About this tour
Seven to eight hours exploring three of Tuscany's medieval gems in a private car. Start in Siena wandering past the Duomo, Santa Caterina's house, and Piazza del Campo with its famous tower. Then head into the countryside to lunch inside Monteriggioni's castle walls before visiting a working Chianti vineyard for tastings. The return route passes Piazzale Michelangelo overlooking Florence. An English, Italian or Spanish-speaking guide accompanies throughout.
Highlights
- Siena's Duomo, towers and Renaissance palaces on foot
- Lunch within medieval castle fortifications at Monteriggioni
- Chianti vineyard cellar tour and wine tasting session
- Piazzale Michelangelo viewpoint on the drive back
- Air-conditioned private vehicle for the full day
- Vegetarian, vegan and gluten-free meal options available
What to expect
The morning focuses on Siena's compact medieval core. Your guide leads you past the cathedral, the Basilica of San Domenico, and palatial Renaissance mansions, with photo stops at elevated vantage points over terra-cotta rooftops. Around midday you'll drive into rolling farmland and eat a traditional Tuscan lunch inside Monteriggioni castle. The afternoon shifts to wine country: a vineyard cellar visit includes education on production methods followed by tastings of local reds and whites with the option to purchase bottles. On the return leg, you'll pause at the hilltop lookout above Florence before heading home.
Good to know
Comfortable walking shoes essential for Siena's cobbled streets. The pace suits all fitness levels. Children can use prams in town; specialised infant seats fit the car. Dietary requirements—vegetarian, vegan, coeliac—are accommodated if you request ahead. Public transport is nearby if needed.
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.