Tuscany Private and Small Group Guided Tours
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.
Looking for something special?
Tuscany custom tours
starting at $1,475.
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
110 Reviews
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Reviews can only be left by Context customers after they have completed a tour. For more information about our reviews, please see our FAQ.
Stella gave us an engaging walk through Siena, providing a good historical perspective as well as how the city became organized. Her experiences provided a deeper understanding of the community and history. Well done!
Jonathan
Dec. 31, 2021
Rita was excellent. Knowledgeable, informative and brought wonderful local color.
Deborah
Dec. 15, 2021
I believe that our guide was Stella, not Viviana.
Your company is well named - your guides really provide a context for what we are viewing. The background really helps the sites come alive. Stella was very knowledgeable and friendly. We genuinely enjoyed our trip to Sienna.
Re: future trips, I hope that you will re-introduce your semi-private tours. With private as the only option available, the tours are pricier than before.
Phyllis
Oct. 17, 2021