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The central location makes San Sano the ideal point to discover the different facets of Tuscany, from the vineyards and Chianti villages to the Crete Senesi, passing through cities of art such as Siena, Arezzo and Florence up to the crystalline sea of the Maremma.

You can take a cue from our suggestions to plan your personalized itinerary and visit places not to be missed!

Within 30 min
Within 1h
Within 1h and 30min

Within 30 min

San Sano

1km 10min

The hamlet of San Sano dates back to Etruscan and Roman times but flourished in the Middle Ages, when a fortress and a church were built. In the 16th century its strategic location made San Sano the subject of a bloody dispute between Siena and Florence, which concluded with the sacking and burning of the village. In the end it became a farming village included in the Grand Duchy of Tuscany, and ... Info

Gaiole in Chianti and the nearby villages

10km 10min

San Sano is part of the municipality of Gaiole in Chianti, historically an important centre of trade and a crossroads between the Chianti country and the upper Arno Valley. The town is now the renowned starting point of the Eroica, a vintage bicycle race on unpaved country roads held on the first Sunday of October each year. You will of course want to take a selfie with the beautiful iron ... Info

Pievasciata and the Chianti Sculpture Park

6km 10min

The village of Pievasciata is only a few kilometres from San Sano. Contemporary art installations blend into the landscape even along the road to the village, which is home to the Chianti Sculpture Park, a permanent exhibition of contemporary art installations and sculptures integrating art and nature. For info, go to https://www.chiantisculpturepark.it/ Info

Radda in Chianti

12km 15min

A beautiful village enclosed by walls on the top of a hill. There are traces of Etruscan, medieval and Renaissance history to be found all over the Chianti district, but even more so in Radda. The town offers a variety of splendid views over the vineyards, olive groves and oak woods typical of the Chianti countryside. Don’t miss the nearby hamlet of Volpaia. Info

Castellina in Chianti

24km 30min

The village is surrounded by a covered walkway, now known as Via delle Volte. Whether you come to the town from Radda, Siena or San Donato in Poggio, the roads leading to Castellina travel through beautiful landscapes, ideal for touring by bicycle or motorcycle. Info

Siena and the Palio

25km 30min

Siena needs no introduction: a timeless city that has preserved its medieval layout, the historic centre of which is a UNESCO World Heritage Site. The city is small enough to get around on foot, and we recommend wandering aimlessly among the narrow lanes of the city centre, following your instincts! Sooner or later you will be sure to end up at the Cathedral, the highest point in the city, and ... Info

Within 1h

Panzano

27km 30min

About half an hour from San Sano, towards Florence, is the town of Panzano. Tour the town’s historic centre and piazza, without forgetting to stop and admire the vineyards, olive groves and woods of the Chianti countryside, extending in all directions as far as the eye can see. If you like cycling or motorcycling, ride to Panzano on the Chiantigiana road! Info

Rapolano Terme

35km 35min

Rapolano is home to two natural hot springs where you can spend a truly relaxing day. The Terme di San Giovanni (https://www.termesangiovanni.it/it) hot springs are surrounded by the landscape of the Clay Hills of Siena, while Terme Antica Querciolaia (https://www.termeaq.it/index.php) hot springs are closer to the town centre. The nearby hamlet of Serre di Rapolano is a splendid concentration of ... Info

Greve in Chianti

35km 40min

Continuing along Via Chiantigiana towards Florence, a few kilometres from Panzano is the biggest town in the Florentine part of the Chianti district, Greve in Chianti. Piazza Matteotti is the centre of the town, with its long arcade under which the town’s many boutiques sell handcrafts and local specialties. If you go to Greve, visit Montefioralle, classified as one of the most beautiful ... Info

Monteriggioni

35km 40min

A perfectly preserved medieval hamlet surrounded by a characteristic circle of walls perfectly following the natural slope of the hill on which the village is built. Visitors may walk on two sections of the ancient chemin-de-ronde atop the walls, enjoying amazing views over the Chianti country and the hills of the Montagnola Senese. The town square is the starting point for a 20-kilometre stage ... Info

The Clay Hills of Siena: The Site Transitorie and Asciano

38km 45min

The Clay Hills of Siena are just over half an hour from San Sano: vast expanses of clay planted with endless fields of wheat. The landscape changes radically with the seasons: from the lunar appearance of winter to green fields of young wheat in spring, the golden sheaves of summer and the warm hues of autumn. Don’t miss the road from Arbia to Asciano, with its winding curves following the ... Info

Montebenichi

38km 45min

IMPORTANT! Travel guidebooks will not tell you about this little hamlet with only a handful of inhabitants, but we’re quite sure that the town square and Montebenichi castle will leave you gaping with astonishment! If you don’t believe us, go and see… Info

Colle Val d'Elsa and Parco Fluviale dell'Elsa, the Elsa River Park

38km 45min

Colle Val d’Elsa, with its historic centre perched atop a high knoll, is Italy’s most important centre for the making of crystal glass. The town was a flourishing centre of trade in medieval times due to its location on the Via Francigena, in a position that made the town the subject of repeated disputes between Siena and Florence. Elsa River Park is well worth visiting (info at: ... Info

Abbey of Monte Oliveto Maggiore

46km 55min

Not far from Asciano is the Benedictine Abbey of Monte Oliveto Maggiore, a monastery open to visitors located in the midst of the scenic Clay Hills of Siena. We recommend stopping by for a visit on the way to San Giovanni d’Asso. More information at https://www.monteolivetomaggiore.it/ Info

