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Top Ten Things To Do

Even if Castellina itself is a key attraction on the Chiantigiana, the Chianti Way also leads to forays to neighbouring Chianti wine hamlets, as well as to San Gimignano, Siena and Florence. Castellina makes a great base for activities as varied as cycling and museum-visiting, wine-tasting and ice cream-slurping. Sample a cookery course or visit a sculpture park: Castellina has it covered.

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, Radda, Castelnuovo Beradenga. Our additional Chianti guides cover Castagnoli, Volpaia, San Gusme, San Donato in Poggio, and Vagliagli.

Top Ten Things To Do

Eat experimental ice cream – Gelateria Castellina

Experimentation with curious flavours is the way to foodies’ hearts in the region’s best ice-cream shop. Gelateria Castellina is run by Simone, a passionate foodie with a creative touch. For over twenty years Simone has been making ice-cream, pasteurising, churning and blast freezing, with interested onlookers watching him concoct the day’s ices in his show kitchen. The welcome by Simone and Chiara is the friendliest ever. The couple also make semifreddi cold desserts or semi-frozen ice cream cakes. As for the ice cream, flavours range from ricotta and fig to chilli and chocolate, raspberry and rosemary, lemon and kiwi fruit, or coffee and dark chocolate. If you prefer water ices, then choose sorbets concocted from lemon and sage or lime and basil. The strangest creation ever was probably the anchovy and spring onion sorbet, which wouldn’t be for all tastes. Simone’s favourite creation? “That would be cantuccini and Vin Santo: almond biscuits with sweet Tuscan wine.” There’s no escaping wine in the Chianti so just give in and eat up.

After your ice cream, walk off the calories by exploring Castellina’s warren of backstreets. In particular, stroll down via delle Volte, an 800-metre-long stone-vaulted passageway built into the side of the hill. Apparently, this moody alley was created to permit horsemen to do the circuit of the fortress on horseback. Today the arched alley is home to small boutiques and cafes. From the window slits pierced in the outer you can admire the sheer drop and glimpse the Chianti countryside beyond.

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Etruscan life at Castellina Archaeological 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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Castellina cycling or wine-tasting tour

Consider a cycle ride if you want more than the familiar wine-tasting experiences. Variants include picnicking in the vineyards or lingering in the Dievole wine estate for lunch or dinner. South of Castellina, around the hamlet of Vagliagli, is an appealing cycle route that takes you past rolling vineyards in leisurely fashion. Expect flitting butterflies, trilling birds and the smell of baked earth as you cycle. The route begins in Vagliagli, with an intriguing 26 km trail around vine-clad slopes. At its heart is the Dievole wine estate, a 400-hectare property 12 km north of Siena. Although it’s a private estate, anyone is welcome to ride the trail, which has recently been revamped and signposted. The `new’ trail was devised by an estate-worker, who knows the land like the back of his sun-leathered hand. In one sense, the trail is as ancient as the hills and was used by Tuscan sharecroppers for almost a thousand years. Ideally consult the Dievole estate before setting off on the trail and consider booking the gourmet picnic option.

The Dievole 80-hectare wine estate has been cultivated since 1090, when it was a monastic holding. Today, the property also produces award-winning olive oil. From the highest point of the vineyards stretch views of olive groves, deep woods and cascading vineyards planted with the grapes required for Chianti Classico. The estate offers gourmet picnics and cycle tours, as well as wine and olive oil tastings, complete with Pecorino cheese and crostini drizzled with olive oil. If won over by the spot, linger over a romantic gourmet dinner at Ristorante Dievole, or just a light lunch in the same place. The fallback restaurant, Giardino del Tasso, is another recommended spot for a candlelit dinner.

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Castello di Fonterutoli - wine-tasting & fine dining

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)
T: 0577 741385
www.mazzei.it

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Ballooning over the Chianti

If weary of wine estates or in search of romantic memories, consider an amazing balloon ride over the Chianti. This works well for most people, from couples to families. Being on board a hot air balloon should provide a magical new perspective on Tuscany along with great photo opportunities.

Very probably you will float above the hills of Castellina in Chianti and recognize the tower and the walled medieval fortress. That said, the precise route isn’t decided until the balloon launch as it all depends on the weather, especially the winds. Given the strategic location of the launch site in Tavernelle Val di Pesa, you should be able to admire the highlights of southern Chianti. This might range from Tuscan castles and Renaissance villas to aerial views of San Gimignano and the prettiest Chianti hamlets and wine estates. Certainly, there will be memorable views of silvery olive groves, vineyards and rolling hills. On a clear day, if the balloon flies high enough, you may even glimpse the Mediterranean reflecting the morning sun.

The launch site is Tavarnelle Val di Pesa, in western Chianti, west of Badia a Passignano, San Donato in Poggio and Panzano. The hot air balloon rides take off in the early morning when the air conditions are best. Ballooning is never cheap (around € 250 per person, with a basket holding from four to ten people) but it makes for an unforgettable experience. For more, consult Balloon in Tuscany, the operators, or the Castellina tourism consortium, Associazione Amo Castellina in Chianti.
Balloon in Tuscany. T: 055 8077940
www.balloonintuscany.com

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Castello di Ama for contemporary art

This leading Chianti Classico producer lies east of Castellina as the crow flies, but not as the winding Chianti roads take you. 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 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 31 km west of Castellina 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 worthwhile. 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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Rocca delle Macie wine-tasting or cookery course

Set around 6 km south of Castellina, this stellar wine estate was a tumbledown farmstead until being revitalised by spaghetti western film producer Italo Zingarelli in 1973. The Rocca delle Macie project fulfilled his lifelong dream of owning vineyards in the heart of Chianti Classico. The estate is now run by Sergio, his youngest son and current head of Consorzio Vino Chianti Classico, the Chianti Classico Consortium. This young, forward-looking estate produces best-selling wines. The 500-hectare estate is spread over the Castellina and Scansano areas, with four wine estates in the Chianti and a further two in the prized Morellino di Scansano wine area. As well as 200 hectares of vineyards, the estate produces excellent olive oil on its 40 hectares of olive groves.

The 93-hectare Tenuta Le Macie estate, set in the south-west part of the Chianti, forms the heart of the company and occupies the loveliest vineyards. The terraces are mainly planted with Sangiovese grapes, along with some Cabernet Sauvignon, Merlot and Colorino. As well as the prized Chianti Classico wines, you can sample some IGT Super Tuscans. Unlike more inward-looking estates, this one believes in collaborating with others, whether in San Gimignano or Orvieto, to produce particular wines. For a true taste of the region, sample one of the estate’s best Chianti Classico wines, which reveal fruity notes of blackcurrant and cherries. Either do the basic wine-tasting (of Chianti Classico or the Super Tuscans) or opt for the three-hour wine-tasting tour which includes dinner, ending with dessert and Vin Santo.

Alternatively, come back for dinner at Ristorante Riserva di Fizzano, the estate’s restaurant. If impressed, consider booking a cookery course with Aldo, the resident chef. Typical dishes to master include pici all’aglione, (stubby pasta in garlic sauce), pappa al pomodoro (thick bread and tomato soup) and typical cantuccini almond biscuits.

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Seductive Siena

Siena is a mere thirty-minute drive from Castellina so makes a magical day trip. Siena frames the southern end of the Chianti and so is far more convenient for Castellina. 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.
Centro Guide (guided Walks)
T: 0577 43273
www.guidesiena.it

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Art-filled Florence

Florence is only an hour’s drive from Castellina so still makes a perfect outing. 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 (www.firenzecard.it) and also book a time slot at the Uffizi Gallery.

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