PRIVATE Full-Day Siena, San Gimignano and Chianti from Florence

Siena Highlights. Siena is famous throughout Italy for its remarkably well-preserved medieval architecture. During your visit, explore the city’s highlights, including the iconic shell-shaped Piazza del Campo and the impressive Siena Cathedral. Enjoy free time to wander through historic streets, browse local artisan shops, taste regional specialties, or shop for authentic Tuscan souvenirs.

Cathedral of Siena.. The Cathedral of Santa Maria Assunta (Siena Cathedral) is Siena’s main place of worship and one of the most outstanding examples of Italian Gothic architecture. Located in the historic city center, this iconic landmark is celebrated for its impressive design, rich history, and artistic beauty, making it a must-see highlight of any visit to Siena.

Piazza del Campo, Siena.. Piazza del Campo is Siena’s main square and one of the most iconic medieval piazzas in Italy. Renowned for its distinctive shell-shaped layout and perfectly preserved architecture, it is also the famous setting of the Palio di Siena, the historic horse race held twice a year.

Castello di Monteriggioni. Enjoy a charming stop in Monteriggioni, a small medieval fortified village still enclosed by its original walls. Just a short drive from Siena, it’s the perfect spot for a leisurely walk and to soak in the historic atmosphere, especially after lunch at one of the local restaurants..

Optional Full Lunch Winery Lunch Experience. Enhance your Tuscan tour with a full lunch at a small, family-run boutique farm or winery. During your visit, the farm owner will guide you through the property while a traditional multi-course Tuscan meal is prepared. You’ll also visit the cellar to admire their Super Tuscans and Chianti Classico wines.Enjoy your meal with stunning views of the Tuscan countryside, savoring local specialties such as lasagna with traditional sauces, crostini, cold cuts, legumes, seasonal vegetables, honey, and cheeses. Each course, including dessert, is thoughtfully paired with different local wines, creating a complete wine-paired lunch.The selected wineries are authentic, small-scale, family-run establishments with organic production, not commercialized operations. Menus vary from one winery or farm to another, but every option guarantees a full and genuine Tuscan experience. The specific location will be chosen based on availability. Because these are boutique venues with limited capacity, early booking is strongly recommended.Please note: Choosing this lunch option slightly reduces time in Siena and San Gimignano and excludes the stop at Monteriggioni.

San Gimignano "The medieval Manhattan". Our final stop of the day is the beautiful walled town of San Gimignano, one of Tuscany’s most popular destinations. Known as a pearl of medieval architecture, the town has remained almost unchanged since the 1300s. San Gimignano is especially famous for its ancient towers, which dominate the skyline and have earned it the nickname the “Manhattan of the Middle Ages.” Take time to wander the charming streets, admire historic buildings, and don’t miss the famous Dondoli Gelateria, awarded multiple times for producing some of the best ice cream in the world. After exploring San Gimignano, we head back to Florence, completing your full day of Tuscan discovery.

Strada del Chianti "the Chiantigiana Road". Discover one of Italy’s most scenic roads: the SS222, also known as the Chiantigiana, stretching across the Chianti region from Siena to Florence. This panoramic route immerses you in dreamy Tuscan landscapes, with rolling green hills, endless vineyards, and charming medieval villages.We’ll travel from south to north, exploring picturesque villages along the way. Stop to capture stunning photos of cobblestone streets, historic towers, and quaint village squares that showcase the heart of Tuscany.Perfect for travelers who love history, nature, and iconic scenery, with plenty of opportunities to experience local traditions and taste the flavors of Chianti.