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Top Ten Things to Do

Radda makes a great base for activities as varied as visiting a Chianti cashmere goat farm or taking in a centre for contemporary art. As well as drinking up wine estates, you could visit a wine museum or try a wine appreciation class. Or perhaps cycle to a vineyard. Even if Radda itself is a key attraction on the Chiantigiana, the Chianti Way also leads to forays to neighbouring Chianti wine hamlets, such as atmospheric Volpaia. As for culture, consider day trips to San Gimignano, Siena and Florence.

This is just a taster to the Chianti. See our specific guides to top Chianti towns and villages nearby, all accessed through our Destinations listings, For starters, check out our guides to Gaiole, Greve, Panzano, Castellina, Castelnuovo Beradenga. Our additional Chianti guides cover Castagnoli, Volpaia, San Gusme, San Donato in Poggio and Vagliagli.

Top Ten Things to Do

Wine class, tasting and lunch in Casa Chianti Classico

Casa Chianti Classico, an exceptional concentration of wine expertise, 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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Chianti Cashmere Goat Farm

If you’ve got young children in tow or are simply tired of wine estates, then visit the quirky Chianti Cashmere Goat Farm, just north-east of Radda. Run by American-born Nora Kravis, this long-established cashmere farm goes from strength to strength. It’s fun but also represents sustainable farming at its best. Founder Nora Kravis left New York’s Long Island for Italy long ago and never looked back. She knows all the shepherds, herders, growers and weavers and cares for her goats as if they were family. At this stone farmhouse with a view, the kids can hold, pet and bottle-feed the kid goats. The goats are guarded by fluffy white Abruzzo shepherd dogs who act as guard dogs to keep any wolf pack at bay.

After getting your fill of cute goats and puppies, turn your attention to the cashmere itself. In colour, the superior cashmere goats are shades of cream, hazelnut, brown, grey and charcoal so the yarn can be used undyed in its original shade. Cashmere is the fine, fluffy, downy undercoat produced by a cashmere goat and is apparently ten times lighter and warmer than wool. Knitters can choose some lovely fibres and sustainable cashmere yarn. You can also buy home textiles hand-made in Tuscany as well as hand-woven, scarves, shawls, throws, hats, socks and baby blankets.

If you’re won over, the farm can organize spinning, weaving, knitting or embroidery classes with local Italian artisans who already work with them. Best of all, there’s the new `be a shepherd for the day’ experience. This is fun for all the family, with full-immersion in the life of a cashmere goat shepherd. Guests get to accompany a herd of goats through the fields and woods surrounding the farm, stopping for a wine-tasting at a neighbouring farm, and coming back to the cashmere farm for a lavish farm lunch. The farm and gift shop are open in the afternoon from Easter to October.

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Visit Volpaia, a quaint hilltop village

Volpaia, an enchanting medieval hamlet just north of Radda, is reached along a scenic winding road. Framed by walls and towers, this fortified hamlet has retained its medieval layout and defensive character. Book an unusual wine-tasting and cellar tour in the Castello di Volpaia estate in the heart of the hamlet. The cellars start from a sacristy and end up in yet more cellars hidden below churches. In Volpaia, once sacred spaces are now given over to wine-making. It’s a mysterious process. The wine is moved by means of a maze of interconnected stainless steel pipes. Even to reach the tasting room involves traipsing along narrow corridors and ancient staircases. The crypt of the Renaissance-era Commenda di Sant’Eufrosino church is now used to store barrels of the estate’s ageing wine.

Book a visit to the olive press and wine cellars, with a tasting of Volpaia’s exciting organic wines, along with an olive oil tasting and a sampling of local produce. Castello di Volpaia honey, speciality vinegars and Extra Virgin Olive Oil make tempting gifts. Bear in mind that cellar visits are usually conducted at 11.30am, 3pm and 5pm but it’s best to check with the estate directly.

For lunch or dinner, head to Piazza della Torre, the main square in Volpaia. Book ahead for a table on the terrace at La Bottega, which serves special but unfussy Tuscan dishes. After a salad picked from the kitchen gardens you could opt for the wild boar stew or Florentine T-bone steak.  Or, for fine dining, book at the gastro inn of L’Osteria Volpaia, noted for its creative cuisine and organic wines. In more casual mode, consider a light lunch in Bar Ucci, which is a cross between a wine bar and a homely inn. Set in former stables, this welcoming spot serves platters of cured meat and cheeses or pasta with wild boar. For a snack, sample the fruit tarts or cakes made by the resident granny pastry chef. For more on this fascinating fortified village, including dining options, see our Volpaia guide.

