Wine Tasting Experiences

TUSCANY

10 Best Wine Tasting Experiences In Tuscany

Tuscany's standouts.

The 10 wine tasting experiences travellers book most often across Tuscany. Each one with the price you pay, the operator behind it and the day you actually get when you turn up.

10 Best Wine Tasting Experiences In Tuscany

Florence: Chianti Wineries Tour with Wine Tasting

Florence: Chianti Wineries Tour with Wine Tasting - Piazzale Montelungo Meeting Point: Easy to Find, Close to the Action

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

Rome: Tuscany & Montepulciano Day Trip with Lunch & Wine Tasting - Tempio di San Biagio: Renaissance architecture you can spot right away

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

4.5

Rome to Tuscany for Montepulciano, Pienza, and Val d’Orcia views, plus a Tuscan farm lunch with wine tasting incl. Brunello.

“The lunch was mediocre at best. 5 measly sips of wine. Probably one glass of wine total. They really needed to have some bottles in the tables. The drive itself was nice and the tour guide was great.”

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

SMALL-GROUP Wine Safaris: Tuscan Wine Tasting Tours from Florence - Val d’Orcia for Brunello and Montepulciano: A Longer Day With Two Big Reds

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

5.0

Off-road Tuscan wine safaris from Florence with 4WD vineyard drives, expert tastings, olive oil, and a real farm lunch or dinner.

“This was a fun experience. Tony was a great guide and gave us enough information but not too much. I would recommend for anyone looking for a nice way to spend an evening.”

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Chianti Wine Tour from Florence

Chianti Wine Tour from Florence - First Winery Stop in Chianti Classico: Organic, Cozy, and Food-Forward

4.Chianti Wine Tour from Florence

4.5

Two organic Chianti wineries, expert-led tastings, and Via Chiantigiana views from Florence. Food included and you can buy bottles home.

“Very organized wineries. They had everything prepared for our visit and gave us all the important information. Beautiful landscapes and friendly staff.”

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From Florence: Small Group Wine Tasting Tour to Tuscany

From Florence: Small Group Wine Tasting Tour to Tuscany - The Minibus Ride: Views, Stories, and Why Small Groups Matter

5.From Florence: Small Group Wine Tasting Tour to Tuscany

4.9

Small-group wine and olive oil tasting from Florence to Chianti Classico, visiting 2 estates with food pairings and cellar tours.

“The tour was fantastic. Having a small group of people meant that we got to easily hear the people explaining how they made the wine. When we all sat down to taste, it was quiet enough that we could all talk unlike a very large group. The vineyards they picked were all delicious in historical.…”

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

From Florence: San Gimignano, Siena, and Chianti Wine Tour - Fortezza Medicea stop: the small walk that sets the tone

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

4.5

Tuscany day trip from Florence with Siena, Chianti wine tastings and lunch, plus San Gimignano towers. Small-group transport and 5 wines.

“Amazing small group tour! We saw so much and we loved that we were able to walk around by ourselves instead of being stuck in a tourgroup. The only small negative we have is that we wished we had a little bit more time in Siena. We had wished to see more of the city!”

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

Florence: S. Gimignano, Siena, Chianti & Wine Tasting Lunch - Getting From Florence: Piazzale Montelungo and the Bus Rhythm

7.Florence: S. Gimignano, Siena, Chianti & Wine Tasting Lunch

4.6

Florence day trip to San Gimignano and Siena UNESCO sites plus a Chianti winery lunch with three wine tastings and optional cathedral entry.

“Nice charter bus, knowledgeable, fun guide, amazing sites with time to see and buy gifts. We loved our lunch and wine tasting and we bought a couple bottles of wine. We met many fun people and would recommend this tour.”

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Half day Chianti Vineyard Escape from Florence with Wine Tastings

Half day Chianti Vineyard Escape from Florence with Wine Tastings - The big coach reality: group size, walking, and comfort

From Florence: Chianti Wine Tour with Tastings

From Florence: Chianti Wine Tour with Tastings - Two winery stops in one half-day: why this format works

9.From Florence: Chianti Wine Tour with Tastings

4.4

Half-day Chianti wine tour from Florence with two wineries, ancient cellars, Chianti tastings, pecorino snacks, and scenic Chianti roads.

“Everything went great. The first winery was small, cozy, and overall it was not bad. The second winery was simply the best part. An interesting and funny employee who told us about wine and all the processes. He joked with us, let us try many of his products. He answered all the questions. The tour…”

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Tuscany Wine Tour: 2 Wineries & San Gimignano from Florence

Tuscany Wine Tour: 2 Wineries & San Gimignano from Florence - Winery stop one: the Chianti-region tasting school experience

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

5.0

Florence to Chianti and San Gimignano in 7 hours: tastings at 2 wineries, oil and vinegar, plus 1.5 hours in the medieval town.

“Amazing day with Valentina, who provided great information not only about our tour, but for other aspects of my trip. The vineyards and wine were excellent and the time in San Gimignano was a fun side quest. Fun day that was the perfect amount of time.”

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