About this tour
Your private driver collects you from your Florence hotel and drives into Tuscany's rolling countryside for an eight-hour loop through two medieval strongholds. San Gimignano's skyline of towers comes first—walk the compact centro at your own pace—then settle into a family winery for lunch paired with local wines and vineyard views. Siena follows, where your driver shares local knowledge before you wander the brick-built streets and Piazza del Campo solo. Return to Florence as the light fades.
Highlights
- San Gimignano's 14 surviving medieval towers and narrow lanes
- Tuscan vineyard lunch with regional wines and countryside setting
- Siena's shell-shaped piazza and Gothic architecture
- Private car throughout; no coach crowds or fixed schedules
- Both towns UNESCO-listed; centuries of art and architecture intact
- Driver commentary on Tuscan history and local stories
What to expect
You'll spend roughly two hours each in San Gimignano and Siena, enough to hit the main squares and basilicas without rushing. The winery stop—about 90 minutes—includes a light meal and walk through the cellar or estate. Drives between locations take 45 minutes to an hour on quiet country roads; bring a book or watch the landscape shift. The car is comfortable but not a tour bus; your driver won't narrate every village or vineyard you pass. If you want deeper context on frescoes, history, or architecture, upgrade to include a guide who travels with you all day.
Good to know
Lunch includes non-alcoholic options if you prefer to stay sober for the afternoon driving. Wear comfortable shoes—cobblestones and hills are unavoidable in both towns. The route is manageable for most fitness levels, though Siena's centro has stairs and slopes. Infant seats and prams are available if needed. Tips aren't included.
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.