From Florence: PRIVATE Trip to Pisa, San Gimignano, & Siena｜Italy

Itinerary

Stop at: Pisa, Tuscany
After a scenic one-hour drive through the rolling Tuscan hills, you’ll arrive in Pisa, a city where history whispers from every corner. Wander through its charming historic districts and discover Piazza dei Cavalieri, once the medieval political heart of the city. Transformed by Cosimo I de’ Medici into the headquarters of the Order of the Knights of Santo Stefano, this square is steeped in stories of courage, power, and Renaissance beauty. Every building, every cobblestone seems to echo tales of a time when Pisa defended the Mediterranean from pirates and Turkish fleets.
-Leaning Tower of Pisa
No trip to Tuscany is complete without stepping into the magic of Piazza dei Miracoli. Admire the iconic Leaning Tower, whose extraordinary tilt and timeless charm have captivated visitors for centuries. Capture playful photos “holding up” the tower, and let yourself be swept up in the joy and wonder of this unforgettable landmark.
Duration: 1 hour

Stop at: Historic Center of San Gimignano, Tuscany
Next, arrive in San Gimignano, a medieval gem seemingly frozen in time. Its towers rise proudly above the skyline, offering a glimpse into life in the 1300s. Stroll through charming streets filled with artisan shops, and don’t miss a stop at the world-famous Dondoli Gelateria, where some of the best gelato in the world awaits.
Piazza della Cisterna, San Gimignano
At the heart of the city, Piazza della Cisterna, dating back to 1287, was once a bustling hub for markets, festivals, and tournaments. Today, it still radiates the lively spirit of medieval life, inviting you to pause and imagine the stories that unfolded here centuries ago.
Duration: 2 hours

Stop at: Historic Center of Siena
Your journey concludes in Siena, a city where medieval architecture is perfectly preserved and every street tells a story. Explore the stunning Piazza del Campo, shaped like a seashell, and admire the magnificent Cathedral of Santa Maria Assunta, a Gothic masterpiece that leaves visitors in awe. As you stroll through the historic center, you’ll discover charming local shops and elegant boutiques, perfect for a bit of shopping, and don’t miss the local pastry shops where you can taste the famous ricciarelli, traditional almond and sugar cookies that are a true symbol of the city.
Piazza del Campo pulses with centuries of tradition and excitement, hosting the legendary Palio di Siena twice a year, while the Cathedral stands proudly at the city’s spiritual heart.
Duration: 2 hours

An exclusive and authentic experience, created especially for your private group, blending wine, culture and scenery into a memory you’ll cherish for years to come