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
-
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.
20 experiences -
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.
20 experiences -
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.
20 experiences -
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.
20 experiences -
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
Organic and Biodynamic Chianti Small Family Wineries: Greve, Montefioralle and Two Estates
Only organic or biodynamic family wineries, with stops in Greve, Montefioralle and the Falorni butcher shop, starting from a bistro in Piazza Torquato Tasso.
Organic and Biodynamic Wine, Olive Oil and Lunch Day in Chianti Classico, Max 8 Guests
Groups are capped at 8 on this Chianti Classico day: an olive oil tasting, a biodynamic organic winery with 4 wines, and a winery lunch with 3 more wines.
Organic Chianti Classico Farm Tasting: Small-Group Tour on a Terrace Above the Vines
A family-run organic farm with a tasting terrace facing the vines behind the wine, and groups kept small so there is time for questions and slow sipping.
Organic Winery Tour and 3 or 6 Wine Tasting between Radda and Panzano in Chianti
Organic vines and cellars are the focus, with bread, the estate's own olive oil and Grappa alongside the wines. Guests choose a tasting of 3 or 6 wines.
Perseto Chianti Classico Farm near San Casciano: Winery Tour and Four Wines with Crackers
A short winery tour past machinery and barrels, then four wines poured with Tuscan crackers at seated tables in a large tasting room near San Casciano.
Poggio ai Laghi Tasting near Monteriggioni: Chianti Wines, Olive Oils and Vinegars
One estate, three products: guided tastings of wines, olive oils including white truffle and chili, and vinegars made with balsamic and Valdelsa onions.
Private Chianti 4x4 Safari from Florence: Off-Road Backroads, Two Villas, Rignana Lunch
Backroads in an air-conditioned 4WD, cellars reached by underground tunnel and lunch at Rignana set this private Chianti day apart from a standard wine tour.
Private Chianti Afternoon Wine Tour along the Via Chiantigiana with Hotel Pickup
A private driver collects the group at the hotel, and a winery is picked from Guidi, Rocca delle Macie or Poggio ai Laghi. Vermentino and Riserva feature too.
Private Chianti and San Gimignano Day Trip by Minivan with Farm Lunch and Wine Tasting
An organic family farm serves lunch with wine, oil and vinegar tastings, after 90 free minutes in San Gimignano. The minivan and driver are for the group alone.
Private Chianti Classico Day from Florence: Luiano, Savignola, a Young Estate, 9:30 Pickup
Three family-run estates, from Luiano's Renaissance cellars to a winery that began producing in 2012, with a multi-course lunch and pairing tips from guides.
Private Chianti Classico Tour by Mercedes E-Class: Poggio Amorelli Lunch, Gabbiano Castle
A Mercedes E-Class and English-speaking driver, with lunch and tastings at Poggio Amorelli and Gabbiano castle paid on the spot, picked up anywhere in Florence.
Private Chianti Tour: Two Boutique Wineries, Three-Course Lunch and Greve, 5 Hours
Two family wineries, an organic estate among them, and a three-course lunch with wine fill this private Chianti half day, with a driver-guide and time in Greve.
Private Chianti Wine Day: Radda Lunch Pairing, Two Wineries and Six Hill Villages
Two winery tastings bracket a homemade Tuscan lunch paired with Chianti wines near Radda, with stops at Badia a Passignano, Greve and Montefioralle on the way.
Private Chianti Wine Region Day by Minivan with Winery Lunch and Medieval Hamlets
A private minivan for the group, a small winery for lunch and tasting paid on the day, and slow roads through the Tuscan hills to medieval hamlets in Chianti.
Private Chianti Wine Tour from Florence Through Rolling Hills and Small Towns
Travel with your own group, not a coach load, through the hills and small towns that gave the world Chianti wine. Private eight-hour departure from Florence.
Private Chianti Wine Tour from Livorno Port: Greve, Panzano and a Hilltop Winery
A private driver-guide takes you from the Livorno cruise dock to Greve in Chianti and a hilltop winery, with Chianti Classico, Riserva and olive oil tastings.
Private Day Trip from Florence: Greve in Chianti, a Chianti Winery Tasting and Siena
A driver who adapts the route takes you from Florence to Greve, a Chianti cellar tasting and Siena's two main squares, with pickup at your accommodation.
Private Day Trip from Florence to San Gimignano and Chianti by Deluxe Minivan, Commentary
A deluxe minivan and an English-speaking driver who narrates the road to San Gimignano's medieval towers and the Chianti hills, with an optional winery lunch.
Private Driver Tour from Florence: San Gimignano, Two Chianti Wineries, Michelangelo Stop
An itinerary you can adjust, a private driver, two Chianti wineries and a morning in San Gimignano, with a photo stop at Piazzale Michelangelo in Florence.
Private Grape Stomping at a Chianti Farmhouse: Meet in Castellina, Harvest and Tasting
Meeting at the company office in Castellina, guests pick or stomp grapes on a farm with a cellar dating to 1825, then taste four wines and grappa at lunch.
Private Grape Stomping on a Chianti Family Farm with Lunch and Florence Hotel Transfer
Barefoot grape stomping or picking on a family farm with a cellar dating to 1825, a home-cooked lunch, a stop in Castellina and hotel pickup in Florence.
Private Half-Day Tour of San Gimignano and Chianti by Car with Wine Tasting
A private car for your group only, the medieval towers of San Gimignano and a Chianti winery tasting among old vineyards. A full lunch is not included.
Private Land Rover Defender Wine Tour from Castellina in Chianti, Strade Bianche
A private Land Rover Defender ride on the gravel strade bianche of Chianti Classico, with three winery stops and a light lunch paired with wine at the second.
Private San Gimignano and Chianti Classico Wine and Food Day from Florence by Mercedes
An English-speaking driver, a Mercedes with Wi-Fi and refreshments, and Monteriggioni's walls before San Gimignano's towers, on a private eight-hour day.
Ratings collected by Viator and Tripadvisor