Little Cayman’s Pirates Point resort for sale for US$7.5 million

One of Little Cayman’s longest established resorts, Pirates Point, is up for sale with an asking price of US$7.5 million.

The popular all-inclusive dive resort has been in operation since the 1980s, when it was bought by the late Gladys Howard.

Howard’s daughter Susan, who has been running the business since her mother passed away in October 2015, said it was with a “heavy heart” that she was selling the resort.

“When my mother, Gladys Howard, purchased Pirates Point in 1986, never did she or I envision we would be here 37 years later,” she told the Compass.

Explaining why she is selling up, she said, “Caymanian ownership laws have changed, we have survived a world-wide pandemic, and my daughter has graduated from college, all while Pirates Point has flourished. I cannot stop time, however, and it is my desire to return to my home in Dallas and hand Pirates Point to its next generation of owners and guests.”

The listing of the resort for sale comes as interest in purchasing land and property in Little Cayman is at an all-time high, after many residents of Grand Cayman discovered the charms of the tiny secluded island when the borders were closed during COVID, and the Sister Islands became popular ‘staycation’ options.

It also comes shortly after an announcement that Little Cayman’s marine parks have been shortlisted for UNESCO heritage status, which honours places of outstanding natural or cultural value.

A real estate listing for Pirates Point states that for US$7.5 million, the new owner would get 9.95 acres of beachfront property, with six residential buildings for overnight accommodation and two additional facilities for entertainment and operations. The resort has 12,250 square feet of living space, with 11 bedrooms and 13 bathrooms.

Like the other resorts on Little Cayman during the pandemic, Pirates Point relied on customers from Grand Cayman to keep operations running, but now it’s back to business as usual, and the resort has bookings through to next year, the Cayman Property listing notes.

Many of those who stay at Pirates Point are repeat guests, who return year after year to dive Bloody Bay Wall, relax on the resort’s hammocks, and indulge in its prize-winning cuisine. Gladys Howard, who trained as a chef at renowned Parisian cooking schools Le Cordon Bleu and La Varenne, had a passion for cooking and good food, a tradition at the resort which has continued.

Pirates Point has changed considerably over the years since 1986. Now a regular winner of the TripAdvisor Certificate of Excellence and considered one of the ‘best of the best’ by Fodor’s Travel, it was a far different story back in the ’80s.

Gladys Howard, in a 2012 article, recalled her first visit to Pirates Point, saying, “The buildings were quite termite eaten. The furniture was shot, windows were broken, the roof seeped rain, the kitchen was part of the front room and it had an apartment-size stove with a stick propping the door on the oven shut. The one Zodiac rubber dive boat had so many holes in it that the guide who took us out on our two dives stayed in the boat the entire time blowing up the raft so it wouldn’t sink.”

The property listing reflects the series of upgrades and additions made to the resort since it first opened, but states that it “still has room, both figuratively and literally, to grow”.

As well as the land and buildings, the sale includes vehicles, a new dive boat, a dock, dive operation, booking system, retail store and inventory, as well as the guest contact list.

Looking back at her years running the resort, Susan Howard said, “What a remarkable ride it has been on the most pristine and tranquil island of Little Cayman.

“I love the resort, always will, and my heart goes out to all the guests that visited over the years. I look forward to welcoming the new owner and wish them every success.”