Category Guided

Siena · GUIDED

12 Standout Guided Tours in Siena

12 reviewed

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

From Siena: Brunello di Montalcino Guided Wine Tour W/ Lunch - Meeting in Siena and getting into the day’s rhythm

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

★★★★★★★★★★4.9 · 357 reviews · from $203Our pick

A small-group Brunello di Montalcino day from Siena with three winery visits, tastings, a winery lunch, and a stop at 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 each vineyard instead of the stop in Montalcino. An enjoyable day out and highly recommended”

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Discover Siena: Guided Walking Tour and Cathedral Visit

Discover Siena: Guided Walking Tour and Cathedral Visit - The Palio Thread: Contrade Stories That Make the Festival Click

2.Discover Siena: Guided Walking Tour and Cathedral Visit

★★★★★★★★★★4.3 · 314 reviews · 1 hour · from $34

Siena on foot with a local guide: Piazza del Campo, palio stories, and Siena Cathedral entry included for $34.

“Coming to Siena just for a day, this 2-hour tour was perfect: it gave us enough important information in the very beginning of the day, after which we could explore the city and its treasures on our own. Highly recommend for first-time one-day travelers.”

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Siena: Private Custom Tour with a Local Guide

Siena: Private Custom Tour with a Local Guide - How the custom walk works: pickup, timing, and pacing

3.Private Custom Tour with a Local Guide

★★★★★★★★★★4.3 · 101 reviews · 2 - 8 hours · from $65

Private custom Siena walking tour with a local guide. See key sights and Palio stories, get food tips. From $65.

“With only one day to visit Siena, this tour was filled with color, history and an extensive traverse of the city inside the wall. It provided us with the opportunity to learn about Siena and all that it had to offer us to do following the tour. Our guide spoke wonderful English.”

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Montepulciano: Historical Cellars Guided Tour & Wine Tasting

Montepulciano: Historical Cellars Guided Tour & Wine Tasting - Walking Montepulciano’s historic center with a wine lens

4.Montepulciano: Historical Cellars Guided Tour & Wine Tasting

★★★★★★★★★★4.4 · 83 reviews · 2.5 hours · from $77

Guided tour of Montepulciano’s underground brick cellars and tasting of Vino Nobile DOCG and Rosso DOC in 2.5 hours.

“Our tour was a lovely addition to our week in Tuscany. We learned a lot about Montepulciano and the history of wine cellars and of the town. We also learned a lot about the process of wine making.”

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Siena: Half-day Guided Hike to Monteriggioni

Siena: Half-day Guided Hike to Monteriggioni - Meeting point at Siena train station: what to do at 08:55

5.Half-day Guided Hike to Monteriggioni

★★★★★★★★★★4.8 · 57 reviews · 4 hours · from $71

Guided hike from Siena to Monteriggioni on the Via Francigena, ending with wine tasting in the fortress village. $71, 4 hours.

“Our family enjoyed both the local history and nature on the tour. Our guide was enthusiastic, knowledgeable and engaging throughout the hike. A great way to spend half a day in the Tuscany countryside!”

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Florence: Wine Tasting and Paring Class Guided Tour

Florence: Wine Tasting and Paring Class Guided Tour - What You Taste in This Florence Wine Tasting Class

6.Florence: Wine Tasting and Paring Class Guided Tour

★★★★★★★★★★4.9 · 56 reviews · from $52

Guided Florence wine tasting with Chianti pairings and Tuscan appetizers. Learn wine stories with a sommelier in 90 minutes.

“It was really really nice. We got to try a few nice wines and the guide had a lot of interesting information and fun facts about the wine, production, and the area overall. We got to try a few Italian snacks, which were all really good. Looking back, it was a nice experience, but I'm not sure if it's really worth the money. We spend over €100 for 3 wines (not full glasses), and two rounds of snacks, which makes us feel like we did overpay a bit.”

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Guided Winery Tour and Wine Tasting in Siena

Guided Winery Tour and Wine Tasting in Siena - Cellar Stop: Quality Winemaking from Destemming to Aging

7.Guided Winery Tour and Wine Tasting in Siena

★★★★★★★★★★5.0 · 52 reviews · 2 hours 30 minutes (approx.) · from $90Top rated

Guided Siena wine tour at La Lastra in English: vineyard and cellar walk, 5 organic wines, plus seasonal food and organic olive oil.

“From start to end this event was not only educational but sensational - learning from the roots to the glass was inspirational and really showed the dedication and respect they offer as an organic winery in Tuscany. Thanks for the delightful meal wonderful wine and excellent guide Maya!”

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Guided tour of the cellars with wine tasting and lunch

Guided tour of the cellars with wine tasting and lunch - Winery walk-through: how their wine is born and aged

8.Guided tour of the cellars with wine tasting and lunch

★★★★★★★★★★5.0 · 40 reviews · 2 hours 30 minutes (approx.) · from $77

Visit a restored family church, tour San Giorgio a Lapi cellars, then enjoy lunch plus multiple Tuscan wine tastings near Siena.

“This was without a doubt the best day out ever! The vineyard is absolutely beautiful and learning about the history of their family run business and the surrounding areas was truly amazing. The wines we tasted were incredible and the little food platters - so tasty!! Our Tour guide Albrezzo was so lovely and so attentive, we would most definitely do the tour again just to enjoy the views and the delicious wine. I wish they sold their wine in London, I would definitely buy it!”

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Siena Medieval Power Quest: Self-Guided Family Feud Game

Siena Medieval Power Quest: Self-Guided Family Feud Game - Getting Started at Piazza del Duomo: Fast Setup Beats Frustration

9.Siena Medieval Power Quest: Self-Guided Family Feud Game

★★★★★★★★★★4.5 · 38 reviews · 1 hour to 1 hour 30 minutes (approx.) · from $7Best value

Self-guided medieval family feud quest in Siena. Solve 9 puzzles at top landmarks in English, offline, about 1–1.5 hours.

“App was pretty buggy and difficult to use and English translation and overall story was poor. This was an okay way to walk through old Siena and see some of the major sites.”

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Discover Siena: Guided Walking Tour and Cathedral Visit

Discover Siena: Guided Walking Tour and Cathedral Visit - The Palio Thread: Contrade Stories That Make the Festival Click

Chianti: 4 Wines +1 Oil Guided Tasting & Tour

Chianti: 4 Wines +1 Oil Guided Tasting & Tour - The 25-Minute Guided Tour: Wine and Olive Oil From the Ground Up

11.Chianti: 4 Wines +1 Oil Guided Tasting & Tour

★★★★★★★★★★4.8 · 32 reviews · 1.5 - 2 hours · from $41

A guided Chianti Classico winery and farm tour with 4 wine tastings plus Terre di Perseto olive oil, paired with Tuscan bruschetta.

“Our tour was interesting and informative. Our tour and the tasting was the exact vibe that my daughter and I had hoped for. Our guide, Simona (sp), was delightful and welcoming. Her personality made the atmosphere relaxing and fun. Thank your for a wonderful afternoon!”

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Siena Walking Tour with Audio and Written Guide by a local

Siena Walking Tour with Audio and Written Guide by a local - Price and what it buys you: $7.20 for a day of structure