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A bedroom inside the Chequit. (Credit: Julie Lane)
A bedroom inside the Chequit. (Credit: Julie Lane)

“We found the Chequit again after it was lost for 60 years.”

That’s how David Bowd describes the $2 million transition that has quietly taken place inside the Chequit since he and Kevin O’Shea acquired the grand Shelter Island hotel from James and Linda Eklund last fall in a $3.35 million deal.

When the doors open on the first 21 guest rooms and suites in the main building on Friday, May 8 — an opening Mr. Bowd refers to as “trial by fire” — the first thing repeat guests will notice is floors have been redone and hallways painted a subtle grey. 

Darker hallways encourage people who may come back to the hotel late at night to keep their voices low so they don’t disturb other guests, Mr. Bowd explained.

All floors have been redone and sleeping rooms have been redecorated. The main building is almost entirely booked for opening weekend.

In designing the hotel rooms, the two heavyweights in the hospitality industry were reaching for a combination of the warmth and intimacy of a bed and breakfast with the independent feel of a hotel.

Mr. Bowd calls it “reinventing the bed and breakfast experience.”

It’s a lesson the men learned with two Salt Hotel properties they operate in Provincetown on Cape Cod.

“A hotel is about great service, a great bed and a great shower,” said Mr. Bowd, who along with Mr. O’Shea, has worked alongside some of the most influential people in the hospitality industry.

Toward that end, 60 percent of his staff comes from Shelter Island with another 20 percent from nearby Greenport to the north and Sag Harbor to the south. That assures guests will get “an insider’s knowledge of Shelter Island,” he said.

Rachel Medina is house manager and he said he wishes he could clone her because of her knowledge of the Island and gracious approach to people. He’s determined that she will be training others who work there to bring the same sensibility to their jobs.

He hopes that the fact that he’s hiring people for year-round employment will give them a feeling of loyalty and belonging that workers in the hospitality field don’t always have because so many can get only seasonal jobs.

“The biggest mistake you can make is not looking after your guests,” Mr. Bowd said about the awareness he and Mr. O’Shea have about successful operation of a hotel like the Chequit.

In tackling the work, Mr. Bowd and Mr. O’Shea wanted to assure that the Chequit would “have a sense of place” reflecting Shelter Island. What they believe they are creating is an inn “on the Island for the Island,” Mr. Bowd said.

He showed off a redecorated room that mirrors what has been done in other rooms throughout the main building.