Chianti Wine Tours
100 tours read one by one, from 15 to 980 EUR and sorted into five formats. The median runs from 39 EUR for a cellar visit to 388 EUR for a private day.
A cellar visit in Chianti costs a median 39 EUR. A private day with a driver costs 388 EUR. Both are sold under the same two words, and three more formats sit between them, each answering a different question: how much of the day you want to spend in a vehicle, who does the driving, and how many people share the bill. This page is about the place itself, the Chianti Classico hills between Florence and Siena. You will find a map of the wine villages, cellar-door prices read on the estates' own sites, a timeline and the harvest calendar. The 100 tours are on the five pages linked below, each read one listing at a time.
Prices by format, the tour-by-tour reading and the mistakes people make at booking live on the format pages. One warning before the map: the word Chianti in a tour title is a label, not a location. The most reviewed Vespa listing here spends its day on the hills above Florence, and the Vespa, Fiat 500 and e-bike page says where.
A note on the numbers. They describe the 100 listings we read on 30 September 2026, not the whole market, and they are medians, because one 980 EUR listing would drag an average out of shape. Sixty-three operators are behind the page. One of them, Walkabout Florence Tours, holds 33% of all the reviews, so the 4.79 rating is partly its rating.
Choose a destination in Chianti
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Chianti by Vespa, Fiat 500 & E-Bike
Twenty Chianti days by Vespa, vintage Fiat 500 or e-bike, 45 to 333 EUR. Who drives, how far each route gets into the wine country, and the alcohol limit.
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Full-Day Chianti Wine Tours from Florence
Twenty full-day Chianti wine tours from Florence compared: 45 to 980 EUR, median 220, lunch in 15, and what the extra money buys over a half day.
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Private Chianti Wine Tours
Private Chianti wine tours read one by one: 160 to 795 EUR, median 388. What the price covers, what it leaves out, and the cost per guest at two, four and six.
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Half-Day Chianti Wine Tours from Florence
Half-day Chianti wine tours from Florence compared: 33 to 880 EUR, median 124. Why the page rates 4.43, which tours are coaches, and which are small groups.
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Chianti Winery Visits & Tastings
Twenty Chianti winery visits and tastings read one by one: 15 to 393 EUR, median 39.
20 experiences
Wine Tours Experiences in Chianti
Private Siena and Chianti Day Trip from Florence by Mercedes Minivan, 8 Hours
Eight hours in an air-conditioned Mercedes minivan with a licensed driver, a Falorni cold cuts tasting in Greve and an optional farm lunch in Chianti.
Private Slow-Living Day in Chianti: Montefioralle, Castello di Verrazzano and Estate Lunch
The hilltop town is the guests' choice, San Gimignano or a Chianti village, and the long lunch is at a historic boutique winery. A private guide leads the day.
Private Small-Group Bike Tour from Florence: Chianti Hilltop Towns and Tastings
A guided full-day ride from Florence for groups of up to 8, through Chianti hilltop towns with winery tastings and a light Tuscan lunch along the way.
Private Tuscany Minivan Wine Tour: Three Sommelier-Picked Wineries and Pairing Lunch
Three wineries chosen by a Level 3 sommelier, owner-led tastings with Super Tuscans and olive oil, and a pairing lunch in a private minivan with a wine guide.
Quiet Private Chianti Classico Tasting at Two Family Wineries with a Local-Born Guide
Producers host you themselves at two family wineries, and a guide born in Chianti drives the private car, with cheese, cold cuts and olive oil at every tasting.
San Giorgio a Lapi Morning Winery Visit near Siena: Four Wines and a Tuscan Lunch
A 10:45 a.m. start at a family winery near Siena, then four wines and a four-course Tuscan lunch under a white mulberry tree on a terrace above Chianti.
Self-Drive Vintage Fiat 500 Convoy to a 15th-Century Villa with Picnic Lunch and Wine
Drivers go in convoy along quiet private roads from a Scandicci clubhouse to a Renaissance villa, with 2.5 hours at leisure, a picnic lunch and a wine tasting.
Self-Guided E-Bike Loop from Florence to Fiesole, Settignano and a Chianti Vineyard
A GPS route on e-bikes links Fiesole, Settignano and a Chianti vineyard, where wine, cheese, cured meats and oil can be bought and enjoyed on the estate.
