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San Gimignano: Unleash Your Medieval Magic in Tuscany!

Discover the medieval charm of San Gimignano, where history comes alive in every cobblestone.

28 August 2023

San Gimignano, located in Tuscany, Italy, is a medieval hilltop town renowned for its stunning medieval architecture and encompassing panoramic views of the surrounding vineyards and rolling hills. Famous for its 14 remaining medieval towers, San Gimignano offers tourists the opportunity to immerse themselves in the rich history and charm of the past, while also indulging in the delicious local wines and authentic Tuscan cuisine found in its numerous trattorias and enotecas. Whether exploring the maze-like cobblestone streets, visiting the striking frescoes in the Collegiate Church, or simply enjoying a glass of Vernaccia wine in one of the picturesque squares, a trip to San Gimignano promises a memorable and enchanting experience for any history or culture lover.

Travel plan

• Check-in at Hotel La Collegiata, a charming 13th-century former monastery turned hotel with stunning views of the Tuscan countryside.
• Take a leisurely stroll through the enchanting town, where time seems frozen. Get lost in the maze of cobblestone streets, secret alleys, and medieval towers.
• Admire the breathtaking frescoes at the Collegiate Church of San Gimignano, a UNESCO World Heritage site, and feel the medieval vibes seep into your soul.
• Savor the local delicacy, saffron-infused Pici pasta, at Osteria delle Catene. Let every twirl of the pasta transport you to pasta heaven.
• Conclude the day with a sunset visit to one of the iconic towers, Torre Grossa. See the town from a different perspective and enjoy the golden hues painting the Tuscan horizon.

• Embark on a wine tasting adventure at Fattoria San Donato, a family-run winery located in the heart of the Tuscan countryside, producing world-class Vernaccia di San Gimignano.
• Immerse yourself in the vineyards, learn about the winemaking process, and sample their exquisite wines, feeling each note dance on your taste buds.
• Visit the Museum of Medieval Torture Instruments (Museo della Tortura). This quirky museum offers a glimpse into the dark side of history, where sadistic devices were used.
• Enjoy a leisurely picnic lunch at Piazza della Cisterna, surrounded by ancient buildings and centuries-old history.
• Wander through the luscious vineyards of Rocca delle Macie winery, just outside the town, and be treated to a sensory overload of flavors during another wine tasting session.
• Indulge in a gastronomic feast at Ristorante Le Tre Stelle, savoring traditional Tuscan dishes like Florentine steak and wild boar ragu. Buon appetito!

• Start your day with a hearty breakfast at Caffè Porta San Giovanni, a local gem offering mouthwatering pastries and rich Italian coffee.
• Lace up your hiking boots and venture out into the rolling hills surrounding San Gimignano. Follow the trail to the panoramic viewpoint of San Gimignano 1300, where the past meets the present.
• Explore the ancient ruins of the Rocca di Montestaffoli, a medieval fortress offering sweeping views of the vineyards and olive groves below.
• Recharge with a rustic lunch at Locanda Viani, an authentic trattoria nestled in the countryside, serving traditional Tuscan dishes using locally sourced ingredients.
• Visit the impressive Palazzo Comunale, adorned with beautiful frescoes, and climb the Torre del Diavolo for a bird's-eye view of the town.
• End your day with a magical sunset from the panoramic terrace of Osteria Il Campagnolo, accompanied by a glass of local Vernaccia wine. Bliss!

• Immerse yourself in the world of Renaissance art at the Museum San Gimignano 1300, showcasing a stunning miniature replica of the town as it appeared in its heyday.
• Wander through the charming Piazza del Duomo, surrounded by ancient buildings and the awe-inspiring Cathedral of San Gimignano, housing stunning frescoes.
• Treat your taste buds to a gelato extravaganza at Gelateria Dondoli, the gelato world champion institution. Savor unique flavors like saffron and truffle, and let your tastebuds rejoice.
• Discover the hidden gem of Torre Chigi, a lesser-known tower that offers panoramic views of San Gimignano's skyline without the hustle and bustle.
• Enjoy a leisurely lunch at Osteria del Carcere, housed in an old jailhouse, serving mouthwatering Tuscan classics with a modern twist.
• Dive into the medieval past with a visit to the Torture Museum Il Bastione, where you'll learn about ancient methods of obtaining confessions. Intriguing and spine-chilling!

• Start your day with a leisurely breakfast at La Cisterna Bar, savoring a cappuccino and warm cornetto while absorbing the vibrant atmosphere of the town awakening.
• Take a scenic drive through the Tuscan countryside, visiting the nearby town of Volterra, known for its Etruscan origins and stunning medieval architecture.
• Sample Volterra's traditional alabaster craftsmanship, and find a unique piece to take back home as a memento of your Tuscan adventure.
• Revisit your favorite spots in San Gimignano, capturing the last snippets of magic before bidding farewell to this enchanting town.
• Savor a farewell dinner at Ristorante La Mangiatoia, indulging in a feast of traditional Tuscan specialties while reminiscing about the enchanting days spent in San Gimignano.
• As the night falls, raise a glass of Chianti to toast the memories created and the promise to return to this medieval gem in the heart of Tuscany. Salute!