Tuscany is full of countless darling towns scattered through the rolling hills of the countryside. On a trip to Tuscany, you’re sure to be memorized by scenes of cypress trees and Tuscan villas. Strolling by outdoor cafes, gelato shops and cobblestoned alleys, it’s easy to fall in love with any Tuscan town, but these are a few of my favorites.
Tuscany as a whole is known worldwide for amazing wine, but Montepulciano and Montalcino specifically produce Brunello. Be sure to try this specialty when visiting the region. E Lucevan le Stelle is a nice wine bar near one of many lookout points in Montepulciano.
Insider Tip: You wouldn’t know from the front, but Caffè Poliziano has the most darling balcony in the back facing the countryside.
I’m not going to lie to you, I really only visited San Gimignano for the gelato and the gelato alone. Gelateria Dondali has won several gelato world championships and there’s a line out into the piazza to prove it. Go later in the evening after the crowds have died down. If you’re after more than world famous gelato, the town is also known for its fourteen medieval towers.
Built of medieval brick, Siena is a university city in central Tuscany. I think of Siena as the younger, hip sister to the more refined city of Florence. Head over to Fortezza Medicea for views of the city painted in shades of burnt sienna after grabbing a pastry and caffé at Bar Pasticceria Nannini. In the evening, Piazza del Campo fills with socializing students, locals on their evening passeggiata and tourist taking their part in the celebrated Italian pastime of aperitivo.
This little town is a must if you are fan of Under the Tuscan Sun. I adore that movie and Eat, Pray, Love (really any movie with a female protagonist in Italy!). You can stay at Villa Laura where they filmed the movie or drive by the actual Bramasole, the private home of author Frances Mayes. After strolling through the shops and taking in the views, relax on the steps in the main piazza and watch the town walk by.
No list of places in Tuscany would be complete without the capital city, Florence. I especially like Florence during December with its charming Christmas decorations. There’s also a quaint Christmas market in Piazza Santa Croce selling local and German specialties like cheese, panettone, ornaments and glühwein. Lines to Florence’s treasures like Michelango’s David and the Uffizi (and to get a panino at All’Antico Vinaio) are much shorter in the off-season too.
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