About this tour
Seven to eight hours exploring Tuscan wine country in a private Mercedes with your own driver, departing Florence. Visit two Chianti wineries at your pace, take in San Gimignano's medieval towers, and stop briefly at Piazzale Michelangelo for views over the city. Roll through cypress-lined valleys and stone villages while your driver handles the roads. Wine tastings cost extra but the countryside itself is the main event.
Highlights
- Two winery visits in Chianti region at your chosen pace
- Medieval San Gimignano with its signature tower skyline
- Piazzale Michelangelo viewpoint overlooking Florence
- Private Mercedes with English-speaking driver throughout
- Customise stops based on your interests and timing
- Air-conditioned comfort on winding Tuscan roads
- Hotel pickup and drop-off included
What to expect
Your driver collects you from your Florence hotel in the morning and heads into rolling Chianti hills. You'll pull into at least two working wineries where you can wander the grounds, chat with staff, and decide whether to pay for tastings separately. San Gimignano appears suddenly—a fortified medieval town perched on a ridge with 14 towers poking skyward. Wander the narrow streets, grab lunch (your cost), browse local shops. On the return, the driver stops at Piazzale Michelangelo so you can photograph Florence from above. You're in a vehicle for substantial stretches; the journey itself is part of the experience.
Good to know
Wine tastings aren't included—budget accordingly if you want to taste at the wineries. Lunch is on you, though San Gimignano has decent options. Wear comfortable shoes for cobbled streets. Travel time counts toward the 7–8 hour total, so actual winery time is less than it sounds. Infant seats available if needed.
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.