Things to do
Castelnuovo Berardenga makes a mellow base for exploring Siena and the southern Chianti. As well as driving to wine estates, you could visit others by bicycle. The Chiantigiana, the Chianti Way, is made for forays to charming Chianti hamlets and castles doubling as wine estates or centres of contemporary art. To wallow in a tempting thermal spa resort, visit neighbouring Rapolano Terme. Or get on an electric bike or Vespa and explore the countryside. As for cultural trips, consider outings to Montepulciano, San Gimignano, Siena and, though further afield, Florence, a two-hour drive.
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.
Things to do
Chianti cycle rides from Castelnuovo
Based in Castelnuovo Berardenga, Chianti Bicycles offer both straightforward independent bicycle hire or well-planned 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 Castelnuovo. 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.
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
exertions, then head to a spa in Rapolano Terme, Castelnuovo, just a fifteen-minute (14 km) drive away. 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.
Castello di Brolio – birthplace of Chianti Classico
Set around 13 km north of Castelnuovo Beradenga, 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 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.
Chianti Sculpture Park for an engaging art trail
The Chianti Sculpture Park, set in Pievasciata, 20 km west of Castelnuovo, makes a refreshing change from eating and drinking your way through the Chianti, lovely though that is. This harmonious Sculpture Park, also known as the Parco Sculture del Chianti, occupies an oak wood between Pievasciata and Vagliagli, about 10 km north of Siena. If arriving from Castellina you will be drawn to the scenery, a patchwork of olive groves and hills draped in vineyards, sublime views unfolding around every hairpin bend. Once there, simply follow the wooded trail that winds past sculptures cast in a multitude of materials and styles.
The Sculpture Park is curated by art-dealers Piero and Rosalba Giadrossi, who often help out so you might well meet them. The concept comes from the ancient Italian tradition of creating site-specific artworks for the outdoors. Around 40 contemporary sculptures by different artists are dotted through the woods of this 17-acre site. Along the way, you can spiral through a life-size labyrinth made of glass cubes, and gaze at a sculpted cypress-like sculpture that looks more vivid than the real thing.
Given such a diverse collection, some sculptures will speak to you while others won’t. Most are thought-provoking. Thinker by Ichwan Noor from Indonesia is a homage to Rodin's Thinker but features a workaday character rather than a noble being. Suspended Stone by Mauro Berrettini is ingenious, a light-seeming sculpture made from travertine quarried from neighbouring Rapolano, south of Siena. Energy, by the Greek sculptor Costas Varotsos, reveals a cypress-like structure perched on a rocky location. Labyrinth, by the British artist Jeff Saward, was inspired by a stone labyrinth in stone found in Val Camonica, Naquane dating back to 700-800 BC. This one is octagonal, not round like the original. In general, the materials used range from true marble and granite sculptures to more modern installations involving neon lights and sound. There’s also a bridge of bright blue tiles that, on clear days, frames the distant skyline of Siena. Some works are now found outside the park so look out for the artily incongruous British red telephone boxes, for instance.
There’s also an amphitheatre in the park for outdoor summer concerts, with genres embarcing classical, opera, jazz, folk, Gospel and tango. Even the amphitheatre is arty, made of slabs of white Carrara marble from Michelangelo's quarry, black granite from Zimbabwe and the stage covered with lava-stone. Definitely pick up an audio guide to the Sculpture Park from the entry kiosk or download the app before you visit.
Guided riding trails - with Centro Ippico della Berardenga
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, north of Castelnuovo and just east of San Gusme. This is a reliable riding school, from the well-trained horses to the rides and 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.
Seductive Siena
Siena is a twenty-five minute (13 km) drive from Castelnuovo and makes a magical day trip. You could even cycle there and back on a tour with Chianti Bicycle. (See Chianti cycle rides from Castelnuovo). Siena frames the southern end of the Chianti and so Castelnuovo 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 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.
