Immersive Italy Tour Designer Offers Trip Planning Services
by Richard D’Ambrosio
Photo: ValerioMei/Shutterstock.com
For several years now, travel agents have been hearing how they need to curate immersive travel experiences in order to deliver complete, unique vacations for their clients.
This has led more agencies to seek out specialized tour operators like The Roman Guy, a small company known for going to the extreme in finding unique local Italian experiences – such as visiting the catacombs three stories below the homes and businesses of private families in Rome.
Faced with the same pressures agents feel to offer a total package, The Roman Guy, based in Rome and Philadelphia, is responding to consumer demand by offering trip planning services.
When you visit the company’s website, there is now a Trip Planning tab, informing the visitor that, “You’ll be matched to a personal Italy trip planner who will work with you to build your dream vacation itinerary,” including accommodations, train tickets, ground transportation and other travel services.
The company has designated seven of its approximately 35 team members specifically to trip planning duties, helping travelers book their entire visit to Italy (though the company does not make airline reservations).
“We have always had to be a travel agency since we started,” said Co-Founder Sean Finelli, who holds dual Italian/American citizenship. “People would call us looking for an amazing tour, or a driver to take them around, and they would ask us about hotels, and trains, and transfers. We’ve now grown to the point where we can handle the influx of that kind of business.”
From humble beginnings
In many ways, the launch of trip planning reflects The Roman Guy’s humble beginnings. Fresh out of college, virtually homeless, and hustling as a tour guide in front of Rome’s Colosseum in 2007-2008, Finelli learned how to ask clients the right questions, leveraging his local expertise and delivering results.
“I wasn’t satisfied just taking them for a tour around the Colosseum. I’d ask, ‘What else do you want to see and do? What kind of dinner are you looking for?’”
After a few weeks of working what he calls the “fold-up tour trade,” he was finally able to afford an apartment. “My client base and knowledge grew. We would send people to our favorite restaurants, and our clients would come back saying ‘They treated us so well.’ One of the biggest things about traveling to Europe is to eat well but not get ripped off. And the demand grew,” Finelli said.
“We took the same approach when we launched The Roman Guy [with Co-Founder Brandon Shaw]. That is where we differentiated, the ‘trust me’ factor.”
Unique local Italian experiences
The company started with their first rudimentary website in 2009, and has been upgrading it ever since, focusing mostly on specialty activities, like a Colosseum Tour at Night that descends into the “Hypogeum” (commonly known as the Colosseum Dungeons), a walk under the “Porta Libitina” or “Gate of Death,” and out onto the reconstructed Arena Floor. Guests spend 75 minutes inside the Colosseum alone, capped off with a champagne toast.
Today, Shaw runs the main operations center from Italy, where the trip planners and tour guides are based, while Finelli lives most of the time in New York City. Finelli said sales have been doubling every year, with much of the proceeds being reinvested into product development and marketing, as well as building new experiences.
The shift towards more trip planning has caused the company to upskill their team members. “It has been a huge undertaking, consolidating all of that product for a whole country,” he said, versus the curated activities in a handful of cities.
“At first, we were playing it by ear. We offered the hotels we like to work with because we know they can serve our customers well. But over the course of the last few years, we’ve had to expand and reorganize our product to meet a broader clientele.”
The Roman Guy is still actively courting travel agencies looking to customize FITs or provide activities and tours for their own customers. “We work best with specialized agencies, family travel, European specialists,” Finelli said.

