Italy · WINE TASTINGS & VINEYARD TOURS

The 15 Best Wine Tastings & Vineyard Tours in Italy

126 tours  ·  ★★★★★★★★★★ 4.7 average  ·  from $52

Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery - Siena Cathedral and Piazza del Campo, Where the Art Has a Reason
1-Day Tours, Day Trips from Florence, Florence Tours, Lunch Experiences, Pisa Tours, Tour Reviews, Tuscany Countryside Day Trips, Wine Tastings & Vineyard Tours, Wine Tastings in Florence, Wine Tastings in Pisa, Wine Tours

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

Florence: Pisa, Siena, San Gimignano, and Chianti Experience - Meeting Point: Santa Maria Novella, Then a Smooth Start
Florence Tours, Pisa Tours, Tour Reviews, Tuscany Countryside Day Trips, Wine Tastings & Vineyard Tours, Wine Tastings in Florence, Wine Tastings in Pisa

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

A full day loop through Pisa, San Gimignano, Siena, and Chianti with optional Pisa tickets, a Siena guide, and wine-lunch.

“I enjoyed every moment of this tour. Barbara is an amazing guide and told us everything about the places we visited and where to find the best gelato and coffee (and bathrooms😅). For the Siena tour, Chiara was an amazing tour guide and the lunch at Poggio Ai Laghi was paired with some of the best wines I tasted. The whole tour was an amazing experience and I recommend it to anyone who wants to see the highlights, just so they can visit those places by themselves again and fully enjoy everything about Toscana.”

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Florence: Chianti Wineries Tour with Wine Tasting - First cantina: Chianti Classico, barrels, and your first tasting flight
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Florence: Chianti Wineries Tour with Wine Tasting

Small-Group Wine Tasting Experience in the Tuscan Countryside - Stop 1: The first Chianti Classico winery and your olive-oil tasting
Florence Tours, Food & Drink, Tour Reviews, Tuscany Countryside Day Trips, Wine Tastings & Vineyard Tours, Wine Tastings in Florence, Wine Tours

Small-Group Wine Tasting Experience in the Tuscan Countryside

Rome: Tuscany & Montepulciano Day Trip with Lunch & Wine Tasting - Val d’Orcia stop: where the views start doing the talking
1-Day Tours, Food & Drink, Lunch Experiences, Rome Tours, Tour Reviews, Tuscany Countryside Day Trips, Wine Tastings & Vineyard Tours, Wine Tastings in Rome, Wine Tours

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

Rome to Montepulciano and Pienza with Tuscan farm lunch, wine tastings, and Val d’Orcia views by air-conditioned coach.

“It was such a beautiful and lovely tour. Our tour guide is Anna and the driver is Luca. They make such a great team! We love all the places included in the tour. Food and drinks were excellent.”

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SMALL-GROUP Wine Safaris: Tuscan Wine Tasting Tours from Florence - Chianti Classico full-day: two villas, cellars, and off-road photo breaks
Day Trips from Florence, Florence Tours, Food & Drink, Tour Reviews, Tours, Tuscany Countryside Day Trips, Wine Tastings & Vineyard Tours, Wine Tastings in Florence, Wine Tours

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

Go off-road from Florence into Chianti or Val d’Orcia for guided tastings, olive oil and cheese stops, and a classic Tuscan meal.

“Gloria and Roberto were amazing guides. Not only were the wineries diverse, but the knowledge shared was informative and interesting. Gloria also took the time to answer questions and ‘get to know the group’. Roberto was a smooth and careful driver.”

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From Florence: Siena, San Gimignano, Pisa & Lunch at Winery - Siena Walking Tour: Duomo, Piazza del Campo, and That Old-Bank Detail
Day Trips from Florence, Florence Tours, Lunch Experiences, Pisa Tours, Tour Reviews, Tuscany Countryside Day Trips, Wine Tastings & Vineyard Tours, Wine Tastings in Florence, Wine Tastings in Pisa, Wine Tours

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

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

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

Full-day Tuscany tour from Florence: guided Siena, Chianti winery lunch and wine tastings, San Gimignano towers, Pisa sights and Leaning Tower.

“Sara was informational and warm. Our guide in Sienna was helpful to understanding the local art and history. Enjoyed the friendly rivalry between Florence and Sienna. While we felt hurried, each stop was just the right amount of time. Each site felt like a day unto itself.”

