Siena

ITALY · CITY

15 Best Siena Tours In Italy

The most popular, first.

The 15 most popular siena tours, with what each one includes, who runs it, and what you can expect on the day.

15 Best Siena Tours In Italy

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

From Florence: San Gimignano, Siena, and Chianti Wine Tour - Siena first: Piazza del Campo, Santa Maria Assunta, and Palio vibes

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

Most Popular 4.5

Florence to Tuscany in a small group: Siena sights, a Chianti estate with five wine tastings and lunch, then San Gimignano’s towers.

“Oh such a lovely day it was and our guide Lyla was very communicative and made the tour very fun. Our driver, Antonio, was also a very sweet person. She explained about the very interesting history of places and the wines too. There was intern from the company who also gave a lot of information…”

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Siena: Siena Cathedral and Piccolomini Library Entry Ticket

Siena: Siena Cathedral and Piccolomini Library Entry Ticket - The major sculptors you can actually spot: Donatello, Michelangelo, Nicola Pisano

2.Siena: Siena Cathedral and Piccolomini Library Entry Ticket

4.5

Skip the line in Siena Cathedral and visit the Piccolomini Library with Pinturicchio frescoes, plus an official QR-code audio guide.

“Admirable example of medieval architecture and art. This cathedral as well the entire Siena city is a must if you love art and culture as well as the entire Italian country...very hard to find anywhere in the world.”

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

Siena: Cathedral Complex Pass with Audio Guide (OPA SI PASS) - First stop: exchanging your voucher at Cripta del Duomo di Siena

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

4.4

OPA SI PASS lets you explore Siena’s Duomo complex with a self-guided digital audio guide and access to crypt, libraries, museum and viewpoint.

“The Opa Si Pass (self-guided with audio) is definitely worthwhile. The comprehensive narration at your own pace with an easy-to-use map on the audio download (bring your own cell phone) was best to absorb the magnificence of the Duomo in a sensible manner. The understanding of the Duomo as an historic, architectural, cultural, civic, and…”

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

Siena: Walking Tour and Skip-the-Line Duomo Tickets - Where to start: Piazza San Domenico and the clothing rule you can’t ignore

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

Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena - Stop 1: vineyard walks, cellars, and your first Brunello comparisons

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

5.0

Small-group Brunello di Montalcino day trip from Siena with 3 winery visits, winemaker lunch, town time, and Abbazia di Sant’Antimo.

“Spent a wonderful day with our exceptionable guide Georgia! Georgia was incredibly knowledgeable and entertaining throughout our day trip to experience Brunello wine and the producing region. Great winery picks! Very easy pickup/dropoff in Siena. Highly recommend!”

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Skip the Line: Siena Duomo and City Walking Tour

Skip the Line: Siena Duomo and City Walking Tour - Basilica Cateriniana Di S. Domenico: Red Brick and Real Atmosphere

From Siena: Chianti and Castles Tour with Wine Tastings

From Siena: Chianti and Castles Tour with Wine Tastings - Hotel Minerva to the minivan: the comfort setup

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

4.6

A 5-hour small-group van tour from Siena through Chianti towns and vineyards, with 2 winery tastings and classic Tuscan stops.

“Both wineries were lovely but we felt the tour could visit the second winery Lornano first as this winery is a little more affordable, also family run and a more relaxed experience. The two locations you’re dropped in are also nice but there’s not a lot to do in either. Our driving Fabio very friendly…”

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Florence: Siena, San Gimignano and Chianti Small Group Tour

Florence: Siena, San Gimignano and Chianti Small Group Tour - Meeting at Montelungo without losing time (or your sanity)

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

4.9

Small-group Florence day trip to Siena, San Gimignano and Chianti with guided walks, winery lunch and tastings, plus time to explore.

“Beautiful day in Tuscany! Our guide and driver were both wonderful. The winery staff were great too; the food and wine at lunch were delicious. We had such a great day.”

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Total Immersion Wine Tour in Chianti

Total Immersion Wine Tour in Chianti - Organic Chianti at a Small Family Winery: What You’re Really Paying For

9.Total Immersion Wine Tour in Chianti

4.9

A 2-hour Chianti organic winery tour in Tuscany with vineyard and cellar visits, 5 wine tastings, olive oil snacks, and optional grappa.

“Francesco is very nice guide! the experience is insane, we totally liked the tour, and of course, wine degustation! Totally recommended place to visit!”

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Siena: 3h Private City Walking Tour with Optional Cathedral

Siena: 3h Private City Walking Tour with Optional Cathedral - Piazza del Campo and Palazzo Pubblico: Siena’s Civic Heart

10.Siena: 3h Private City Walking Tour with Optional Cathedral

4.7

3-hour private Siena walk with a local guide and optional Duomo visit. UNESCO stops, Palio stories, and photo-worthy sights.

“The tour guide was very knowledge, very personable and spoke very clearly. She was very sensitive to what we might want to do and see. We can’t think of anything to improve.”

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From Siena: Brunello di Montalcino Guided Wine Tour W/ Lunch

From Siena: Brunello di Montalcino Guided Wine Tour W/ Lunch - Vineyard walk and cellar time: where Brunello gets real

Siena: A Wine Tour and Tasting Experience

Siena: A Wine Tour and Tasting Experience - Getting to Azienda Agricola La Lastra: Meeting Point and Timing

13.Siena: A Wine Tour and Tasting Experience

5.0

Small-group organic wine tour outside Siena: vineyard walk, cellar science, tasting 4 wines, and a light Tuscan lunch with olive oil.

“Informative tour of an organic winery; so much to learn about what goes into making a good, organic wine. The wine was delicious and so was the lunch. The grounds are beautiful and picture postcard worthy.”

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Tuscan Cooking Class in Central Siena

Tuscan Cooking Class in Central Siena - The menu changes, but the structure stays classic

14.Tuscan Cooking Class in Central Siena

5.0

Hands-on Tuscan cooking in central Siena with chef Francesco, a full 4-course menu, and wine at the end in a small group.

“I was so excited to take a cooking class as I am a self-taught cook and wanted to learn more about the art of Tuscan cuisine. However, I honestly was disappointed. The class was in English, which was very helpful when learning the various dishes and techniques. The recipes that were given to take home…”

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From Siena: Tuscany Hills Wine Tour

From Siena: Tuscany Hills Wine Tour - Monteriggioni and the Chianti winery: where wine meets olive oil

15.From Siena: Tuscany Hills Wine Tour

4.1

Full-day wine tour from Siena with two winery tastings, plus Pienza and Montepulciano in Val d’Orcia. Great views, long day.

“The tour was wonderful! It was really more about seeing the three towns than about food. The bus was modern and comfortable. The guide was very nice. We were basically left on our own to explore which was very nice. I recommend it.”

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