Montepulciano for smooth Tuscan living
Gorgeous Montepulciano is only a 45-minute (48 km) drive south from Castelnuovo. There is a loftiness about Montepulciano that makes itself felt in the noble palaces and equally noble wine. Even the citizens consider themselves superior, somehow above the fray. But ultimately Montepulciano is a smooth operator, delivering the true Tuscan lifestyle. Begin with a coffee in Caffè Poliziano, a lovingly restored Art Nouveau café which feels like a great Mitteleuropean café that wouldn’t be out of place in Vienna.
Begin your explorations with the historical splendour of the Piazza Grande, Montepulciano’s showy stage set. The tower of the Palazzo Comunale, modelled on that of Florence’s Palazzo Vecchio, surveys the Val d’Orcia, Monte Amiata and Siena, with further vistas across to Lake Trasimeno in Umbria. Il Corso, Montepulciano’s main street, is dignified and reserved, much like Montepulciano itself. En route are snapshots of history, from solemn Renaissance mansions to recycled Etruscan artefacts, and the ancestral cellars of local wine families.
There’s no escaping wine, the most popular purchase in town, especially when linked to a relaxed tasting in rock-hewn vaulted cellars or in a modish wine bar that doubles as a wine shop. Do a wine-tasting of Vino Nobile di Montepulciano in Contucci Cantine, possibly with a member of the family who has been making wine here since Renaissance times. Montepulciano is about both wine and heritage but this wine dynasty combines both from its ancestral stronghold on the main square.
Don’t leave Montepulciano without admiring its star Renaissance church. Tempio di San Biagio stands below the city walls, at the end of a long line of cypresses, and is the Renaissance church most at ease with its setting. This domed masterpiece was designed by Antonio Sangallo in 1518. If food is on your mind, consider a hearty lunch in L’Osteria del Conte, a friendly inn known for its Tuscan home-cooking. See our Montepulciano guide for full recommendations of attractions and restaurants.
Castello di Fonterutoli - wine-tasting & fine dining
This impressive ancestral wine estate is a forty-minute, 32 km drive west of Castelnuovo. Castello di Fonterutoli is the first significant wine estate south of Castellina, a former Florentine outpost. This 21-hectare estate forms the ancestral heart of the Mazzei land-holdings, which the Mazzei marquesses have owned for 24 generations, ever since 1435. Even though the estate is 6 km south of Castellina, the views extend to Siena. From this timeless stone-built hamlet you can make out Siena’s Torre del Mangia and the outline of Siena Cathedral. These Fonterutoli estates are largely planted with Sangiovese, with a far smaller proportion of Merlot, Malvasia Nera, and Colorino. Fonterutoli’s award-winning Chianti Classico wines are matched by their grappa, olive oil and Tuscan cuisine. If tasting the wine barons’ vintages is not enough, then buy the estate lavender and natural Tuscan beauty products, created by Carla Mazzei, scion of the estate’s great wine dynasty. Stay for lunch or dinner at L’Osteria di Fonterutoli, the estate’s acclaimed restaurant.
The estate is also a pretext to delve into local history as Fonterutoli was, for both the Florentines and the Sienese, a significant battleground. In the early 13th century the warring Republics of Florence and Siena fought over Chianti territory, sandwiched as it was between the two great rivals. To determine fixed borders and end this dispute forever, it was determined that two knights would depart from their respective cities and fix the boundary point at wherever they met. Dawn was the agreed departure, with the signal to ride announced by the rooster’s crowing. The Florentines cheated and won.
Their symbolic black rooster was kept in a dark coop and practically starved so crowed as soon as it was released. The Florentine knight set off immediately and, with this huge head start, met the Sienese knight at Fonterutoli, just 12 km from the gates of Siena. The Sienese white rooster faithfully followed instructions but was vanquished by Florentine trickery. As a result, most of the Chianti was brought under Florentine control, far earlier than the defeat of Siena itself in 1555. A triumphant Florence brought its border to Fonterutoli along a new border marked by Castellina, Radda and Gaiole, and established the Chianti Military League, with the Black Rooster as its shield. History has given the Sienese the last laugh: Castellina, Radda and Gaiole are now Sienese territory once more.
L’Enoteca, Castello di Fonterutoli (wine tastings and tours):
0577 741385
