About this tour
This 11-hour private tour departs Rome early to explore two of Tuscany's most distinctive hilltop settlements. Your driver navigates the 2.5-hour journey to Siena, where you'll wander its brick-laid piazzas and medieval streets at your own pace. From there, San Gimignano awaits with its famous tower-house skyline and narrow alleyways. The day concludes in the countryside at a winery for lunch and tastings, before returning to your Rome hotel by evening.
Highlights
- Siena's Piazza del Campo and medieval architecture
- San Gimignano's distinctive 14 surviving towers
- Tuscan countryside wine tasting and lunch
- Private vehicle with English-speaking driver throughout
- Hotel collection and drop-off from Rome
- Flexible exploration time in both towns
What to expect
Expect an early 7:30am departure followed by a long coach journey into Tuscany's rolling hills. In Siena, you'll have roughly two hours to navigate the centro storico—steep cobbled streets and sudden plazas reward wandering. San Gimignano is more compact; most travellers cover the main sights in an hour, sampling local gelato and souvenirs along the way. The afternoon shifts to a more relaxed pace at a valley winery where you'll sit down for a light meal paired with regional wines. Bring comfortable walking shoes, water, and sunscreen; the towns are hilly and exposure is unavoidable.
Good to know
Wine tasting and lunch cost €55 per person, paid on-site. Inform the operator of dietary requirements when booking. The tour runs regardless of weather—dress appropriately. Moderate fitness needed for town exploration. Prams and wheelchair-accessible vehicles are available; confirm accessibility needs in advance.
Tour sold and operated by Viator via Viator. Descriptions on this page are original Global Hobo summaries written by our team — not copied from the operator. Prices and availability are confirmed at checkout.