The Chianti trip planner
The tall, vine-striped hills between Florence and Siena is one of the most famous—and beautiful—wine regions in the world
The Badia a Passignano in the Chianti region of Tuscany.
The hills of the Chianti stretching between
Florence and
Siena comprise one of the world's most famous wine-producing regions.
The steep slopes are cloaked in terraced rows of vines and peppered with medieval castles and cypress-shrouded abbeys.
The narrow valleys are laced with tiny rivers along which are sprinkled small market towns: Greve in Chianti (the unofficial capital of the Chianti), Radda in Chianti, Gaiole in Chianti.
The Chianti is the perfect place for a countryside getaway—and a great base for exploring Tuscany for the comfort of a rental villa or country hotel. At the very least, avoid the speedy SS2 Via Cassia highway to get between Siena and Florence and instead take the slow road (the SS 222, a.k.a. the Chiantigiana) on a day-long tour of the Chianti's wineries, winding your way leisurely though these misty, wine-sodden hills between Florence and Siena.
Visiting the vineyards
Call ahead before visiting a winery
As a general rule you'll want to call ahead at least a day or two before heading out to any winery.
Some of the slicker commercial operations allow you just to drop by and get on a tour, but many require you to book a tour in advance, often a day or two (sometimes a week).
However, almost all of them have tasting rooms and direct sales outlets that are open to all comers, though often only during business hours on weekdays.In the Chianti, some of the most visitor friendly wineries—from castles to monasteries to Renaissance country villas—include:
Castello di Verrazano
The 12th century Castello di Verrazano is the hilltop castle where Giovanni da Verrazano was born in 1485 (later to sail out of the Chianti and discover New York harbor, which is why we named that big old bridge after him).
Hour-long tours of the gardens and cellars run Monday through Friday from 11am to 3pm). Book ahead at least a day in advance (tel. +39-055-854-243 or 055-290-684; www.verrazzano.com).
Badia a Passignano
The monks who live in the postcard-perfect thousand-year-old Badia a Passignano, a castle-like monastery wrapped in a cypress grove atop vine-stripped hills and olive groves, no longer tend to the wine-making; that's in the hands of the massive Antinori wine empire (www.antinori.it).
Monday to Friday you can visit its osteria (tel. +39-055-807-1278, www.osteriadipassignano.com) to tour the cellars and buy the wines produced here (tel. +39-055-807-1622).
Tours of the monastery itself are only given Sundays around 3pm.
Villa Vignamaggio
The Russet-orange villa surrounded by cypress and elegant gardens called Villa Vignamaggio will look oddly familiar to Kenneth Branagh fans. This is where he filmed Much Ado About Nothing—but the 14th-cetnury villa's fame goes back much further; this was, after all, the childhood home of a young girl who would grow up to pose for a painting by Leonardo da Vinci and become known as the Mona Lisa.
Now the joint's owned by a Milanese former banker, who has revived the wine making (and turned most of the out buildings in a rather chic agriturismo, or farm stay operation » more).
Book ahead at least a week ahead to tour the cellar and those ornate gardens, on Tuesdays and Thursdays only (tel. +39-055-854-661; www.vignamaggio.com).
Castello di Volpaia
The Castello di Volpaia is another looker, a medieval stone borgo (village) around a crenellated tower, and the winery is actually installed in the series of houses and buildings of the village itself (all connecting pipes, tubes, and electrical wires have been seamlessly hidden underground and within walls, so the exterior effect is as medieval as it gets).
Tours are run every day but Saturday, but call ahead—and try to do so a week in advance (tel. +39-0577-738-066; www.volpaia.com).
Castello di Monsanto
My favorite Chianti is that produced by Dr. Laura Bianchi on her family's Monsanto estate in Barberino Val D'Elsa—one of the first two wineries to switch over to producing a fully Sangiovese Chianti (actually, they started doing it back in 1974, waaaay before it was legal to deviate from the official grape formulas). They also do a mean Chardonnay.
The cellars are also pretty evocative, modeled after an Etruscan tomb found on the premises, and including a hall of niches covered by iron grates—and hovering between being Cask of Amtillado-creepy and aw-isn't-that-sweet cute—where bottles are set aside for each family member when they are born, to age and be ready for them to celebrate a wedding or some other major life event in the future.
They also now run an agriturismo on the property.
Reserve a tour at least a few days ahead of time (tel. +39-055-805-9000, www.castellodimonsanto.it).