Buonconvento

47km 50min

At the point where the Ombrone and Arbia rivers flow together stands Buonconvento, a mid-sized town included in the list of the “most beautiful villages in Italy”. The first thing you notice upon arriving in Buonconvento is the town’s imposing walls, built for defensive purposes. There were originally only two gateways in the walls, one at the northern end of town, towards ... Info

San Giovanni d'Asso

51km 1h

Located where the Clay Hills of Siena meet the Orcia Valley, San Giovanni is a centre for truffle-hunting: if you love truffles, you must visit for the truffle festival. The calendar is published at https://www.tartufodisangiovannidasso.it/ In San Giovanni d’Asso you can also visit the Bosco della Ragnaia, a wooded park and garden created in 1996 by American artist Sheppard Craig, who ... Info

Abbey of San Galgano

62km 60min

While you’re in the area, you’ll be sure to want to visit the famous Cistercian Abbey of San Galgano! Or at least what is left of it, since the roof fell in after the belltower was struck by lightning in 1786. The hermitage and abbey are now open as a tourist attraction. In the hermitage you can see the famous sword in the stone: legend has it that one Christmas night in the 12th ... Info

Within 1h and 30min

Reggello and Vallombrosa Abbey

50km 1h 15min

Heading towards Florence and the Arno Valley, at the foot of the Pratomagno mountain range, is Reggello, famous among gourmets for its fagiolo zolfino beans and extra virgin olive oil. Climb to an elevation of 1000m above the town of Reggello to the imposing Vallombrosa Abbey, surrounded by the forests of the Pratomagno mountain range. Next door to the abbey there is a convent of cloistered nuns, ... Info

San Gimignano

55km 1h 10min

A UNESCO World Heritage Site, San Gimignano is one of the top sights to see in the province of Siena. Nicknamed the Medieval Manhattan, the town had 72 towers in the 13th century, of which only 14 remain standing today. The town’s nobility competed to build the highest tower and demonstrate their power. You will feel like you’ve gone back in time to the Middle Ages as soon as you ... Info

The Via Francigena

55km 1h 10min

The Via Francigena, the historic walking route from northern Europe across France to Rome, is just over an hour away from San Sano, near San Gimignano. Today’s 3,000 km Via Francigena is a walking and cycling route joining Canterbury in England with Santa Maria di Leuca in Puglia, at the southern tip of the heel of Italy. The route features an incredible variety of landscapes and history. ... Info

Montalcino and the Abbey of Sant’Antimo

60km 1h 10min

Montalcino will need no introduction, as it is one of Tuscany’s top attractions. The town stands at the top of a high hill, with views over the immense expanses of vineyards producing the town’s famous Brunello wine. Don’t miss the town’s imposing fortress and historic centre, with its many traditional craft, food and wine boutiques where you can sample and purchase the ... Info

Volterra

65km 1h 20min

Volterra is a town in the province of Pisa packed with history: the city walls and gates date back to Etruscan times! A flourishing centre of trade in medieval times, the town is still perfectly preserved, and its 7th century B.C. Etruscan acropolis is open to visitors. More information at https://volterratur.it/en/poi/the-etruscan-acropolis/   Info

Val d’Orcia: San Quirico, Castiglione, Rocca D’Orcia and Bagno Vignoni

65km 1h 15min

Val d’Orcia, the Orcia river valley, is definitely worth a visit! Drive along the historic highway following the route of the ancient Roman road known as Via Cassia, enjoying the views of little villages perched atop the hills along the way. One of these that you will definitely want to stop and visit is San Quirico. You will surely have seen the famous photograph of a Tuscan hill topped ... Info

Montepulciano

70km 1h 10min

A town in the Chiana Valley bordering on the region of Umbria, not far from Lazio. Visit the Town Hall and Piazza Grande in front of it. Montepulciano is renowned for its Nobile di Montepulciano DOCG wine and its hot springs. The town holds its traditional Bravìo delle botti, a contest between the 8 districts of the town, on the last Sunday of August every year. Another local tradition is ... Info

Firenze e Fiesole

70km 1h 15min

What more could be said about Florence? No trip to Tuscany would be complete without a visit to its magical capital city. It would take pages and pages to describe everything there is to see in Florence, so here we shall simply list a few of the city’s principal attractions. Don’t miss Piazza della Signoria with Michelangelo’s David, only minutes away from the Uffizi Gallery ... Info

Pienza

75km 1h 20min

This town in the Orcia Valley was declared a UNESCO World Heritage Site in 1996. The perfectly preserved historic town centre was commissioned in the fifteenth century by Pope Pius II, who wished to transform his birthplace into a papal residence in true Renaissance style. Now considered a symbol of the Renaissance, Pienza is home to countless boutiques selling traditional crafts and foods, where ... Info

Arezzo, Cortona and Castiglione del Lago

85km 1h 10min

Arezzo - Cortona - Castiglione del Lago is a recommended itinerary for a day trip to the east of San Sano. Arezzo was home to one of the oldest universities in Tuscany, or indeed anywhere in Europe, and is now the capital of one of the provinces forming the region of Tuscany. The city abounds in artistic treasures and was home to some of Italy’s most prominent poets and artists, including ... Info

Shopping: the best luxury outlet stores

90km 1h 30min

If you like shopping and are looking for good bargains on top luxury brands, San Sano is close to the top three outlet stores in Tuscany. You’ll find well-known luxury brands at The Mall in Leccio (Florence), lots more prominent brands at the Designer Outlet in Barberino del Mugello, and still more at Valdichiana Village in Foiano della Chiana. Find out more: The Mall (loc. Leccio, 50km ... Info