Known as the capital of Tuscany, Florence’s ideal location makes it a prime starting spot for many exciting day-trips to nearby cities. These six are sure to make their way onto your itinerary!


Head to Siena for its celebration of Gothic architecture and its open-air architecture, easily recognized by the rusty red bricks and tiled roofs. The buildings in Siena date back to the medieval age and visitors can explore the contrade (districts) that retain just as much color and culture as they did nearly three hundred years ago. Stroll through the cobbled streets and shop for special goods, pastries, and other food products. Be sure to visit the Duomo, the Museo Civico, the Piazza Del Campo, and the Pinacoteca Nazionale!

Accessing Siena from Florence is easy by either the bus or train: by non-stop (“Rapida”) bus, it’s about 1 hour and 15 minutes. By train, the journey will take about an hour and 30 minutes. A one-way train ticket will cost under eight euro.


Bologna is a city of dualities: a tech-fueled, fast-paced society in the economically prosperous Po valley, and a more gritty, graffiti laden city filled with edgy college students who attend the world’s oldest university. A high speed train covers the 50 miles between Florence and Bologna in half an hour, and costs less than seven euro one way.

Photo by Omar Cordovani of Bologna.
Photo by Omar Cordovani of Bologna.

Head to Bologna for its lively atmosphere, bustling cafes, and Medieval and Renaissance architecture, including the City Hall, Basilica di San Petronio, Asinelli and Garisenda towers, and the Fountain of Neptune. There’s a reason this city is designated as a UNESCO “City of Music” — the city has a long history with musical tradition and hosts musical festivals throughout the year.


Known for its eponymous leaning tower, Pisa has more to offer than this failed architectural endeavor. Pisa is home to a renowned university that has graced the region since the 1400s, a host of gorgeous Gothic churches, and an open Piazza with a Cathedral and Baptistery that’s worth a visit with a camera in tow.

Photo by Gabriele Colzi.

Stroll on the banks of the Arno river and explore the Piazza dei Cavalieri, once known as the city’s heart. Hungry? Pisa is known for its delicious snack called “cecina” — a thin bread made from chickpea flour, water, oil, salt, and black pepper (and it’s naturally gluten free). If you visit during June, you’ll be sure to experience one of the many festivals of Pisa. The city is only 40 miles away, and an hour long train ride from Florence will get you there in no time.


The natural beauties of the Chianti region are renowned: the rolling green hills, golden light, and rustic stone architecture. But there’s another element of this region that draws tourists: the wine. That being said, wine tours in Chianti are a must, as are any outdoor experiences.

There’s a small outdoor art museum in the small town of Castlenuovo Berardenga, which is easily accessible by car. Chianti was also well traveled by generations of artists, so its museums are full of incredible art. Visit the Museum of Sacred Art, the Museum of the Treasure of Santa Maria dell’Impruneta, the Antiquarium di Sant Appiano a Barberino val d’Elsa, and the Wine Museum. There are just 40 miles between Florence and Chianti, and travelers can catch a SITA bus that covers the distance in about half an hour.


An ancient gold-smithery, Arezzo is a wealthy city in the region of Tuscany, between the valleys of Val Tibertina, Casentino, Valdarno, and Valdichiana. You won’t see much Medieval architecture here — it was destroyed in WWII, but the city still has plenty of Renaissance splendor, exemplified best by its Church of San Francesco, Piazza Grande, Medicean Fortress, Roman Amphitheater and Church of San Domenico.

Visitors can also tour some of the smaller towns and castles in the area (including the Poppi Castle) and the villages of Anghiari and Sansepolcro. Trains from Florence to Arezzo are under seven euro one-way and take less than 30 minutes total.

Tuscan Countryside

For those wishing to explore the beauty of the Tuscan countryside from the comfort of their own vehicle, renting a car is not difficult from either Siena or Florence. Note, however, that non-resident cars may not be allowed in the city centers themselves, so it’s best to stay in a small town near these cities and pick up the car there.

Once you’re on the road, be prepared to pass by olive groves, historic castles, vineyards, and medieval hamlets. Explore Val d’Orcia’s rolling hills, San Gimignano’s medieval towers, Bagno Vignoni’s thermal baths, Elba’s white sand beaches, Montepulciano’s fruitful vineyards, and Monte Argentario’s hiking trails.