15 Top-Rated Tuscany Wine Tours To Experience

When you think of Tuscany, what comes to mind? For me, it’s rolling hills, sun-drenched vineyards, and, of course, the finest wines.

If you’re planning a trip to this beautiful region in Italy, I’ve got you covered with the best Tuscany wine tours. I’ve sifted through countless sources and personally sampled some of the top tours to bring you a curated list that stands out.

From Chianti’s robust reds to the delicate whites of San Gimignano, I’ll guide you to experiences that are more than just tastings—they’re unforgettable journeys into the heart of Tuscan culture.

Simply choose your desired location and jump to my recommended three top-rated tour experiences.

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3 Best Wine Tours in Tuscany from Florence

table and chairs on a tuscany wine tours

1. Chianti Wineries Tour with Food and Wine Tasting

⭐️ RATING: 4.5/5 Stars | ⏳ TOUR LENGTH: 5.5 hours

Head to the heart of the Chianti region and visit two wineries, one steeped in tradition and the other showcasing modern techniques, both offering a delightful taste of local wines.

What’s included in this Tuscany wine tour:

Guided wine tasting at 2 different wineries
Tasting of 7 different wines
Charcuterie board-type snacks

“My group and I wanted to do a wine tasting tour while in Florence that would not take 10+ hours. We came across this tour that was about 4-5 hours: includes AC bus transport to and from (the bus was a big, & nice charter bus) and 2 winery tours. Each tour was about 1 hour each.

Our tour guide Stefano was so fun and gave us facts while en route. In addition, we got small snacks in each winery. Overall, it was a GREAT tour. We had a great time, and karaoke’d on the way home once we were all feeling the wine 😆 I would absolutely recommend this tour. Hopefully you get lucky and have a great guide like Stefano!!!”
Yvette from USA

Ideal for wine enthusiasts: Check Prices and Availability!

2. Wine Tasting and Dinner in Chianti Vineyards

⭐️ RATING: 4.5/5 Stars | ⏳ TOUR LENGTH: 6.5 hours

Begin with a visit to a family-run wine estate tour. Sample some Chianti wines along with some fresh olive oil. Next end your day at another wine estate and enjoy dinner with local Tuscan specialties.

“10/10 day. We had such a good time – it was stinking hot so the afternoon/evening was much more pleasant. Both wineries had wonderful guides who spoke to us in great detail about the wines. Antipasto platters at both. The dinner was delicious and SO much food. 6 tastings at the second winery!

Good value despite the cost. It was nice to see Greve in Chianti town as well. Bus nicely air conditioned. Would highly recommend!”
Sophie from Australia

Perfect for Foodies: Check Prices and Availability!

3. Tuscany Wine & Food Tour with Guide

⭐️ RATING: 4.9/5 Stars | ⏳ TOUR LENGTH: 8 hours

One of the reasons to visit Florence is its proximity to wine country. Visit three wineries, taste local wines and olive oil, enjoy a group lunch with local specialties, and explore Greve in Chianti.

“It was an extraordinary day. Our guide Sofia was outstanding. She gave us a lot of interesting, exciting and relevant information. She was funny, caring and attentive. The ride was smooth, the driver was professional and knowledgeable. The 3 vineyards visited were well chosen. I loved the 1st. The resource person was A1. Super interesting and knowledgeable.

The 2nd, beautiful site and good food, dinner was very good. The guy knew his products well. Good tasting. The 3rd… a big wow, no spoilers. Good wines and, again. The resource person was really good. I highly recommend this activity.”
Patrice from Canada

Ideal for Experience Collectors: Check Prices and Availability!

3 Best Wine Tour in Tuscany from Montalcino & Montepulciano

rooftops with moutains on tuscany wine tours

1. Guided Winery Tour & Gourmet Tasting

⭐️ RATING: 4.8/5 Stars | ⏳ TOUR LENGTH: 2.5 hours

From Montalcino, enjoy 2 wine tasting options of 6 wines in total accompanied by some local specialty bites.

