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Tuscany Private Tours and Tuscany Small group Tours

Tuscany 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 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
116 Reviews (4.69)

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Stella is an excellent guide. Her being a Siena native added so much richness to the tour. She was able to share her vast knowledge of Sienese history as well as impart much of the culture.
Martino was an excellent, well-informed guide who was happy to adapt to interests and pace. He was generous with his time and we greatly appreciated his insights. He even gave us tips for our trip to Florence next year. A note to Context: I would have liked to have known beforehand that entrance fees were not included in the cost of the tour.
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.