San Gimignano, whose 13th-century walls have borne witness to events of immense historical significance, is a “must-see” for many visitors to Tuscany. But this beautiful medieval city suffers a little from its success and popularity. For about nine months of the year, the UNESCO World Heritage site swarms with tourists who come to see this remarkably preserved hilltop town and its 14 towers, rising out of the walled city like a “medieval Manhattan.”

Visiting renowned tourist sites like San Gimignano in the off-season (on a weekday especially) offers a chance to really have them “to yourself.” It’s a rare opportunity to see the place quietly, slowly, and without crowds. Savour the atmospheric light fog and slip into a shop for a coffee or aperitivo as you watch the winter shoppers, mostly locals, go by.

You don’t have to go far to imagine stepping back in time by a thousand years.

While visiting medieval cities in summer has its own joys–the sun, winter can provide for a deeper experience that leaves a more lasting impression. The ancient streets are uncrowded, the mood is peaceful, and the locals are more relaxed. Start the winter visit with coffee and pastries, and spend the next hours slowly wandering, admiring the famous “case torre” (tower houses), panoramic views from the edge of the city walls, peeking into ancient courtyards and taking in medieval architecture, all at your leisure.

For an even deeper cultural immersion, taking the walk with Camilla, art historian and guide of San Gimignano and Siena for over 30 years, makes the city’s history and the frescos at the collegiate church of Santa Maria Assunta, or the cathedral of San Gimignano, truly come alive.

When tummies start rumbling, head to one of our favorite restaurants and warm up with delicious, comforting bowls of Ribollita (Tuscan vegetable soup) or an indulging plate of lasagne, homemade bread, and plenty of wine