Semi-Private Pisa, Siena and Chianti Tour with Lunch and Wine Tastings

One extraordinary day across medieval hilltowns, rolling vineyards, and a legendary leaning monument

This Tuscany day tour takes you through three of the region's most celebrated destinations — Siena, San Gimignano, and Pisa — while weaving in a sit-down lunch and wine tasting at a working Chianti winery. The semi-private format keeps group sizes small, allowing for a more personal experience with your guide. Every stop on this itinerary has earned its place on the UNESCO World Heritage list or in the pages of Italian history.

Siena opens the day with its extraordinary medieval streetscape and the iconic shell-shaped Piazza del Campo, the stage for the Palio horse race that has defined the city's identity for centuries. A licensed guide walks you through the city's architectural highlights, including the exterior of the black-and-white marble Cathedral, before you have time to explore at your own pace.

After a lunch break in the Chianti countryside — complete with local wine, bruschetta, fresh pasta, and seasonal sweets — the afternoon brings you to San Gimignano. This walled town, crowned by its surviving medieval towers, offers cobbled lanes, artisan shops, and what is widely considered Italy's finest gelato. The day closes at the Piazza dei Miracoli in Pisa, where the Baptistery, Cathedral, and Leaning Tower stand together in one of the most photographed squares on earth.

Traveling through the Chianti region by panoramic road connects each destination naturally, offering sweeping views of cypress-lined hills, vineyards, and farmhouses that define the Tuscan landscape most visitors come to see.