About this tour
An eight-hour private drive through Tuscany's rolling hills to the medieval towers of San Gimignano and the vineyard-striped Chianti region. You'll explore hilltop villages and countryside that has hardly changed in centuries, with a break for lunch at a family-run winery where you can taste local wines and eat alongside locals. The landscape shifts constantly—cypress groves, terracotta farmhouses, endless vine rows—making the journey itself as rewarding as the stops.
Highlights
- Medieval San Gimignano with its iconic stone towers
- Chianti vineyards stretching across rolling Tuscan hills
- Lunch at a working winery with regional dishes
- Private car and driver for eight hours
- Countryside viewpoints and quiet village walks
- Accessible throughout—all surfaces, transport, facilities
What to expect
You'll be collected for a leisurely drive through Tuscany's most photographed landscape. San Gimignano appears suddenly—a cluster of 14 medieval towers rising from a hilltop, largely unchanged since the 1300s. Time here is unrushed; wander the narrow streets, visit a couple of churches or the central square. Then you'll head into Chianti proper, where vineyards dominate the view. Lunch happens at a genuine winery, not a tourist trap—expect honest Tuscan food (pasta, roasted meat, local cheese) and the chance to taste and buy wines if you wish. The drive back takes in more countryside, stopping for photos as light changes.
Good to know
Wine tastings and meals are separate costs—budget accordingly. Bring comfortable walking shoes for cobbled streets and uneven village paths. The car is air-conditioned and can accommodate prams and wheelchair users. Nearby public transport exists but the private vehicle gives you flexibility to linger without rushing.
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.