Wine Tasting in Italy: The 15 Best Cellar Visits

Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery - A Tuscan Farm Lunch at Fattoria Poggio Alloro

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

Review of a full-day Tuscany tour from Florence to Siena, San Gimignano, Pisa, and a Chianti winery lunch with wine tasting.

“The day was great! Our tour guide was absolutely amazing! He even helped me find my phone when it went missing! The tour is perfectly described on the Viator app as to what you will do for the day. Personally all in our group said if we did it again we wouldn’t go to Pisa and would have really wanted to stay longer in the other two towns. The wine tasting and lunch is an absolute must!!”

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Florence: Pisa, Siena, San Gimignano, and Chianti Experience

2.Pisa, Siena, San Gimignano, and Chianti Experience

★★★★★★★★★★4.5 · 8,393 reviews · 12 hours · from $52Best value

See Pisa, San Gimignano, Siena, and Chianti in one full day from Florence, with optional Siena guiding, tower tickets, lunch, and wine tasting.

“We loved the activity, but the change in plans made us think we weren’t going to like the activity, as our main reason to going to Siena was pilgrimage and we arrived very early and many churches were closed. However, the experience was amazing. The destinations, the group we found and continued being friends for the rest of the stops, was EXCELLENT! The tour guide in the winery (Davide) was great, our bus driver was so nice and the tour guide knew a lot. Very much recommended”

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Florence: Chianti Wineries Tour with Wine Tasting

3.Chianti Wineries Tour with Wine Tasting

★★★★★★★★★★4.5 · 8,301 reviews · from $56

Tour two Chianti wineries from Florence, taste up to seven wines, sample Tuscan foods, and enjoy rolling vineyard views in half a day.

“Tour was amazing. The transportation was easy and accessible to find. The guide was informative throughout the whole ride there. Our favorite part were the two wineries. We loved our experience and would want to book again!”

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Small-Group Wine Tasting Experience in the Tuscan Countryside

4.Small-Group Wine Tasting Experience in the Tuscan Countryside

★★★★★★★★★★5.0 · 7,392 reviews · 4 hours 45 minutes (approx.) · from $107

Compare two Chianti wineries on a scenic half-day trip from Florence, with wine, olive oil, Tuscan specialties, and a small-group setting.

“We had a great guide. The two winery visits included just enough time to enjoy what they had to offer and company of the participants. There were only eleven of us!”

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1-Day Tours, Food & Drink, Lunch Experiences, Rome Tours, Tour Reviews, Wine Tastings, Wine Tastings in Rome

Rome: Tuscany & Montepulciano Day Trip with Lunch & Wine Tasting

5.Tuscany & Montepulciano Day Trip with Lunch & Wine Tasting

★★★★★★★★★★4.5 · 5,232 reviews · 12 hours (approx.) · from $83

Trade Rome for Montepulciano and Pienza on a 12-hour Tuscany day trip with a farm lunch, regional wines, and Val d'Orcia views.

“It was extremely educational and the lunch and wine tasting was quitr worth it. Only dad part was that in the off season (winter) all the shops and stores are closed.”

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SMALL-GROUP Wine Safaris: Tuscan Wine Tasting Tours from Florence

6.SMALL-GROUP Wine Safaris: Tuscan Wine Tasting Tours from Florence

★★★★★★★★★★5.0 · 5,088 reviews · 7 to 9 hours (approx.) · from $157

Ride off-road through Chianti or Val d’Orcia, taste top Tuscan wines, tour old cellars, and enjoy a farm-fresh meal from Florence.

“Guide was informative and fun. The wines were good as was the food served. The grounds and estate were lovely. Met lovely people from across the world and had great conversations. Only adults on this tour but they were of all ages. Highly recommend”

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Evening Experiences, Florence Tours, Food, Food & Drink, Tour Reviews, Tours, Wine Tastings, Wine Tastings in Florence

Winner 2025 Florence Sunset Food & Wine Tour by Eating Europe

7.Winner 2025 Florence Sunset Food & Wine Tour by Eating Europe

★★★★★★★★★★5.0 · 5,015 reviews · 3 hours 30 minutes (approx.) · from $149

Taste Tuscan wines, Negroni, pasta, cheese, soup, wild boar, and artisan gelato on a lively 3.5-hour Florence evening walk.