Castello di Volpaia, Piazza della Cisterna, Volpaia, 53017 Radda in Chianti
T: 0577 738066 & www.volpaia.com

La Bottega, Piazza della Torre 1, Volpaia, 53017 Radda in Chianti
T: 0577 738001 & www.labottegadivolpaia.it

L’Osteria Volpaia, Vicolo della Torre 2, Volpaia, 53017 Radda in Chianti
T: 0577 738066 & www.osteriavolpaia.com

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L’Accademia del Buon Gusto in Panzano for Chianti fun

In the Chianti, the people often make the difference, especially as regards wine-tastings. A perfunctory tour of a great estate is still a perfunctory tour. In neighbouring Panzano in Chianti, they do wine in style and make it memorable. L’Accademia del Buon Gusto is a wine shop with a difference thanks to its entertaining and effervescent owner. The lasting feeling is one of meeting a friend who cares passionately about both wine and Tuscany and wishes to share his knowledge.

Multilingual Stefano Salvadori is an engaging personality, a gracious, old-school host who entertains and informs about the wine wonderland that is Chianti. Stefano offers free tastings of Tuscan wines, olive oils and vinegars, all the while waxing lyrical about Chianti wines, Slow Food, Tuscan life, traditions, art, politics, the universe and everything. The wine shop is not called `The Academy of Good Taste’ by chance. Visitors leave uplifted and usually laden down with both wine and new knowledge.

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Castellina in Chianti for a foodie foray

Visit neighbouring Castellina in Chianti, a charming town just west of Radda. Wander down via delle Volte, a quaint stone-vaulted street built into the side of the hill. Devour delicious ice cream at Gelateria Castellina, known for its experimental ices. The flavours range from ricotta and fig to chilli and chocolate or lemon and kiwi fruit. There’s also the owner’s favourite creation, cantuccini and Vin Santo: almond biscuits with sweet Tuscan wine. There’s no escaping wine in the Chianti.

Consider your first wine-tasting as Castellina is awash with Chianti Classico. The trademark on bottles of Chianti Classico is the Black Rooster (or Black Cockerel), the historic symbol of the Chianti Military League. In the late 13th century, Castellina was the first site of the Chianti League, a group of three Florentine feudal castles. Call into L’Antica Trattoria alla Torre for lunch. Set on the main square, this old-fashioned inn serves Tuscan treats on a summery terrace. Tuck into the Florentine T-bone steak, grilled meats and Pecorino cheeses, all washed down with Chianti Classico wines.
Go shopping for Tuscan foodstuffs, including of cheeses, biscuits, cured meats and pastries. (For shopping suggestions, see our guide to Castellina in Chianti).

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Badia a Coltibuono – dreamy abbey wine and oil estate

Set just north of Radda and Gaiole, this former Benedictine abbey surveys gorgeous estate vineyards. The tranquil oil and wine estate commands landscape that has been cultivated since time immemorial. In Tuscany it is hard to separate the wine and oil from the scenery. The aptly named Badia a Coltibuono (Ab¬bey of the Good Harvest) is framed by pines, oaks, chestnuts and vines. Founded in 1051, the medieval abbey belonged to reformist Vallambrosan monks who established viticulture here. Little did they know that their estates would still be flourishing so many centuries later. Since the Dissolution of the Monasteries in 1810, this medieval abbey has belonged to one family. The forward-looking Stucchi Prinetti family started off as Florentine bankers before pioneering the commercialisation of quality Chianti here. The family remains committed to sustainable farming.

The beguiling 15th-century clois¬ters, chapel and frescoed ceilings can be viewed as a guest of the Tuscan cookery school, while the 12th-cen¬tu¬ry walls and bell-tower are open to all. You can also book a tour of the original monastic cellars and frescoed villa, followed by a wine-tasting. Below the former abbey are cellars filled with Chianti Classico, the abbey’s traditional living. No less famous are the aromatic ¬chestnut honey and olive oil, the delicious Extravergine Badia a Coltibuono. Much of the produce can be bought on the premises or savoured in Ristorante Chianti, the ex¬cel¬lent abbey restaurant. You can also do a cookery course run by Benedetta Vitali, founder of the noted Florentine restaurant Cibreo. within the former Romanesque abbey.

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Castello di Ama for contemporary art

As one of the leading Chianti Classico producers, this working wine estate just south of Radda is known for its superb, full-bodied reds. Castello di Ama is not even a castle but a hilltop wine estate and villa restaurant, doubling as a centre of contemporary art. At first sight it’s yet another traditional borgo, a stone-built hamlet nestling in the Chianti hills. Slowly, it becomes clear that wine, food and contemporary art are all part of the picture. This was the wine estate that entranced the Obamas on their post-presidential tour of Tuscany.

The wine is master-minded by Tuscan Marco Pallanti, regularly crowned wine-maker of the year, with wines often in the world’s top ten lists. The estate’s San Lorenzo is a Chianti Classico gran selezione DOCG, a category considered the finest expression of its kind. The 80 hectares of vineyards cover different terroirs, from rocky schist to clay and gravel, with another 40 hectares given over to olive groves. The olives end up in the estate’s extra-virgin DOP Chianti Classico olive oil.