Semi-Private Chianti Classico and Montalcino Day from Siena, Max 6 Guests, Licensed Guide
Six guests at most share a vehicle with a licensed guide from Siena, for an organic Chianti winery, a cellar tour and Montalcino's fortress, Brunello optional.
Semi-Private Mercedes Van Wine Day from Florence: San Gimignano and Prosecco
Travel by black Mercedes van from Florence to San Gimignano and two wine stops, with a farmhouse lunch, WiFi on board and a Prosecco toast at the end.
Semi-Private Supertuscan Tour from Florence: Castello di Gabbiano and Greve
Taste Supertuscans at three wineries near Florence with an oenophile guide, from Castello di Gabbiano to a boutique estate, then sit down to a Tuscan lunch.
Siena Chianti Sunset at San Giorgio a Lapi: Winery Visit, Tasting and Terrace Dinner
A family winery between Chianti and the Crete Senesi: vineyard walk, 11th-century church, cellars, then wine and a Tuscan dinner on a terrace at sunset.
Siena Small-Group Tuscany Day: Chianti Classico, Brunello Winery, Pienza and Lunch
Six guests at most, two family-run wineries and a Tuscan lunch. Chianti Classico at Castellina, Brunello at Montalcino, then the Val d'Orcia and Pienza.
Six-Hour Chianti Vespa Tour from Florence via Castellina, Fonterutoli and a Winery Meal
Six hours on a Vespa take in Castellina, Monteriggioni and Fonterutoli, with a winery visit, a wine tasting, an oil tasting and a two-dish Tuscan meal.
Small-Group 50cc Vespa Day near San Gimignano with Three-Course Lunch at a Winery
The ride starts from a base deep in Chianti rather than the hills next to Florence, then stops at a winery for a three-course Tuscan lunch and a wine tasting.
Small Group Chianti Classico Wine Day with a Certified Sommelier and Farm-to-Table Lunch
A certified sommelier leads a small group through three family wineries in Chianti Classico, with a farm-to-table lunch and departure from central Florence.
Small-Group Chianti Day from Florence: Riseccoli, Casa Emma, Poggio Torselli
Three estates, from organic Riseccoli to Villa Poggio Torselli, plus Greve in Chianti and a light Tuscan lunch, on a small-group day trip from Florence.
Small Group Chianti Day Trip from Florence with Cellar Visits at 2 Top-Rated Wine Estates
Cellar tours at two top-rated Chianti wineries, with tastings that add balsamic vinegar, olive oil, cheese, salami, prosciutto and bruschetta to the wine.
Small Group Chianti Day with an Italian Sommelier: 3 Family Wineries and Local Lunch
Three family-owned wineries away from the main tourist routes, a sommelier guiding the group and a lunch with paired wines, starting at Piazza Lorenzo Ghiberti.
Small-Group Chianti Half-Day: Two Family Wineries, 8 Wines and Home-Cooked Lunch, Max 8
A wine-professional driver leads eight guests at most to two family-owned wineries, with at least eight wines poured and lunch cooked at the second one.
Small-Group Chianti Tasting from Florence at a 12th-Century Villa: Seven Wines and Lunch
Departs central Florence at 10am with a bilingual guide. Seven Tuscan wines at a private Chianti property, followed by a traditional lunch with more wine.
Small-Group Chianti Wine Tour from Florence in a Mercedes V-Class Van, 2 Wineries
Both wineries are small estates rather than commercial operations, and an extra virgin olive oil tasting joins the cellars and vineyards. Drivers speak English.
Small-Group Chianti Wine Tour from Florence: San Gimignano and Two Farm Wineries
Two working farm wineries, a guided visit of San Gimignano and its famous gelato, and a Tuscan farm lunch, on a family-friendly small-group day from Florence.
Terre di Perseto Cellar Visit and Chianti Classico Riserva Tasting with Pecorino Cheeses
Two IGT Toscana wines, a Chianti Classico and a Riserva, each explained by the host and paired with two sheep's-milk pecorinos, plus a look at the cellars.
Ratings collected by Viator, Tripadvisor, Civitatis and Tiqets