Kailoa Passages

Kailoa is a sailing vessel traveling down the east coast to the Bahamas.

scenes from the dockside town in the Berry Islands

The Berry Islands, Great Harbour Cay, Bullock’s Harbour Settlement, January 9, 2025

“If you want something you’ve never had, you must be willing to do something you’ve never done.”
— Thomas Jefferson.

Imagine living in a home on the water (aka a sailboat) and then moving your house from place to place every few days, knowing not a soul at your destination. Imagine knowing very little about where you will live other than what you read in a guidebook and then picking up and moving. There is a thrill and excitement for us in visiting a new place, and with that, there is also an associated set of adjustments as we reorient ourselves to our new temporary home every few days.

We took a leap of faith as we approached the inlet to Great Harbor in the Berry Island chain. The opening was not visible until we were within 100 yards because it was at a ninety-degree angle from the point of approach. The 50-foot coral-lined channel led to the Bay of Five Pirates. As Kailoa motored through the cut, our minds conjured images of the characters in “Pirates of the Caribbean” hiding in hidden coves to avoid capture by the Crown.

We threw lines to a dock staffer with a broad smile and a knitted hat (Trameco), and he delivered the practiced run down. “We have fuel and water; there is a grocery down the street, you can borrow our bikes, and food is served at Da Warf. Upon check-in at the Marina staff handed us a copy of a hand-drawn map; “The town is dis way. Don’t miss Shelling Beach; you can walk through the Old Club House ruins on your way.” Walking down the street, we saw a shop sign outside a house: “T’ings Necessary.” You can read a cruising guide but can’t know a place until you see it with your own eyes.

As with any new place, getting accustomed to the surroundings takes a few days. Our immediate neighborhood, the harbor, was bordered by 1960s-style townhomes equipped with docks. Some were in good condition, and some were not. We counted fifteen sailboat masts from Maine, New York, Massachusetts, Rhode Island, Michigan, Texas, Virginia, and Canada, as well as trawlers and long-range sport fishing boats. We learned that most visitors return and spend weeks, if not months, here, drawn by the friendly, laid-back atmosphere and stunning isolated landscapes.

Da Warf (aka the local restaurant) served food in a tiny 10-by-20-foot building. One woman cooked all the meals, which were served outside at two tables. The dual purpose fuel dock had one attendant who filled vehicles, boats, and/or jerry cans.

On our first night, we went to dinner at Da Warf, where the apologetic owner offered meals of either cracked lobster or hamburgers. “We have been swamped today and have limited supplies.” We ordered the cracked lobster tail, which is breaded and fried in the shell. During dinner, we talked with Pile Drivers from Alaska who were on a 2-year assignment to install docks for the Norwegian cruise line on Stirrup Cay (now known as Coco Cay). As we munched on our meal, a flatbed truck sprayed for mosquitoes and delivered a fog of insecticide. We learned later of the food shortage.

Food is delivered once per week via ferry. Because of the holidays, the usual delivery was delayed two weeks, leading to an island-wide shortage. “There’s been no eggs, no produce, only frozen and non-perishables available to everyone on the island.” The boat beside us relayed the rumor that the food boat had arrived that day.

We completed our settlement tour on the rusty bikes in less than an hour, including the ride down and back. The town had a police station, ferry dock, church, school, and medical center that served the island’s 350 residents. The Berry Island chain, named after the Thatched Palm, a species that produces a white flower and berry, is another world experience. We purchased a basket from Trameco, who maintains the cultural practice of using the palm’s foliage to make baskets to sell to infrequent visitors. Recall that Trameco also works part-time at the Marina.

There is an abbreviated history on the Great Harbor Cay webpage, but one must rely on the locals to fill in the gaps. The story says that Great Harbor Cay became the “Rat Pack’s” new playground after the revolution in Cuba in the 1960s. At this time, a thirty-eight-million-dollar investment was made in a club, villas, an airport, and a golf course to create a hideaway for a very privileged few. The Club became the hangout for Cary Grant, Brigitte Bardot, Frank Sinatra, Dean Martin, Douglas Fairbanks, Ingrid Bergman, and the Rockefeller clan. When Great Britain did not approve the gambling license for the casino, the dream began to crumble; drug runners overtook the island, and the amenities fell into disarray. The island is still in recovery from the drug runner days and has had a resurgence in development in recent years.

On the way to the beach, we made a wrong turn and ended up at an open landfill dump. Roads and beaches are littered with plastic bags, cans, fishing lines, Styrofoam, pallets, and boards because trash management is not a priority on this small, isolated island. On the beaches, trash is woven into the dried eel grass that has washed ashore. Seeing the extent of the litter in such a beautiful place was overwhelming and painful. It would take several lifetimes to collect it all.

We visited an artifact of an ill-fated drug run at the site of a DC-3 plane crash in about 5 feet of water off Cistern Cay. We walked the ruins of the former Club.

We trekked on foot to Shelling Beach, which has shallow, clear waters and white sand that stretches for miles in the uninhabited landscape. The aquamarine, isolated beaches brought an unparalleled experience of peace and tranquility. And yes, we found some of the most beautiful little shells there at low tide.

While alluring, Instagram posts paint a fraction of the story. The travel guides get you there and mark the highlights, but there’s so much detail that’s not there that you can only see by being there. We thoroughly enjoyed our stay here.


Kailoa signing off!!

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