My dinner with ‘Mr. Italy Jr.’

ROME — Two orders of cacio e pepe and a half-eaten plate of suppli wasn’t going to cut it. 

I was two dishes deep into my dinner conversation with “Mr. Italy Jr.” and I needed to get my hands on more valuable information than what I had gotten so far, which was shop talk: prices are up in Europe, finding hotels in Italy is tough, travel advisors are everything. 

What I really wanted to know from Steve Perillo, third-generation owner of Perillo Tours, seemed much more urgent: What’s he watching on TV right now? Is he on TikTok? Does he have plants? His thoughts on dog hotels. Fettuccini Alfredo or cacio e pepe?

Those answers eventually came to light over the course of our two-hour dinner at Il Segreto here, where along with the tasty meal we had a hearty, expectedly funny and wildly meandering conversation with a vibe similar to the popular YouTube series “Chicken Shop Date.”

It turns out Perillo is TikTok-curious; he’s obsessed with hydroponic gardening and the proud owner of a new AeroGarden; he’s plotting his entrance into the dog hotel market and wonders what the competition is like; and most importantly, he’s team cacio e pepe. 

Our conversation touched on everything from family to cooking to his personal observation that people might just be getting a little nicer in the world. 

But it was Perillo who asked me the all-important TV show question: “Are you watching ‘Ripley’?” he said with the casual seriousness people adopt moments before revealing just how much they love their favorite show on TV.

“No,” I replied about the hit Netflix show that was nevertheless on my list to watch. The latest adaptation of Patricia Highsmith’s novel “The Talented Mr. Ripley” is set in southern Italy.

“This is where my family comes from — Sorrento, Maiori, Positano, Salerno, Naples,” Perillo said, almost gushing in what felt like a rare sentimental moment coming from someone I know to be deeply and hilariously deadpan. “That whole Neapolitan feeling [of “Ripley”] — I just love it. You would like it.”

And indeed, I have. I’ve enjoyed the first few episodes and the set-jetting wanderlust it conjures in me. But I also enjoyed actually seeing southern Italy for myself on my first trip with Perillo Tours, which kicked off from the Eternal City the day after our dinner.

Mr. Italy pays a visit

Perillo had flown here to meet me for the first couple of days of the 10-day Vesuvius Tour I joined in late April. The trip starts in the capital and visits Sorrento and Florence, making stops in Pompeii, Capri and Venice along the way. 

He said he only visits Italy about three times a year, a seemingly small number for someone nicknamed Mr. Italy Jr. (The original Mr. Italy was Steve’s father, Mario Perillo, the late second-generation owner of the 79-year-old company.)

Perillo’s infrequent Italy visits make his appearances on tours all the more special for guests, tour guides and the company’s longtime supplier partners. That much was evident on my tour when Perillo greeted guests and joined them for dinner at Meo Patacca, a lively medieval-themed restaurant in Trastevere that Perillo Tours has been bringing travelers to for more than 40 years. 

They were pleasantly surprised to be meeting the man who has graced small screens across the New York tri-state area for decades, promoting vacations to Italy in local commercials, just as his father did for years before him. 

A couple from North Carolina introduced themselves to Perillo during dinner, telling him how they’d discovered Perillo Tours through the staunch recommendation of friends and how much they were already enjoying the trip, all of which Perillo seemed humbled by and appreciative to hear.

Even our tour director, Irene Capano, had only met Perillo two or three times over the course of her 17-year career with Perillo Tours. Her last run-in with him happened to be earlier this year, in March, just a few weeks prior to the tour we were on. 

Seeing a window of opportunity, Capano decided to pitch an idea to Perillo at dinner about adding a short cruise element to itineraries that visit the southern part of Italy, particularly the Amalfi Coast.

“The idea is to spend a few days on a yacht where you can really enjoy the experience of this place from both perspectives — the mainland and the ocean,” Capano said to Perillo.

Intrigued by the possibility of adding yacht experiences to Amalfi Coast and other southern Italy itineraries, Perillo grew increasingly starry-eyed as Capano spoke. He peppered her with follow-up questions about small-ship companies to partner with, the wheels clearly turning in his head.

