Oneil Khosa took the long way to a small hotel

Oneil Khosa went looking for somewhere to spend his holidays and came back with a hotel. Casa Morada, in Islamorada in the Florida Keys, was a rather elaborate answer to the question of where to put a second set of house keys. Most people buying a retreat acquire a place to escape work. A hospitality entrepreneur can apparently acquire more of it.

The purchase became the beginning of a collection. Other inns followed, and eventually a name: Enthusiast Hotel Collection. Khosa had spent years working with ships, their passengers and their financing. Now he was assembling places where a guest might arrive carrying binoculars, a fishing rod or a very firm opinion about the correct way to take a corner.

That move makes more sense when you look past the change of scenery. His working life has repeatedly brought together a journey, a destination and the business that joins them. The vehicle has changed. The interest in getting people somewhere they want to be has endured.

A sailor learns the price of a ship

Khosa’s maritime career included serving as a first officer with Royal Caribbean and aboard the Semester at Sea ship, which takes students around the world. On Explorer of the Seas, he worked aboard a vessel that, in 2000, represented the enormous scale of modern cruising. A ship is a workplace with a destination attached; for its passengers, that relationship is reversed.

He also studied at Rotterdam School of Management, Erasmus University, earning a master’s degree with a university scholarship. His education included merchant marine training. The combination matters to his later career: he could approach a vessel as an operating environment and as an asset someone had to finance.

At DVB Bank, his work included developing and managing a $1.5 billion cruise asset debt portfolio and managing a $150 million private equity fund focused on cruising and yachting. He spent five years with the bank in London and Amsterdam. Those figures describe portfolios he managed, rather than personal wealth. The distinction is useful in a business where a photograph of a yacht can invite all sorts of arithmetic.

He went on to found Blue Ocean Cruises in India. That company was sold to a local buyer in 2009. By then his experience covered work aboard ships, the financing behind them and the effort of building a cruise business himself. He had occupied several seats around the same table.

Two nights, one very particular business

In December 2016, Khosa joined forces with former Norwegian Cruise Line chief executive Kevin Sheehan to buy Bahamas Paradise Cruise Line. Khosa held a minority stake and became CEO. The line had a clear proposition: short trips from Palm Beach to the Bahamas, with two nights aboard a ship doing the work of a compact holiday.

In August 2017, he expected Grand Celebration to carry roughly 250,000 passengers that year. An older ship could be a busy ship. The opportunity depended on using it repeatedly for a narrowly defined trip, close to a market that could reach the departure port. There is a practical appeal to a holiday that does not require negotiating an entire week off.

Grand Classica joined the operation in 2018. That October, Khosa hosted a Palm Beach North Chamber of Commerce gathering aboard the vessel, with lunch and a tour. He told the story of his rise through the industry with humor. The setting suited the subject: a CEO explaining his business while his audience sat inside it.

The next conspicuous change was a name familiar well beyond the cruise terminal. Bahamas Paradise became Margaritaville at Sea in May 2022, with Khosa continuing as CEO. A business built around a short escape had acquired a brand whose songs had been inviting people to take one for decades.

Beach balls, then a different departure

At the launch festivities, Khosa appeared alongside Margaritaville CEO John Cohlan and cruise line president Kevin Sheehan Jr. Shaquem Griffin served as the ship’s godfather. The ceremony included the traditional bottle breaking, followed by streamers and beach balls. Maritime ritual had found room for inflatable accessories.

Jimmy Buffett gave a surprise poolside performance. The first passenger sailing followed on May 14, 2022, taking travelers from the Port of Palm Beach to Grand Bahama Island. For an executive whose work had included debt portfolios and ship operations, it was a distinctly public expression of the product: people gathered on a vessel to have a good time.

Later that year, Khosa left. He has dated his departure to October 2022, explaining that he wanted to concentrate on his hotel business. Enthusiast Hotel Collection made its public debut in 2023. The move brought an existing personal interest to the center of his working life.

His explanation of the connection was straightforward. Ships take people to distant places; he wanted to pursue that pleasure on land as well. Boutique hotels offered a way to build around particular interests, with nature close enough to shape what guests actually did during their stay.

“Our clientele is enthusiastic about something they do.”

Oneil Khosa · 2023

The road gets a room, too

The name Enthusiast gives the business an organizing idea. A guest can choose a place because of what surrounds it: a forest, water, a stretch of road. A hotel becomes part of an activity someone already cares about. The interesting question is what will bring that particular person here.

Khosa’s own shorthand is “travel-inspired hospitality.” He includes the approach to the hotel in the experience. Driving toward the Keys, through Northern California or into the mountains provides time together before check-in. In a 2025 interview, he said, “I almost put as much emphasis on the journey as I put on the destination.”

There is something pleasantly inconvenient about that idea. Hospitality usually promises to remove friction. Khosa sees value in a destination that takes some effort to reach. The drive can belong to the holiday, rather than sitting outside it as a regrettable preliminary.

318 reasons to take the long way

Historic Tapoco Lodge in North Carolina makes the proposition easy to understand. Near the lodge, the Tail of the Dragon packs 318 curves into 11 miles. Drivers and motorcyclists have their own reason to come. A hotel close to that road has an audience before anyone has described the thread count.

The lodge has a working history, too. Built in 1930 by the Tallassee Power Company, it housed workers associated with local hydroelectric projects. Its later life includes rooms and cabins along the Cheoah River, with hiking, fishing and other outdoor pursuits nearby. It joined the National Register of Historic Places in 2004.

Khosa’s hotel idea fits a place with several stories already in progress. There is the industrial history, the river and the motoring community. The operator’s task includes understanding the reasons those communities show up. One guest’s scenic detour is another guest’s entire itinerary.

Places with a previous life

In Camden, Maine, the Hartstone Inn offers another maritime connection. Its building began in 1835 as the home of Captain Joseph C. Stetson, a shipbuilder credited with launching more than 70 vessels. A former ship officer’s hotel collection now includes a shipbuilder’s house. The sea has a way of getting back into the conversation.

The house survived Camden’s 1892 downtown fire and later became a bed-and-breakfast. Its present history identifies Khosa and Enthusiast as owners. For guests, those layers give a stay a setting more particular than a room number. For an operator, they are also an inheritance that predates the brand on the booking page.

At Brewery Gulch Inn in Mendocino, history is in the timber itself. Redwood logs left in the silt of the Big River were later recovered, and 15,000 board feet of salvaged wood became a major component of the inn’s 2001 construction. Mineralization helped give its paneling its varied color.

The property looks toward Smuggler’s Cove and borders the meadows and redwoods of Jackson Demonstration State Forest. Here, the building and the landscape offer connected stories. Khosa did not invent them. Bringing such properties together means recognizing why their existing character might matter to a traveler.

The scenery still needs a back office

Khosa’s more recent work also offers a reminder that a collection of individual places must function as a business. In October 2026, he described consolidating the hotels’ customer relationship systems into one ZEPIC account, allowing the group to retire four redundant platforms and better understand the origins of direct bookings.

“Tool sprawl is a massive data problem for hospitality brands,” he said. The vocabulary is a long way from a riverside lodge, but the concern belongs to the same operator. Guests encounter a place through booking, arrival and service as well as through its view. Someone has to make those parts talk to each other.

That combination is the revealing part of Khosa’s career. He has worked on a ship’s bridge and on its financing, led a cruise line through a change of identity and built a hotel collection around the reasons people travel. The scenery keeps changing. He keeps paying attention to the journey that gets a guest there.