Siena

15 Best Siena Wine Tours

The wine country at Siena’s gates: Brunello tastings in Montalcino, Chianti immersions and the Montepulciano-Pienza loop with pecorino between cellars. Three of Italy’s greatest reds grow within an hour; the designated driver comes included.

1.Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena

Discover authentic Brunello di Montalcino wines on this small-group day trip from Siena, including visits to three charming wineries, a Tuscan meal, and the Abbey of Sant'Antimo.

Most Popular★ 5.0

“This tour was beyond what I had expected. It was a memorable experience with a small group. We visited 3 different wineries, each had excellent selection of wines. We could see the cellars, they explained us the wine making process in depth. Our minivan driver…”

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2.Total Immersion Wine Tour in Chianti

Experience authentic organic Chianti wines with stunning vineyard views, expert guides, and delicious local snacks on this immersive two-hour tour in Tuscany.

★ 4.9

“This tour was amazing! I can’t say enough good things about this place! The tour was rich with knowledge of the winery itself and the history behind the region and the wine. We can’t wait to share our experience with our friends back home as…”

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3.Siena: A Wine Tour and Tasting Experience

Discover Tuscany’s wine heritage with a small-group tour from Siena. Taste organic wines, learn from a passionate guide, and enjoy a scenic countryside lunch.

★ 5.0

“I'm so glad I chose to book this at the last minute. La Lastra winery is stunning and picturesque, just what I pictured when I planned a visit to Tuscany. Maya was a knowledgeable and warm guide who gave us lots of engaging information about…”

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4.Small-Group Montepulciano and Pienza Day Trip from Siena

Discover the charm of Tuscany with this small-group day trip from Siena to Pienza and Montepulciano, including wine tastings, a cheese farm, and stunning scenery.

★ 5.0

“Guiliana is an expert guide, making our trip so interesting. She is an absolute rock star! She knew so much history about the area and answered any questions we had. The views through the winding roads on our trip to Pienza and Montepulciano were spectacular.…”

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5.Wine Class – Tuscan Classics

Discover Tuscan wines through an engaging 2-hour class in Siena, learning from local experts, tasting regional wines, and pairing with delicious bites.

★ 5.0

“We had only two couples in this tour. One was from a combined food and wine tour and us, who were supposed to be just in the wine class. It was All Saints Day and things weere supposed to be winding down in Siena. Since…”

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6.A Brunello Cooking Class with Vineyards View Winery

Experience a hands-on Brunello wine region cooking class on a scenic Tuscan vineyard terrace, combined with castle tours and wine tasting near Siena.

★ 5.0

“From our tour of the winery to our cooking….SO great. We learned about the winery, cooking techniques……then put the food and wine together for a really great experience!”

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8.San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting

Discover Tuscan charm on this full-day tour visiting San Gimignano, Siena, and Monteriggioni with wine tastings, lunch, and expert guides from Florence.

★ 4.5

“This tour helped us see three towns when we had a short few days in Florence! Our guide Fabi was fantastic and walked us through each area carefully. We had insight into each area and a lovely wine tasting with a small accompanying lunch. Best…”

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10.San Gimignano, Chianti, and Montalcino Day Trip from Siena

Discover Tuscany’s highlights on this small-group day trip from Siena, including San Gimignano, Montalcino, and Chianti wine tastings—perfect for wine lovers and history buffs alike.

★ 4.5

“Our driver, Giovanni, was prompt and provided a clean vehicle but he was NOT a guide as the trip was advertised. Rather than talk about Italy, he wanted to engage about politics and his heavy smoking between stops made the van stink. Our tour left…”

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12.Tuscany Hiking Tour from Siena Including Wine Tasting

Explore Tuscany on this scenic half-day hike from Siena, including a walk along the historic Via Francigena and a delightful wine tasting in Monteriggioni.

★ 5.0

“Fabulous! Great guide, perfect weather (late October), great like minded group of hikers. Was a good few hours (almost 4) of hiking but fairly flat and not a fast pace. Definitely recommend. The town of Monterriggioni at the end was the icing on the cake.”

