About this tour
This eight-hour private tour threads through Chianti's rolling countryside to medieval Siena and the hilltop towers of San Gimignano. Your driver navigates the scenic back roads of Tuscany whilst sharing historical context about these two cornerstone towns. Along the way, you can request stops at local wineries for tastings or lunch—these are arranged and paid separately, giving you flexibility to linger or move on as you prefer.
Highlights
- Scenic Chianti roads through Tuscan countryside
- Siena's mediaeval piazza and historic centre
- San Gimignano's iconic tower-house skyline
- Optional winery visits and wine tastings
- Private air-conditioned vehicle throughout
What to expect
Your day begins with pickup in a comfortable, climate-controlled vehicle. The drive winds through characteristic Chianti landscape—vineyards, cypress-lined hills, stone villages—as your driver shares local knowledge. You'll spend time exploring Siena's compact historic core and its famous piazza, then head north to San Gimignano, perched on a hilltop and distinctive for its cluster of medieval towers. Between towns, if you wish, the driver can detour to a winery where you taste local wines or grab lunch. Otherwise, the journey is direct.
Good to know
Lunch, drinks and wine tastings are not included and paid on the day. The vehicle is wheelchair accessible; prams and specialised infant seats available. Suitable for all fitness levels. Public transport options exist if you prefer independent travel between stops.
Tour sold and operated by Viator via Viator. Descriptions on this page are original Global Hobo summaries written by our team — not copied from the operator. Prices and availability are confirmed at checkout.