Private Full-Day Siena, San Gimignano & Chianti Tour

Tour Overview

Siena San Gimignano and Chianti with private GUIDE 9hrs

Start your morning with a guided tour of the enchanting city of Siena, accompanied by an expert licensed guide who will bring the city’s medieval streets, iconic Piazza del Campo, and stunning cathedral to life.

In the afternoon, explore the heart of the Chianti wine region, discovering both famous vineyards and charming family-owned wineries. Tour the cellars, meet the winemakers, and taste their exquisite wines and local specialties🍷✨

Finally, wander through the breathtaking medieval town of San Gimignano, renowned as one of Italy’s most beautiful historic villages.

Add an optional lunch at a local organic farm or winery, savoring traditional Tuscan dishes paired with exceptional wines 🌿🍝

9-hour full-day private tour of Tuscany from Florence
Private tour for a maximum of 6 travelers (your party only)
Licensed tour guide in Siena included
Visit the medieval cities of Siena, Monteriggioni and San Gimignano
Craft Chianti Classico wine tasting at a local vineyard
Private air-conditioned minivan for your group

What's Included

Pick-up and drop-off at your selected hotel or location in Florence downtown Licensed tour guide in Siena for 2–3 hours Private minivan with air-conditioning for maximum comfort 🚐English-speaking licensed driverUnlimited cold mineral water 💧WiFi on board 📶Panoramic photo stop to capture the breathtaking views 📸

What's Not Included

A full lunch at the winery is available at an additional cost of €60–€70 per person to be paid on site.A restaurant lunch in Monteriggioni, as per the standard itinerary, is available at an additional cost depending on what you order.
Food and drinks

Your Itinerary

Discover the medieval beauty of Siena

Followed by an authorized guide, who will be at your disposal for the entire time you spend in Siena, you will explore the stunning city. Renowned throughout Italy for its medieval architecture, Siena is a feast for the eyes at every corner. Upon arrival, admire the iconic Conch-shaped Piazza del Campo and the magnificent Siena Cathedral, true gems of Tuscan heritage. Stroll along the historic streets, where charming local shops invite you to taste authentic Tuscan food or pick up unique souvenirs 🌿✨

Visit the stunning Siena Cathedral (DUOMO)

Here too, you will be accompanied by an authorized guide, who will meet you on site to explore the Cathedral of Santa Maria Assunta, the main Catholic place of worship in Tuscany and the bishopric of Siena. Located in the square of the same name, in the heart of the city, this Italian Gothic masterpiece is one of the most remarkable and awe-inspiring churches in Italy. 🌿✨

Discover the iconic Piazza del Campo

Step into Piazza del Campo, the heart of Siena and one of the most beautiful squares in the world. Famous for its unique shell-like shape, the square is a masterpiece of medieval architecture and a gathering place full of life and history. Twice a year, it becomes the stage for the famous Palio di Siena, an unforgettable horse race that fills the city with color, tradition, and excitement. 🌿✨

Optional Full Lunch at a local organic winery

Enjoy an unforgettable lunch experience at a charming organic farm or small family-owned winery. While the owner shows you around the property, his family will prepare a delicious homemade lunch featuring fresh pasta, crostini, local meats and cold cuts, legumes, seasonal vegetables, honey, and cheeses. Taste the farm’s own organic wines, including small-production craft wines, perfectly paired with each course. Sit back and savor your meal while enjoying a breathtaking Tuscan panorama 🌿🍷 ⚠️ This optional experience may slightly reduce time in Siena and San Gimignano and will replace the visit to Monteriggioni Fortress. If the winery lunch is not requested at the time of booking, the tour will follow the original program, including the stop at Monteriggioni Fortress.

Explore the charming village of Monteriggioni

Make a delightful stop in the small medieval fortified village of Monteriggioni, still surrounded by its original walls. Just a short drive from Siena, Monteriggioni is the perfect place for a leisurely stroll, soaking in the historic atmosphere after lunch at one of the local restaurants 🌿🏰

Discover the magic of chiantigiana road

Discover the magic of the Chiantigiana Road (SS222), one of Italy’s most beautiful routes 🇮🇹, winding through the heart of Chianti from Siena to Castellina in Chianti. Every turn offers breathtaking views, with green rolling hills, endless vineyards, and charming medieval villages 🏰. A journey along the Chiantigiana is more than a drive—it’s an experience for all your senses: the scent of wine, the colors of the hills, and the charm of ancient villages… an adventure that will stay in your heart ❤️.

San Gimignano, the medieval Manhattan

Here we are in the stunning stronghold of San Gimignano 🏰, a true jewel of medieval Italy, known as Medieval Manhattan for its multiple towers 🏙️. Walking through its streets is like stepping back in time to the 1300s, where every corner tells a story and every stone whispers history. Famous for its tower houses, San Gimignano rises proudly over the surrounding Tuscan hills, offering breathtaking views 🌄 that will stay in your memory forever. Take your time to wander the narrow streets, admire the medieval architecture, and capture the perfect photos 📸. Please note: there will be no authorized guide during this stop—this is a self-guided experience, so you can explore at your own pace and fully immerse yourself in the town’s magical atmosphere ❤️. This is our last stop of the day before returning to Florence, so savor every moment—the charm, the history, and the feeling of a town that seems frozen in time.