PRIVATE Full-Day GUIDED Tour: Siena, San Gimignano and Chianti

About this tour

A private nine-hour Tuscan circuit departing Florence that sweeps through three medieval strongholds and wine country. Your licensed guide shepherds you through Siena's Gothic core, then the afternoon pivots to Chianti's rolling vineyard estates where you'll taste Classico wines straight from small producers' cellars. San Gimignano's tower-studded skyline closes the day. A Mercedes minivan handles transport; lunch at a working farm or winery is optional but revelatory for wine enthusiasts.

Highlights

• Licensed guide leads two-hour Siena walkthrough through piazzas and palaces
• Taste Chianti Classico at a family-run vineyard with cellar visit
• San Gimignano's medieval towers rise from rolling Tuscan hills
• Optional farm lunch pairing local wines with organic Tuscan fare
• Private nine-seater Mercedes with WiFi and chilled water included
• Monteriggioni fortress stop (or skip for extended winery lunch)
• Hotel pickup and drop-off within Florence city centre

What to expect

You'll be collected from your Florence hotel at 9am and travel in air-conditioned comfort through Tuscan countryside. In Siena, your expert guide unpacks the city's Renaissance layers—the striped cathedral, the Palio square—across two to three hours. The drive south enters Chianti proper: vineyards cascade downslope, and you'll stop at a producer to walk their cellars and taste their output. San Gimignano awaits late afternoon, its fourteen towers piercing the horizon. If you've booked farm lunch, expect three courses with wine pairings at an organic estate, though this swaps out the Monteriggioni fortress stop. Rain brings umbrellas; the pace suits all fitness levels.

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