Pisa, Siena and San Gimignano Day Trip with Optional Lunch and Wine Pairing
One day, four legendary destinations, and the rolling hills of Tuscany as your backdrop.
This Tuscany day trip from Florence brings together four of the region's most celebrated destinations into a single, expertly guided journey. From the shell-shaped piazza of Siena to the medieval towers of San Gimignano, the iconic Leaning Tower of Pisa, and an optional wine lunch at a family estate, this tour is designed for travelers who want to experience Tuscany without compromise.
The route follows the scenic Chianti countryside, giving passengers a window onto the vineyards and olive groves that have defined this landscape for centuries. A professional guide accompanies the group throughout the day, providing historical context and local insight at each stop along the way.
For those who select the optional lunch and wine pairing, the experience extends to a rustic estate in the foothills of San Gimignano, where a three-course Tuscan meal is paired with high-quality local wines. The combination of guided culture, free exploration time, and a farm-to-table meal makes this one of the most complete introductions to Tuscany available from Florence.
Tour Highlights
Walk through Siena's UNESCO-listed historic center, including Piazza del Campo and the Gothic Cathedral, with a professional local guide.
Enjoy an optional three-course Tuscan lunch paired with quality local wines at a family-owned estate near San Gimignano.
Photograph the celebrated Leaning Tower of Pisa and the surrounding Square of Miracles, one of Italy's most recognized landmarks.
Explore the cobbled streets and medieval towers of San Gimignano, a hilltop village that has preserved its 13th-century skyline.
Take in panoramic views of the Tuscan countryside from a scenic viewpoint above San Gimignano before entering the ancient gates.
Return to Florence along scenic Tuscan roads as the sun sets over the vineyards, rounding off the day with a memorable evening vista.
Itinerary
Meet your guide at Piazzale Montelungo Bus Terminal, located a five to ten minute walk from Santa Maria Novella train station. Board the air-conditioned coach and settle in for the approximately one-hour drive to Siena, with commentary from your guide along the way.
A professional city guide meets the group at Piazza del Campo for a one-hour walking tour covering Siena's history, its famous annual Palio horse race, and its status as a UNESCO World Heritage Site. The tour concludes at the Siena Cathedral, where visitors have time to explore independently before rejoining the group.
Drive approximately one hour through the Tuscan hills to a family-owned winery in the countryside outside San Gimignano. Those who selected the optional lunch enjoy a three-course meal of local charcuterie, pasta, and dessert, paired with a tasting of high-quality Tuscan wines amid olive groves and vineyards.
A fifteen-minute drive brings the group to the hilltop town of San Gimignano, where your guide leads you to a panoramic viewpoint before you pass through the ancient city gates. One hour of free time allows visitors to explore the cobbled streets, small squares, and local artisan shops at their own pace.
After approximately one hour of travel, the group arrives at the Square of Miracles in Pisa. Free time allows visitors to admire the Cathedral, Baptistery, and Monumental Cemetery, and to photograph the Leaning Tower; those who wish may climb the tower independently (subject to queue availability).
The coach departs Pisa for the approximately one-hour return journey to Piazzale Montelungo in Florence. Relax and enjoy the evening light over the Tuscan countryside as the day draws to a close.
What Is Included
Included
- Professional English-speaking tour guide throughout the day
- Air-conditioned coach transport between all destinations
- Professional local guide for the Siena walking tour
- Guided visit to Piazza del Campo and Siena Cathedral square
- Guided panoramic viewpoint stop in San Gimignano
- Free exploration time in San Gimignano and Pisa
- Optional three-course Tuscan lunch with wine pairing at family estate (if selected)
Not Included
- Entrance ticket to Siena Cathedral interior
- Leaning Tower of Pisa climb ticket
- Entrance fees to Baptistery and Monumental Cemetery in Pisa
- Gratuities for guides (discretionary)
- Personal expenses and souvenirs
- Lunch and wine pairing (available as an optional add-on)
Important Information
Book Your Tuscany Day Trip
Secure your place on this full-day journey through Siena, San Gimignano, and Pisa, and discover why Tuscany continues to captivate travelers from around the world.
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