Chianti vineyard tours
- Tours leaving from Florence
- Tours leaving from Siena
Chianti Classico winery tours from Florence
Combine wine-tasting and a country drive through magnificent Tuscan landscapes on an afternoon excursion to Chianti. You'll discover a magical world of woods alternating with vines and olive trees, Romanesque churches, medieval farmhouses, Renaissance villas and castles, and one of Chianti's most renowned wine-growing estateswhere you'll sample Chianti Classico, Chianti Reserve and Vin Santo dessert wine accompanied by local traditional snacks...
Duration: 6 hours; Cost: $54 per person
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Combine Tuscan wines with incredible scenery on a full-day Tuscany wine-tasting tour from Florence! Led by a sommelier guide, travel by luxury minivan to the heart of Italy's Chianti region, famed for its ruby-red wines and rolling hills. Tour two exceptional Chianti wineries, sample six local wines and enjoy a classic Tuscan lunch before visiting a medieval town with your guide. There is a maximum of 16 people on your Tuscany wine-tasting tour, ensuring you'll enjoy an intimate day with a small-group of Iike-minded wine lovers...
Duration: 6 hours; Cost: $142 per person
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Tidy rows of vineyards, silvery-green olive trees and the inky exclamation points of cypresses are the scenic backdrop for this shared, full day excursion to the Chianti area where one of the world's most famous wines is produced. You will stop at two celebrated wineries where sommeliers will show you around the cellars where you will taste wines made from Sangiovese, Canaiolo and other varieties of purple grapes (as well as spome of the excellent olive oils produced in this region). Lunch will be at a lovely trattoria serving local Tuscan specialties. A short stop in a medieval Tuscan town ensures that this tour is a perfect blend of food, wine and culture...
Duration: 6 hours; Cost: from $159 per person
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Follow the scent of the Great Wines through the most stunning landscapes of Chianti, Val d'Orcia and Val di Chiana. From the market in Greve in Chianti to wineries and vineyards in Castellina in Chianti, we'll continue to the Crete Senesi of the Val d'Orcia and a lunch with guided tasting of Montalcino wines. Round out the day with a visit to Montepulciano and its storied wine cellars...
Duration: 11 hours; Cost: from $224 per person
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Wine-tasting at one of Chianti's most renowned castle-farm estates, scenic drives through magnificent Tuscan landscapes, visits to ancient villages, and a traditional dinner an old village among the Tuscan hills - is there a better way to spend the afternoon in Tuscany?
Duration: 9 hours; Cost: $91 per person
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Enjoy personalized attention on your private visit to an artistic old village famed for its castle farms. You'll stop at one to sample its prestigious wines accompanied by light snacks. Choose to end your tour here returning to Florence, or continue to visit a beautiful Romanesque church and complete your private tour with a traditional Tuscan Dinner in a historic village set in the hills. Weather permitting you'll dine under the stars, toasting the finest Chianti wine...
Duration: 4 or 8 hours; Cost: from $95 per person
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Drive a vintage Fiat 500 to a gorgeous 15th-century Renaissance villa nestled in the picturesque Tuscan hills just outside of Florence. Traveling in a convoy behind an expert guide, you’ll drive along quiet private roads and then enjoy 2.5 hours at leisure. Swim in the villa’s pool, indulge in a picnic lunch with wine tasting, or upgrade to include a winemaking session in which, yes, they will let you stomp the grapes. (No one actually makes wine this way anymore, but c'mon: Who doesn't want to try it? Lucille Ball impressions are optional.)...
Duration: 5 hours; Cost: $180 per person
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Famous for a wealth of art, history, striking landscapes and outstanding produce, Tuscany really does have the best of all worlds! With only a day to spare, see the best Tuscany has to offer on this full-day guided coach trip from Florence, including: Gothic Siena, Chianti vineyards, Tuscan lunch and wine-tasting class amongst the Sienese hills, medeival San Gimignano, and Pisa...
Duration: 12 hours; Cost: $103 per person
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Produced in the undulating hills of the Tuscan countryside between Florence and Siena, the famous Chianti Classico wine is known and celebrated all over the world. Departing from and returning to your Florence hotel, first stop is the town of Greve in Chianti with its picturesque, asymmetrical main piazza. After a tour of Greve you'll head to the Casaloste Vineyards, known for their fine Chianti Classico and Riserva wines. A visit to the cellars and a guided wine tasting are included. Then you'll visit the cellars of the Setriolo estate in Castellina in Chianti to learn how grapes become wine; a guided tasting follows...
