Private Tour Siena San Gimignano and Chianti from Cortona




Private Tour Siena San Gimignano and Chianti from Cortona
Discover Tuscany's gems on a private tour from Cortona. Explore Siena's historic streets, taste exquisite Chianti wines, and stroll San Gimignano's medieval towers. An unforgettable day.
Experience Details
Kick off your day with a comfortable ride through the stunning Tuscan countryside. First, we’ll arrive in Siena, one of Tuscany’s most beautiful towns. Explore Piazza del Campo, famous for the Palio di Siena horse race, admire the breathtaking Duomo (Cathedral), and wander through the charming, narrow streets of the historic center. Wine Tasting & Light Lunch Next, we’ll head to a renowned winery for a light lunch paired with an amazing wine tasting experience. A sommelier will guide you through five exceptional wines, plus an olive oil tasting.
After lunch, we’ll continue our journey with a spectacular drive through the rolling Vernaccia di San Gimignano vineyards, home to Tuscany’s most famous white wine. Stop in San Gimignano you’ll have free time to explore this medieval gem, known for its 14 towers dating back to the 13th century. The town’s atmosphere will transport you back to the Middle Ages! And of course, you can’t miss the world’s best gelato at Gelateria Dondoli.
What You Get
Good To Know
- Infants and small children can ride in a pram or stroller
- Public transportation options are available nearby
- Suitable for all physical fitness levels
- Specialized infant seats are available
What You’ll Experience
Piazza del Campo
Duomo di Siena
Monteriggioni (Pass By)
San Gimignano
Meeting & Pickup
Cancellation Policy
Cancel your booking at least 24 hours before the experience start time to receive a full refund.
This was seriously the most amazing experience of my entire life Max was the funnest, funniest and coolest guide. He was so knowledgeable, so attentive so caring and so positive. I will use this co...read more









Max was great and helped us so much to navigate through with precise directions and enough time to enjoy a few different cities. He was such a great guide for our first time in Italy Would recomme...read more




Amazing trip with Luca. Made the trip memorable for our family of 4 and still managed to fit in a bit of time a local winery! Loved both San Gimignano and Monteriggioni and really enjoyed Luca’s ...read more
Luca provided outstanding customer service throughout the entire tour. He was patient professional and explained contextualized historical information so that we understood the importance of what w...read more
Luka was wonderful! The time allocation accross each of the three places was exactly right. It was entertaining and also relaxing. We didn’t feel rushed or overwhelmed and had time to explore. I hi...read more



