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Circumnavigating Jamaica

Three weeks to explore a diverse island nation.


When Christopher Columbus first discovered Jamaica in 1494, he named it “Santa Gloria” and declared it the most beautiful island he’d ever seen. In the centuries that followed, droves of visitors seemed to agree, and today the island is a mish-mash of the towns, villages and marinas they established along Jamaica’s shores. From deserted coastal hamlets to gleaming tourist ports full of the rich and the famous, we knew Jamaica had plenty to offer exploring sailors. That’s why we gave ourselves three full weeks to circumnavigate the country’s shores.

Sailing aboard Seaquest, a Gulfstar 50, my crew of four friends, all in our 20s, cast off from the Montego Bay Yacht Club on the northwest coast of Jamaica. Several months into our cruising adventure, we’d just completed some much-needed repairs and were finally ready to set off again. Light morning winds propelled us to our first stop, Discovery Bay, which was also Columbus’s first landfall in Jamaica. The bay remains as secluded as when he arrived, although the looming bauxite plant onshore added a rather ugly scar.

We didn’t mind sailing away along the north coast to Ocho Rios, a tourist town that caters to the many visitors that pour in off cruise ships. The famous Dunns River Waterfalls offers a taste of nature onshore, but even it has been made tourist-friendly, with peddlers selling their wares all the way up to the very mouth of the falls.

Oracabassa offered four days of tourist reprieve with a refreshing taste of “true” Jamaica: a small manmade bay that is home to a number of local fishing boats, a fish sanctuary and a turtle-hatching program. Oracabassa, which means “Golden Head,” is also famous for its incredible sunsets, which attracted Ian Fleming, author of the James Bond series, who once owned a house here, now a rental called the “Goldeneye Resort.”

We enjoy traveling at night and chose to make the next 32-mile leg of our journey to Port Antonio under a peaceful starry sky. History has it that in 1942, actor Errol Flynn’s yacht washed ashore near Port Antonio, and he took refuge there, where he fell in love with the colonial architecture that lined the winding riverways. Today, traditional bamboo rafts still travel the rivers, laden with bananas, tourists or both.

Four days later, a 24-hour sail took us around the eastern tip of the island to the capital, Kingston. One quirk of cruising in Jamaica is that you have to clear in at each port of call; just as Columbus’s first attempts to reach shore were at first thwarted by hordes of Taino Indians in their canoes, these days, cruisers are met by coastguard officials carrying M-16s. Fortunately, just as the Indians eventually welcomed in Columbus, the coastguard soon offered up some friendly banter.

Kingston is dizzy with activity. The historical port town, once a pirate enclave, later a British naval base, is now the main supply port for Jamaica, servicing an endless line of huge tanks and container ships. Downtown is a bustling mayhem of wholesalers and suppliers, buying their wares to sell in the tourist centers around the country.

Salt River was only an 18-mile sail west of Kingston, but felt like a world away. Onshore, rusty warehouses and sugar mills served as a reminder of the former sugar exportation days. Aside from the handful of spear fishermen in canoes, Manatee Bay was the only beach I saw in Jamaica with no development and no people, just the crew of Seaquest and a barbecue on the beach. Nearby Big and Small Pelican islands featured white, sandy beaches surrounded by beautiful reefs, where nurse sharks slithered and eagle rays soared. Though “Cow Bay” was named for the manatees, or sea cows, that Columbus observed there, we didn’t see a single one: a painful reminder of the degradation of marine habitat around this island, courtesy of invasive species and dramatic overfishing.

Continuing along the southern shore, we sailed another 54 miles east and discovered Treasure Beach, with its European look and feel. Legend has it that a Scottish boat laden with prospective slave owners left Panama a few centuries ago, sailing for home. When their boat wrecked nearby and they stumbled ashore, they found Jamaica a more livable landscape than Scotland and decided to stay there. After observing the gorgeous rocky coastline, I could hardly blame them.

After that, all that was left from there was a short stop in picturesque Bluefield Bay and four nights in Negril, dodging beach hustlers and eating jerk chicken, before sailing back to Montego Bay Yacht Club. Our loop was complete: three weeks and 382 nautical miles. From the over-developed tourist centers to the small fishing communities, we had to agree with Columbus: this was truly Santa Gloria. 

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