“That’s the best idea I’ve ever heard,” Perillo said — something he said more than once that night, I might add. 

Perillo Tours headquarters

The Vesuvius Tour, Perillo said, is one of the company’s bestsellers among about a dozen signature itineraries it offers in Italy. But Janice Charowsky, office manager for 10 years at the company’s Woodcliff Lake, N.J., headquarters, told me that the most popular tour by far is the 15-day Italy North Classic. 

Like the Vesuvius itinerary, it visits Rome, Sorrento and Florence, but it also includes daytrips to Naples, Pisa, Padua and the lake regions of Como and Lugano. There also is a two-night stay in Venice before the trip concludes with two nights in Milan.

Regardless of which is more popular, I imagine it’s hard to go wrong with a Perillo Tours itinerary given the higher-end quality and amenities the company strives to deliver. Delivery of an upscale land tour and motorcoach experience with four-star hotel accommodations in the heart of Europe’s city centers is what Perillo called “our differentiation.” 

Staying true to that playbook might be the reason Perillo Tours has achieved somewhat of a cult following in its nearly 80-year history. Between the memorable TV commercials that turned Perillo Tours into a household name across the Northeast U.S. and entering the pop culture zeitgeist after Adam Sandler’s 2019 “Saturday Night Live” sketch inspired by those ads, it’s no wonder Perillo Tours’ popularity has yet to run its course.

One of the biggest testaments to its success, Charowsky said, is when past guests go out of their way to visit headquarters and personally thank Perillo and the team for their trip to Italy, something I witnessed while at the company’s office late last month, when a couple that was very satisfied with their trip stopped by to say so. 

“It’s been happening more often lately; people know we’re here,” Charowsky said. “We’ve had people come from Connecticut, from the [Jersey] shore. They just want to come and see somebody’s face.”

Perillo’s headquarters gives visitors an immersive preview of Italy without needing to leave New Jersey. There’s a replica of Michelangelo’s statue of David in the front courtyard; a stained-glass dome and rotunda in the lobby that’s reminiscent of the churches in Rome; there are marble statues and marble floors throughout, emitting the kind of baroque opulence that the Italians pull off so well.

“It doesn’t feel like work here,” Charowsky said.

The road ahead

Despite its almost 80 years of success, Perillo Tours is not resting on its laurels. 

In the past year, the company has made several moves to secure its future. 

It brought on Keith Baron, former president of luxury tour brand Abercrombie & Kent, as its COO and has plans to expand its portfolio to offer more immersive itineraries in existing destinations as well as new regions in Europe — an idea Perillo seemed adamantly against two years ago when I first interviewed him. 

“This has been the biggest question of my career, about how much we should veer away from Italy,” Perillo said back then. “If we start going to 15 other destinations, we won’t be the Italy specialist anymore.”

Perillo is singing a more upbeat tune now about expansion and the company’s future, and he largely credits Baron’s arrival. 

“Our office has always been informally run, by my grandfather, by my father, then me. But Keith is bringing it up to 2024 business standards that every company should be following,” Perillo said, adding that “every family company could use an outsider.” 

“That’s really the lesson of the decade,” Perillo said. “[Keith] is professionalizing our business.”

Under this new direction, Baron told me earlier this year, the company will first start to dig deeper into its existing destinations by offering regions where it hasn’t previously operated, including in Italy, Spain and Greece, which has become one of its most popular destinations. 

Then they’ll start to look at other European destinations that might make sense for Perillo Tours to offer, which Perillo said could one day include Germany. He has also told me a few times that faith-based itineraries will be part of the company’s new focus, which may mean the addition of destinations with rich religious history and sights. 

But probably more important than where Perillo Tours might add tours is who will be by the company’s side in its expansion efforts.

The answer, Perillo said, are travel advisors. Perillo Tours is going to be more focused than ever on its trade relationships. 

“To open up Germany for Perillo Tours — we can’t do that without travel advisors,” Perillo said at our dinner in Rome, reflecting on the past while considering the company’s future. “Why can’t Perillo Tours be one of the major international tour operators? There’s no reason.”

“That’s what I’ve discovered,” he added. “We can do it, and we can do it with travel advisors.”