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Cruiser’s Guide to Key West

This tiny island in the Florida Keys has it all.

October 15, 2009
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Michael McCloud’s lyrics, “I came down here for the weekend 25-years ago,” imply that Key West can have a captivating grip on visitors. Normally, this fun loving, wise guy musician can be found at the Schooner Wharf Bar, entertaining tourists and locals with his raspy voice and raunchy lyrics. But, there’s little else about Key West that is normal. After recovering from a major hurricane years ago, the city ran an ad campaign to lure tourists back “VISIT KEY WEST. WE’RE BACK TO ABNORMAL.”

What is so special about this 2-mile by 4-mile island at the tip of Florida that has attracted the likes of Ernest Hemingway, Tennessee Williams, Harry Truman as well as thousands of tourists, artists, sailors, fishermen and cruisers every year? It starts with the weather. Located between the Gulf of Mexico and the Gulf Stream, Key West boasts a frost-free, tropical climate. Average lows in January are 67 degrees, and thanks to prevailing easterly trade winds and cool sea breezes, the summers rarely experience temperatures above the low-to-mid 90s.

Hurricanes are relatively rare, although Wilma packed a wallop in 2005, flooding homes and businesses. But among its many claims to fame, Key West is Florida’s driest city, experiencing mostly early morning showers during the wet season of May through October.

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While great weather and beautiful water may have been the initial attraction of celebrities and famed politicians, today the attraction lies in the diversity of its population and its variety of recreational activities. You need to have an open mind to fully enjoy Key West, because you’ll find all types, shapes and sizes here. From pale cruise ship passengers riding the Conch Train to transvestites handing out drink coupons on Duval Street, and from sun-crazed street performers on Mallory Square to college kids hanging out at Sloppy Joes during Spring Break, you’ll find everything and anything-but all sharing the same philosophy of being yourself and having an absolutely wonderful time.

Beyond people watching there are lots of things to entertain you, especially if you love the water. During January, Key West Race Week brings a fleet of top sailing yachts and accomplished sailors to compete in this world-class event. Diving and snorkeling trips to colorful, bountiful reefs can easily be arranged on a variety of dive and tour boats. If you’ve come for the fishing, you’ve come to the right place, as there are numerous charter operations that offer a wide choice of angling. Flats fishing, light tackle reef and wreck fishing and deep-sea fishing are popular activities and readily available. For the more leisurely minded there are schooner and catamaran day cruises as well as ever-popular sunset cruises.

If you’re arriving on your own boat, you’ll have plenty of options of where to stay. Navigation into the harbor is easy and well marked. There are several first-class marinas conveniently located in the Old Town area, some of which offer resort-like amenities. Anchoring out is an option, but you’ll be exposed to shifting winds, strong currents and wakes from heavy traffic. Directly across the harbor is a popular anchorage off the southwest side of Wisteria Island. Set your anchor well, because the holding ground is poor. I prefer dropping the hook just west of Fleming Key, where the reversing currents encourage the use of two anchors Bahamian style. In either case, you’ll want a substantial tender to get to town. When it gets too windy and rough, call for the Key West Water Taxi.

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I’ve been visiting Key West regularly for over 20-years, and I don’t remember ever having a bad meal here. Duval Street is known for its great bar and café scene, but you’ll also want to venture beyond this strip for fine cuisine. Two of my most recent favorites are Camille’s and Sarabeth’s, both on Simonton Street.

Before dinner, of course, you have to celebrate sunset on Mallory Square where crowds gather each evening to be entertained by the street performers and rejoice in their good fortune of having lived another day in this eccentric, festive place also known as The Conch Republic.

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