Tuscany Private Tours and Tuscany Small group Tours

Tuscany Tours and Experiences Hosted by Local Experts

From the Renaissance of Florence to the hilltop towns of the wine-producing countryside, it would be difficult to overstate the role of Tuscany in Italy’s history.
Whether visited as a day trip from Florence or arranged as a standalone trip, our favorite cities of Tuscany—Lucca, Siena, Pisa, Val d’Orcia, as well as the Carmignano countryside—are magnificently distinct, each offering a different glimpse into Italian life and culture. Explore the diversity of Tuscany with Context's private and small group guided tours.

Tuscany Private Tours and Tuscany Small Group Tours

Lucca is one of our favorite towns in Tuscany, and our half-day Lucca Tour is a great way to explore it. With a super-knowledgeable local historian at our side, we'll immerse ourselves in a mixture of history, language, local tradition, and contemporary life. Coming on a cruise ship and visiting Pisa for the day? Our insider Pisa Tour pairs us with a historian for three hours in order to make the most of the trip. For those renting a villa in Tuscany and spending more time exploring, we highly recommend our all-day Val d'Orcia Tour and our culinary adventure in Carmignano, two excursions for getting off the beaten path.
What Context Tuscany Travelers Say
137 Reviews (4.67)

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We learned so much! If you are going to Siena, I cannot recommend this tour enough. Having a guide walk around with you and provide so many details and lessons on the spot is invaluable. Our guide, Domenico, is truly passionate and knowabout what he does which made our experience so enjoyable and fun. Given the limited time that we had in Siena, I feel that we were able to make the most of it because of our tour. My only regret is that the time went by too quickly.
First and foremost, I'd like to highlight that my friends and I have taken several tours with Context Travel in the past few days, and each one of them was an outstanding experience. The guides were engaging, knowledgeable, and made our visits truly memorable. However, I must express my disappointment with the tour in Siena. The primary concern was the guide proficiency in English. It was exceptionally challenging for anyone in our group to grasp what he was trying to convey. Furthermore, his presentation style lacked cohesion, often feeling disconnected and confusing. By the end of the tour, most of us were genuinely relieved that it had concluded. I chose to rate the tour 2 out of 5 instead of 1 out of 5 because, despite the glaring issues, it was evident that he had good intentions. It was clear he wanted to deliver a positive experience, but sadly, he was not equipped to do so for an English-speaking audience. Considering this, it might be more beneficial for both the guide and the tourists if he is assigned to groups that speak Italian. He might be able to offer a far better experience in his native language. I genuinely hope this feedback will be useful for enhancing your future offerings.
Alessandra was absolutely wonderful! Extremely knowledgeable.. a perfect tour!