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TUSCANY

10 Best Siena & Tuscany Experiences

Most booked first.

The 10 most-booked experiences out of Siena, ranked by what travellers actually rated. Brunello days, hilltop villages, the Duomo, cooking with Sienese grandmothers — the shortlist worth your week.

10 Best Siena & Tuscany Experiences

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.

“Marco our tour guide was amazing! He was very knowledgeable and explained everything clearly. He also made sure to talk and connect with many of the people on the tour individually, so it felt very personalized! The tour itself was also incredible - being able to see all the beautiful areas that I did in…”

3,762 reviewsFrom $164.26by My Tour in Italy

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Siena: Siena Cathedral and Piccolomini Library Entry Ticket

Siena: Siena Cathedral and Piccolomini Library Entry Ticket - Siena Cathedral Interior: Dome, Marble Mosaic Floor, and Cathedral Scale

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

Siena: Cathedral Complex Pass with Audio Guide (OPA SI PASS) - Exchanging your voucher at Cripta del Duomo di Siena (without losing your momentum)

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

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

Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena - Stop 1: Tuscan vineyards, cellars, and your first Brunello tasting

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

6.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.

“Super informative tour of Siena. The tour guide was knowledgable and we found everything so interesting! We learnt so many things that we would never have known about, the different areas that people live and the origins of the famous horse race and of course many things about the famous churches!”

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

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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

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

8.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.

“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.”

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

9.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.

“The tour was great! We have not only received a detailed information about the winery but also tried a lot of different (including aged) wines with a tasty plate of cheese/cold cuts. Big thanks to our guide Francesco for making this tour fun!”

430 reviews2 hoursFrom $47by Fattoria di Montemaggio

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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 to Palazzo Pubblico: Siena’s political heartbeat on foot

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