There are lots of hill towns in Tuscany, but San Gimignano gets much of the attention. Why? It's special in a few ways - all those towers make it incredibly picturesque from anywhere outside the city and it's not accessiable by train which does help keep the huge crowds away. It can still feel overrun during the daytime in the high season, mainly because big tour buses drop day-trippers off for a few hours at a stretch, so if you really want to experience these medieval streets at their most charming, you'll want to stay over at least one night.
What to Do
Wandering through the whole city will only take you a couple of hours, so you'll want to savor your stroll. Take your time, gaze over the improbably perfect Tuscan views stretching out in all directions, stop for coffee or gelato. There are a couple churches worth spending a little bit of time in, and some museums as well. But the primary attraction of San Gimignano is without a doubt San Gimignano. If you've got a car, it's an ideal base for exploring this part of Tuscany.
If your starting point is outside Europe, it's likely that you'll be flying into Rome's Fiumicino Airport. From there, you can rent a car and drive directly to San Gimignano or you can take a train to a larger city like Florence or Siena and then take a bus (or rent a car there) to get to San Gimignano. If you're starting point is in Europe, Florence or Pisa is probably an easier airport to fly into. Search for deals on airfare to Italy.
Where to Stay
Many of the properties in San Gimignano are agriturismo, and most of those are outside the city itself. The good news with this is that you're likely to have spectacular views of San Gimignano's famous towers, but it means that you'll have to hop in your car or put your feet to good use to wander its pretty cobbled streets. There are a few hotels right inside the old city which are reasonably priced, so if you want to have the medieval streets right outside your door, that's the way to go. Start by looking through these San Gimignano hostels and San Gimignano hotels and book a room today.
For more information on San Gimignano and the rest of Italy, don't forget to check out our Italy Travel Guide.