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Top Ten Things to Do

Enjoy a meaty feast in Panzano, which is a restaurant hotspot, before embarking on wine trails in the Chianti hills nearby. Visit a Renaissance villa and gardens linked to Leonard da Vinci or fly over the Chianti in a hot-air balloon. More simply, enjoy a great circular hiking trail between Greve and Panzano, along with scenic drives to medieval castles and estates. Panzano, set more or less halfway between Siena and Florence, makes a great base for exploring both cities, as well as San Gimignano.

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

Top Ten Things to Do

Panzano stroll, wine-tasting and meaty feast

Panzano is the place to indulge in a passion for Tuscan meat, including Florentine T-bone steak. On the food front, this Tuscan bastion belongs to Dario Cecchini, a cleverly eccentric celebrity butcher with a mini empire in these parts. No one can wield a bloody meat cleaver better, still less while reciting Dante. Part butcher, part showman, Dario keeps his audience entertained as well as over-fed.

Work up an appetite by strolling along the walls and admiring the Chianti countryside. Restaurants lining the walls offer views of the Chianti hills and vineyards. Before lunch, call into L’Accademia del Buon Gusto for a wine-tasting with one of Tuscany’s most colourful characters. Stefano Salvadori is a gracious, old-school host who offers free tastings of Tuscan wines, olive oils and vinegars, all the while waxing lyrical about Chianti wines. Expect to leave enlightened, amused and possibly laden down with wine.

The café-lined main square is the place for lapping up the small-town atmosphere and contemplating lunch. With several restaurants in town, all clustered round his famous butcher’s, Cecchini is still doing a brisk trade. The restaurants are fairly priced so there’s no sense of being caught in a tourist trap. The winning format appeals to most visitors, as does the conviviality and showbiz side. T-bone steak predominates, at least in L’Officina della Bistecca. For any beef-loving Tuscan, bistecca alla fiorentina – a huge, tender T-bone steak, grilled over an open fire and seasoned with nothing more than crushed pepper¬corns, salt, and a hint of garlic and olive oil, served very rare – is the ultimate steak. Bear in mind that all is not bleak for vegetarians: there are strong meat-free menus for those of a more squeamish disposition. Basic wine is included in the price but you can also bring your own.

After lunch, work off the calories by walking upto the Pieve di San Leonino, Panzano’s loveliest church, set on a hilltop just outside Panzano. Inside the Romanesque pieve are precious artworks, including della Robbia terracotta tabernacles and a medieval triptych of the Virgin and Child.

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Vignamaggio – Renaissance villa estate and gardens

This Renaissance villa estate is linked to great art. Set around 5 km north-east of Panzano, the wine estate is delightful enough to have starred as a film set, based on Shakespeare’s Much Ado About Nothing. The romantic villa lords over its Italianate gardens and vine-clad hills. The serene landscape supposedly inspired Leonardo da Vinci. The castle was remodelled as a patrician villa in the 14th century and belonged to the Florentine Gherardini family. Monna Lisa Gherardini, better-known as Leonardo da Vinci’s Mona Lisa, married into this family in the 14th century.  The villa boasts a crenellated tower, 16th-century corbelled arches and courtyard, with the top of the tower remodelled in Neo-Gothic style.

Centred on the lovely Renaissance villa, this tenuta is an established 65-hectare wine estate, and one of the oldest in Tuscany, dating back to 1404. The award-winning wines range from Chianti Classico and trendy Super Tuscans to a fresh Rosé, a Cabernet Franc, Vin Santo and grappa. Orchards, herb gardens, wheat-fields and thirty hectares of olive groves reflect the estate’s commitment to biodiversity. The villa grounds showcase Italianate, Renaissance-style gardens, complete with cypresses, clipped box parterres and rose-draped statuary. French owner and architect Patrice Taravella has recently spruced up the grounds, adding orchards, classical pool fountains and pergolas.

Vignamaggio now offers garden and cellar tours, as well as a free wine-tasting. The farm-to-table Ristorante Monna Lisa serves produce from the surrounding organic estate. Wine-pairing lunches are recommended, as are guided tours of the estate, ending in a sunset dinner. The seasonal menu celebrates Tuscan fare, from vegetable platters drizzled in home-produced olive oil to pasta with pistachio and garden-mint pesto. The pork and cured meats come from the estate's happy herd of cinta senese pigs.

