Chianti Wine Tours

TUSCANY · DESTINATION

10 Best Chianti Wine Tours From Siena

Most booked first.

Our shortlist of the 10 highest-rated ways to spend a day in the Chianti hills. Castle estates, family-run vineyards, lunch under the cypress — the wine roads that start half an hour out of Siena.

10 Best Chianti Wine Tours From Siena

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

From Florence: San Gimignano, Siena, and Chianti Wine Tour - Starting point in Florence: meet near the Baptistery

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

Most Popular★ 4.5

Florence to Siena, San Gimignano, and Chianti in one full day with guided history, five wine tastings, and a Tuscan lunch.

“We had an incredible adventure through Chianti and surrounding towns. Marco was an excellent guide who is very knowledgeable of Tuscan and Italian history. San Gimingnano was the highlight filled with delicious treats and sights of the picturesque rolling hills.”

3,762 reviewsFrom $164.26by My Tour in Italy

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From Siena: Chianti and Castles Tour with Wine Tastings

From Siena: Chianti and Castles Tour with Wine Tastings - Castellina in Chianti: Walled-Town Energy Without the Full Hike

2.From Siena: Chianti and Castles Tour with Wine Tastings

★ 4.6

5-hour Chianti tour from Siena with a small minivan, Castellina and Monteriggioni, plus two winery tastings with snacks and views.

“The guide was wonderful and explained to us all the places we were going to visit. We stopped in small towns along the way that were very picturesque and scenic, which really added to the atmosphere. The wineries were amazing and the wines were truly excellent — I enjoyed every moment.”

631 reviews5 hoursFrom $100by My Luxury Drive

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Florence: Siena, San Gimignano and Chianti Small Group Tour

Florence: Siena, San Gimignano and Chianti Small Group Tour - Siena’s Guided Walk, Cathedral Option, and the Palio Piazza

3.Florence: Siena, San Gimignano and Chianti Small Group Tour

★ 4.9

Small-group Tuscany day trip from Florence to Siena and San Gimignano with guided walk, Chianti wine tasting, lunch, and free time.

“Siena and San Gimignano were beautiful. Lorenzo, our guide, was excellent. He was a great storyteller and told us ahead of time ( on the bus) what to expect, where to meet etc. And then showed us in-person and pointed out important details like washroooms and scenic viewpoints. I have been on many tours and…”

433 reviews9 hoursFrom $175by Prestige Rent - Tours in Italy

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Total Immersion Wine Tour in Chianti

Total Immersion Wine Tour in Chianti - Rooftop Introduction: Black Rooster Story and Chianti Views at 600 Meters

4.Total Immersion Wine Tour in Chianti

★ 4.9

2-hour organic Chianti Classico tour at Fattoria di Montemaggio with a vineyard-and-cellar walk, tasting course, snacks, and optional grappa.

“Stefano and Francesco were excellent guides. Great information about the Classico Chianti region and how to taste wine. I would love to go again!”

430 reviews2 hoursFrom $47by Fattoria di Montemaggio

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Siena: San Gimignano, Chianti & Montalcino Small-Group Tour

Siena: San Gimignano, Chianti & Montalcino Small-Group Tour - A small-group van with a bilingual escort (and why that helps)

Hidden Castles & Chianti Wine Experience– Small Group

Hidden Castles & Chianti Wine Experience– Small Group - Where You Meet in Siena (and Why It Matters)

Siena: Small group Cooking Class in Chianti Farmhouse

Siena: Small Group Cooking Class in Chianti Farmhouse - The Tuscan Menu Focus: Pasta Skills Plus Starters and Tiramisu

San Gimignano, Chianti, and Montalcino Day Trip from Siena

San Gimignano, Chianti, and Montalcino Day Trip from Siena - Price and time: 11 hours, and why the early start matters

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

★ 4.5

An 11-hour Siena day trip hitting San Gimignano, Chianti wine country, and Montalcino for Brunello tastings plus classic Tuscan stops.

“Montalcino was not worth a stop. Brunello wine was good but host’s English was not good enough. The stop at Poggio Al Laghi Was good. Driver was very nice and accommodating.”

150 reviews11 hours (approx.)From $168.96by myTour in Italy

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Siena: Small Group Cooking Class in Chianti Farmhouse

Siena: Small Group Cooking Class in Chianti Farmhouse - The Tuscan Menu Focus: Pasta Skills Plus Starters and Tiramisu

9.Siena: Small Group Cooking Class in Chianti Farmhouse

★ 4.9

Cook classic Tuscan dishes at a Chianti farmhouse with Chef Simone. Small group lesson, wine, and a meal you make in 4 hours.

“We had a little delay getting there; you really have to put the full address, and sometimes even better with the name of the place Simone greeted us with a warm smile and good red wine We had a large, fun group Simone and his helpers were amazing The instructions were clear and easy to…”

146 reviewsFrom $130.28by My Tour in Italy

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Vespa Tour with Lunch&Chianti Winery from Siena

Vespa Tour with Lunch&Chianti Winery from Siena - Meeting point and “where do I actually start?”

10.Vespa Tour with Lunch&Chianti Winery from Siena

★ 4.0

Vespa through Chianti from Siena with wine tasting, vineyard cellars, and quick hill towns. Driver or passenger options.

“This day was amazing!!!! There are some things you should know before hand. It doesn’t leave from Siena. It is a little town about 20 mins away. If you don’t have a car you need to spend the extra for pick up and drop off. I didn’t see that until the night before and we…”

126 reviewsFrom $168.36by myTour in Italy

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