Italy · SIENA TOURS

8 Siena Tours to Build a Day Around

8 tours  ·  from $9 a head

The 8 best siena tours you can book today, with what each costs, how long it runs and who it suits. Number one is top for a reason; start there.

From Florence: San Gimignano, Siena, and Chianti Wine Tour - Siena: grand squares, narrow lanes, and a tight clock
Siena Tours, Tour Reviews, Tours, Wine Tastings, Wine Tastings in Siena

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

1.San Gimignano, Siena, and Chianti Wine Tour

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

Explore Siena, Chianti, and San Gimignano from Florence with wine, Tuscan lunch, free time, and an air-conditioned ride.

“12 hours very well splited which led to beautiful memories. We were lucky to have Marta as a guide. She shared with us the history of the region and some old legends. Sienna, Colle di Val d’Elsa and San Gimignano worth for sure spending more than one day to feel them.”

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Siena: Cathedral Complex Pass with Audio Guide (OPA SI PASS) - Inside the cathedral: marble stories and famous sculpture
Audio Tours, Guided, Self-Guided Tours, Siena Tours, Tour Reviews

Siena: Cathedral Complex Pass with Audio Guide (OPA SI PASS)

Siena: Walking Tour and Skip-the-Line Duomo Tickets - Meeting under the tree at Piazza San Domenico
Siena Tours, Skip the Line, Skip-the-Line Tickets, Tickets, Tour Reviews, Tours, Walking Tours

Siena: Walking Tour and Skip-the-Line Duomo Tickets

4.Walking Tour and Skip-the-Line Duomo Tickets

★★★★★★★★★★4.8 · 1,116 reviews · 2 hours · from $47

Walk medieval Siena with a local English-speaking guide, learn the Palio story, and enter the spectacular Duomo without the ticket-line wait.

“Elio is fantastic! V informative. Next time I’d choose a longer tour as 2 hours is not enough. Nothing to do with the guide, but we paid almost $100 for the two of us and I thought that was a bit steep for only 2 hours (granted, it included entrance to the duomo). Highly recommended!”

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Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena - The first winery: vineyards, cellars, and an introduction to Brunello
Food & Drink, Siena Tours, Tour Reviews, Wine Tastings, Wine Tastings in Siena

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

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

★★★★★★★★★★5.0 · 952 reviews · 9 hours (approx.) · from $217Top rated

Taste Brunello at three Montalcino wineries, enjoy a homemade Tuscan lunch, visit Sant’Antimo Abbey, and return to Siena by minivan.

“This tour was a wonderful experience! We visited three distinct wineries and tasted a variety of Rosso and Brunellos. We had a great lunch that was homemade in the family kitchen. The drive was beautiful and Emanuel, our “professional drive” (as he calls himself), is fantastic! He made our day showing us the sights and offering lots of history about the area. Don’t miss this tour!”

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Skip the Line: Siena Duomo and City Walking Tour - Starting at Basilica San Domenico
City Tours, Siena Tours, Skip the Line, Skip-the-Line Tickets, Tour Reviews, Tours, Walking Tours

Skip the Line: Siena Duomo and City Walking Tour

6.Skip the Line: Siena Duomo and City Walking Tour

★★★★★★★★★★5.0 · 689 reviews · 2 hours (approx.) · from $48

Explore Siena’s contrade, Piazza del Campo, and the Duomo with a local guide, skip-the-line entry, and two hours of focused walking.

“We learned about many of the unique traditions of Sienna and its "animal" neighborhoods, along with wonderful tidbits about the cathedral and the Duomo. 2 hours was a perfect amount of time for us, and gave us a wonderful overview of the beautiful and long history of Siena and its people. Claudia is a learned and upbeat guide and a proud lifelong resident of the city. Go, Unicorns!”

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From Siena: Chianti and Castles Tour with Wine Tastings - Castellina in Chianti and the appeal of a walled hill town
Siena Tours, Tour Reviews, Tours, Wine Tastings, Wine Tastings in Siena

From Siena: Chianti and Castles Tour with Wine Tastings

7.Chianti and Castles Tour with Wine Tastings

★★★★★★★★★★4.6 · 631 reviews · 5 hours · from $100

Tour Chianti from Siena in a small van, visit Castellina and Monteriggioni, and taste regional wines at two Tuscan wineries.

“Daniel was a fun informative guide . We visited beautiful little villages and 2 wonderful wineries with amazing views of the Chianti wine region .The wine we tasted was lovely and each winery gave us a different experience. Highly recommended.”

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Florence: Siena, San Gimignano and Chianti Small Group Tour - Meeting the minibus at 7:45 AM
Siena Tours, Tour Reviews, Tours, Wine Tastings, Wine Tastings in Siena

Florence: Siena, San Gimignano and Chianti Small Group Tour

8.Siena, San Gimignano and Chianti Small Group Tour

★★★★★★★★★★4.9 · 433 reviews · 9 hours · from $175

Spend a day in Tuscany visiting Siena, a family winery, and San Gimignano, with lunch, wine tasting, guided walks, and free time.

“Lorenzo was a fantastic tour guide and Alessio made the ride very comfortable. Such a great day well spent at a comfortable pace with a good amount of historical information and lots of free time to shop around and take photos.”

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