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Tuscan Day Trips

Craving adventure beyond the confinement of my cubicle I embarked on a journey to Florence in 2016. Even after nearly five years of taking advantage of my expat life and ensuring my weekends are spent exploring everywhere from the Dolomites to Le Marche to Calabria, I’m still not immune to the unparalleled magic of Italy. But the hillsides that surround my home of Firenze house the most beautiful hidden gems. Stepping foot in any one of these Tuscan towns–where the perfect combination of rolling green hills and charming cobblestone streets–make for an incomparable day or weekend trip. A bonus: visiting them in Autumn really allows you to savour what makes them so special. 


I’ll never forget the views from the bus the first time I pulled up to Siena. Colourful apartments stacked tetris-style painted the skyline on a chilly November afternoon; my friends and I took in the breathtaking view from our AirBnB’s rooftop over a glass of Chianti. Siena, though slightly smaller than Florence, is just as alive — especially in Piazza del Campo, the heart of the city. Exit the piazza from pretty much any direction and you’ll find yourself on a narrow corridor where mom-and-pop shops alternate with local restaurants, completely devoid of cars but full energy. And if at any point you need to find your way back to a landmark, just look up for signs of Siena’s magnificent marble Duomo, a masterpiece that will have you completely enamoured.



Once you ride a bike in Lucca, no other bike ride will compare. There is truly no better way to explore this medieval-walled city. When you’re ready for lunch, pull over in the oval-shaped Piazza dell’Anfiteatro for a plate of black truffle pasta and world-class wine for 5€ a glass. One of the most beautiful places in Lucca is its botanical garden, full of lush greenery and exquisite flora.

San Gimignano

San Gimignano, also known as “The Medieval Manhattan,” is famous for its towers that can be spotted from the winding road leading up to the gates of the city. Recognized as a UNESCO World Heritage Site since 1990, this picture-perfect Tuscan town is the perfect day-trip from Florence. Go for the Vernaccia di San Gimignano, stay for the world-famous gelato (no really, Gelateria Dondoli is a gelato world champion).


One weekend where I had my heart set on traveling but had no clue as to where I looked at the map and chose Arezzo — close enough to Florence, but far enough away to make a day out of it. I happened to venture out during Fiera Antiquaria Arezzo, the city’s monthly antique fair, when boutique owners, painters and jewelers lined Piazza Grande and spilled over into the neighboring streets. I highly recommend visiting Arezzo during this fair, when the city is energetic and enthusiastic to kick off a new month. After losing yourself in the beautiful antiques, visit the newly restored Medicean Fortress or the Church of San Domenico before settling down by the Roman ruins to soak up a perfect fall day.


From thermal springs to its famous Vino Nobile, Montepulciano has it all. This Renaissance city boasts unmatched panoramas overlooking the Val d’Orica that — as if you had any doubt — confirm you are indeed in Tuscany. There’s no better way to see the city and take in the sights of the surrounding vineyards than to walk it. True to Tuscan form, there are plenty of churches to stop in and marvel at throughout your day.