About this tour
A seven-hour private drive through central Tuscany linking two medieval hilltop towns separated by centuries of history. Start in Volterra with its Roman theatre and sweeping countryside views, then lunch at a working winery farm where you'll taste five wines and sample local oils and vinegars. Afterwards, wind through Chianti's vine-covered slopes to San Gimignano, famous for its cluster of surviving towers. Finish with gelato in the main piazza before returning mid-afternoon.
Highlights
- Roman theatre in Volterra, one of Tuscany's finest viewpoints
- Lunch and five-wine tasting at a certified organic farm
- Drive through Chianti vineyards, olive groves, cypress-lined roads
- Medieval towers of San Gimignano and Black Rooster legend
- Vernaccia white wine, Super Tuscan, local balsamic and truffle oils
- Award-winning gelateria stop in San Gimignano's main square
What to expect
Your driver collects you and heads north into rolling Tuscan hills. Volterra sits high and exposed; you'll walk the historic centre and stand at the Roman theatre with views across farmland to distant ridges. At midday you reach a family-run biodynamic estate nestled among vines. Lunch is simple and seasonal—cured meats, cheese, bread—paired with tastings of Chianti Rosso and Riserva, Sangiovese, and crisp Vernaccia. You'll also sample their bottled oils, aged balsamic, and truffle products. After two hours, you drive south through classic postcard landscapes: vineyard parcels separated by cypress windbreaks. San Gimignano's towers rise suddenly from the valley. You explore the town's narrow medieval streets, admiring tower-houses, then sit down for gelato. By 5pm you're on the road home.
Good to know
The tour is fully private, not group-based. Five wines over lunch is substantial; eat well and pace yourself. Infant seats and prams are available. Wheelchair access confirmed. A professional guide is not included but can be arranged a week ahead for extra cost. Bring comfortable walking shoes for cobbled streets.
Tour sold and operated by Viator via Viator. Descriptions on this page are original BugBitten summaries written by our team — not copied from the operator. Prices and availability are confirmed at checkout.