From Florence: Siena, San Gimignano and Pisa day trip｜Italy

Explore the Best of Tuscany in One Unforgettable Day

Follow in the footsteps of the 18th-century Grand Tour travelers and uncover the very best of Tuscany in a day packed with art, culture, food, and iconic views.

Your day begins at 8:00 AM in Florence, where you'll meet your local tour leader and set off aboard a luxury Mercedes minivan, equipped with air-conditioning and free Wi-Fi. Glide through the picturesque Chianti countryside as you head toward the first stop: Siena.

Here, you’ll join a guided walking tour through one of Italy’s most enchanting medieval cities. Admire Gothic landmarks like the Basilica of San Domenico, stroll along ancient alleys to Piazza del Campo, and learn about Siena’s legendary Contrade—its fiercely proud neighborhoods that come alive during the famous Palio horse race. End the tour near the majestic Duomo, after a delightful local tasting of typical specialties.

Next, the journey continues through a scenic route dotted with vineyards and hilltop towns, reaching the iconic skyline of San Gimignano. Known as the "Medieval Manhattan," this UNESCO gem offers free time to wander cobbled streets, admire the soaring towers, shop for artisan crafts, or simply take in the postcard-perfect views.

By early afternoon, you’ll stop to enjoy a typical Tuscan lunch (included), where you’ll sample regional flavors in a charming countryside setting. Expect fresh pasta, cured meats, and local wine—the essence of Tuscan cuisine.

The final stop of the day brings you to Pisa, home of the world-famous Leaning Tower. You'll have time to explore the impressive Piazza dei Miracoli, a masterpiece of medieval architecture featuring the Cathedral and Baptistery. While entry tickets to climb the tower are not included, you’re free to purchase them on-site if time allows.

As the sun begins to set, relax in comfort on the return drive to Florence, arriving around 7:30 PM with your camera full and your heart fuller.

SHORT ON TIME?
Don’t have a full day to spare? Choose our afternoon experience "Siena & San Gimignano with Dinner" instead! Departing at 2:00 PM and lasting around 8 hours, this option does not include Pisa, but takes you to the same iconic Tuscan towns in a small group (max 20) aboard a comfortable minibus. Cap off the day with a magical sunset dinner in the Chianti hills — ideal for travelers on a tighter schedule who still want the full Tuscan vibe.