About this tour
A nine-hour private tour through Tuscany's medieval heartland, combining wandering time in San Gimignano's towers and alleyways with a countryside winery experience. You'll taste eight wines and oils alongside a proper sit-down lunch in the cellar—lasagna or ribollita, roasted meats, local cheeses and cured cuts—before heading to Siena for two hours exploring its cathedral and famous piazza. Private car and driver included throughout.
Highlights
- Hour to wander San Gimignano's medieval streets alone
- Eight-wine and oil tasting at a working Tuscan estate
- Cellar lunch: ribollita, roasted meats, cantuccini biscuits
- Gothic cathedral and Torre del Mangia in Siena
- Private vehicle with air conditioning and WiFi
- Piazza del Campo, the shell-shaped civic heart
What to expect
You'll start with a drive to San Gimignano, where you've got an hour to explore the medieval towers and stone streets at your own pace. Then it's on to a countryside winery for a guided walk of the grounds, followed by lunch in the cellar itself—a rustic setting with proper Tuscan food and plenty of wine to taste alongside. After eating, you'll sample oils and taste through eight wines with a small spread of appetisers. The final leg takes you to Siena, where two hours allows a decent look at the cathedral's intricate Gothic facade and the sloping Piazza del Campo where the famous horse race unfolds each summer.
Good to know
Wear comfortable walking shoes; medieval villages involve cobbles and slopes. The winery lunch happens in the cellar itself, so dress warmly if you're sensitive to temperature. Small children can bring prams; specialised infant seats available in the car. Gratuities not included.
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.