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Greve to Panzano hiking circuit

A 14-km hilly hiking circuit from Greve in Chianti to Panzano and back forms a gentle loop that should take around five hours, not allowing for a lunch stop. However, a lunch stop is recommended in Panzano, at one of the places we suggest in our Eating & Drinking section.  The map and full route description is visible at the link at the bottom so this is merely a summary. The route gives a sense of the Via Chiantigiana and its offshoots, passing farms, cypresses, olive groves and chestnut groves. Expect olive groves, gently rolling hills and dark cypresses standing sentinel.

From Greve, the first leg is a short, steep but rewarding 2km hike before reaching Montefioralle and its wonderful views. In Greve, take via Roma and via San Francesco to the medieval village of Montefioralle, passing through classic Chianti landscape. Although there are stretches of asphalted roads, these are generally peaceful and cypress-shaded. The winding route leads to the walled settlement, once the feudal castle, perched on the hill. Although no longer a military outpost, Montefioralle is still fortified. The walls were once octagonal, bounded by four gates, parts of which survive. The village was the birthplace of Amerigo Vespucci (1415-1512), who followed Columbus’ route to America. The explorer’s ancestral home lies along the main street, and is indicated by his coat of arms, incorporating a wasp. Wander along narrow alleys and secret passageways past well-preserved stone-built houses. Leg two of the hike then goes through silvery olive groves to Panzano, where you’ll probably stop for lunch. (See our suggestions below). Continue the walk back to Greve. Fortunately, leg three, the final leg, is all downhill. It takes you back to Greve through yet prettier countryside.

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Castellina in Chianti for a foodie foray

Visit neighbouring Castellina in Chianti, a charming haunt south of Panzano. 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 di Passignano - medieval abbey and Antinori wine estate

Set north-west of Panzano, this moody hamlet incorporates a Benedictine monastery founded by the Vallambrosan order in 1049. All around Badia di Passignano are vineyards belonging to the Antinori Chianti estates. This particular Antinori wine estate is given over to vineyards of Sangiovese grapes and olive groves. This Florentine-based wine dynasty have been peddling the `nectar of the gods’ in Tuscany since 1385.  Before succumbing to the wine option, spend a bit of time in the fortified abbey where the great Galileo Galilei taught in the 16th century. Pre-book a guided tour with one of the handful of remaining Vallambrosan monks to admire a refectory decorated with a magnificently restored Last Supper by Domenico Ghirlandaio.

If more earthly concerns are on your mind, then the abbey can also sustain you. The Antinori’s Michelin-starred restaurant occupies part of the vaulted abbey, with the so-called `historical cellars’ located immediately below the abbey. At the estate you can sample Antinori signature wines, whether Chianti Classico wines or Super Tuscans. Famous names are Tignanello, Guado al Tasso, and Solaia, as well as Chianti Classico Riserva Badia a Passignano. Book an Antinori wine-tasting and cellar tour, possibly even an oil-tasting, followed by lunch or dinner in their onsite fine-dining restaurant, L’Osteria di Passignano or their far simpler Trattoria della Fonte in a farmhouse nearby. Instead, L’Antica Scuderia is the best dining option for families or anyone fancying a pizza.

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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 around Panzano or Castellina in Chianti and recognize Castellina’s 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 the 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 the western Chianti, west of Panzano and San Donato in Poggio. The hot air balloon rides take off in the early morning due to the ideal air conditions found at that time. 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.

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San Gimignano – medieval Manhattan

San Gimignano is only 40 km south-west of Panzano 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

A charming wine estate-lined route leads south from Panzano to Castellina and Rocca delle Macie, which is around 5 km south of Castellina. This stellar wine estate was a tumbledown farmstead until revitalised by spaghetti western film producer Italo Zingarelli in 1973. The 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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Art-filled Florence

Florence is only 40km from Panzano so 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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Seductive Siena

Siena, which frames the southern end of the Chianti, is 35 km from Panzano so makes a magical day trip. 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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