Long Weekend in Tuscany, Italy, in Spring 2026, Visiting Lesser Known Places

So this is a spring trip during a long weekend to Tuscany, to lesser known places in the area, beyond Florence, Pisa, and Siena.

We went around by car, rented from Sicily by Car (quite cheap! Around 40 euros per day). We landed in Bologna to get a cheaper flight and stayed at an Ibis in Prato.

On the first day, we drove to Colle di Val d’Elsa with its beautiful medieval old town on top of the hill. Then we descended to Sentiero d’Elsa, a beautiful hike by the river with turquoise water due to calcium carbonate. It reminded me of Plitvice in Croatia or Kuang Si Waterfalls in Laos. Most visitors were Italians enjoying the long weekend, with some Dutch groups. At one part, you can jump into a formation that looks like a cenote. Sometimes you have to take off your shoes to cross the river.

Then we drove to San Gimignano. I went there once in 2014. I think this charming medieval town has become much more crowded and touristy. I remember eating one of the best gelatos in Italy, but when I wanted my husband to try it, the queue was so crazy that we decided to skip it. The further you go from the main square though, the fewer people there were. It was still beautiful with all the towers that were built by rich medieval families to show off.

The next day we drove to Volterra. It’s also popular but not as crazy as San Gimignano. I think it’s much more beautiful, particularly the viewpoint overlooking the city.

We also saw the typical Tuscan landscape with cypress trees and flower bloom. So stunning!
We then drove to a place that nobody knew of: Monterotondo Marittimo. Italy is a volcanic region, but here you can see hydrogen sulfide fumes coming out of the ground. The landscape looked lunar, with yellow colors and a sulfur smell. There were also geothermal power plants.

On the last day, we went to Prato city before heading to Bologna airport. It was really surprising because the city was not in any travel guide, but it was really beautiful, with a castle from Emperor Barbarossa and a cathedral. We also had no idea, but it has a big Chinatown with delicious food!

Overall it was a really interesting experience. I feel like you can never finish exploring Italy. In Tuscany alone, there are so many places to discover beyond Florence or Pisa. I particularly love going to a borgo medievale in the middle of nowhere that’s still inhabited by locals.