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Top Things to Do

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, For starters, check out our guides to Greve, Panzano, Castellina, Radda and Castelnuovo Beradenga. Our additional Chianti guides cover Castagnoli, Volpaia, San Gusme, San Donato in Poggio and Vagliagli.

Top Things to Do

Chianti country cycling

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. If Vespa rides are more appealing, then see Vineyards on a Vespa.

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Horse-riding trails around San Gusmè

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.

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Castello di Brolio - birthplace of Chianti Classico

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.  For more on the castle history, see Castello di Brolio in our general Chianti guide.

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Rapolano Terme for a spa day in the hills

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.

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Radda in Chianti for a wine class, tasting and lunch

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.

Casa Chianti Classico is housed in an 18th-century Franciscan monastery in the upper part of town. Itself attached to a medieval church, this sacred complex is now a shrine to wine, with a Wine Museum on the first floor. Sign up to a 90-minute wine class or restrict yourself to learning all about Chianti before facing an entertaining multimedia wine quiz. After doing a wine-tasting and dutifully going through your tasting notes, you deserve lunch in the Enoteca. Even better, it features a charming terrace surveying the Chianti vineyards.

As a major wine centre, Radda has been quietly prosperous since the 16th century when it was already exporting wine to England. Later, in 1716, Cosimo III, Grand Duke of Tuscany, officially delimited the production zone of Chianti wine. Along with Radda, the main centres in Chianti Classico remain Greve, Panzano, Castellina, Gaiole and Fonterutoli. The boundaries and strict rules still apply, even if the responsibility for enforcing them has passed to the Chianti Wine Consortium.  The Consortium was established in 1927 by a group of wine producers in the Provinces of Florence, Siena, Arezzo and Pistoia. Easily accessible off the scenic route SS222, the grandest, castle-like estates have often been run by the same families since medieval times, as is the case with the aristocratic Antinori, Frescobaldi, Mazzei and Ricasoli dynasties. Tuscany’s aristocrats are still over-represented in the wine business, including in the Chianti Classico Wine Consortium. On the board are a clutch of Tuscan nobles, ancient wine dynasties who have moved with the times. The great names include Marquess Lodovico Antinori, Count Lorenzo Guicciardini, Prince Emmanuele Corsini and Count Guido Chigi-Saracini.

Even so, the wine is bigger than the individual families, no matter how glorious their pedigree. The wine’s `soul’ is Sangiovese. The rules for Chianti Classico wine allow for a minimum ratio of eighty percent of Sangiovese, the typical red regional variety. A maximum of twenty percent of other local red grapes can be added to the blend. These varietals include native grapes such as Canaiolo and Colorino, along with `international’ Cabernet Sauvignon and Merlot, all permitted in this Chianti Classico production zone. In essence, Chianti Classico is made from Sangiovese grapes, or a Sangiovese blend, and aged for 14 months in French oak barrels followed by at least seven months in the bottle, or two years for a Riserva.

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Seductive Siena

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.

As a Gothic city built on a human scale, Siena is effortlessly civilised and at ease with itself. All roads lead to Il Campo, the beguiling, shell-like central square, shaped like an amphitheatre. Sit at a terraced café on the sloping side of the square and spot the division of the paved surface into nine segments, recording the wise Council of Nine who governed Siena from the mid-13th century to the early 14th. Consider climbing the slender Torre del Mangia, with sultry views over a pink piazza and Siena’s rooftops, even if the views from the Cathedral rooftops are even better.

After an early lunch, a leisurely stroll leads to the Duomo, Siena’s pinnacled Gothic cathedral. The facade is a riot of green, pink and white marble, like a glorious iced cake. Siena Cathedral and the Cathedral Museum should be seen as one entity as they share several spaces. The Museum displays Pisano’s original statues for the façade along with Siena’s best-loved work, Duccio’s Maestà, the Virgin Enthroned. For many visitors, equally impressive is the rooftop walk, known as the Panorama from the Unfinished Façade. These are arguably the finest views of Siena. Facing the cathedral is the Spedale di Santa Maria della Scala, the most extraordinary building in Siena. It began as a hospital a thousand years ago and continued as one until it was reborn as a magnificent museum in recent years. In medieval times, it was always far more than a hospital. The art-studded complex embraces a former pilgrims’ hostel, an orphanage, frescoed churches and granaries.

Don’t let Siena’s art-studded museums blind you to the beauty of the backstreets. Here, the city history unfurls like a medieval banner. Walkable Siena has well-preserved walls and inviting gateways. Wind through a tangle of medieval streets and stumble across secret courtyards, fountains and surprisingly rural views. Check our Siena guide to see what appeals most.

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