Key West - In search of the islands in the stream…

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Key West, at just 90 miles north of Cuba, daring to jut out into the might of the Gulf Stream, is the perfect setting for an end of the world story, or the beginning of another for sailors bound south through the emblematic “islands in the stream”, as Hemingway called them. The famous American author, winner of the Nobel Prize for Literature in 1954, actually lived in Key West from 1927 through 1939. And it was here that he penned some of his most famous works, including Green Hills of Africa, To Have and Have Not, and For Whom the Bell Tolls. Sailing south-west from Miami along the glistening 125-mile chain of islands that make up the Florida Keys is a fascinating voyage in this region of shifting sandbanks and storm-pummeled beaches where few monuments to men outlast the hurricane season. The storm season generally runs from June until November. In August 2019, Hurricane Dorian - destroyed much of the northern Bahamas with 185 mph winds.

Located at 24° 33’ 35’’ N, 81° 47’ 01’’ W, Key West sits just above the Tropic of Cancer and enjoys a privileged climate – outside of hurricane season…


Getting intimate with the Keys and the nearby Bahamas is best done on a shoal draft boat, or a lifting keeler, though the ideal boat of course is a multihull, as I did recently on a new Seawind 1260 catamaran from Sailaway Charters. The route is the southern end of the 3,000-mile Intracoastal Waterway (ICW) that takes boaters safely south from Boston in north eastern USA. The shallow yet beautiful coral-strewn Bahamas are the most popular cruising ground for those sailors departing Miami, a mere 115 miles south-east. The city of Miami at the southern end of Florida is the gateway to the Keys and a fascinating city, often referred to as the ‘capital of Latin America’ because of its dominant Cuban and Caribbean demography. Arguably, the best rum in the world can be found here, with my favorites being pungent and slightly sweet Guatemalan and Venezuelan varieties, that are served by friendly expatriate Cubans. One of America’s most recent cities, as the entire region was a Spanish colony until the 1820s, Miami is pinned to the coast by the surrounding swamps of the Everglades to the west and the Gulf of Mexico to the south. As a major cruise ship port, its vast harbor throbs with large vessels and a busy container quay. Marinas for recreational craft abound as well, including the one on the island of Key Biscayne where I boarded our charter boat. Crandon Park marina charges my friends on a 35 footer, US$ 79 per night for casual marina berthing but the cheaper option is to use the swinging mooring in its sheltered bay then take an Uber across the causeway to downtown Miami for shopping.

Located at 24° 33’ 35’’ N, 81° 47’ 01’’ W, Key West sits just above the Tropic of Cancer and enjoys a privileged climate – outside of hurricane season…


After visiting Miami to attend the three major boat shows that run simultaneously in ...

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