After years of trial runs and testing adorable Tuscan towns, I think I finally figured out the perfect day trip from Florence! With so many charming town, it can be hard to choose which to visit. While there are certainly a ton worth seeing, I think Siena, San Gimignano, and the Poggio Alloro winery really make for the perfect day.
Get an early start and head via bus or car to Siena. Siena is a charming Medieval town with tons of history, incredible architecture, and delicious food. You won’t want to miss the stunning striped cathedral, the incredible fresco in the Piccolomi library (located inside the cathedral), the head of Saint Catherine of Siena (in the church of San Domenico), and the main town square (Piazza del Campo) where the crazy Palio horse race is run every year. I also love visiting the local archive, which is partly open to the public. Before departing, be sure to grab a bite at Ristorante La Taverna del Capitano near the cathedral. They have a stracchino (a type of delicious cheese) and sausage pasta that will rock your world.
After exploring Siena, head to the adorable town of San Gimignano. This medieval town is pretty much frozen in time. San Gimignano flourished from the 11th to 14th centuries, but sadly never recovered from the Black Death in 1348. Today the town is famous for 2 things – its medieval towers (it is nicknamed “medieval Manhattan”) and the worlds best gelato. No seriously, the own of Dondoli won the world championship of gelato not once, but twice (and yes, that exists). While in town you will also want to sample this tiny region’s specialty and one of the few white wines produced in Tuscany — Vernaccia.
Speaking of wine, no Tuscan day trip is complete without a visit to a winery. End your day at the beautiful Fattoria Poggio Alloro where you can enjoy a wine tasting and dinner on their stunning vineyard overlooking the medieval skyline of San Gimignano. If this isn’t a perfect day, I really don’t know what is!