The 15 Best Vineyard Tours in Italy

1-Day Tours, Florence Vineyard Tours, Italy Vineyard Tours, Lunch Experiences, Tour Reviews, Vineyard Tours, Wine Country Day Trips, Wine Country Day Trips in Florence, Wine Country Day Trips in Italy

Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery

1.Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery

★★★★★★★★★★5.0 · 21,634 reviews · 11 to 12 hours (approx.) · from $114Our pick

Travel by air-conditioned coach from Florence to Siena, San Gimignano, Pisa, and a Chianti winery. You’ll tour Siena Cathedral, enjoy free time in three towns, and can add a farmhouse lunch with four wine tastings and a Leaning Tower climb.

“We went on this day trip during our honeymoon in October 2025. This excursion was an outstanding experience thanks to our tour guide, Giancarlo. He was engaging, informative, funny, and knowledgeable. Siena, San Gimignano, Pisa, and lunch at the winery were beautiful. It is a long day so be sure to dress comfortably. This day trip was one of the highlights of our trip. We highly recommend going on this tour.”

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Florence: Chianti Wineries Tour with Wine Tasting

2.Chianti Wineries Tour with Wine Tasting

★★★★★★★★★★4.5 · 10,071 reviews · 5 - 5.5 hours · from $41

Travel from Florence to two Chianti wineries by comfortable GT bus, meet local producers, walk through vineyards, and taste three to four wines at each stop. Guides such as Ana, Alex, Martina, and John add local context, while cheese, salami, olive oil, bread, and balsamic vinegar round out the tastings.

“Both wineries were beautiful and had excellent tastings. Both also offered the option to ship wines if you decided to purchase any. Emma and the driver (sorry I forgot his name) made the trip fun and informative. Both of them handled traffic well and kept us on schedule.”

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From Florence: Siena, San Gimignano, Pisa & Lunch at Winery

3.Siena, San Gimignano, Pisa & Lunch at Winery

★★★★★★★★★★4.8 · 4,538 reviews · 12 hours · from $112

Join guides such as Sara, Alessandro, or Giancarlo for a full day through Tuscany. Walk Siena’s medieval center, taste four wines over a farmhouse lunch in Chianti, explore San Gimignano, and finish beside Pisa’s Leaning Tower. Choose the lunch and tower-entry options carefully.

“The pace was perfect. We were able to see a variety of the cities and countryside, without rushing. Our guide, Gabriel, did a great job and our driver, Domenico, was fantastic as well. Lunch was pasta, and some appetizers, which were tasty. Will recommend to all our friends!”

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Half day Chianti Vineyard Escape from Florence with Wine Tastings

4.Half day Chianti Vineyard Escape from Florence with Wine Tastings

★★★★★★★★★★4.5 · 2,196 reviews · 5 hours (approx.) · from $53

Ride from Florence to two Chianti estates with an English-speaking guide, taste three to four wines at each, sample olive oil, cheese, and balsamic vinegar, and tour vineyards and cellars. Guides such as Alex, Lorenza, and Cecilia have led especially engaging outings, though groups can reach 43 people.

“We had a great time. Our tour guide Cecilia, was charming and informative. The two wineries were different from each other, so it was interesting. Great driver too.”

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Tuscany Wine Tour: 2 Wineries & San Gimignano from Florence

5.Tuscany Wine Tour: 2 Wineries & San Gimignano from Florence

★★★★★★★★★★5.0 · 1,007 reviews · 7 hours (approx.) · from $229

Leave Florence at 10am for two winery visits, guided tastings of Chianti, Vernaccia, rosé, and more, plus olive oil and balsamic pairings. Your guide drives the scenic Chianti Road, then gives you 90 minutes to explore San Gimignano before returning around 5pm.

“The communication, and experience as a whole was excellent. Emanuele was superb and the two different wine experiences made it even more enjoyable. The views, amazing and finishing off at San Gimignano was a delight being able to have some free time to venture out.”

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From Florence: Private Chianti Hills Tour with Tasting

6.Private Chianti Hills Tour with Tasting

★★★★★★★★★★4.3 · 809 reviews · 6 hours

Spend six hours in Chianti with a guide and minivan, stopping at two wineries and a wine shop in Radda. Taste six local wines with olive oil, cheeses, bread, and cured meats, then stroll Radda’s lanes. Hotel pickup may be requested in central Florence.

“It was fantastic. We had a great time. The wine were great, the views, Marina and Luigi... Overall a wonderful time discovering Chianti and its wine.”

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Chianti Wineries Tour with Tuscan Lunch and San Gimignano

7.Chianti Wineries Tour with Tuscan Lunch and San Gimignano

★★★★★★★★★★5.0 · 793 reviews · 8 hours (approx.) · from $229

Spend about eight hours visiting two Chianti wineries, tasting local wines, sharing a Tuscan lunch, and exploring San Gimignano. Guides such as Lorenzo, Daniel, Christian, and Cecilia are praised for their warmth and local stories, while the group size is capped at 16.

“Tour was excellent! Daniel the tour guide was the best, he explained everything, took pictures, played great car music & so polite. Wineries were amazing, breads, cheeses, meats, vegetables & the best pasta we ever ate, so much delicious wine & food.”

