About this tour
A seven-hour private tour through two of Tuscany's most striking hilltop towns. Start in Volterra, where Etruscan walls and a well-preserved Roman theatre anchor centuries of history, then drive through the cypress-dotted Chianti landscape to San Gimignano's famous medieval towers. Lunch at a working vineyard includes five wine tastings and local specialities—olive oil, balsamic, truffles—giving you a genuine taste of how the region eats and drinks.
Highlights
- Roman theatre and Etruscan ramparts in Volterra
- Five distinct Tuscan wines tasted at a family winery
- Lunch featuring local oils, truffles, and aged vinegars
- San Gimignano's iconic towers rising above rolling hills
- Vernaccia white wine, Chianti Riserva, and Super Tuscan varietals
- Private transport with air conditioning and expert commentary
What to expect
Your driver collects you and heads northeast toward Volterra, where you'll wander the historic centre and stand before the Roman theatre—a genuine ruin, not a reconstruction. Around midday you arrive at a vineyard tucked into the Chianti hills. Here you'll sit down to a proper Tuscan lunch: bread rubbed with tomato, cured meats, cheeses, and hot dishes, paired with five different wines poured by someone who knows the soil they come from. You'll taste balsamic on its own, sample estate olive oil, and understand why truffles matter. The afternoon drive to San Gimignano feels like stepping backward; the town's stone towers crowd the skyline exactly as they have for 700 years. You'll explore the piazza, spot the gelateria, and have time to absorb the quieter corners before heading back.
Good to know
Wear comfortable shoes for walking cobbled streets. The tour runs seven hours total with pick-up and drop-off included. Lunch and all five wine tastings are part of the package. Infant seats and pram facilities are available. The vehicle is wheelchair accessible.
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.