San Gimignano earned a spot on our Tuscany day trip itinerary with its nickname: The Medieval Manhattan. As a lifelong New Yorker, I’m always curious to see anything that’s compared to New York. San Gimignano is a small town, but it’s famous for its tall stone towers (pictured above) look like skyscrapers. Only 14 remain, but there used to be 70 and you were able to walk around the town on the rooftops, which sounds pretty cool. You definitely can’t do that now…

We had left Florence that morning, drove through wine country, ate lunch in Volpaia, walked around Siena and then wound up in San Gimignano. Luckily, we took the highway to get there and didn’t have to deal with the windy roads we navigated from Volpaia to Siena. Trains don’t go to San Gimignano, so the only way to get there is by car or bus. It’s only 35 miles from Florence, so it’s an easy trip.

San Gimignano may be touristy, but it’s one of those places that’s touristy for a reason. It’s very charming and you feel like you’re back in time as you walk around the main square.

You don’t need to plan to spend a lot of time in San Gimignano, but you may find that you don’t want to leave too quickly once you get there, especially if you’re lucky enough to find it fairly uncrowded as we did. Most of the town’s little shops sell ceramics — there’s a good variety but I have no idea if they’re competitively priced compared to the larger cities. If you’re on a budget, then just window shop because that’s always free. Or even better, take in the views of the rolling Tuscan hills.