3-Day San Gimignano Itinerary: Explore Tuscany's Medieval Gem

price per person From

274 €

Based on 2 adults

Created: Wednesday, November 12, 2025 - Departure: Friday, February 13, 2026

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About the destination

Welcome to San Gimignano, a gem nestled in the Tuscan hills! You are in an extraordinary medieval village, celebrated throughout the world for its imposing thirteen towers that create an unmistakable skyline. This unique feature has earned it the nickname “Medieval Manhattan.” Walking here is like taking an authentic journey back in time: the ancient walls and cobbled streets whisper stories of knights and merchants. You cannot miss visiting the heart of city life, consisting of the beautiful Piazza della Cisterna and the majestic Piazza del Duomo. If you want to admire a breathtaking view of the surrounding countryside, I recommend climbing the Torre Grossa, the tallest tower and the only one open to visitors. But San Gimignano is not just about history and views: it is also a paradise for foodies. You are in the territory of Vernaccia di San Gimignano, a dry and fragrant DOCG white wine, famous since the Middle Ages. Try it in the typical taverns accompanied by local cold cuts such as Cinta Senese, a prized native pig, and pecorino cheeses. And to finish on a sweet note, treat yourself to a moment of pleasure with an award-winning homemade ice cream. Enjoy this unique mix of art, history, and authentic flavors.

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13 Feb

Accommodation

2 Nights

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Locanda Il Pino

8.6

Very good

759

San Gimignano - At 0.3 km from the centreROOM ONLYVia Cellolese 4, San Gimignano 53037

Double Room

With a stay at Locanda Il Pino in San Gimignano (San Gimignano City Centre), you'll be steps from Sant'Agostino Church and Archaeological Museum - Spezieria Santa Fina - Raffaele De Grada Modern and Contemporary Art Gallery. This bed & breakfast is 0.1 mi (0.2 km) from Rocca of Montestaffoli and 0.2 mi (0.3 km) from Fortress of Montestaffoli.

Make use of convenient amenities such as complimentary wireless internet access, shopping on site, and a communal living room.

Stay in one of 5 guestrooms featuring LED televisions. Complimentary wireless internet access keeps you connected, and digital programming is available for your entertainment. Conveniences include complimentary bottled water, and housekeeping is provided daily.

At Locanda Il Pino, enjoy a satisfying meal at the restaurant. Local cuisine breakfasts are available daily from 7:30 AM to 10:30 AM for a fee. Children aged 8 and younger eat free breakfast.

Featured amenities include multilingual staff, luggage storage, and ATM/banking services.

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13 Feb

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