Where to drink · ITALY

The 15 Best Wine Tastings & Drinks Tours in Italy

143 tours  ·  from $18 a head

Chianti in the south of Tuscany, Prosecco on the ridges above Venice, Barolo in the Piedmont fog, limoncello on the Amalfi coast. These 15 sort the Italian tasting days by region, price and how much of each one is lunch.

Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery - Siena begins with banking, rival neighborhoods, and Piazza del Campo
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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

From Florence, visit Siena with a local guide, admire its marble cathedral, eat and taste wine at Fattoria Poggio Alloro, wander San Gimignano, and finish at Pisa’s Square of Miracles. The $114.88 tour lasts 11 to 12 hours and offers a Leaning Tower upgrade.

“Unreal. Go on this. All I have to say. With my boys and having the best time. The tour hasn’t even finished and I wanna come back!”

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Florence: Chianti Wineries Tour with Wine Tasting - Meeting the coach near Santa Maria Novella
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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 $41Best value

Ride from Florence to two contrasting Chianti wineries with an English-speaking guide such as Ana, Alex, or John. Tour vineyards and cellars, taste up to seven wines with cheese, salami, olive oil, and bread, then return by comfortable coach in about five hours.

“James Is our guide on the boat Thank you very much”

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Small-Group Wine Tasting Experience in the Tuscan Countryside - First winery: vineyard, cellar, and three wines
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Small-Group Wine Tasting Experience in the Tuscan Countryside

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

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

Leave Florence from Piazzale Montelungo for two Chianti Classico wineries. Your English-speaking guide, such as Leo, Jonathan, Matteo, or Leonardo, leads tastings of regional reds, olive oil, cheese, cured meats, and bruschetta. Expect a social half-day with fine views and time to shop.

“Leonardo was a wonderful guide, so knowledgeable and so kind, the wineries were exquisite! Would highly recommend this tour!”

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Rome: Tuscany & Montepulciano Day Trip with Lunch & Wine Tasting - What the coach ride adds, and what it costs
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Rome: Tuscany & Montepulciano Day Trip with Lunch & Wine Tasting

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

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

Travel from Rome to Montepulciano and Pienza by air-conditioned coach, with a guided hill-town walk, Tuscan farm lunch, regional wine tasting, and free time for pecorino, photos, and gelato. Guides such as Anna, Barbara, and Antonino have earned praise, though the wine pours and free time can feel limited.

“It was a long day. The towns visited were nice and pleasant. Worth the trip. Just be aware the food at the selected restaurant leaves alot to be desired. I would suggest bring along some food to eat. Be sure to utilize bathrooms when you can as both towns it was difficult to find public restrooms (which is normal in Europe). The tour guide was very pleasant and communicative.”

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SMALL-GROUP Wine Safaris: Tuscan Wine Tasting Tours from Florence - Val d’Orcia: Brunello, Pienza, and Montepulciano
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SMALL-GROUP Wine Safaris: Tuscan Wine Tasting Tours from Florence

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

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

Leave Florence with an English-speaking wine expert and explore Tuscany by air-conditioned 4x4. Choose Chianti or Val d’Orcia, taste wine, olive oil, cheese, and salumi, visit family-run estates, and enjoy a full Tuscan lunch or dinner.

“Good tour with a nice tasting of wines at the fist winery and a nice lunch with wine at the restaurant.”

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Winner 2025 Florence Sunset Food & Wine Tour by Eating Europe - Cheese, dairy, and the neighborhood specialist
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Winner 2025 Florence Sunset Food & Wine Tour by Eating Europe

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

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

Spend 3.5 hours walking Florence’s Oltrarno with an English-speaking guide such as Alice, Sara D., Antonella, or Martino. Taste Prosecco, four Tuscan wines, local cheeses, gnudi pasta, Tuscan soup, wild boar stew, a Negroni, and artisan gelato at family-run spots.

“Sarah D was amazing! She’s a local with lots of experience. So much fun with our group. Lots of local food dishes and wine. A must do for sure!”

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From Florence: Siena, San Gimignano, Pisa & Lunch at Winery - The coach ride from Florence to Siena
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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

Spend a full day in Tuscany with guided Siena, free time in San Gimignano and Pisa, and an optional Chianti winery lunch with four wines. Guides such as Sara, Alessandro, and Giancarlo bring the history to life, while comfortable coach travel handles the long distances.

“Our trip was excellent and my friends and I really enjoyed our day. The guide was brilliant with so much knowledge of the areas we visited and really made our trip special. We loved seeing the Tuscan countryside and towns we visited.”

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San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting - San Gimignano: towers, alleys, and free time
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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

Leave Florence at 8 a.m. for San Gimignano, Monteriggioni, a Chianti winery lunch, and Siena. You get free time in the medieval towns, three Tuscan wines plus vin santo, and optional Siena guiding and cathedral access. Guides such as Sandro, Marta, and Ilaria are often praised for clear, friendly help.

“Hilaria was our guide, she did a wonderful job, she gave us a lot of information without being overwhelming. The visit to the winery and lunch was delightful. I 100% recommend this tour .”

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Chianti Wine Tour from Florence - The road into Sienese Chianti Classico
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Chianti Wine Tour from Florence

9.Chianti Wine Tour from Florence

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

Ride from Florence into Chianti on an air-conditioned coach, visit two organic family wineries, taste six or seven Tuscan wines with local foods, and return in about five hours. Guides such as Aaron, Alessandra, Cristina, and Maria Luisa have led recent departures, though the guide can vary.