“All 14 members of our family including grandchildren were lucky enough to attend this lovely wine tour with wonderful wine tastings paired with appetizers. The winery itself is beautiful on acres of rolling countryside as is the building you get to experience the wine and food.

The guide was very informative on the process of making wine but kept the outside experience quick as it was extremely hot The 3 bruenella wines they served were fantastic. They also had a merlot and rose that were quite good all paired with delicious appetizers. A great family memory for us and we highly recommend the tour!”
Liz from Canada

For the red wine enthusiast: Check Prices and Availability!

2. Montepulciano Wine Tasting and Cellar Tour

⭐️ RATING: 4.8/5 Stars | ⏳ TOUR LENGTH: 1 hour

Delight in a flight of five meticulously selected Montepulciano wines showcasing the region’s distinct terroir served with local Pecorino cheeses, bruschetta and olive oil.

“I highly recommend this tour! Absolute fantastic guide, who not only had a great knowledge of the wine, but was also able to put it in context with the history of Montepulciano. The wine cellar is much more impressive than I had imagined. The tour lasted a little longer than indicated; I would say that the wine and snacks alone were worth the money”
Thomas from Germany

Quick sip and savour: Check Prices and Availability!

3. Brunello Wine Tasting & Lunch in a Tuscan Castle

⭐️ RATING: 4.8/5 Stars | ⏳ TOUR LENGTH: 1.5 hour

Enjoy a 3-course lunch with wine pairing within a medieval castle’s walls.

“We had one guide to the pair of us which was fantastic – and he had a great knowledge of both the wine making process & the Ricci family which was fabulous. Substantial selection of meat & cheese after the tour, and the staff were very generous with the top ups. Would definitely recommend.”
Sarah from Canada

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3 Best Tuscan Wine Tours from Rome

2 chairs and rolling hills on tuscany wine tours

1. Bagnoregio & Orvieto Day Trip with Wines & Lunch

⭐️ RATING: 4.7/5 Stars | ⏳ TOUR LENGTH: 12 hours

Explore Bargnoregio and Orvieto for the day from Rome. Enjoy a stop for wine tasting and lunch in Montepulciano at a Tuscan farmhouse and winery.

“Great excursion! The guide Natasha knows her business perfectly and readily answers all questions. In addition to the program, she gave useful tips for traveling around Rome: about the metro, cafes, etc. The driver Emilio accompanied us on the trip – a true professional in his field, he drove very gently and safely.

Orvieto is a chic town with its own atmosphere. Traditional lunch at Trattoria Pulcina with tasting of wine, cheeses and sausages – a gastronomic orgasm! Everyone explained in such an interesting and detailed way what wine to drink after what. The most memorable thing on this tour, of course, was Bagnoregio – an authentic town in the mountains. The atmosphere there is magical!!! I highly recommend it! The day was amazing!
Mag from Spain

For an authentic experience: Check Prices and Availability!

2. Tuscany Day Trip with Lunch and Wine Tasting

⭐️ RATING: 4.7/5 Stars | ⏳ TOUR LENGTH: 13 hours

From Rome, you’ll experience the best of Tuscan towns worth visiting. This day trip includes:

Guided tour of Montepulciano
Guided tour of Abbey of Sant’Antimo
3-course lunch with local wine pairings, seated in an authentic vineyard wine cellar
Free time in Pienza

“The day trip was amazing especially due to our excellent guide Andreas. He was well educated about the regions history and was able to deliver the info in easygoing way. We learned a lot about Rome and Tuscany. The schedule was reasonable and we got to see a lot without being in a hurry. The food and drinks at the winery were also great.”
Jukka from Finland

For Tuscany lovers: Check Prices and Availability!

3. Private Day-Tour of Tuscany

⭐️ RATING: 4.5/5 Stars | ⏳ TOUR LENGTH: 10 hours

Get the VIP treatment when you book this exclusive private tour from Rome that whisks you away to Montepulciano and Pienza for wine tastings. Note, that this tour does not include lunch.

