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.