About this tour
Spend five hours exploring San Gimignano's medieval towers and the surrounding Chianti hills with a private driver. After wandering the village famous for its Vernaccia wine, you'll head to a family-run estate nestled between vineyards and olive groves. There you'll descend into the cellar, taste five distinct wines spanning Vernaccia to Chianti Classico Riserva and Supertuscan blends, plus sample their own extra virgin olive oil. Hotel transfers included.
Highlights
- Medieval San Gimignano village with iconic tower skyline
- Cellar tour at a generations-old family winery
- Five wine tastings from Vernaccia to Supertuscan
- Estate-made extra virgin olive oil tasting
- Scenic drives through rolling Tuscan countryside
- Private group, dedicated local driver
- Hotel pickup and dropoff
What to expect
Your morning begins with collection from your hotel. The drive into Tuscany sets the tone—rolling hills, cypress lines, vineyards stretching toward the horizon. San Gimignano reveals itself gradually, its towers rising above the landscape like a medieval chess set. You'll have time to walk the compact medieval streets before reconvening. The second leg takes you deeper into wine country, to an estate where generations have farmed the same slopes. A winery staff member will walk you through their cellars, explain the differences between vintages and styles, then guide you through five tastings. The olive oil rounds things out. Throughout, your driver remains on hand for the return journey.
Good to know
Water and air conditioning provided. Prams and infant seats available if needed. The tour suits all fitness levels—San Gimignano's streets are cobbled but manageable. Wear comfortable shoes. Wine tastings typically include food pairings; confirm dietary needs beforehand.
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.