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13.Brunello di Montalcino Wine Tour of 2 Wineries with Pairing Lunch

Discover Tuscany’s finest Brunello wines on this small-group tour visiting two historic wineries with tastings, scenic drives, and a delicious pairing lunch.

★ 5.0

“I booked this tour based on the reviews I'd read here, expecting a personalized, custom feeling experience. I expected wineries that I couldn't otherwise find, an engaged tour guide, and a generally great day. While the tour technically included all the pieces in the listing,…”

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14.Siena walking tour with lunch & Chianti wine

Discover Siena’s charm on a guided walking tour with authentic Tuscan food, regional wines, and hidden sights—perfect for lovers of history and cuisine.

★ 5.0

“Off the beaten track….where locals find the best pasta,gelato and vino. Ancient tomb attached to an enoteca. Minimal historical information but learn about the 17 contrada and life as a resident Guide Morad 5 STARS”

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15.Tuscany Wine & Hills from Siena

Discover Tuscany's charm on this full-day Siena-based tour featuring visits to Pienza and Montepulciano, with wine tastings, stunning views, and free time.

★ 4.0

“Signed up for a minibus tour six months ago. Ended up on a full tour bus. Stopped at one winery.the entire day. “Snacks” were a packet of saltine crackers. I guess I misread the description? Enjoyed the other people on the bus and the towns…”

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More Siena Wine Tours

5.0Full-Day 2 Wineries Tour in Montepulciano with Tasting and Lunch6 to 8 hours (approx.)$265.49 5.0“CLASSIC” Wine Tasting and Typical Tuscan Products1 hour (approx.)$33.79 5.0Small-Group Chianti Trip with Wine Tasting from Siena8 hours (approx.)$217.22 5.0Chianti and San Gimignano – 2 Wineries with Pairing Lunch$423.77 5.0Siena: winery tour, wine tasting and lunch2.5 hours$77 4.0Small group Brunello di Montalcino Wine Tour from Siena5 hours 30 minutes (approx.)$142.97 5.0Small-Group Chianti and San Gimignano Sunset Trip from Siena8 to 9 hours (approx.)$217.23 4.0Tuscan Chianti Hills Horseback Riding Tour1 hour 30 minutes (approx.)$90.11 4.5Montalcino: Brunello Wine Tasting Experience1 hour 30 minutes (approx.)$39.05 4.5Vintage Fiat 500 Tour from Siena: Tuscan Hills and Winery Lunch$191.58 5.0Guided Winery Tour and Wine Tasting in Siena2 hours 30 minutes (approx.)$90.51 4.9Siena: Tour and Wine Tasting in a Tuscan Private Castle2 hours$51 5.0Siena Underground Wine tasting in a Medieval Cave1 hour 15 minutes (approx.)$90.11 4.0Vespa Tour in Chianti Small Group from Florence$167.68 4.8Montepulciano: Cinta Senese Tour With Food Tasting1.5 hours$65 5.0Guided tour of the cellars with wine tasting and lunch2 hours 30 minutes (approx.)$77.89 5.0Savor Siena Food and Wine Tour2 hours (approx.)$71.90 5.0Pienza, Val d’Orcia, Montalcino wine and Pecorino cheese PRIVATE TOUR from SIENA8 hours (approx.)$527.24 4.0Montalcino Castle and Vineyards tour with tasting1 hour (approx.)$46.86 4.7Chianti: Wine and Olive Oil Tasting with Cellar Tour1 hour$41 5.0Small Group E-Bike Chianti Tour with farm lunch from Siena6 hours (approx.)$216.25 5.0Exclusive Wine Tasting in the Historic Center of Siena1 hour (approx.)$42.05 5.0Small group Chianti, Montalcino & Monteriggioni castle from Siena5 hours 30 minutes (approx.)$198.95 5.0Private Tour: Pienza and Montalcino Organic Cheese and Wine Tour8 hours (approx.)$840.98

Explore Siena

A striped Duomo, a shell-shaped square and Brunello next door.