7 best experiences in Italy, according to a third-generation tour operator

Italy has long been a top global vacation destination and much loved by travelers seeking history, culture, stunning coastlines and, of course, delicious cuisine. While first-time visitors would be well advised to stick with the well-known trio of Rome, Florence, and Venice, those returning to Italy might seek out 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 who go on vacation to Italy. Steve gave us his take on under-the-radar experiences, as well as places you may not have heard of but should consider visiting.

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

A trulli residence in Puglia

Photo credit: francesco de marco / Shutterstock.com

1. Enter Trulli Residences


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

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

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

Well, I’m intrigued.

It turns out that the trulli are truly remarkable – so much so that UNESCO named them in its World Heritage Convention, which defines the type of natural or cultural sites that can be considered for inscription on its famous World Heritage List. Built without mortar, the trulli are made of limestone blocks with these characteristic conical roofs. Many have symbols painted on the tops to bring good luck to those who live inside. They are architectural marvels and worth seeing!

Locorotondo;  Puglia, Italy


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2. Walk through a mysterious whitewashed maze city


Also located in the Puglia region, the small town of Locorotondo is another star on Perillo’s “hidden gems” list. Many consider it one of the most beautiful villages in Italy, with its historic houses and unique design. Locorotondo means “round square” in Italian, and when you enter the streets you will quickly see this charming place that lives up to its name. The city center radiates out in circles, creating an incredible maze.

All the buildings in the village are whitewashed which, along with the light colored cobblestones, 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.

A wine window in Florence marked "Vundita di Vino" (Wine for sale)

A wine window in Florence marked “Vundita di Vino” (Wine for sale)

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3. Have a drink in a wine window


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

“Wine dispensed through a window in Florence is part of an old ‘plague’ tradition,” Steve told me. “There are tiny hidden windows dotted all along the side streets – to this day! They reopened to avoid contagion during COVID-19.

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

A further nod to this fascinating wine tradition has just opened in Florence: a new restaurant, Babaehas reopened one of Florence’s old wine storefronts in the Santo Spirito district, serving customers in this ancient way.

Piazza Martiri d'Italia in Cagliari, Sardinia

Piazza Martiri d’Italia in Cagliari, Sardinia

Photo credit: lorenza62 / Shutterstock.com

4. Visit a Blue Zone


Of course, Italy is known for its wine, pizza, and pasta, which admittedly aren’t the healthiest things to eat in large quantities. However, did you know that there is an area of ​​the country considered blue zonewhere people live the longest and are considered among the fittest in the world?

Sardinia, a beautiful island off the west coast of Italy, is one of only five such areas. The others are in Okinawa, Costa Rica, Greece and Loma Linda, California.

While a genetic marker prevalent among Sardinians results in nearly ten times more centenarians than in the United States, their diet and lifestyle also play a role. A dietary focus on grains, omega-rich dairy sources — including goat’s and sheep’s dairy — plus plenty of vegetables (not so much meat) make a big difference. Sardinians also receive adequate doses of daily exercise, which has been proven to help improve 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 boost your longevity tips while in Italy!

Alta Acqua Liberia in Venice

Alta Acqua Liberia in Venice

Photo credit: Annik Susemihl / Shutterstock.com

5. Discover Alta Acqua Liberia


Venice has always had a quirky, quirky vibe. If you’ve been there, you know there’s something about the city that’s so special, so different, so unlike anywhere else on the planet. The magnificent buildings, the rich history, the delicious food, the art, the culture, the romantic gondolas and… don’t forget the books in the bathtubs.

Wait what?

It also raised my eyebrows until Steve explained the reason for the Alta Acqua Libreria. Unfortunately, floods have become more frequent in Venice, but this small bookstore – whose name translates to “high water bookstore” has decided to address the events with some preventative measures.

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

I will definitely be back the next time I have the chance to travel to Venice!

the island of Procida;  Napoli, Italy

Island of Procida

Photo credit: Boris Stroujko / Shutterstock.com

6. Roam the island of Procida like a local


A stone’s throw from the charming coastal town of Sorrento, Steve says the island of Procida is a hidden gem well worth the ferry ride and a day’s visit.

“You can almost swim there from Sorrento,” Steve said. “Nobody’s ever heard of it, and it’s so colorful, so beautiful. And you have the advantage of avoiding the crowds.

It has always been home to fishing villages, a fact revealed as soon as you spot Marina Corricella. The bright pastel colored houses have been painted in such a way that boats can easily find their way home.

Tiny Procida is entirely walkable and its narrow streets are wonderful to walk through. The Abbey of San Michele Arcangelo was first built in the 11th century as a house for monks, then became a church in the 16th century. Here you will find magnificent works of Renaissance art. If there is a better view somewhere than the one you will see from the balcony of the abbey, we have a hard time naming it. There is also the medieval village of Terra Murata and many beaches to explore.

Santa Maria della Concezione dei Cappuccini

Santa Maria della Concezione dei Cappuccini

Photo credit: TK Kurikawa / Shutterstock.com

7. Check out one of the spookiest churches


Last but not least, if your Italy vacation takes you through Rome – and chances are it does – there’s a church you might want to take the time to see, but its crypt isn’t. 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 built with rather… shall we say, creative building materials.

“Built in 1631, it is one of the rarest churches in Rome thanks to the skeletal remains of thousands of Capuchin monks taken from the local monastery,” Steve explained.

It’s true: the crypt contains the bones of thousands of monks and poor Romans. Many of them were used to create symmetrical patterns, much like macabre mosaics. The monks prayed in the five chapels of the crypt, which use the 206 bones of the human body in intricate but rather macabre ornamentation. Today, this place is an incredibly historic and rather hidden destination in Rome, although perhaps not for all travelers.

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

He also offers this sage advice, especially for returning travelers: “Spend a week in one place and really live. The biggest lesson from Italy is the lifestyle. Getting off the beaten path gives you the chance to see what life is really like there.

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