Sign in

Top Things To Do

Castagnoli lies in the southern Chianti and so, despite its sleepiness, is well-placed for cultural outings to Siena, Gaiole in Chianti and Radda in Chianti. Montepulciano, San Gimignano and Florence are further away but still make tempting day trips for culture-lovers. Closer to home, it’s all about dining in delightful inns and indulging in wine-tastings, often in castles or abbeys. Luckily, you can also explore the Chianti in a more energetic way, whether by Vespa, on an electric bike, or even on horseback.

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

Vineyards on a Vespa

Tired of museums and madonnas? Head for the wine-producing hills on a Vespa. The rolling slopes are planted with olive groves that shimmer dark green and dusty silver. Spanning the hills between Florence and Siena, Chiantishire is a gentle vision of olive groves, cypresses, vineyards and villa gardens.  This is the perfect terrain for exploring on a Vespa or even a vintage scooter.  A typical Vespa tour will follow the Chianti trail and feature a rustic lunch on a wine estate. Tuck into Tuscan antipasti and red wine. You can even ride pillion with a guide if you think you might overdo it on the Chianti. Iconic and utterly Italian, the Vespa scooter is a fun and authentic way to explore Tuscany.

The scooters are cheerful, colourful, stylish and easy to operate. At Tuscany Scooter Rental, based in Radda in Chianti, the fleet includes Piaggio scooters, red Vespas and even vintage scooters with sidecars. This is the only Vespa rental agency in the heart of the Chianti wine-growing region but is only 13 km north west of Castagnoli. On request, you can book a door-to-door pick-up service from your villa, within a reasonable radius of the rental base. The helpful staff speak Italian, English and French and can assist on route-planning.

As for the itinerary, vary it over a couple of days. Delightfully torn between tradition and creativity - like the contradictory Tuscans themselves - the wine scene allows for a duality between provenance and personality. If you’re interested in important estates that double as castles, abbeys or villas, then there’s a great choice locally. Try the abbey estate of Badia a Coltibuono to the north, or the grand estate of Castello di Brolio to the south.

Also visit a few smaller wineries, where the mood is more hands-on than at grander Tuscan estates. Near Lecchi in Chianti the family-run wine and oil estate of Azienda Agricola Casanuova di Ama is homely and hard to leave. The tour may well be with the owner, Daniela, and include a light lunch. Also close to Lecchi is the Castello di Ama winery, perfect for combining with a contemporary art and sculpture tour of the grounds. Just south, slightly closer to Vagliagli, are the wine estates of Dievole and Castello di Selvole, both of which have recommended restaurants.

Read more

Easy electric-biking before dinner in Gaiole in Chianti

Castagnoli is a mere 6 km south of Gaiole in Chianti, a sleepy Chianti market town. The attractions mostly lie outside town and are best viewed on a smooth cycling trail that takes in the countryside, castles and wine estates south of Gaiole. This is prime cycling country so make the most of it, even if you are not a fitness fiend on a racing bike. Best of all, you can do it on an electric bike on a full-day or half-day tour. These power-assisted bicycles are easy to use, even for first-timers or families.

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. 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 includes a light lunch and 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 available.

After returning your bikes, consider dinner in L’Osteria al Ponte in Gaiole, a fuss-free, family-friendly inn. As a reward for your cycling exertions, dine on crostini neritagliatelle with truffles, wild boar stew, or pasta with porcini mushrooms. Sit on the summery terrace and knock back a glass or two of the underrated local Chianti Classico from Rocca di Castagnoli or Castello di San Sano estates.

If you’d rather cycle in the countryside south of Castagnoli, closer to Castelnuovo Beradenga, then book a guided cycle ride with Chianti Bicycles, including a sunset tour on hybrid bikes.

Read more

Castello di Brolio – birthplace of Chianti Classico

Set around 7km south of Castagnoli, 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. 

Read more

Radda in Chianti day trip - for wandering, wine and a goat farm

Neighbouring Radda in Chianti, 13 km north west of Castagnoli, makes for an entertaining outing, whether for couples or families.  In this charming market town, begin with a visit to the region’s foremost shrine to wine, the Casa Chianti Classico. After an interactive wine induction there, including a wine quiz at the Wine Museum, stay for a wine-tasting and rustic lunch in the centre. Then head to the Chianti Cashmere Goat Farm, just north-east of Radda, to meet (and pet) the region’s silkiest and best-loved cashmere goats. Learn how sustainable farming is producing the finest cashmere and be tempted to buy a keepsake. Then either return to Castagnoli or drive a few kilometres north to explore Volpaia, one of the Chianti’s moodiest villages, and stay for dinner there.

Begin in Radda’s Casa Chianti Classico, housed in an 18th-century Franciscan monastery in the upper part of town. In its Wine Museum sign up to a 90-minute wine class or restrict yourself to learning all about Chianti before facing an entertaining multimedia wine quiz. Learn how 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. Members include some of the same families that have been wine barons since medieval times, including the aristocratic Antinori, Frescobaldi, Mazzei and Ricasoli dynasties. 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.

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. It’s fun but also represents sustainable farming at its best. 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. The American-born owner knows all the shepherds, herders, growers and weavers and cares for her goats as if they were family. After getting your fill of cute goats and puppies, turn your attention to the cashmere itself. Cashmere is the fine, fluffy, downy undercoat produced by a cashmere goat and is apparently ten times lighter and warmer than wool. At the goat farm you can buy home textiles hand-made in Tuscany as well as hand-woven casmere scarves, shawls, throws, hats, socks and baby blankets. From here it’s home to Castagnoli or onto atmospheric Volpaia, just north of Radda, for a memorable stroll in the medieval hamlet and dinner there, with homely or fine-dining options covered in our Volpaia guide.

Read more

Badia a Coltibuono – dreamy abbey wine and oil estate

Set just north of Castagnoli 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 (Abbey 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 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 cloisters, chapel and frescoed ceilings can be viewed as a guest of the Tuscan cookery school, while the 12th-century 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 excellent 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.

Read more

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.

Read more

Join us


Do you want to receive weekly inspiration, villa recommendations and travel tips from our Tuscany experts?

Find out more

© 1998-2023 To Tuscany Ltd. All rights reserved.

Can we help you?