The verdict
Our pick
Chianti Classico: Organic Winery Tour & Wine Tasting★ 4.90 (135) · 2h
Best price
Montalcino Wine Tasting: 6 Wines & Tuscan Terroir★ 4.75 (8) · 45m
Top rated
Montalcino: Brunello Wine Tasting & Vineyard Tour★ 5.00 (16) · 2h 30m
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Private experiences (3)
Livorno to Chianti: Private Tuscany Wine Tour & PickupYou’ll ride from Livorno into classic Tuscany with a local driver, stroll Greve’s lively piazza, sample Chianti wines straight from the cellar, and taste fresh olive oil with bread. There’s time for lunch at a family-run restaurant if you want it. You’ll leave with new stories (and maybe a red-wine stain), plus that quiet sense you’ve really touched Tuscan life.
Radda in Chianti: Private Cooking Class & Wine TastingYou arrive at a working farmhouse in Radda in Chianti, taste Giorgia's olive oil and local wine on the patio, then spend two hours learning to make three traditional dishes using her family's recipes. You cook the meal yourself, then eat it together at the outdoor table with Giorgia and Luigi. The whole experience is private, lasts about half a day, and includes everything — wine, food, instruction, and the kind of conversation that only happens when you're sitting down together after cooking.Is it for me?Right for anyone who wants to learn real Italian cooking in a home kitchen rather than a commercial class, and who values time with local hosts over a polished performance. The private format means Giorgia can adjust the pace and the menu to what you actually want to learn.
Montalcino & Chianti: Private Wine Tasting Small Group TourYou spend the morning walking Montalcino's fortress and learning why Brunello di Montalcino commands its price, then taste wines at two small wineries chosen for what you're interested in. The private group format means no crowds and no fixed schedule — your guide adjusts based on how long you want to stay at each stop. You leave with two tastings included and a real sense of how the region's soil and tradition shape what's in the glass.Is it for me?Book this if you want to taste real Brunello and Chianti without the standard tour-group experience — the private format and small winery selection mean your guide can actually respond to what you're curious about instead of moving everyone through the same stops.
Up to 2 hours (8)
Greve in Chianti: Organic Winery Tour & Wine TastingYou walk the vineyard, learn how Chianti Classico is produced from cellar floor to barrel, then taste the wine paired with local cheese and salami. The group stays small — no more than 15 — and the whole experience moves at a pace that lets you actually absorb what you're seeing instead of rushing through a checklist.Is it for me?Right for wine drinkers who want to understand how Chianti is actually made, not just taste it. The small group size and family-run setting mean you get real conversation with the people who made the wine, and the cellar tour is hands-on enough that you'll remember the process when you drink it later.
Chianti: Montefioralle Winery Tour & Wine Tasting with SnacksYou’ll sip different vintages of Chianti Classico right where they’re made, walk through Montefioralle’s small cellar with a local guide, and try Tuscan snacks overlooking the countryside. Expect warm conversation, honest flavors, and plenty of stories — plus a view you might keep thinking about long after you leave.
Montalcino Winery Tour & Wine Tasting ChiantiYou walk through Brunello vineyards with views of Montalcino, learning about biodynamic methods and terroir from trained staff. You tour the grape processing area and cellar, then sit down to taste 6 wines in 3 flights at your own pace. Water and all fees are included, and you choose from 4 tasting options before you arrive.Is it for me?Right for anyone who wants to understand Montalcino wine by standing in the vineyard and tasting it seated, without arranging transport or choosing wines blind — the walk through the vines and the structured tasting do both at once.
Radda in Chianti: Wine Tasting, Cellar Tour & Tuscan LunchYou arrive at a family-owned winery in Radda in Chianti, tour the historic cellar and castle, taste three estate wines plus Vinsanto, then sit down to a three-course Tuscan lunch with vineyard views. The whole day is structured but unhurried, and includes everything — transport logistics and meal timing are handled so you just show up and eat.Is it for me?A good fit if you want to understand Chianti winemaking without arranging a separate lunch or navigating the estate yourself — the guided structure and included meal mean you spend the afternoon tasting and eating instead of planning.
Chianti: Organic Wine Tasting & Vineyard Tour with LunchYou tour the vineyards and cellar with one of the three brothers or their team, taste four organic wines paired with local cheeses and cold cuts, sample their olive oil, and eat seasonal produce from their garden. The guide speaks English or Italian, and the whole experience happens at their property without needing to arrange transport separately. You leave with a clear sense of what makes their wines different and which ones to reorder.Is it for me?Right for anyone who wants to understand how organic wine is actually made, not just taste it—the brothers walk you through their vineyard and cellar, so you leave knowing the story behind each bottle.
Montalcino: Brunello Wine Tasting & Vineyard TourYou walk through the vineyards, tour the aging cellar with a sommelier, and taste four wines — Rosato, Rosso di Montalcino, vintage Brunello, and a Super Tuscan — paired with local pecorino and bruschetta. The winery keeps groups small and the pace relaxed, so you're learning without feeling rushed. Plan for three to four hours in the hills above Montalcino.Is it for me?Right for anyone who wants to understand Brunello without the crowds of a commercial tasting room — the small-group format and family-run setting are what make the sommelier's attention and the pace actually yours.
