What is the best town to stay in Tuscany?

If you were to listen to the Maestro (Seinfeld S7, E3), you would be led to believe that Tuscany is full.

And, in a way, the Maestro was right. Tuscany is full: full of wondrous cities and charming villages, rolling hillsides and cultural heritage that challenges Rome itself for the jewel of Italian travel.

But with so many picturesque towns dotting the region’s bucolic landscape, where is the best town to stay in Toscana? The truth is, it is impossible to name one town as the best to stay in Tuscany, as there are so many with their own fascinating characteristics.

So let’s take a look at a handful and let you decide once you’re there.

• Siena

  Siena is a wonderfully compact city with a huge wealth of sites. The city is a must for lovers of Medieval art, with the Museo Civico, Museo dell’Opera del Duomo and the Oratorio di S.Bernardino all offering an abundance of stunning works and frescoes from the Sienese School. If incredible artworks aren’t enough to satisfy your Siena sojourn, climb to the top of the Torre del Mangia, taking in the stunning views of the picturesque town. Siena is also home to some of the finest restaurants in Tuscany, so you know they must be good.

• Lucca

  Lucca is an incredibly romantic city that boasts impressive city walls that are worth touring in their own right. The high, thick fortifications date back to the Middle Ages, and are so immense that the only way to truly experience their majesty is by hiring a bike from one of the city’s cheap rentals. Lucca seems to be a city untouched by time, perhaps owing to this to the grandness of its walls. It’s also a charming getaway to the more touristy Florence, Pisa and the aforementioned Siena.

• San Gimignano

  San Gimignano is small, so small in fact that it makes the perfect place to stay, see in one day and then use a base for experiencing Tuscany’s grander locales. But this charming town is awash with its own vitality and makes for one of the best visits in the region. Here you can take in the town’s stunning towers, which were once built as part of a competition of the patriarch families to display their wealth. San Gimignano also boasts a wonderful Tuscan food culture, with elegant wine bars serving some of the best of the region’s world class produce.

Related article: What is the best time of year to go to Tuscany?