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Italy has long been a top global and much-beloved vacation destination for travelers looking for history, culture, stunning coastlines, and of course, terrific food. While first-time visitors would be well-advised to stick to the well-known trio of Rome, Florence, and Venice, those returning to Italy might be looking for other off-the-beaten-path destinations and experiences.

I recently had the chance to chat with Steve Perillo, president and owner of Perillo Tours. For three generations, his family has been preparing fabulous itineraries for Americans headed to Italy on holiday. Steve gave us his insights for under-the-radar experiences, plus places you might not have ever heard of, but should consider checking out. 

Here are seven of his top recommendations and why you’ll want to add them to your must-see Italy list.

Puglia, a region in the southeast portion of the country (think the heel of Italy’s “boot”), is perhaps best known for its olive oil and wine production. What’s more, the crowds aren’t intense here, and you’ll still get all the gorgeous beaches and blue-green seascapes. Win-win!

However, there are unique lesser-known sights in Puglia that you might want to make time for during your next trip, including some interesting architecture. Trulli residences dot the region and are especially concentrated in the town of Alberobello.

“These are whitewashed stone huts with conical roofs that have been around for centuries,” Perillo told me.

As it turns out, the trulli truly are remarkable — so much so that UNESCO has named them in its World Heritage Convention, which defines the kind of natural or cultural sites that can be considered for inscription on its famed World Heritage List. Constructed without mortar, the trulli are made of limestone blocks with those signature conical rooftops. Many have symbols painted on the tops to bring good luck to those who live inside. They are architectural marvels and worth checking out!

Also located in the Puglia region, the small town of Locorotondo is another stand-out on Perillo’s “hidden gem” list. Many consider it to be one of Italy’s most beautiful villages, with its historic homes and unique design. Locorotondo means “round place” in Italian, and when you step into the streets, you’ll quickly see this charming spot live up to its name. The city center radiates out in circles, creating an incredible labyrinth.

All of the village’s buildings are whitewashed, which along with the light-colored paving stones also contributes to the ethereal effect. Chances are you’ve never seen a place like this, and Steve says you won’t soon forget it, either.

We all know Italy is known for its fine wines and rich winemaking traditions. However, a speakeasy-style experience that dates back to the Black Plague is still practiced today, especially around Florence.

“Wine handed out through a window in Florence is part of an old “plague” tradition,” Steve explained to me. “There are tiny hidden windows sprinkled all along the side streets — to this day! They reopened to avoid contagion during COVID-19.”

These wine windows — called “buchette del vino” — can be attributed to the infamous de’ Medici family. In the 16th century, the Medicis allowed families of similar status (noble, of course) to sell wine from their vineyards directly out of their palaces. Anyone on the street could knock on the windows to purchase wine and a servant would handle the transaction through the window.

An additional nod to this fascinating wine tradition has recently opened in Florence: a new restaurant, Babae, has reopened one of Florence’s ancient wine windows in the Santo Spirito neighborhood, serving its customers in this ancient way.

Sure, Italy’s known for its wine, pizza, and pasta, which admittedly aren’t the most healthful things to consume in large quantities. However, did you know that there’s a region in the country considered a Blue Zone, where people live the longest, and are considered among the fittest in the world? 

Sardinia, a beautiful island off Italy’s western coast, is one of only five such zones. The others are in Okinawa, Costa Rica, Greece, and Loma Linda, California.

While a genetic marker prevalent among the Sardinians results in nearly ten times the number of centenarians there than in the U.S., their diet and lifestyle also play a role. A food focus on grains, omega-rich sources of dairy — including goat and sheep milk products — plus ample amounts of vegetables (meat not so much) make a big difference. Sardinians also get adequate doses of daily exercise, which has been proven to help boost both health and happiness. The island is also known for its gorgeous beaches and sparkling sunsets, making it the perfect place to visit if you’re looking to level up on longevity tips while in Italy!

Venice has always had a quirky, off-beat feel to it. If you’ve been there, you know there’s just something about the city that is so special, so different, so unlike anywhere else on the planet. The gorgeous buildings, the rich history, wonderful food, art, culture, romantic gondolas, and… don’t forget about the books in bathtubs.

This was an eyebrow-raiser for me as well until Steve explained the reason behind the Alta Acqua Libreria. Sadly, flooding has become more prevalent in Venice, but this little bookshop — the name of which translates to “high water bookshop” has decided to lean into the occurrences with some preventative measures.

“This Venice bookstore has resigned itself to constant flooding by keeping its books in bathtubs and boats,” Steve told me. “It’s worth a visit!”

I’ll certainly be stopping by next time I’m fortunate enough to travel through Venice!

Just a stone’s throw from the charming coastal city of Sorrento, Steve says Procida Island is a hidden gem that’s well worth the ferry ride, and a day’s visit.

“You can almost swim there from Sorrento,” said Steve. “No one’s ever heard of it, and it’s so colorful, so beautiful. And you get the advantage of avoiding the crowds.”

It’s always been home to fishing villages, a fact given away as soon as you spy Marina Corricella. The bright pastel-colored homes were so painted to allow boats to easily find their way back home.

Tiny Procida is completely walkable, and its narrow streets are wonderful to wander. The Abbey of San Michele Arcangelo was first built in the 11th century as a home for monks, then became a church in the 16th century.  Here, you’ll find gorgeous works of Renaissance art. If there’s a better view anywhere than the one you’ll glimpse from the abbey’s balcony, we’re hard-pressed to name it. There’s also the medieval village of Terra Murata, and many beaches to explore.

Last but certainly not least, if your Italian holiday has you going through Rome — and chances are it might — there’s a church that you might want to take the time to see, but its crypt is not for the faint of heart. Much like its Czech counterpart in Sedlec, the Chiesa di Santa Maria della Concezione dei Cappuccini on the famous Via Veneto was constructed with rather… shall we say, creative building materials.

“Built in 1631, it’s one of the most uncommon churches in Rome thanks to the skeletal remains of thousands of Capuchin monks excavated from the local monastery,” Steve explained. 

That’s right: the crypt contains the bones of thousands of monks and poor Romans. Many of them were used to create symmetrical designs, much like macabre mosaics. The monks would pray in the crypt’s five chapels, which utilize all 206 bones of the human body in intricate but rather ghoulish ornamentations. Today, this spot is an incredibly historic and rather hidden destination in Rome, although admittedly perhaps not for every traveler.

Pro Tip: Perillo says that travel trends to Italy right now include up close, personal, and authentic experiences that a solo traveler — or an entire family — can enjoy. Popular offerings from Perillo Tours have included truffle hunts, mozzarella-making classes, and cooking classes with Italian nonnas. Consider these experiences when you’re planning your next trip to this charming country. You might want to make sure you work one or two in.

He also offers this sage advice, especially for return travelers: “Spend a week in a single place and really live. The biggest lesson of Italy is the lifestyle. Getting off the beaten path gets you the chance to see the way life there really is.”

For more information on traveling to Italy, check out these articles:

Communication done well has always been Erika’s career focus. She’s served as a publicist and PR expert for several non-profit organizations based in St. Louis. Prior to that, she was an Emmy Award–winning television newscast producer.

When she’s not training for her next race or packing for another trip, you’ll find Erika hanging out with her husband, son, and personal zoo, which includes a King Charles Cavalier Spaniel, two cats, and a grumpy pygmy hedgehog.