About this tour
Venture into Tuscany's medieval heartland on a 12-hour private drive from Rome, visiting three distinctive hilltop settlements. Explore Monteriggioni's ring-walled fortress, wander San Gimignano's tower-studded streets, and discover Castellina in Chianti's wine country charm. A leisurely lunch and local wine tasting anchor the day, with your own vehicle and driver throughout.
Highlights
- Monteriggioni's complete medieval walls and compact piazza
- San Gimignano's 14 surviving towers rising above Tuscan hills
- Castellina in Chianti wine estate with tasting included
- Private transport with English-speaking driver throughout
- Lunch in one of the three towns
- Flexible itinerary customisable before departure
What to expect
You'll be collected from your Rome hotel and driven into Tuscany's rolling landscape. The day moves at a relaxed pace—each town rewards a couple of hours on foot, climbing cobbled streets and ducking into galleries or shops as you choose. Monteriggioni is compact; San Gimignano demands more time if you climb its towers or visit museums. Lunch happens around midday, typically within one of the towns. The wine tasting occurs at a local producer, usually in Castellina, where you'll sample a few pours with light snacks. Return to Rome happens in the evening.
Good to know
Minimum age for wine tasting is 18 (soft drinks available). Wear comfortable shoes—cobblestone streets dominate all three towns. An infant car seat can be arranged on request. The tour operates as a private group; you can request route adjustments before booking.
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.