About this tour
A full-day drive from Florence through medieval Tuscany, visiting Siena and San Gimignano with your own English-speaking driver. You'll navigate both towns at your own pace, absorb local histories and traditions, and choose between lunch in Siena or at a Chianti wine estate with house-made food and local wines. The journey includes panoramic routes through the rolling hills that define the region. Eight to nine hours total.
Highlights
- Explore Siena's monuments and piazzas independently
- Climb Torre Grossa for views across San Gimignano
- Optional lunch and wine tasting at a Chianti estate
- Private vehicle and driver throughout the day
- Panoramic drive through Tuscan countryside
What to expect
Your driver collects you from your Florence accommodation and handles all navigation. In Siena, you'll have blocks of free time to wander the cathedral, admire the Palio square, and duck into local shops—your driver stays available to answer questions about customs and local food culture. Lunch is yours to shape: stay in town or venture to a working wine property in the Chianti hills for a seated meal with Tuscan specialities and glasses of the estate's own bottles. San Gimignano follows, where you can scale the tower, visit the duomo, or simply sit with gelato and watch the light change across the Val d'Orcia. The return journey gives you time to absorb the landscape before dropping back at your hotel.
Good to know
Admission fees to monuments and meal costs are not included. A guided walking tour of Siena can be arranged on request and is recommended if you want deeper context. The vehicle is air-conditioned and fully accessible. Infant seats are available; prams and service animals are welcome.
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.