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Tuscany Private Tours and Tuscany Small group Tours

Tuscany Private and Small Group Walking Tours

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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
120 Reviews (4.71)

Reviews can only be left by Context customers after they have completed a tour. For more information about our reviews, please see our FAQ.

Viviana was great. We enjoyed her flexibility and relaxed attitude as she told us great stories about Sienna. We learned a lot and saw the most spectacular sites to be seen.
Our guide was Vincent and he was terrific! Knowledgable, flexible, very pleasant and patient. Gastone was ill. My only criticism was that the price of the tour SHOULD have included tix to the monuments (cathedral and baptistry). It was made clear in advance that the tower was NoT included, but I was under the impression that the other sites were.
Stella is an amazing guide!!! We all appreciated her intimate knowledge of the Palio and she made that part of our trip so much more informative.