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Private Self-Guided E-Bike Ride in Tuscany with Vineyard Visit

8.Private Self-Guided E-Bike Ride in Tuscany with Vineyard Visit

★★★★★★★★★★5.0 · 775 reviews · 4 to 7 hours (approx.) · from $96

Set out from central Florence with John’s e-bike team, then follow a GPS route through Fiesole, olive groves, forest roads, and Tuscan hills to a boutique vineyard. Wine, food, and tastings cost extra. You ride independently, so solid bike skills and comfort with traffic are essential.

“This was brilliant. Easy to follow and exceptionally beautiful route. The bikes give as mush assistance as you want and worked well. Lovely accommodating host who gives a great explanation of everything to expect on bike ride.”

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Florence: Chianti Wine Region Vespa or Fiat Topolino Tour

9.Chianti Wine Region Vespa or Fiat Topolino Tour

★★★★★★★★★★4.8 · 739 reviews · 6 - 6.5 hours

Join an English-speaking guide such as Niccolo, Julia, Yo, or Heather for a 6 to 6.5-hour Chianti outing from Florence. Ride a 50cc Vespa on quiet paved roads, or choose the electric Fiat Topolino. Stop in medieval villages, visit a winery, and enjoy lunch with wine and olive oil.

“Overall, the experience was great! Riding the vespa around the countryside was great! Yhe sightseeing was absolutely incredible! The tour guides were helpful with teaching you how to safely ride the vespa, and kept you safe on the road by having one guide in the front of the pack and another at the back. You got to ride the vespa long enough to really enjoy the experience. It was also really nice being able to have a little free time in Greve to shop around and enjoy a little break! That was an unexpected surprise! The wine tasting olive oil tasting and lunch was really nice! The lunch was simple,…”

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Milan Urban Winery: Taste & Tour at Cantina Urbana

10.Milan Urban Winery: Taste & Tour at Cantina Urbana

★★★★★★★★★★4.7 · 683 reviews · 1.5 hours · from $47

At Cantina Urbana Milano, a sommelier leads you through a small city winery, wooden barrels, terracotta amphorae, and steel tanks. Taste four or six house wines with local food, and hear guides such as Andrea, Irene, Francesco, and Nello explain how each bottle is made.

“Fantastic experience. We really enjoyed it. Our guide Andreas was fun friendly and informative. The wines were delicious as was the accompanying food. I would definitely recommend this tour. Great value and a fun way to spend an evening Thank you Urban Cantina 😊”

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Lucca: Guided Winery Tour with Wine Tasting

11.Lucca: Guided Winery Tour with Wine Tasting

★★★★★★★★★★4.7 · 611 reviews · 1.5 hours · from $29

At Tenuta Adamo, tour the cellar for about 20 minutes, then taste local wines and extra virgin olive oil on a hilltop terrace above the vineyard. English-speaking hosts such as Lisa, Julia, Luisa, and Antonio explain the wines in a friendly shared setting. Breadsticks are included, with optional food platters.

“Definitely recommend! All the wines were so different from each other. A very good variety.”

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Tuscany Wine Tour : 2 Wineries & San Gimignano from Florence

12.Tuscany Wine Tour : 2 Wineries & San Gimignano from Florence

★★★★★★★★★★4.8 · 594 reviews · 7 hours · from $201

Leave Florence at 10:00 for two contrasting Chianti wineries, tasting up to seven wines, olive oil, balsamic, and local foods. Your English-speaking guide, perhaps Dom, Valentina, or Alessandro, handles the roads while you enjoy the countryside and 1.5 hours in San Gimignano.

“The stop at Tenuto Torciano winery was the highlight of the trip. The experience was excellent as we're the wines. we bought four bottles to enjoy back at home.”

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Montepulciano: Wine Tasting and Cellar Tour

13.Wine Tasting and Cellar Tour

★★★★★★★★★★4.8 · 545 reviews · 1 hour · from $38

In central Montepulciano, an English or Italian guide such as Emilio, Debi, Mirko, or Ron leads you through historic underground cellars before a tasting of five DOC and DOCG wines, pecorino, bruschetta, olive oil, and crostini.

“This is my favorite winery! Such rich history and amazing to see. The wine is amazing and the tasting was a lot of fun. So happy they ship the wine now. This is a must do tour.”

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Olbia: Gallura Winery Guided Tour with Tasting

14.Olbia: Gallura Winery Guided Tour with Tasting

★★★★★★★★★★4.7 · 451 reviews · 1.5 hours · from $61

At family-run Cantina Murales near Olbia, guides such as Greta and Arianna lead you through the vines, winery, and barrel cellar. You will taste three local wines with Sardinian snacks, then meet the rescued donkeys, goats, chickens, ducks, and dogs on the property.

“The vineyards are absolutely beautiful. our guide, Greta was informative, friendly and knowledgeable. I have never done a wine tasting experience previously but I really believe that any others I do will be disappointing compared to this one. I highly recommend 👌 ☺️”

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Private 6-Hour Tour of Three Etna Wineries with food&wine tasting

15.Private 6-Hour Tour of Three Etna Wineries with food&wine tasting

★★★★★★★★★★5.0 · 417 reviews · 6 hours (approx.) · from $375

Spend six hours visiting three Etna wineries with a private driver-guide such as Marco, Massimo, Alessandro, or Bruno. Taste reds, whites, rosés, and dessert wine with Sicilian food, while passing lava-stone villages, citrus groves, and views of Mount Etna.

“Great day out worth the money Carmelo our sommelier/ driver was very informative The wineries we visited were great hosts serving us amazing wines and beautiful food to complement”

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