Tours

TUSCANY

10 Best Tours In Siena

Most booked first.

Our shortlist of the 10 most-booked tours around Siena, ranked by what travellers actually rated. Who runs them, how long they take, what they cost.

10 Best Tours In 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.

“The experience couldn’t get any better. Marco is an excellent guide and a person! Highly recommended. I went by myself, but made very good friends along the way 💫 Italy is mesmerizing and do not hesitate to take this tour 🥰🌟 p.s. I would recommend to get lunch at the winery. Grazie”

3,762 reviewsFrom $164.26by My Tour in Italy

Check Availability →Read the review →

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

Siena: Walking Tour and Skip-the-Line Duomo Tickets - Basilica di San Domenico: more than a stop on the map

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

★ 4.8

2-hour Siena walking tour with skip-the-line Duomo access, San Domenico stories, Contrade and Palio context, plus major Renaissance art.

“Starting point was great. The guide was terrific, interesting, knowledgeable, and enthusiastic. Excellent all around. I would recommend this to anyone. You really got a feel for sienna, the history and the culture of sienna..”

1,116 reviews2 hoursFrom $47by Tuscan Escapes by Papilio

Check Availability →Read the review →

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 Gothic and Catherine relics

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

★ 5.0

A 2-hour Siena walk with skip-the-line Duomo entry, contrade stories, major piazzas, and art inside the cathedral for about $48.

“Very good tour guide—knowledgeable and entertaining. Beautiful sights and saw a lot of Siena and learned about the different family heritages. . Highly recommend this tour.”

689 reviews2 hours (approx.)From $48.37by Tuscan Escapes by Papilio SRL

Check Availability →Read the review →

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

4.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 viewing points that Chico showed us were great, especially with the autumn colour to the trees and they showed off the Chianti area superbly. The tour of Lornano winery and the tasting were delightful, as were the wines and snacks at Poggio Al Laghi. Our hosts were brilliant.”

631 reviews5 hoursFrom $100by My Luxury Drive

Check Availability →Read the review →

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

5.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.

“Davide was an excellent tour guide. He was knowledgable and gave us a wealth of information, while we were on route to prepare us. At the same time, he gave us time to rest and process the information. This tour was well worth the money. It was clear that Davide enjoys guiding tourists and wants…”

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

Check Availability →Read the review →

Total Immersion Wine Tour in Chianti

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

6.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

Check Availability →Read the review →

Siena: 3h Private City Walking Tour with Optional Cathedral

Siena: 3h Private City Walking Tour with Optional Cathedral - Piazza del Campo to Palazzo Pubblico: Siena’s political heartbeat on foot

Siena Walking Tour with Cathedral and Crypt & Museum Option

Siena Walking Tour with Cathedral and Crypt & Museum Option - Contradas, Old Ghetto corners, and the Palio story that actually clicks

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

From Siena: Brunello di Montalcino Guided Wine Tour W/ Lunch - Montalcino Hill Town Time: Fortress Views and Easy Browsing

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

★ 4.9

Small-group Brunello day trip from Siena to Montalcino: 3 winery tastings, a family lunch, medieval town time, and Sant’Antimo Abbey.

“Enjoyable day out, and Georgia was a fantastic, knowledgeable guide. The vineyards were all the kind of postcard settings we imagined and the lunch was excellent! The wines - and winemakers - were interesting but not to our taste - which is a very subjective assessment! We would happily have spent a little more at…”

357 reviewsFrom $203.91by Tuscan Escapes by Papilio

Check Availability →Read the review →

Siena: A Wine Tour and Tasting Experience

Siena: A Wine Tour and Tasting Experience - Stop 2 in the Cellar: From Crushing to Bottling (and Why It Matters)

10.Siena: A Wine Tour and Tasting Experience

★ 5.0

Organic vineyard and cellar tour outside Siena with four wine tastings, olive oil, and a light lunch in a small English group.

“Found this wine and food tour and loved it. Beautiful setting in the winery. We toured the vineyard and cellars. Then the wine pairing!!! So good my husband bought a case to take away and one shipped home. Loved the fact that it was organic. Our guide. (Sorry can’t remember her name!) was very knowledgeable…”

352 reviews3 hours (approx.)From $102.84by Az. Agr. La Lastra

Check Availability →Read the review →

Most recent

Explore Siena & Tuscany

Siena

Day Trips

Wine & Food

Experiences