Private Chianti Wine Tour from Florence with Siena and San Gimignano Visit

Meet your private driver at Piazzale Montelungo

Your day starts at Piazzale Montelungo in Florence, next to the Piccolo Ristoro kiosk. Meet your tour leader, hop into your private vehicle, and head south through Tuscany's cypress-lined roads.

Explore Siena

Arrive in Siena, home to the twice-yearly Palio horse race that packs the shell-shaped Piazza del Campo with roaring crowds. Walk the sloping piazza and spot the tower that looms over medieval brick buildings. After, enjoy free time to visit the black-and-white striped cathedral on your own.

Chianti winery tour and tasting

Drive into Chianti's vine-covered hills to meet a family that's made wine here for 13 generations. Walk the Sangiovese rows, peek into aging cellars, and taste six wines, including crisp Vernaccia and bold Super Tuscan Riserva, paired with artisanal olive oil.

Tuscan 3-course lunch

Sit down to a traditional feast that starts with Tuscan cheeses, cured meats, and bruschetta. Next comes lasagne al tartufo and ribollita, the hearty bread-and-vegetable soup that's fed families here for centuries. Finish with cantucci dipped in sweet Vin Santo.

Free time in San Gimignano

Continue to San Gimignano, nicknamed Medieval Manhattan for the 14 stone towers that once showed off rival families' wealth. You'll have free time to wander cobbled lanes and climb to viewpoints where towers frame the hills in every direction.