Radda in Chianti: Wine Tasting & Winery Tour SangioveseYou walk through a working barrel cellar with an expert guide, learn how Sangiovese ferments and ages, and taste four wines—three Chianti expressions and a Vermouth—in a winery surrounded by vineyards in the medieval village of Radda. The tour includes the full winemaking process from fermentation to bottle, so you leave knowing how the wine you're tasting actually got made.Is it for me?Book this if you want to understand how wine is actually made rather than just taste it—the cellar tour and expert explanation are what set this apart from a standard tasting room visit.
Chianti Wine Tasting & Dinner with SommelierYou taste four wines guided by a sommelier who explains tannins, aromas and food pairings, then sit down to a three-course dinner at SiChef Villa overlooking the Tuscan hills. The tasting teaches you to recognize flavors and match wines to food; dinner puts that knowledge to work. Pickup and transport are not included, so you'll need your own way to the villa or arrange it separately.Is it for me?Book this if you want to learn how to taste wine properly and eat dinner in the same evening without arranging the experience yourself — the sommelier and the villa handle both, and the pairing between the two makes each one better.
2 to 5 hours (5)
Chianti Winery Tour & Vineyard Picnic with WineYou'll tour the vineyards and cellar at your own pace, taste wine in a cozy setting overlooking the vines, and eat a picnic of homemade Tuscan food with a bottle of wine included. The private format means no group timing, and you can skip the tour part if you'd rather go straight to eating.Is it for me?Pick this if you want to taste Chianti wine where it's made without the logistics of arranging transport, finding a restaurant, or sitting in a crowded tasting room—the private setup and included picnic basket handle all three at once.
Montalcino: Brunello Wine Tasting & Tuscan Lunch TourYou get picked up from your hotel, driven through Montalcino's vineyards to three different estates, guided through cellars and vines, taste Brunello in two separate tastings, and sit down to a four-course Tuscan lunch with wine pairings—all in five hours, with the driver handling the route and the timing so you don't have to.Is it for me?Book this if you want to understand Brunello without arranging transport, cellar access, or timing between estates—the five-hour structure and fixed schedule handle all three, leaving you free to actually taste and listen.
Chianti: Etruscan Winery, 4-Course Lunch & Wine TastingYou tour an ancient Etruscan cellar and learn how the winemakers select grapes and manage fermentation; then sit down to a four-course lunch where each dish pairs with one of six regional wines made on-site. Vegetarian options and allergy accommodations are available if you specify them at booking. Public transport reaches the location, and the experience is shared with a small group rather than private.Is it for me?Book this if you want to understand how Chianti wine is actually made—not just taste it—and eat a proper meal in the place where it happens, without arranging transport or navigating a crowded tasting room.
Montalcino: Pasta Class, Wine Tasting & Sunset DinnerYou arrive at a Montalcino winery in the late afternoon, learn to hand-roll pinci pasta from scratch, tour the wine cellar with your guide, then sit down at sunset for a three-course dinner paired with four regional wines including Brunello di Montalcino. The experience includes round-trip pickup from the meeting point in town, an air-conditioned minivan, and a multilingual guide who stays with you through the whole evening.Is it for me?Book this if you want to cook something with your hands, taste serious wine, and eat dinner in a real place where the producer sits at your table — the small group size and fixed timing are what make an evening in a working winery feel personal instead of rushed.
Chianti: E-Bike Tour & Wine Tasting with SommelierYou ride electric bikes through Chianti's vineyards and olive groves between Florence and Siena, stopping at medieval villages along the way. A sommelier guides you through a tasting at a historic winery, explaining the wines and the region's terroir. The tour includes helmet, bike use, and the tasting itself, so you show up and ride.Is it for me?Right for anyone who wants to see Chianti's landscape without renting a car or planning stops—the e-bike pace lets you absorb the hills, and the sommelier tasting replaces the guesswork about which wine to try and why.
Half day and longer (1)
Montalcino Wine Tour: Brunello Tasting & Tuscan LunchYou spend nine hours moving between four Montalcino wineries, tasting Brunello di Montalcino at each one with a guide who explains what you're drinking. Lunch is a four-course meal at a historic villa with wine pairings, followed by a cellar visit. Transport, snacks, and all entry fees are included, and you return to Montalcino by 7pm.Is it for me?Book this if you want to taste Brunello di Montalcino at multiple producers without arranging transport, timing, or cellar access yourself — the fixed itinerary and included lunch mean you spend the day learning about the wine instead of organizing logistics.
Chianti Wine Tour — what to know before booking
This guide compares 20 bookable options for Chianti Wine Tour, with up-to-date prices and real traveler reviews. Prices start at € 35. The average rating is 4.8 out of 5, based on 560 traveler reviews.
Most options last up to 2 hours. 16 of the 20 options offer free cancellation. 3 private experiences are also available for closed groups. The verdict at the top highlights the travelers' favorite, the best price and the top-rated option, updated with live data.
Frequently asked questions
How much does Chianti Wine Tour cost?
Prices start at € 35. There are 20 options to compare, and the final price depends on the date, group size and the option you choose.
Can I book with free cancellation?
Yes: 16 of the 20 options offer free cancellation, so you can book now and confirm your plans later.
How long do these experiences last?
Most options last up to 2 hours. There are also shorter and longer formats to fit your itinerary.
Which one is the travelers' favorite?
Chianti Classico: Organic Winery Tour & Wine Tasting is the travelers' favorite, rated 4.9 out of 5 across 135 reviews.
Are private options available?
Yes, 3 private experiences are available if you prefer a closed group.
