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Top Ten Things to Do

Hilltop Gaiole makes a great stepping-stone to explorations of local inns, wine estates and ancient abbeys. From the fortified monastery of Badia di Coltibuono to Castello di Brolio. a former Florentine castle with its gaze firmly fixed on its ancient enemy, Siena. The area abounds in wine estates and gourmet inns but there are enough challenging cycle trails to keep you fit en route. As for culture, consider day trips to Siena, Florence or charming Castellina.

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 Ten Things to Do

Easy e-bike rides through the Chianti

Gaiole is cycling country so make the most of it, even if you are not a fitness fiend on a racing bike. The reason the Chianti is so scenic is because it's so hilly. If you lack thighs of steel or the desire to face steepish ascents, then consider an e-bike. Based in Gaiole, Tuscany E-bike Rental run guided or self-guided e-bike tours in the Chianti area. These power-assisted bicycles are easy to use, even for first-timers. On downhill slopes, they work like a conventional bicycle but on long, flat runs or if you’re going uphill, the electric motor cuts in and provides the help you need to reach your destination without breaking into a sweat. The e-bikes can be rented for as little as an hour or as long as a week.

One typical guided route from Gaiole could take in the rolling hills of the Chianti, the Castello di Brolio and distant views of Siena. All this including a light lunch and simple wine-tasting on an atmospheric estate. This particular tour is a three-hour, 46 km affair reaching an altitude of 518 metres. There are plenty of easier or more challenging routes that can be suggested.

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Castello di Brolio - birthplace of Chianti Classico

Set around 10 km south of Gaiole, and 20 km from Siena, Castello di Brolio 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 former 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. This castle is a curious hybrid, a villa remodelled as a neo-Gothic castle.

Tuscan aristocrats, including the Antinori and Frescobaldi families, have often been making wine since Renaissance times. Baron Ricasoli, whose descendants now run the castellated villa, 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 Ricasoli found¬ed the modern Chianti wine in¬dus¬try, 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. For more on the history of Chianti Classico, see our Radda guide and visit the Casa Chianti Classico.

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Badia a Coltibuono – dreamy abbey wine and oil estate

Set just north of Gaiole and Radda, this former Benedictine abbey surveys gorgeous estate vineyards. Much like Antinori’s Badia a Passignano, which is closer to Greve, Badia a Coltibuono is linked to a medieval monastic foundation. It was the monks who established viticulture here, little knowing that their estates would still be flourishing so many centuries later.

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 vineyards, olive groves, chestnut and oak woods. Founded in 1051, the medieval abbey belonged to reformist Vallambrosan monks who established viticulture here. 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 recommended  abbey restaurant, which occupies the former stables. 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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Chianti Cashmere Goat Farm

If you’ve got young children in tow or are simply tired of wine estates, then visit a quirky Chianti Cashmere Goat Farm, north-west of Gaiole. 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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Contemporary art at Castello di Ama

As one of the leading Chianti Classico producers, this working wine estate south-west of Gaiole 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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Serious cycling – as a spectator or participant

L’Eroica – the “heroic” cycling race  – is a Chianti legend but you could do stretches of the routes at any time. You don’t need a handlebar moustache or legs of steel but you might have those by the end of the ride. L’Eroica is the celebrated amateur event that allows cyclists from around the world to experience the beauty and history of the region while riding classic or vintage bikes. The October event starts and finishes in Gaiole and includes week-long festivities, from wine-tastings to food markets.

The routes cover much of the Chianti. including Gaiole, Montefiridolfi, Panzano and Castellina. Riders can choose routes to match their abilities; the shortest option is 46 km (27 miles); the longest is 209 km (130 miles). The race draws Italian and international riders, ranging in age from 15 to 90, with the occasional world champion joining in. Because there are no time trials, stopping for a sandwich and a glass of Chianti is perfectly acceptable. Nor is there any doping - it’s all about the natural highs.

You could do the three-hour “leisure route” over 46 km, which includes views of Brolio Castle and even the skyline of Siena. Other routes are tougher, including the 75-km Radda route. For the more challenging routes, it’s less an easy ride than painful fun. On steel-framed classic or vintage bikes, racing along gravel tracks is not always comfortable. The rides may be low to medium altitude but are full of short, steep, challenging climbs. Expect plenty of bouncing, sliding and braking. The pleasures are about cycling camaraderie and the nostalgia of the vintage ride. There’s also the joy of the rolling Chianti countryside, vineyards and olive groves, small medieval towns and enchanting Renaissance vistas en route. Riding in the Chianti is characterized by quiet, twisting roads, winding ribbons of pleasure, interspersed with sweeping panoramas, short, challenging climbs and thrilling descents. If all this sounds too much hard work, then simply be a spectator. Or choose to hire an e-bike and do a less taxing route. If so, see our Easy e-bike riding through the Chianti.

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Visit Volpaia, a quaint hilltop village

Volpaia, an enchanting medieval hamlet north-west of Gaiole, 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, relax over 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.

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Etruscan life at Castellina Archaeological Museum

Visit neighbouring Castellina in Chianti to get to grips with Etruscan civilisation in the Chianti. Also make time to explore the warren of backstreets and buy an exotic ice cream at Castellina’s best gelateria. Simone, the owner, swears by the cantuccini and Vin Santo combination: almond biscuits with sweet Tuscan wine. There’s no escaping wine in the Chianti, even in the Etruscan museum.

The former medieval castle is now a fortified town hall hiding this small, Etruscan-centred archaeological museum. Known as the Museo Archeologico del Chianti Senese, the museum focuses on finds unearthed in Sienese Chianti, including from Castellina, Gaiole, Radda and Castelnuovo Berardenga. In particular, the museum displays Etruscan finds from the 7th-century-BC Montecalvario tombs, Castellina’s aristocratic Etruscan burial mound. Admire the newly reconstructed Montecalvario chariot, with its bronze and iron decorated plates. Look at the talismanic treasures placed with the dead for their final journey — objects such as a gold earring or a bronze belt.

These Etruscan tombs were built nearly 3,000 years ago but the creators can feel very much like ourselves. On view is an amphora decorated with a scene of revellers at a feast. As in the contemporary Chianti, wine plays a significant role. In Etruscan times, wine was a sign of status, and drunk at rituals and ceremonies. Generally, the wine was mixed with honey and spices but, more curiously, there was also a version featuring grated cheese.

This castle setting is about far more than the Etruscans so you can also explore the fortress, a former stronghold of the Florentine Republic during its century-long war against Siena. End your explorations with the tower-top walkway and sweeping views from medieval Castellina to the Chianti mountains to the east, and San Gimignano and the Val d’Elsa valley to the west.

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Seductive Siena

Siena is a forty-minute drive from Gaiole and makes a magical day trip. Siena frames the southern end of the Chianti and so is convenient for anyone based here. 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 ninety minutes’ drive from Gaiole, Florence still makes a must-see day trip for first-timers to the Renaissance-heavy capital. Despite devouring the checklist of major 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 ( and also book a time slot at the Uffizi Gallery.

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