Tuscany Highlights and Wine Private Car Tour from Florence

About this tour

A twelve-hour private tour sweeping through Tuscany's most storied towns and wine country, departing from Florence. You'll visit Pisa's tilted cathedral, wander the brick towers of San Gimignano and the Gothic squares of Siena, then sample three wines at a working Chianti estate. A licensed guide drives you door-to-door in a private car, handling navigation while you absorb the landscape.

Highlights

• Photograph Pisa's off-kilter bell tower up close
• Walk medieval San Gimignano's hilltop streets and towers
• Explore Siena's shell-shaped piazza and duomo
• Taste three Chianti wines at a traditional producer
• Private sedan or van with hotel pickup and drop-off
• Fluent English-speaking guide for full day
• Wheelchair-accessible stops and transport throughout

What to expect

Your guide meets you at your accommodation and drives south into rolling vineyard country. You'll spend roughly 2–3 hours each in Pisa, San Gimignano, and Siena—enough to see the major monuments and wander quieter lanes without rushing. Expect cobblestone streets, steep hills in some towns, and moderate walking between sites. Mid-afternoon, you'll arrive at a family-run cantina or restaurant where you'll taste three wines paired with the region's landscape. The drive itself is part of the experience: your guide narrates Tuscan history and points out working farms as you pass.

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