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  • TheWayToItaly

Tuscan Hill Towns by Train from Florence

Updated: Nov 13, 2022

I always recommend you do at least a week (in a private villa or B&B) in Tuscany but if your time is limited to several days in Florence and you don’t want the hassle of driving, then a day trip by train is a must. Traveling by train from Florence offers the opportunity to view the scenic changes in landscapes from city to countryside on your way to many historic towns. Here are just a few of my favorites.

Piazza Grande


Producers of gold jewelry, Piero Della Francesca‘s frescoes and it’s antique market Arezzo is heavy on charm and light on tourists.

Exit the train and head uphill on Via Guido to Piazza San Francesco and inside the Chiesa of the same name. This unassuming church holds Arezzo's most treasured pieces. Among the "must-see" is Italy's greatest fifteenth-century fresco cycle "Legends of the True Cross" by Piero Della Francesca.

For the shoppers, from Chiesa di San Francesco cross over two streets to Corso Italia. Did I mention that until recently Arezzo was known as the greatest producer of gold jewelry in Europe? Continue north on Corso Italia to Piazza Grande.

With its spectacular loggias, Arezzo's Piazza Grande is considered one of the most beautiful squares in all of Italy. It has been the center of this city's life since the 13th century and the world-famous antique market. On the first weekend of every month people from all over Italy and around the world shop from more than 500 antique vendors. It's amazing to see!

Stop for lunch at the cozy little Tuscan spot, Antica Osteria L'Angania on Via Mazzini, 10.

If you happen to be in Tuscany in the month of September, Arezzo hosts their annual Giostra del Saracino. This jousting tournament in medieval costume is held in Piazza Grande on the first Sunday in September every year. Perhaps arrange an overnight as it's the best way to experience this local tradition.

There are closer to sixty direct trains from Florence to Arezzo every weekday. Around forty-five on the weekends. The average travel time is about an hour. And a round trip ticket for a standard seat is around $20. You can find Trenitalia train schedules and pricing here.

Piazza dell"Anfiteatro


Take a break from the hills and visit the city of Lucca. Lucca is enclosed by massive 16th-century defensive walls which provide a tranquil promenade for visitors as well as locals. Flat with little car traffic (mostly pedestrian inside the walls) Lucca makes for a tranquil visit. Beware of the hill towns listed here Lucca can be the busiest.

The train drops you right outside the walls of the city. Head north on Piazzale B. Ricasoli and make your way to Via Della Rosa. Once on Della Rosa, you can visit Lucca's Duomo di San Martino which houses Ghirlandaio's Madonna with Saints on the west side. East of Via Della Rosa, nature lovers will find Giardino Botanico quite enjoyable.

Continue north on Via Della Rosa to climb the infamous, unusual oak tree-topped Guinigi tower not only to see some amazing centuries-old trees planted but also the panoramic view of the city below. You can't miss it. Just look up from any area in Lucca and you will see it. The Palazzo was owned by the powerful Guinigi family. For a good perch to photograph the Guinigi tower with its trees chose less crowded Torre Delle Ore (Clock Tower) on Via Fillungo. This tower has kept the town's time for centuries.

From the tower head to the most famous square in town - Piazza dell'Anfiteatro. A gorgeous medieval piazza with shops and cafes. I bought some of my best linens from a tiny underground shop just outside the piazza. Sit for a spell with a glass of prosecco or mid-morning coffee and fresh-baked Buccellato. You can read more about the ancient sweet bread from Lucca here. Enjoy the everyday activities of the locals. Hardly any of the Roman amphitheater (180BC) survives but the piazza still takes the shape of the theater and the medieval houses that surround it were built into the amphitheater walls.

Back to the fully intact ramparts that surround Lucca. They are among the best-preserved renaissance walls in Europe. From Piazza dell'Anfiteatro head east to Via Fillungo and rent a bike from Biciclette Poli (Piazza Santa Maria, 42). Ride the wall's path with the locals.

Trains for Lucca leave Florence every hour and sometimes more frequently depending on the day of the week. The trip takes about seventy-five minutes and tickets start at $10 for one way. The train arrives south of the walls just outside Porta San Pietro. You can walk to the center of town from there. You can find Trenitalia train schedules and pricing here.

Certaldo Alto


Certaldo is divided into two parts: Certaldo Basso (lower) - the more recent part of Certaldo and where the train arrives and Certaldo Alto (upper) - the historic center of Certaldo. Exit the train in the lower part and take the fun funicular(cable car) to the upper part of Certaldo. Or if you feel the need to scratch your legs there is a walking path uphill and you reach the city walls in about ten minutes more or less. I love this town for its size. It is very small and can be seen in its entirety within a couple of hours giving you lots of time to wander the narrow alleys for shops, great eats, and fantastic photo opportunities.

Certaldo Alto built almost entirely of brick is a fortified medieval village very well preserved despite the bombing during World War 2. All the buildings were built facing onto Via Boccaccio which honors its most famous resident- the poet Giovanni Boccaccio. Casa Boccaccio which has been totally rebuilt is now a museum. Climb to the top of the loggia (only a few floors) for a fantastic view of the valley below and as far as San Gimignano.

Facing onto the little piazza is the church of Santi Michele e Jacopo (Saints Michael and James). Built in the 13th century but damaged in the war the interior has been restored to its original Romanesque appearance. Step inside for a quick peek of the Della Robbia shrines on either side of the main altar and locate the bust of the aforementioned poet sculpted in 1503. To the left of the church is the 14th-century cloister.

Continue on up the street to Palazzo Pretoria originally the castle of the Conti Alberti who lived there until the 13th century when it became the residence of the Florentine Delegate. Notice the facade decorated with picturesque coats of arms in stone and glazed terracotta which record the Governors (Vicari) sent from Florence throughout the centuries. There is also a chapel of the doubting St. Thomas off the courtyard.

Train service runs hourly from Florence Santa Maria Novella to Certaldo every hour. It is a 52-minute ride with no changes so it makes it easy. Round trip tickets run about $15 depending on the season and the time of day you travel.

To book your tickets in advance or to check the details for each train itinerary you can click here.





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