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Private and Small Group Guided 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.

Want more than a tour in Tuscany? Talk to our expert planners about custom and multi-day options at +1 (800) 691-8328. 

Tuscany Private and Guided 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
114 Reviews (4.69)

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

Patricia was a great guide. She did a great job of explaining the historic and cultural significance of where we were, making us both laugh and think, and just generally treating us like long-lost best friends. I'd definitely do another tour with her the next time we're in Tuscany.
So happy he met us at our hotel. We were worried that we would miss him at the train station. Great tour of Pisa: informative, good pace, and great guide!
Everything went smoothly thanks to both Context communication and Alessanda’s exceptional knowledge. Her warm personality made us feel almost like friends from the start. She remembered all our special requests, and she answered our questions with patience, insights, and gentle humor. All four of us left feeling that we couldn’t have made a better investment of time or money.