“Dimitri, our guide, grew up in the neighborhood and was superb. The food was at old generational establishments and local specialties, refreshingly not the touristy list. The drink list and exposure/education alone was worth the price. Thank you!”

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Florence Tours, Lunch Experiences, Tour Reviews, Wine Tastings, Wine Tastings in Florence

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

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

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

See Siena, San Gimignano, Pisa, and Chianti in one full day from Florence, with a winery lunch, wine tasting, and expert guides.

“Our guide, Ginnie, was excellent. She kept the tour group on time, informed, and was personable with a good sense of humor. Tour was organized well and interesting.”

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San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting

9.San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting

★★★★★★★★★★4.5 · 4,432 reviews · 11 hours (approx.) · from $83

Review of a full-day Tuscany tour from Florence covering San Gimignano, Monteriggioni, Siena, Chianti wine, lunch, costs, and practical tips.

“It feels very rushed in last portion of tour. We had a guide that walked entirely too fast and our chronic knee and back pain were exacerbated trying to keeep up. Guided tour wasn’t really necessary… save yourself the expense. Meal was delicious! We thoroughly enjoyed San Giiagmano wish it was longest stay of tour.”

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Florence: Pisa, Siena, S. Gimignano, Chianti Wine & Lunch

10.Pisa, Siena, S. Gimignano, Chianti Wine & Lunch

★★★★★★★★★★4.6 · 4,354 reviews · 12 hours · from $77

See Pisa, San Gimignano, Siena, and Chianti in one full day from Florence, with a Tuscan lunch, wine tasting, and guided Siena walk.

“This tour is worth every penny, it’s an entire day of visiting beautiful places and making memories. Our guide Sandro is very knowledgeable and friendly”

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Chianti Wine Tour from Florence

11.Chianti Wine Tour from Florence

★★★★★★★★★★4.5 · 3,979 reviews · 5 hours (approx.) · from $59

Review of the 5-hour Chianti wine tour from Florence, with two wineries, Tuscan tastings, scenic coach travel, practical tips, and honest drawbacks.

“The tour was worth it from beginning to end. The scenery, the trip up the mountain and through the villages, the wine tasting and explanations with the hors d'oeuvres, and the views are Unforgettable.”

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From Florence: Small Group Wine Tasting Tour to Tuscany

12.Small Group Wine Tasting Tour to Tuscany

★★★★★★★★★★4.9 · 3,902 reviews · 4.5 hours · from $105

Taste Chianti wines, olive oils, and Tuscan specialties at two wineries on a relaxed half-day trip from Florence.

“So much fun with driver and tour lead! Such a great time”

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From Florence: San Gimignano, Siena, and Chianti Wine Tour

13.San Gimignano, Siena, and Chianti Wine Tour

★★★★★★★★★★4.5 · 3,762 reviews · from $164

Explore Siena, Chianti, and San Gimignano from Florence with wine, Tuscan lunch, free time, and an air-conditioned ride.

“12 hours very well splited which led to beautiful memories. We were lucky to have Marta as a guide. She shared with us the history of the region and some old legends. Sienna, Colle di Val d’Elsa and San Gimignano worth for sure spending more than one day to feel them.”

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Food, Food & Drink, Food Tours, Food Tours in Rome, Rome Tours, Tour Reviews, Tours, Wine Tastings, Wine Tastings in Rome

Rome Food Tour: Unlimited Tastings with Fine Wine & Barolo

14.Rome Food Tour: Unlimited Tastings with Fine Wine & Barolo

★★★★★★★★★★5.0 · 3,365 reviews · 4 hours (approx.) · from $83

Taste up to 20 Roman specialties in Prati, from truffles and Barolo to pizza, pasta, wine, and gelato, on a four-hour food walk.

“The wine and food were great and Tina was so knowledgeable and fun to be with. There was quite a bit of walking but we never felt rushed. All said it was a very fun experience.”

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Siena, San Gimignano and Chianti Wines Day Tour from Florence

15.Siena, San Gimignano and Chianti Wines Day Tour from Florence

★★★★★★★★★★4.5 · 2,542 reviews · 10 hours 30 minutes (approx.) · from $78

Explore Siena, San Gimignano, Monteriggioni, and Chianti on a full-day Florence tour with guided sightseeing, free time, and wine tasting.

“We had a great time on this tour! Very well organized and packed in a lot of sites for a fun day! The guides were very friendly and there were many add ons to really customize the experience.”

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