The grounds are home to a world-class collection of contemporary art installations. This ambitious collection, Castello di Ama per l’Arte Contemporanea (Castello di Ama for Contemporary Art)
The sculptures respond to the setting, much as the wines do, and are being added to each year. Castello di Ama repurposes original buildings, such as an on-site church and wine cellar, to showcase art installations in a striking way. The art is hard-core contemporary rather than soothingly pastoral. 

The site-specific contemporary art is commissioned from artists of the calibre of Anish Kapoor, Daniel Buren, Louise Bourgeois, Michelangelo Pistoletto, Hiroshi Sugimoto and Lee Ufan. The most engaging and accessible is the show-stopping mirrored installation by Daniel Buren that reflects the rolling hills. A Louise Bourgeois sculpture entitled Topiary is ingeniously hidden beneath a grate in the wine cellar floor and depicts a female form flowering into a male phallus.  Aima, a thought-provoking Anish Kapoor light installation, illuminates the estate’s tiny chapel.

Book a wine tour and tasting, come for lunch, visit the sculpture park, or simply visit the estate’s Enoteca to sample and buy the wines, olive oil and nature-inspired home fragrances.

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San Gimignano – medieval Manhattan

San Gimignano is only 43 km west of Radda so makes a worthwhile trip to see one of the medieval wonders of Tuscany. Given its spectacular setting, San Gimignano is one of the most touristy towns in Tuscany but manages to rise above the masses. With its moody medieval towers and walls, San Gimignano is one of the symbols of Tuscany. Building a lofty tower-house represented one-upmanship, medieval-style. The tower-studded skyline is one of the most spectacular sights in Tuscany. In its heyday, the city had a total of 72 towers, only 14 of which remain. Tower-houses were castle-residences serving as both warehouses and fortresses. A plague in 1348 wiped out much of the local population and the town slumbered as a backwater for centuries. The result is a medieval time capsule, even if the town is far from slumbering today. Its over-popularity and sometimes inflated prices are the only downsides but shouldn’t deter you from joining the throng.

The towers alone make a visit to this medieval time capsule memorable. Make time for Torre Campatelli, a true tower-house you can actually visit. This intriguing tower-house was home to the last resident of an illustrious Florentine clan. Apart from the medieval cityscape, the main sites are churches and public buildings. The best are congregated around the triangular Piazza della Cisterna and Piazza del Duomo. Here, the Palazzo Comunale is the forbidding fortress at the centre of city life since the days when Dante came on an ambassadorial visit from Florence.

Take a short walk along the city walls to la Rocca, the 14th-century fortress, before leaving town. This semi-restored fortress enjoys views over terraced gardens and olive groves winding down to the Vernaccia vineyards. The fortress is home to an enoteca, a wine-tasting experience, which traces the history of Vernaccia, the town’s most famous wine. You can even book a Vernaccia master class through the tourist office. If staying for longer, escape the crowds on a rural walk along stretches of the Via Francigena pilgrimage route outside San Gimignano. This is best booked through the tourist office. See our full San Gimignano guide for more.

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Seductive Siena

Siena is a forty-five-minute drive from Radda and makes a magical day trip. Siena frames the southern end of the Chianti and so is convenient for anyone based in Radda. 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 orig¬i¬nal 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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Art-filled Florence

Although over an hour’s drive from Radda, Florence still makes a perfect day trip. Despite devouring the checklist of must-see sights, steer clear of suffocating under the weight of treasures. Allow time for aimless wandering. Beyond the selfie sticks and statuary awaits a funky foodie haunt with sleek cafes, superb cooking and seriously edible markets. Florence is not fusty. Nor has the greedy city lost its gutsy Tuscan soul: traditional inns still serve earthy peasant fare, including macho steaks. Beware of trying to do too much on a day trip. Balance visits to galleries with wanderings in search of the perfect trattoria or the perfect view.

Begin in Piazza della Signoria, the city’s grandest square, with its copy of Michelangelo’s David and, beside it, the crenellated Palazzo Vecchio, with a well-presented collection. After a coffee at Rivoire, brace yourself for the Uffizi Gallery, the world’s greatest collection of Italian art. As such, the gallery is both a feast for the senses and an indigestible banquet so try and plan your visit in advance or even book a time slot online. After lunch, visit the Duomo, the biggest building for miles around. It is still Brunelleschi’s Renaissance dome that defines Florence. Out of respect for Brunelleschi’s achievement, the city forbade the construction of any building taller than the Duomo.

Clear your head in the Oltrarno, across the river Arno, where the Giardino Boboli (Boboli Gardens) act as an excellent antidote to the suffocating splendours of the Pitti Palace. The Medici dynasty created these statuary-encrusted gardens, which became the model for Italianate gardens for centuries to come. Before dinner, explore the Oltrarno neighbourhood's craft heritage on the so-called Left Bank of the city. This bohemian district is studded with stylish bars and buzzy inns interspersed with antique shops, jewellery-makers, picture-restorers and bijou art galleries.
Check our Florence guide to see what appeals most. If visiting a number of museums, consider buying a Firenze Card online

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