“Way to see the wine country! I’m driving through the terrorist landscape filled with cypress trees and villas was breathtaking! There are miles and miles and miles off vineyards. Our tour guide was versed in several languages, so everyone could understand her words. She was extremely knowledgeable! Thank you for the amazing time!”

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From Florence: Small Group Wine Tasting Tour to Tuscany - The ride into Chianti Classico
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From Florence: Small Group Wine Tasting Tour to Tuscany

10.Small Group Wine Tasting Tour to Tuscany

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

Leave Florence by air-conditioned minibus for two Chianti Classico wineries. An English-speaking guide such as Jason, Leo, Jonathan, or Raffaele explains the region, while each estate serves wine, olive oil, cheese, salami, and bruschetta. Expect a lively, social half-day rather than a quiet private tasting.

“This small group tour was excellent, having been a larger coach regional tour earlier in the week. We took the 2.30 pm option. It was brilliant to get 'up close and personal' in the two wineries and amongst the vineyards. The views were stunning, noticeably more than on our previous large coach experience. Driver Sergio and Guide Marco were both great in their roles and helped make the trip so enjoyable. We would thoroughly recommend this tour to others.”

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From Florence: San Gimignano, Siena, and Chianti Wine Tour - Starting in Florence at Piazza del Duomo
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From Florence: San Gimignano, Siena, and Chianti Wine Tour

11.San Gimignano, Siena, and Chianti Wine Tour

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

Spend nine hours touring Tuscany by air-conditioned minibus, with time in Siena, a Chianti estate, and San Gimignano. Expect five wine tastings, olive oils, balsamic vinegar, and a traditional lunch. Guides such as Marco, Lyla, Marta, and Enrieta are praised for keeping the day friendly and on time.

“Marco our tour guide was amazing! He was very knowledgeable and explained everything clearly. He also made sure to talk and connect with many of the people on the tour individually, so it felt very personalized! The tour itself was also incredible - being able to see all the beautiful areas that I did in one day? 10/10”

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Rome: Pasta Making Class with Wine, Limoncello, and Dessert - Ravioli, tortelli, and fettuccine from one dough
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Rome: Pasta Making Class with Wine, Limoncello, and Dessert

12.Pasta Making Class with Wine, Limoncello, and Dessert

★★★★★★★★★★4.9 · 3,177 reviews · 3 hours · from $48

At Pastamania in Palazzo Grazioli, an English-speaking chef guides you through ravioli, tortelli, and fettuccine from flour and eggs to dinner. The three-hour class includes wine, dessert, limoncello, recipes, and a small group of up to 10 people.

“lovely evening spend with our host georgio.. and others from around the world, informative and fun class on pasta. which you eat with wine, cake and lemonchello at the end. I will never buy dried again. thank you”

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Eat Like a Local: Venice 3-Hour Small-Group Food Tasting Tour - Starting with coffee and pastries at Rialto
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Eat Like a Local: Venice 3-Hour Small-Group Food Tasting Tour

13.Eat Like a Local: Venice 3-Hour Small-Group Food Tasting Tour

★★★★★★★★★★5.0 · 3,137 reviews · 2 hours 30 minutes to 3 hours 30 minutes (approx.) · from $107

Walk from Rialto through San Polo, Santa Croce, and possibly Cannaregio, stopping at eight local bars, shops, and restaurants. Guides such as Anna, Marianna, Greta, Sara, and Carlo lead tastings of cicchetti, seafood, pasta, wine, pastries, cured meats, and gelato. Expect a relaxed, filling introduction to Venetian food.

“We spent a delightful afternoon with our guide Anna and 2 couples. Our family group included my elderly parents, my 2 teenage kids and myself. Everyone in the group was friendly and we mingled well. We shared well wishes and hugs at the end. Anna gave us a great understanding of the history and particulars of local food culture in Venice. Most of the eating occurred standing up outside of the eateries, as is common in Venice. Some places had a restroom. We had a good sampling of pasta, seafood, cured meats, cheeses, street snacks, pastries, wine & coffee. Anna also gave advice on what to look for in eating…”

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Florence: S. Gimignano, Siena, Chianti Wine Tasting & Lunch - San Gimignano and its famous towers
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Florence: S. Gimignano, Siena, Chianti Wine Tasting & Lunch

14.S. Gimignano, Siena, Chianti Wine Tasting & Lunch

★★★★★★★★★★4.6 · 3,102 reviews · 11 hours · from $82

Travel from Florence by air-conditioned coach to San Gimignano, Monteriggioni, Siena, and a Chianti winery. Expect free time in the hill towns, a three-course Tuscan lunch, three wine tastings plus Vin Santo, and optional guided visits in Siena with guides such as Marta, Sandro, and Riccardo.

“We had the trip at 25/10. Our guide was Riccardo and our driver was Antonio. Riccardo gave us much information about the places we visited while also being very funny and friendly, making the trip even better. The free time in each place was enough to see the top attractions. The meal and the wine tasting were perfect. Aristos and Krystallia Riccardo's Greek Friends”

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From Florence: Chianti Half-Day Wine Tour with Tasting - The first tasting at Poggio ai Laghi
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From Florence: Chianti Half-Day Wine Tour with Tasting

15.Chianti Half-Day Wine Tour with Tasting

★★★★★★★★★★4.5 · 3,031 reviews · 6 hours · from $58

Leave Florence by tram and coach for two Chianti wineries, seven wine tastings, Tuscan oil, balsamic vinegar, salami, cheese, and bruschetta. Guides such as Luca, Marco, and Alicia keep the day moving, while Monteriggioni adds a compact medieval stop.

“Everything was amazing — the tour guide, the wine tastings, and the amenities. The wines, oils, cheeses, and bruschettas had excellent presentation and were an absolute delight to taste.”

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