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San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting - The coach ride: comfortable, but plan for a long day
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San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting

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

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

11-hour Tuscany day trip from Florence with San Gimignano towers, Chianti winery lunch and wine tasting, and guided Siena highlights.

“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 - Pisa at the Field of Miracles, what you get and what to plan
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Florence: Pisa, Siena, S. Gimignano, Chianti Wine & Lunch

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

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

Florence day trip to Pisa, Siena, San Gimignano, and Chianti hills with optional guided walks and lunch with wine pairing.

“Great way to see the Tuscany region if you are pressed for time. Good coverage of key regions and take up the lunch offer as the wine tasting and paring of local produce is a great way to understand the beauty of the region.”

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Chianti Wine Tour from Florence - Meeting at Piazzale Montelungo, then leaving the city for good
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Chianti Wine Tour from Florence

10.Chianti Wine Tour from Florence

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

Chianti wine tour from Florence with two organic wineries on the Via Chiantigiana, guided tastings, Tuscan bites, and scenic views.

“Very nice wines and a small bit of food. 3 wines in each place, mainly red wine which is what the area is known for. Guides were very nice and knowledgable, would recommend”

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From Florence: Small Group Wine Tasting Tour to Tuscany - Getting from Piazzale Montelungo to the Chianti Classico hills
Day Trips from Florence, Florence Tours, Food & Drink, Food Tours, Food Tours in Florence, Tour Reviews, Tours, Tuscany Countryside Day Trips, Wine Tastings & Vineyard Tours, Wine Tastings in Florence, Wine Tours

From Florence: Small Group Wine Tasting Tour to Tuscany

11.Small Group Wine Tasting Tour to Tuscany

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

Small-group Chianti tasting from Florence with 2 renowned estates, 6 wine and olive oil samples, and Tuscan bites in under 5 hours.

“Rapha and Sergio provided a friendly and informative tour out to two Chianti wineries in a comfortable bus. The Tuscan landscape and villas dotted around the hills did not disappoint, and the wines were paired with generous antipasto plates. Great tour with fellow travellers from all over the world. Five out of five stars.”

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From Florence: San Gimignano, Siena, and Chianti Wine Tour - How the Tuscany drive actually feels: air-conditioned and time-blocked
Day Trips from Florence, Siena Tours, Tour Reviews, Tours, Tuscany Countryside Day Trips, Wine Tastings & Vineyard Tours, Wine Tastings in Siena, Wine Tours

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

Rome Food Tour: Unlimited Tastings with Fine Wine & Barolo - Price and pacing: what $83.44 actually buys you
Food, Food & Drink, Food Tours, Rome Food Tours, Rome Tours, Tour Reviews, Tours, Wine Tastings & Vineyard Tours, Wine Tastings in Rome, Wine Tours

Rome Food Tour: Unlimited Tastings with Fine Wine & Barolo

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

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

Rome’s Prati food tour with 20 tastings, fine wine and Barolo flavors, small group, truffles, pizza, pasta, gelato in 4 hours.

“This is a great tour. Our guide, Jordano knew everything about our different foods and wines. He was energetic, enthusiastic, and a generally great guy to tour either way. The good and wine choices were well thought-out and presented. Make sure you come hungry!”

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Siena, San Gimignano and Chianti Wines Day Tour from Florence - Monteriggioni: quick hilltop fortress time, photos included
Day Trips from Florence, Florence Tours, Tour Reviews, Tours, Tuscany Countryside Day Trips, Wine Tastings & Vineyard Tours, Wine Tastings in Florence, Wine Tours

Siena, San Gimignano and Chianti Wines Day Tour from Florence

Sorrento Farm and Food Experience including Olive Oil, Limoncello, Wine tasting - Tastings That Make Sense: olive oil, limoncello, honey, and more
Amalfi Coast & Sorrento Tours, Dining Experiences, Farms, Food, Food & Drink, Limoncello Experiences, Tour Reviews, Wine Tastings & Vineyard Tours, Wine Tours

Sorrento Farm and Food Experience including Olive Oil, Limoncello, Wine tasting

15.Sorrento Farm and Food Experience including Olive Oil, Limoncello, Wine tasting

★★★★★★★★★★5.0 · 2,524 reviews · 4 hours (approx.) · from $114

Farm-to-table fun above Sorrento with olive oil, limoncello, wine tastings, and a guided walk through olive and lemon groves.

“This beautiful sunlit family own farm is special. Carved into a hill and is harvesting multiple crops- not just lemons. Family style lunch made from scratch and a great tour of the 12 acre land, divided into terraces.”

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