to Siena and then lunch on Piazza del Campo. The panoramic route home follows the old Chianti road.

If you’re an ultra-fit cyclist, consider the route to Vagliagli, Radda, Gaiole and Castello do Brolio, a 67 km round trip from Castelnuovo Berardenga. It includes some of the legendary L’Eroica route and also allows for a wine-tasting and light lunch at Casa Porciatti.  For more adventurous off-road rides, consult the company’s mountain-bike range and routes.



Address: Via del Chianti, 10 Castelnuovo Berardenga 53019 (SI)

Tel: +39.3315784929
Web: www.chiantibicycles.it

If you like horses and want to appreciate a slower pace of life, then consider a guided ride through the Chianti. Berardenga Horse Riding Centre (Centro Ippico della Berardenga) is based on the eastern border of Chianti, just east of San Gusmè. This is a reliable riding school, from the well-trained horses to the rides over varied terrain. Novices can go on shorter rides while more experienced riders can cover one-day trails, with picnics. These well-planned riding trails take in castles, wine estates and stretches of pilgrimage trails. The instructors, Sadio and Donatella, also speak English and French, and have been in charge of the Horse Riding Centre for a long time. This is an all-weather school so open all year. The riding school is recommended by FISE, the Italian Equestrian Federation.


Address: Strada del Ciglio, 2
Podere Santa Margherita
53019 Castelnuovo (SI)

Tel: +39 339 831 8519
Web: www.chiantiriding.it

Set around 7km north of San Gusmè, Brolio Castle makes for a memorable day out. As well as a ramble through Chianti wine history, take in the sweeping vineyard views from the ramparts. Of the many Florentine castles in the woods, Castello di Brolio is the most impressive – not least because of its views over the original Chianti vineyards stretching as far as Siena and Monte Amiata.

Tuscan aristocrats, including the Antinori and Frescobaldi families, have often been making wine since Renaissance times. Baron Ricasoli, whose descendants now run the castle, first designated the grape mixes to be used in Chianti wine. In the mid19th-century, Barone Bettino Ricasoli capitalised on improvements in production and spearheaded the modernisation of wine-making, with the establishment of the Chianti Classico brand. Essentially, Barone Bettino Ricasoli founded the modern Chianti wine industry, with his wine business continued by the present family. A Chianti consortium, the Consorzio Chianti Classico, acts as a quality control for all Chianti Classico produced in the region. The designated symbol, the gallo nero (black cockerel) designates quality.

Book a visit to the castle gardens and cellars. Tour the estate, taste the wines, and see the family museum. The sunset tour is the most private and includes dinner in L’Osteria del Castello, the Ricasoli’s restaurant. Your castle ticket also allows for a free wine-tasting in the Ricasoli tasting rooms below the castle. Sample Barone Ricasoli Castello di Brolio Chianti Classico 2006.

Information Guided tours: shop@ricasoli.it


Address: Loc. Madonna a Brolio
53013 Gaiole in Chianti (SI)

Tel: +39 0577 7301
Web: www.ricasoli.com

Tuscan spas are arguably the most beguiling in Italy. If you feel like a day off from cultural pursuits and wine-tasting, then head to a spa in Rapolano Terme, just a twenty-five minute drive south of San Gusmè. Landscape as seductive as the history plays a part: you can wallow in sybaritic spas that have been there since Etruscan or Roman times. In the first century AD, Emperor Augustus’ physician issued a prescription to the poet Horace to visit the Tuscan spas, which is one of the first medical prescriptions on record. Rapolano’s original thermal baths date back to Etruscan and Roman times, with the Campo Muri archaeological park set just west of modern-day Rapolano Terme.

In today’s Rapolano Terme, the stylishness of Terme di San Giovanni contrasts with the unpretentiousness of its friendly rival, the old-fashioned, no-frills Antica Querciolaia thermal baths. With its pools set in inviting gardens, Terme San Giovanni makes for a more memorable experience at perfectly reasonable prices. The natural thermal waters come bubbling out of the hot springs at 39c degrees but there are pools of different temperatures. These sulphurous waters are particularly recommended for relaxation, whether from stress or aching muscles. Do one of the day spa options, which include access to the hot thermal pools and maybe a massage.

