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This is a 12-hour Tuscany day trip from Florence that covers Siena, San Gimignano, and Pisa in one day. In Siena, you tour Piazza del Campo and the Cathedral with a local guide, and in San Gimignano, you walk freely around a hilltop town with medieval towers. If you choose a lunch option, you taste 4 wines at a family-run organic winery in the Chianti hills and enjoy a farmhouse-style lunch. Finally, you see the Leaning Tower, Cathedral, and Baptistery up close in Pisa.

Meet your guide in front of Santa Maria Novella train station and take an air-conditioned coach for about 1 hour 30 minutes to Siena. Walk through streets lined with ochre-colored buildings and terracotta roofs, pass the building of Monte dei Paschi di Siena, known as the world's oldest bank, and see the shell-shaped Piazza del Campo, where the Palio horse race is held every year. Enter the Gothic Siena Cathedral, known for its black-and-white striped marble, and see the artworks inside. Free time follows the guided tour.

If you choose a lunch option, you visit a family-run organic winery in the Chianti hills. After tasting Chianti, Vernaccia, and the dessert wine Vin Santo, enjoy a traditional Tuscan lunch with views of the rolling countryside. The meal includes homemade pasta, cured meats such as prosciutto and salami, Italian cheeses, a vegetable salad, and Tuscan biscotti.

After lunch, travel to the hilltop town of San Gimignano for free time. The towers built by noble families in the Middle Ages still form its skyline, earning it the nickname "the Medieval Manhattan," and its historic center is a UNESCO World Heritage Site. Stroll through the squares and alleys, browse artisan shops, and try gelato.

Travel along Tuscan country roads to your last stop, Pisa. See the Leaning Tower of Pisa, famous for its tilting bell tower, along with the Cathedral and Baptistery up close, and explore the historic center of Pisa on a short guided tour. The tour ends when you arrive back in Florence at around 8:30 PM.
* For options without lunch, there is longer free time in San Gimignano instead of the winery visit.
* The Leaning Tower of Pisa entrance ticket is included only if you choose that option.
* If Siena Cathedral cannot be visited because of a religious service, you visit Palazzo delle Papesse instead.
Professional guide
Siena walking guide tour
Siena Cathedral admission ticket
Farmhouse lunch at a Chianti winery estate (when lunch option is selected)
Tasting of 4 local wines (when lunch option is selected)
Free time in Siena, San Gimignano, and Pisa
Leaning Tower of Pisa admission ticket (when option is selected)
Meeting point:
Taxi stand in front of Santa Maria Novella train station
Piazza della Stazione, 50123 Firenze FI, Italy
Meeting point information:
Meet next to the taxi stand outside Santa Maria Novella train station, across from McDonald's. For the semi-private option, check-in is at 8:15 AM, and the guide holds a "WALKABOUT TOURS" sign.
Piazza della Stazione, 50123 Firenze FI, Italy