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Four Fun Days in Medieval San Gimignano

Discover medieval wonders and timeless charm in family-friendly San Gimignano, Italy.

28 August 2023

San Gimignano, located in the heart of Tuscany, is a picturesque medieval town that offers a great family-friendly vacation. The town is famous for its stunning skyline, with its 14 well-preserved towers, providing an enchanting and unique atmosphere. Families can explore the narrow streets, visit the fascinating museums, indulge in delicious local cuisine, and even enjoy outdoor activities such as hiking or cycling in the surrounding countryside.

Travel plan

• Check into your family-friendly hotel, like the quaint Locanda Il Pino, where cozy rooms feel like hugging an ancient stone castle.
• Embark on a guided walking tour through the enchanting streets of San Gimignano, a town frozen in medieval splendor.
• Marvel at the city's 14 famous tower houses and play a game of "who can spot the most charming balcony" (competitive families, here's your chance!).
• Visit the Collegiate Church of Santa Maria Assunta, where even the gods would go "wow" at the intricate frescoes and stunning altarpiece.
• Sample gelato from Gelateria Dondoli, declared the best gelato in the world. You might even shed tears of joy while savoring their divine creations.

• Take a leisurely drive through the Tuscan countryside and pause to admire the rolling hills, vineyards, and fields of sunflowers.
• Sip on fantastic wines at the family-owned Fattoria San Donato, where the vintners will make you feel like long-lost relatives.
• Continue the scenic drive to the hilltop town of Volterra and explore its maze of narrow streets, visiting the Etruscan Guarnacci Museum for a touch of ancient allure.
• Ascend the Torre del Moro—a medieval tower offering jaw-dropping panoramic views. Just be careful not to drop your jaw and knock someone out!
• End the day with a glass of vino at La Cisterna Piazza, and bask in a magical Tuscan sunset. Don't worry about wine mustaches; it only adds to the charm.

• Wander into the Palazzo Comunale, where artists from the Middle Ages to the Renaissance used to showcase their masterpieces. Let the artistic vibes inspire your notoriously terrible family drawings.
• Master the art of making pasta at Fattoria Poggio Alloro, a charming agriturismo. Warning: dancing and singing while twirling pasta dough is compulsory.
• Enjoy a picnic with panoramic views at the charming Piazza Delle Erbe. Bonus points for spotting a pigeon trying to steal your sandwich.
• Discover the secrets of the iconic Vernaccia wine at Tenuta Torciano—an interactive wine experience where you'll sip divine nectar and feel like a tipsy sommelier.
• Head back to San Gimignano and indulge in a delightful family-style dinner at Osteria del Carcere. Your taste buds will thank you later.

• Visit the Museum of Medieval Torture Instruments. Don't worry, no real tortures will be inflicted upon your family, but some sharp improv may ensue.
• Explore the picturesque archaeological park of San Gimignano, where ancient discoveries will make you ponder life, history, and why your kids can't remember where they put their shoes.
• End your stay with a visit to the charming Gelateria Vecchio Forno, where delicious pastries and cakes will prevent any tears from leaving San Gimignano.
• Wave your goodbyes to this enchanting Tuscan jewel, promising yourself you'll return soon. And remember, no souvenir shop is ever complete without a fridge magnet shaped like a tower!