Hidden Gems: Exploring the Lesser Known Cities of Tuscany

When one thinks of Tuscany, images of verdant hills blanketed in vineyards and charming hilltop towns often come to mind. While iconic destinations like Florence, Siena, and Pisa rightfully steal the spotlight, there are hidden treasures waiting to be uncovered beyond the well-trodden tourist paths. These lesser-known cities offer a glimpse into the authentic heart of Tuscany — one that knows kindness, good food, and even holds appreciation for a concert under the stars. 

Florence, Italy

We’ll embark on a journey to explore the enchanting towns of Lucca, Viareggio, and Montepulciano. These destinations might not feature prominently on the itineraries of first-time visitors, but for those who have already fallen in love with the region, they are a logical next step to dive deeper. 

From beach clubs and opera legends, to medieval walls and some of the world’s best wine, there’s something for every kind of traveler to love. So pack your bags, and make sure to brush up on your Italian, we’ve got some exploring to do. Andiamo! 

Lucca

Lucca is a city of music and churches. Of the latter, there are about 100 — many of which are wrapped in striking white stone and adorned with colorful mosaics. It’s also the birthplace of Puccini, the composer behind famous operas like “Madame Butterfly” and “Tosca.” 

That musical legacy carries on today in the form of the Lucca Summer Festival. Held largely inside the renaissance walls that have made Lucca famous, the likes of Bob Dylan, David Bowie, Elton John, and The Eagles have performed here.

If history is more your style, Lucca has plenty to spare. Climb to the top of the Guinigi Tower for unparalleled views of the old city center beneath the oak trees that grow at the top. One of the two palaces below also houses the National Museum. The curiously oval Piazza dell’Anfiteatro, as the name suggests, is all that remains of Lucca’s Roman amphitheater that date from the 2nd century BC. 

San Martino, the Cathedral of Lucca

Of the many churches, San Frediano, with its magnificent mosaic, San Michele in Foro, with its tiered columned facade, and the Cathedral, with its soaring campanile, should be at the top of your list. The cathedral is also the home of the Volto Santo, an effigy of Christ reputedly carved by Nicodemus. It’s paraded though the streets each September 13th. 

To enjoy Lucca like a local, take a stroll down Via Fillungo. Running in a crooked path right through the historic centre, it’s brimming with shops, restaurants, and even the occasional palace. While lovely any time of year, it’s best on an early summer afternoon with a gelato in hand. 

Viareggio

Head towards the Mediterranean coast, and you’ll stumble upon the city created as Lucca’s port. Today, Viareggio is a popular seaside resort. Locals swell the beaches in August as many get at least some part of the month off for Ferragosto — a Catholic holiday that celebrates the Assumption of Mary. While there are public beaches, large swaths of the sand are divided up into small beach clubs who each mark their territories with different colored umbrellas and beach chairs. 

Gaze out over it all from the rooftop pool at the Grand Hotel Principe di Piemonte. Designed during the 1920s, it’s classic aesthetic is a love letter to the era. In addition to the spacious rooms (including a 1,200 square-foot Panorama Penthouse with sweeping sea views), the Il Piccolo Principe restaurant boasts two Michelin stars. The property also sits strategically along promenade for easy beach access and shopping. Booking with us comes with perks like free upgrades, breakfast, a $100 resort credit, flexible check-in/check-out times, and complementary Wi-Fi. 

Grand Hotel Principe di Piemonte in Viareggio, Tuscany, Italy

In addition to lounging on the beach and strolling along the promenade, Viareggio is a prime spot to celebrate Carnival. Every February, gigantic papier-mâché floats take over the streets in a stunning display of craftsmanship and political satire. A tradition since the 1870s, other highlights include masked parties and plays staged throughout the city. 

Finally, while seafood is a staple of the local cuisine, there’s nothing like a hearty snack of focaccia bread adorned with your favorite toppings. Trovò Panettieri near the Viareggio train station is a local favorite. 

Montepulciano 

It’s hard not to think of wine when you think of Tuscany. A region of bold reds and vivacious whites, some of the best are produced around Montepulciano. This medieval hilltop town is known for vino nobile — and locals are more than happy to give you a taste. Some favorites of the area include Icario, Gattavecchi, Cantina Ercolani, and Talosa. No matter which you decide to visit, you’ll enjoy samples surrounded by rolling green hills and craftsmanship that’s centuries in the making. 

Aerial View of Montepulciano, Tuscany, Italy

There’s also plenty to history buffs to enjoy in town — especially with Montepulciano’s roots dating back to the 4th century BC. Strolling the city streets is an excellent way to begin. Begin at the north end of town by entering from Porta al Prato. From there, walk uphill until you reach Piazza Grande. The main street through town is known as Il Corso (although it changes names several times) but is the perfect route to discover side streets and all the hidden gems they have to offer. Other highlights include the Civic Museum with its Etruscan artifacts and sweeping views to be taken in atop the clock tower on Palazzo Comunale. 

The surrounding Val d’Orca is also worth exploring. This ethereal valley is a UNESCO World Heritage City and boasts beautiful sites around every corner. Towns like Pienza, Montalcino and Monticchiello should be at the top of your list. Pienza in particular is known as the ideal city of the Renaissance. It was lovingly reimagined by Pope Pius II who was born there. 

Need more convincing? Check out this testimonial from a client!

“Truly under the Tuscan Sun with stunning views! We explored the charming narrow streets that meander through the hilltops with quaint boutiques and cafes on every corner. Highly recommend visiting the wine shops along the roads. We loved the village that you arranged where we could walk right into town! Thank you for finding the gem! “- Janet

In Conclusion

We hope this deep dive into some of Tuscany’s lesser-known cities has intrigued and inspired you! It’s truly a region that reveals more and more the closer you look. Whether you’re interested in sipping wine in subterranean cellars or soaking up some Mediterranean sunshine, there’s something to please every kind of traveler. If any of these destinations interest you, please don’t hesitate to reach out. We’d love to get the conversation started!