About this tour
This 11-hour private tour sweeps you through three of Tuscany's most compelling medieval towns from a comfortable minivan base in Florence. You'll navigate Siena's atmospheric lanes with a guide, taste four wines at a family vineyard paired with farmhouse lunch, wander San Gimignano's hilltop streets solo, and finish at Pisa's cathedral precinct. The route covers Renaissance palaces, Romanesque churches, and the region's vine-covered countryside in a single arc.
Highlights
- Siena's Duomo and Piazza del Campo with private guide
- Wine tasting and multi-course lunch at working Chianti vineyard
- Medieval tower-studded skyline of San Gimignano
- Pisa's cathedral, baptistery, and Leaning Tower
- Air-conditioned transport between all stops
- Contrada church and museum visit in Siena
What to expect
You'll spend the morning driving through rolling Tuscan landscape to Siena, where your guide walks you through medieval quarters to the cathedral and civic landmarks. Mid-morning, you'll head out to the countryside for a leisurely vineyard tour and four-course lunch with four wine pours, enjoying countryside views from the terrace. Afterwards, San Gimignano offers a few hours of self-directed exploration—narrow stone streets, tiny piazzas, sweeping vistas. The final leg carries you to Pisa, where you'll have time to circuit the cathedral complex and photograph the famous tilted structure. Expect a steady pace with moderate walking.
Good to know
Moderate fitness required due to Siena's steep hills and uneven cobbles. Vegetarian and gluten-free meals available at lunch with advance notice. Infants go on laps; pushchairs work on flatter sections. Not suitable for spinal or cardiovascular concerns. Professional guide stays with you all day except San Gimignano.
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.