As for treatments, wallow in the jets of the various pools or choose from an array of massages and therapeutic mud treatments, including mud facials. You can even have a couple’s massage using local honey, just as messy as it sounds. The spa sells its own line of beauty products, including those made from natural oils, herbs, honey and fruits, as well as mineral-based treatments. For dining, choose between L’Olivo, the gourmet restaurant, and Coffee Relax, the light-dining option, with romantic views over the hills. On Friday and Saturday summer evenings, popular `spa under the stars’ sessions allow you to bathe in the thermal waters at night. Known as Notti delle Terme, these extremely good-value spa evenings often include dinner. The Sunday brunch option is another popular choice, all at very reasonable prices.


Address: San Giovanni Terme Rapolano
Via Terme San Giovanni, 52 
CAP 53040 Rapolano Terme (SI)

Tel: +39 0577.72 40 39
Web: www.termesangiovanni.it

Radda in Chianti, a thirty-five-minute drive north of San Gusmè, once served as the capital of the Chianti. It’s still the place for sensing the Chianti spirit – and for getting to grips with the region’s lifeblood. Stroll round this glorified village with the spirit of a town, framed by its defensive walls. After wandering along the cobblestoned alleys fanning out from the main square, head to Casa Chianti Classico for an illuminating wine induction tour.

Check out our Radda in Chianti guide for more information.


Address: Monastero Santa Maria al Prato
Circonvallazione Santa Maria al Prato 18
53017
Radda in Chianti

Tel: 0577 738187
Web: www.chianticlassico.com

Siena is a thirty-five-minute (13 km) drive from San Gusmè and makes a magical day trip. You could even cycle there and back on a tour with Chianti Bicycle. (See Chianti country cycling).  Siena frames the southern end of the Chianti and so San Gusmè makes a great base.

Check our Siena guide to see what appeals most.



Address: Piazza Il Campo, 1 – 53100 Siena (SI)

Tel: +39 0577 292222
Web: www.terresiena.it

Tuscan food is rustic but robust, nourishing the soul and the spirit as much as the body. This area offers both homely Tuscan cooking and fine-dining options. Although tiny, San Gusme and neighbouring Villa a Sesta and San Felice form a foodie hot spot, with gourmet cuisine the norm, but not always at gourmet prices.

Our recommended wine estates are featured in each of the individual Chianti guides. The following selection is just a taster to the Chianti. See our restaurant recommendations below and also see our other guides to top Chianti towns and villages, all accessed through our Destinations listings.

Set in a stone farmhouse, this Michelin-starred restaurant is in Villa a Sesta, neighbouring San Gusme. This is creative, French-style cooking with Tuscan ingredients, led by a Parisian proprietor.

Diners are encouraged to take the tasting menu to do justice to the cuisine. Typical dishes include: spinach and ricotta ravioli in a truffle sauce; crunchy cod on a bed of kale; pork liver confit with fennel; roasted veal cheek; pappardelle pasta with duck and fennel ragout; maybe with lime and ginger parfait dessert. La Bottega is only open for dinner except for Sunday lunch in summer.


Address: Via di Santa Caterina, 2, 53019 Villa A Sesta SI, Italy

Tel: +39 0577 359226
Web: www.labottegadel30.it

This gourmet inn in Villa a Sesta, neighbouring San Gusme, provides good-value but creative fine-dining. Expect a surprising menu, attentive service, cosy atmosphere and a charming terrace. Typical dishes feature unusual flavour combinations, such as gnocchi in a rabbit and broccoli sauce. Duck, pigeon, venison and quail are often on the menu but so are creative pasta dishes and curious vegetable combinations that work. The good-value tasting menu depends on the chef’s imagination.


Address: Via Nuova, 6 Loc. Villa a Sesta
Castelnuovo Berardenga (SI)

Tel: 0577 359279
Web: www.asinelloristorante.it

Just north of San Gusme, this pricey, fine-dining restaurant specialises in creative Chianti cuisine and beyond, using only local, artisanal ingredients. Saffron from San Gimignano or spring onions from Certaldo find their way into imaginative dishes. Consider risotto with porcini mushrooms, goat’s cheese and cauliflower or seabass with artichokes and chickpeas. This Michelin-starred gastro inn is only open for dinner but for simpler dining, choose the resort’s L’Osteria Del Grigio, which is also open for lunch.


