Two Decembers ago, Keith Waldon was attending the International Luxury Travel Market, pondering what was next for his host agency, Departure Lounge.
The agency (No. 47 on Travel Weekly's Power List) was getting close to $400 million in annual sales, and with its level of staffing and increased buying power, Waldon wondered, "What can we do now that we couldn't get away with five years ago?"
Departure Lounge advisors dining at the Hotel Villa Franca in Positano. Photo Credit: Departure Lounge
He took into account two things that had been most impactful on his advisors' sales: Departure Lounge's exclusive fam trips and attendance at the destination-focused Duco Travel Summits.
After advisors attended those events, Waldon would see their sales "pop" for the destination where Duco was held — "almost immediately" in some cases, he said.
He decided to marry Duco and the fam trips, and MasterClass was born.
Waldon designed MasterClass as an intense, in-destination learning program that brought 35 top producers to the coastal communities of Campania in Italy last month. Over 10 days, they visited the microregions of the Sorrento Coast, Ischia, Capri and the Amalfi Coast.
MasterClass attendees and partners on the rooftop of Hotel Mediterraneo Sorrento. Photo Credit: Departure Lounge
The region was chosen because it "is hard to understand, while high in demand," Waldon said. "We sell it a lot, but it's really difficult to wrap your brain around logistics, geography and small properties that are seasonal and super-expensive, sold out all the time."
On the ground, five-star hotels and resorts offered classroom overviews of the region. Then, the advisors got to work. They stayed in some of the 28 participating hotels and did site visits for the rest of them. Hoteliers were asked to show advisors what is specifically memorable and unique about their properties.
Hotels get into the act
Hoteliers also designed experiences that were something to behold, Waldon said, likely spurred on by a bit of friendly competition. In two instances, properties hired actors to stage performances.
Departure Lounge founder Keith Waldon welcomes advisors to MasterClass 2026 at the Hotel Mediterraneo Sorrento. Photo Credit: Departure Lounge
At Hotel Mediterraneo in Sorrento, an actor portrayed 19th century American novelist F. Marion Crawford, who wrote many of his books in Sorrento. At the Grand Hotel Excelsior Vittoria in Sorrento, a woman dressed as a maid transformed into an opera singer on a suite's balcony.
Advisors also were treated to a watercolor painting class, a lesson in making a limoncello spritz, cooking classes and a shopping spree.
"You could tell that their staffs were really into it, that they had the creative juices to pull it together. There was a lot of pride being exhibited," Waldon said. "These were the best site inspections I've ever been a part of, and this is my 40th year in the business."
Waldon said the experience gave advisors insight into "all the things that we need to know in dealing with a five-star client," such as "what is it that a luxury client will do here? What are the activities? What are the sites? What are the restaurants? What is the shopping like?"
Advisors attended a painting class at Casa Angelina in Praiano on the Amalfi Coast. Photo Credit: Departure Lounge
Departure Lounge's partner destination management company, Essence of Italy, managed the event.
Waldon was told it was the first time all five-star properties in the region had cooperated on any kind of event.
In addition to understanding the properties and activities throughout the region, advisors also got around the way their clients would: in Mercedes-Benz Sprinter vans, yachts and hyrofoil charters. It was an opportunity to experience and understand the benefits of private, chartered transportation, said Waldon.
"At the end of 10 days, this group of advisors knew every property, every great place to eat and do things, and they formed great connections," he said.
Plenty of networking opportunities were provided for advisors and suppliers, and advisors were purposefully split into groups in each region so they'd get to know their peers better.
A local artisan demonstrates his craft at the Hotel Mediterraneo Sorrento during the MasterClass welcome on the hotel’s rooftop. Photo Credit: Departure Lounge
MasterClass was well received by advisors and partners. In post-event surveys, Waldon said it received ratings of 9 and 10 across the board. The return on investment was very good, too.
Andrea Gervasoni, Belmond's area sales manager for Italy and Spain, called it "the future of hotel partners' engagement."
Waldon said advisors were booking trips to the region while they were still on the ground. Their social media posts drew great interest from clients.
Departure Lounge has also been sharing information for its advisors who weren't in attendance, so Waldon even expects a sales bump from those who didn't go to Campania.
The second MasterClass will take place next May with 35 to 40 advisors in the Hawaiian Islands.