About this tour
This 8–9 hour excursion departs Florence to explore two of Tuscany's most distinctive hilltop towns. You'll spend time in Siena wandering Piazza del Campo and its cathedral, then move on to San Gimignano to stroll between its medieval towers. The day culminates at a countryside villa for guided tastings of regional wines and artisanal foods, offering a blend of Renaissance architecture, medieval streetscapes and local gastronomy.
Highlights
- Piazza del Campo: Siena's shell-shaped heart and civic masterpiece
- Siena Cathedral: Gothic interior with striped marble and intricate mosaics
- San Gimignano's tower-lined streets and gelato tradition
- Villa tasting: Tuscan wines paired with regional specialities
- Countryside backdrop and rolling hills between towns
- Private vehicle throughout; no group coach crowds
What to expect
You'll be collected in Florence and driven through undulating Tuscan landscape to Siena, where a guide leads you through the cathedral, then releases you into the piazza and town centre for independent exploration—ideal for lunch stops or lingering in shops. The drive to San Gimignano takes you deeper into wine country; here you have freedom to wander its narrow lanes and sample local ice cream. Late afternoon you arrive at a working villa in the countryside. A sommelier-led tasting introduces you to wines and cured meats, cheeses, or oils sourced nearby, with time to absorb the rural setting before returning to Florence.
Good to know
Wear comfortable walking shoes; both towns involve cobblestone streets and modest inclines. Lunch is on your own—budget accordingly in either town. The villa visit requires reasonable fitness due to uneven terrain. Bring a light layer; countryside venues can be cooler. Gratuities are separate.
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.