Address: Borgo San Felice
Localita San Felice
53019
Castelnuovo Beradenga

Tel: 0577 3964
Web: www.borgosanfelice.it

Set just north of San Gusme, this elegant inn lies in Castello di Brolio, the ancestral castle estate of the Ricasoli wine dynasty. Combine a tour of the castle with lunch in the estate inn. Alternatively, the sunset tour of the castle includes dinner in the Ricasoli’s restaurant. Your castle ticket also allows for a free wine-tasting in the Ricasoli tasting rooms below the castle. With lunch, indulge in the Barone Ricasoli Castello di Brolio Chianti Classico 2006. Dishes are creative twists on traditional Tuscan cuisine. Along with classic Florentine-influenced meat dishes, expect more fish than found in most of the Chianti. Such dishes as olive gnocchi in pecorino sauce or rabbit salad with crispy spelt can also be paired with Ricasoli wines.


Address: Località Madonna a Brolio, Gaiole in Chianti, Siena

Tel: +39 0577 730 290
Web: https://www.ricasoli.com/osteria/

Shopping in San Gusme is very limited so for more varied shopping options, head to neighbouring Castelnuovo Berardenga, Gaiole, Radda, Castellina and, best of all, Siena.

If you want to buy wine and oil at a renowned wine estate, without booking an appointment, then try Felsina, a wine estate south of San Gusme, just before Castelnuovo Berardenga. At this friendly, lovely-looking long-established wine estate you can just turn up. And often get a guided tour as well as a tasting. If you book, then you can also have a light meal of farm produces, such as cured meats, olive oil and wines.


Address: Via del Chianti 101
53019
Castelnuovo Berardenga

Tel: 0577 1523789
Web: www.felsina.it

Castello di Brolio, a famous Chiantishire castle, lies north of San Gusme. The Brolio wine-tasting experience and gift shop can form part of a great day out, as does the route there. This is classic Chianti countryside, with its mix of vineyards, olive groves, oak and chestnut woods. Records attest to the Ricasoli family having been in wine since 1141 so count on buying some fine vintages and possibly even some lovely wine glasses. Along with Chianti Classico, the estate also produces Super Tuscans, such as Casalferro. Even so, the market leader in the Super Tuscan stakes is Ornellaia and Masseto, produced by the rival Frescobaldi wine barons. While at Brolio, book a visit to the castle cellars, tour the estate, taste the wines, and see the family museum.


Address: Loc. Madonna a Brolio
53013 Gaiole in Chianti (SI)

Tel: +39 0577 7301
Web: www.ricasoli.com

For a complete change of scene, designer shopping fans could head to the luxury outlets in the Valdarno area. The Mall Firenze is a thirty-minute drive east from Florence, on the Pontassieve road. There’s also a direct shuttle bus there from Siena. After browsing the designer brands, end your shopping experience in the Mall’s Gucci café and restaurant.


Address: The Mall
Via Europa 8
50066
Leccio Reggello

Tel: 055 8657775
Web: www.themall.it

The public parking in San Gusme is just below the city walls, from where it’s an easy stroll into town. Note that most Tuscan towns operate a strict ZTL system, a Limited Traffic Zone. This means that the Centro Storico (historic centre) is essentially closed to traffic, particularly for non-residents. Cars will need to be left outside the walls. That said, the Chianti towns are small so present far less trouble than such cities as Florence and Siena.

Parking tips: for advice on individual Chianti places, please see our individual Destination guides.

Advice on ZTLs: You may see other cars crossing the ZTL boundary (Limited Traffic Zone) and assume you can proceed. Not so. The drivers crossing into the ZTL zone will probably be locals and have residents’ permits. Visitors do not so are liable to fines. Zones are monitored by cameras, so tickets are issued immediately and automatically, as soon as (and each time) the car crosses the ZTL boundary.

San Gusme is 24 km from Siena and 78 km from Florence so Siena is the natural focal point for visits, though still a saga for parking.
See our Siena guide for more.