“We were so impressed with our adventure into Tuscany! Mauro was a wonderful guide/driver, providing information and insight into the area, the olive groves, vineyards and history. I would go back in a heartbeat and will definitely use get your guide services. A wonderful experience and an exceptional value!”
Sharron from USA

For the VIP traveller: Check Prices and Availability!

From San Gimignano: 3 Wine Tours Tuscany

1. Truffle Hunting with Lunch & Wine Tasting

⭐️ RATING: 4.6/5 Stars | ⏳ TOUR LENGTH: 3 hours

Want a unique experience – go truffle hunting alongside trained dogs. Following the hunt, enjoy an authentic Tuscan lunch accompanied by wine and olive oil tastings.

“This is a must do activity, amazing experience! The guide very nice and friendly, the dogs also smart and friendly. We learnt a lot and had a great time getting and eating the truffles. Winery is also very good and was one of the best wine tasting experiences.”
Erika from Brazil

For unique experience collectors: Check Prices and Availability!

2. Chianti Half-Day Vespa Tour with Lunch

⭐️ RATING: 4.9/5 Stars | ⏳ TOUR LENGTH: 4.5 hours

Take a thrilling adventure through the picturesque Chianti region as you ride Vespas along winding roads featuring stunning hillside vistas. Enjoy a light lunch at a local winery too.

“Our guide, Vincenzo, was extremely patient and knowledgeable. Our group didn’t start the day expecting to learn so much about San Gimignano, but we were pleasantly surprised! This is a great activity for a mix between culture and entertainment.

Vincenzo is the perfect guide for someone who is fairly new to driving a Vespa, but wants a challenge. He is a guide, sommelier, and photographer all in one, and he will make sure everyone enjoys their trip! The food and wine was also incredible.”
Gage from USA

For fun seekers: Check Prices and Availability!

3. Romantic Vineyard Lunch

⭐️ RATING: n/a Stars NEW Tour | ⏳ TOUR LENGTH: 2 hours

Delight in an authentic Tuscan experience with a dinner set amidst the enchanting vineyard rows. Your host will serve their wine and olive oil and traditional Tuscan dinner.

“We had an absolutely amazing time at a romantic vineyard in San Gimignano for a wine tasting experience. It was truly exceptional, with top-quality wines, an intimate atmosphere, and a knowledgeable instructor who guided us through a variety of wine types.

I highly recommend this place for its incredible setting and superb service. Fernando was incredible!! Very generous he went above and beyond to make our experience the best.”
Lauren from UK

For the romantics: Check Prices and Availability!

3 Best Wine Tours of Tuscany from Siena

rolling hills with tall trees on best tuscan wine tours

1. Pienza and Montepulciano Small-Group Tour

⭐️ RATING: 5 Stars | ⏳ TOUR LENGTH: 8 hours

Immerse yourself in the Renaissance charm of Pienza, followed by a delightful lunch at a nearby sheep farm where you’ll discover the art of pecorino cheesemaking. Continue to the hilltop town of Montepulciano, exploring its allure before delving into the world of winemaking with a cellar visit and tasting.

“A lovely trip to Pienza and Montepulciano with stops for coffee in the morning, yummy lunch at a sheep farm where we got to try different local cheeses and a wine tasting in Montepulciano.

Our guide Mattia was great, very friendly with lots of knowledge and information about the places we visited, wine production and also about Tuscany overall. The small group tour is really well-organised. Definitely recommend.”
Shilpa from Germany

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2. Brunello di Montalcino Guided Wine Tour with Lunch

⭐️ RATING: 4.9/5 Stars | ⏳ TOUR LENGTH: 9 hours

From Siena, visit three esteemed wineries featuring Brunello wines, each offering a unique tasting experience. This tour includes lunch at a family-run winery.

“Only a fool would pass up this chance to learn, drink, and enjoy a perfect day in Montalcino. Perfetto per tutti! Mattie made it fun and educational. Book this trip if you want to drink great wine, understand it, and enjoy traditional, fantastic food.”
Traveller from USA

For the ultimate Tuscan experience: Check Prices and Availability!

3. Chianti and Castles Tour with Wine Tastings