About this tour
A 12-hour private drive through Tuscany's trio of medieval towns, departing Florence. You'll explore Pisa's famous leaning tower, wander San Gimignano's stone towers and cobbled streets, then spend time in Siena's brick-built centre. A halt at a top-tier Chianti Classico estate breaks up the drive—lunch and wine tasting included. Your English-speaking driver navigates the route while you take in rolling Tuscan countryside.
Highlights
- Pisa's iconic leaning tower and cathedral square
- San Gimignano's medieval towers and hilltop views
- Siena's duomo, piazza and terracotta rooftops
- Estate lunch and five-wine tasting in Chianti country
- Private Mercedes transport with professional driver
- Bottled water and on-board WiFi throughout
What to expect
You'll start early from Florence and head west to Pisa, where you'll have time to photograph the Leaning Tower and explore the Piazza dei Miracoli. Next, drive into San Gimignano, a fortified village famous for its dozen stone towers; expect narrow lanes and panoramic views. Mid-day arrives at a Chianti Classico winery for a seated lunch and structured tasting of five wines, plus estate products. The afternoon takes you to Siena, where you can climb the Duomo steps, sit in Il Campo, or simply watch the light shift across medieval brick. Your driver handles all navigation and timing; you pace your own exploration at each stop.
Good to know
Wear comfortable walking shoes—each town involves cobblestones and hills. Lunch and wine tasting are separate paid extras (not included in the drive). The 12-hour day is steady but manageable for most fitness levels. Bring a hat and sunscreen for summer visits.
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.