The Chianti itself can be delightful driving country. Its appeal lies in the rolling countryside, array of vineyards and olive groves, relatively quiet roads, and the mix of small medieval towns. Public transport in the Chianti is rather sporadic so car hire makes the most sense if you want to explore the area properly. Driving in the Chianti can be deeply enjoyable experience, especially with a detailed map or GPS navigator to hand. For a great day out, try a customised tour with Chianti Taxi.

Greve, the main gateway from the north, lies on the SR222, commonly known as the Chiantigiana, about 30 km south of Florence and 40 km north of Siena. From Greve, the scenic Chiantigiana meanders through the Chianti, passing through most of the typical villages. This is a charming route to take by day. At night, however, you might encounter wild boars, porcupines or deer crossing the road.

From Florence and the Chiantigiana head towards Greve, then further south to Radda and Gaiole.  Or pick up the Florence-Siena Raccordo Autostradale highway (known as the RA) and take the San Donato in Poggio exit before following the SP101, which becomes the SP76.

From Siena, leave town on the fast Florence-Siena Raccordo Autostradale highway (known as the RA), taking the Badesse exit for the SP 119, which becomes the SR222, the Chiantigiana. Or take the quieter, slower route from Siena: take the SR2, which becomes the more tranquil SR222 until Castellina and then onto Radda and Gaiole.

By private tour: Chianti Taxi, a reliable Panzano-based transport service offers day-long private tours around the Chianti and beyond. These are customised tours that can take in everything from olive oil mills and wine estates to Pecorino farms and hand-painted ceramics. With his comfortable minivan, owner Daniele Mogni has the inside track on what you can do in the Chianti. It’s worth splashing out for a day so you can relax and drink your fill at the wine estates.

Chianti Taxi. T: (+39) 389 8160050 & www.chiantitaxi.com

The Chianti by train: this is not an easy place to reach by rail. The train service barely touches Chianti's attractions, which is part of the reason why the area is so peaceful. The main Chianti station is Castellina in Chianti, which is on the Siena-Florence line but you need to change trains at Empoli.

The Chianti by bus: Buses connect Florence to Greve and Panzano but end there. These buses often provide a more useful service than the trains but the confusing 365 bus service (T: 800373760, freephone only & www.acvbus.it) still means that bus schedules are not always convenient and also operate a limited service on Sunday. Buses also connect Siena and Castellina: a Tiemme bus service (T: 0577 204111 & www.tiemmespa.it) operates around 7 services a day.  Buses also connect Castellina and Radda: a Tiemme bus service (T: 0577 204111 & www.tiemmespa.it). Buses also connect Siena and Gaiole: a Tiemme bus service (T: 0577 204111 & www.tiemmespa.it).

On your bike: The Chianti is a lovely place to explore by bike. The combination of romantic Tuscan scenery and challenging gravel roads is what makes it enjoyable. The cycling races in the region also attract big crowds. Whether as a spectator or a participant, L’Eroica is worth following. This renowned amateur event that allows cyclists from around the world to experience the region while riding classic bikes. The parking in Gaiole is outside the town centre on the Strada Provinciale 408 or in the car park on via Marconi. Note that most Tuscan towns operate a strict ZTL system, a Limited Traffic Zone. This means that the Centro Storico (historic centre) is essentially closed to traffic, particularly for non-residents. Cars will need to be left outside the walls. That said, the Chianti towns are small so present far less trouble than such cities as Florence and Siena. Parking tips: for advice on individual Chianti places, please see our individual Destination guides, including those on Greve, Panzano, Castellina, Radda and Castelnuovo Beradenga.

Nestled near the charming village of San Gusmè, our villa collection invites guests to experience the quintessential beauty of Tuscany. With a history dating back centuries, San Gusmè captivates visitors with its medieval architecture and welcoming atmosphere. Surrounded by rolling vineyards and olive groves, these meticulously selected villas offer a perfect blend of tranquillity and authenticity. From pools overlooking picturesque landscapes to spacious interiors adorned with rustic charm, these accommodations promise an unforgettable escape. So, whether you’re savouring local wines, exploring neighbouring landmarks, or indulging in the renowned Tuscan cuisine, our villas near San Gusmè promise an enchanting experience in this idyllic region. 

Explore our Siena and Chianti villas to start planning your Tuscan holiday today.