Duration: 5 hours; Cost: from $126 per person
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Same as above, only you also get lunch at the Osteria La Scuderia, a lovely place serving typical Tuscan cuisine, and an extra vineyard visit (either to the Antinori vineyards at Badia di Passignano or the small castle of Montefioralle)....
Duration: 7 hours; Cost: $211 per person
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Departing from and returning to Florence, after a tour of San Gimignano, famous for its many 13th century stone towers, you'll head to the Setriolo estate in Castellina in Chianti to tour the cellars and taste their fine Chianti Classico and Riserva wines. Next stop will be lunch at the Osteria di Lornano, a lovely place serving typical Tuscan cuisine. Afterwards, you will drive through the gorgeous Tuscan countryside to Siena. In this cradle of the Italian Gothic style, your expert, private guide will introduce you to...
Duration: 8.5 hours; Cost: $280 per person
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Small Group Chianti Wine Region Day Trip from Florence
Tour the beautiful Chianti and hill towns of Tuscany on a small group day trip from Florence. Group consist of a maximum of eight people for individual attention from your expert driver guide at vineyards, medieval castles, artisan villages, and market towns...
Duration: 8 hours; Cost: $212 per person
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Chianti Classico winery tours from Siena
Combine Chianti's fine wines with its impressive castles on a full-day trip from Siena! Giving the rugged Tuscan landscape a remarkable grandeur, these stunning Italian castles are a must-see for any visitor to the region. With your expert guide, visit Castello di Brolio, renowned as the birthplace of Chianti wine, and explore Castello di Meleto. Sample the esteemed Chianti Classico wine, enjoy an authentic Italian lunch at a Tuscan farm and tour the region’s best wineries. Numbers are limited to eight people on your small-group trip, ensuring you'll receive personalized attention from your guide...
Duration: 8 hours; Cost: $161 per person
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Departing from and returning to your Siena hotel, first stop is the town of Radda in Chianti which has its preserved medieval urban design. After a walking tour of Radda, you'll head to the Buondonno Vineyards, known for their fine Chianti Classico and Riserva wines. A visit to the cellars and a guided wine tasting are included. Then, if you choose the morning departure, the last stop will be lunch at the Osteria Le Panzanelle. If you choose the afternoon departure, you'll do a short walk through the village of Vagliagli and then head to the Monteraponi Vineyards for a guided tasting...
Duration: 5 hours; Cost: from $153 per person
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This small-group tour from Siena takes you to Tuscany’s northern Chianti region, known as the Florentine Chianti, where you’ll visit the pretty villages of Castellina and Greve. During this full-day trip, see breathtaking landscapes, enjoy a traditional lunch and visit two wineries with your expert guide. Meet the area's famously welcoming inhabitants and get a taste for life in the Florentine Chianti! Numbers are limited to eight people on this small-group tour, ensuring you'll receive personalized attention from your guide...
Duration: 8 hours; Cost: $161 per person
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On this afternoon and evening tour from Siena to Chianti and San Gimignano, explore the beautiful Chianti region – an area rich with dense oak forests and cypress trees – and discover its famous wine cellars. Visit village of Castellina in Chianti, a Chianti wine estate where you'll tour the grounds and wine cellars while learning about the winemaking process, and Monteriggioni, a perfectly preserved medieval town with a complete ring of walls and turrets built in the 13th century. Then head to the UNESCO World Heritage-listed town of San Gimignano after the day’s crowds have dispersed. During the sunset, dine in a beautiful farmhouse overlooking the San Gimignano towers and the rolling, vine-covered hills. Numbers are limited to eight people on this small-group tour, ensuring you'll enjoy personalized attention...
Duration: 8.5 hours; Cost: $172 per person
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Departing from and returning to your Siena hotel, first stop is the town of Radda in Chianti which has its preserved medieval urban design. After a walking tour of Radda you'll head to the Buondonno Vineyards, known for their fine Chianti Classico and Riserva wines. A visit to the cellars and a guided wine tasting are included. Next stop will be lunch at the Osteria Le Panzanelle, then a tour or either to the village of Vagliagli or to Castelnuovo Berardenga. Then you'll visit the cellars of the Monteraponi estate for a guided tasting...
Duration: 7 hours; Cost: from $228 per person
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Tips & links
Useful links & resources
- Car resources
- Emergency service/tow: tel. 803-116
- Highway agency: Autostrade.it (traffic info, serivce areas, toll calculator, weather)
- Italian automotive club (~AAA): Aci.it
- ZTLs: Ztl-italia.blogspot.com (lightly outdated, but handy, links to cities' traffic-free zones)
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