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 distincct, each offering a different glimpse into Italian life and culture. Explore the diversity of Tuscany with Context's private and small group guided tours.co

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
134 Reviews (4.68)

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Stella was very knowledgeable and passionate about Siena. We enjoyed her depth of knowledge and personal stories, which brought Siena to life!
Gastone was excellent. His knowledge of Pisa and the history of Tuscany was unparalleled. Tremendous energy which kept the tour alive and fun.
Wow! We went to this tour on Palio weekend and we were SO GLAD we did. Stella was a true expert in all things Palio, and she gave us so much context (yes, the name works here!) for everything we were about to see. This tour exceeded our expectations, and we found ourselves explaining things to people when we went to see the trials and of course, the big race! We felt like real "insiders." Stella was so smart, knowledgable and fun, too. Could not recommend this enough!