Sipping a tropical drink in Mallory Square, watching a schooner slip past the setting sun, is something everybody should experience at least once in their lives. But this island city, once home to pirates, fishermen and high-sea traders, has more to offer when it comes to the great outdoors.
Sailors gather here each winter for Key West Race Week, an international sporting event second only to the America's Cup. Powerboat racers come in droves each year as well for the Key West World Championship Powerboat Races, one of motor sports' most prestigious events.
Sea kayakers, windsurfers, swimmers, anglers and cyclists also love Key West – for the water, the beach, but most of all, the hospitality of the native "Conchs," who for generations have made their livelihoods from the sea.
Wet a Line
Captain Bill Wickers, a third-generation charter boat captain, challenges his customers to name another place in the world where anglers can catch as many different species of fish in one location.
"We've got it all," says Wickers, who runs two boats out of Key West's famous Charter Boat Row. "It doesn't matter what month you come down, there is always something biting."
Wickers' grandfather helped pioneer blue-water fishing "beyond the reef." Legendary anglers such as Ernest Hemingway and Zane Grey ventured to the southernmost point in the United States for marlin, tuna and wahoo, the fastest fish in the sea.
"We have two 40-foot, diesel-powered sportfishermen that we take to the gulfstream, wrecks and the reefs," he says. "We don't have to run very far to put you on the fish."
More world records have been set in Key West than any other location in the world. Tournament fishermen come for the king mackerel when the winter wind blows. In the spring, the sailfish begin to bite, and as the water warms, the action heats up with big, bull dolphin, known to diners as mahi mahi.
"I'll just ask what do you feel like catching, then you let us take it from there," he says.
Bob Holston and CeCe Roycraft have been ferrying scuba divers and snorkelers to nearby wrecks and reefs for over 40 years.
"We have the best diving in the world," says Roycraft. "But it's about to get a whole lot better."
In late May of 2009, a World War II-era warship called the Vandenberg was sunk less than five miles from shore. Scuba divers are able to access the the main deck at approximately 95 feet below surface in the crystal clear water.
"Most of the truly spectacular wrecks lie in such deep water that they are out of reach to everybody except the most advanced divers," Roycraft explains.
The Vandenberg, which also saw service as a missile-tracking ship during the Mercury, Jupiter and Apollo programs, is just outside the reef line, about a half-hour ride from the marina.
"This ship has varied relief so it attracts a wide variety of marine life," she says. "It is the largest wreck in the Keys."
Roycraft's company, Dive Key West, runs regular trips to the Vandenberg.
Catch Some Air
Thrill seekers have always made Key West a destination vacation. Nestled between the Atlantic Ocean and the Gulf of Mexico, there is always a breeze blowing on the water from one direction or another.
"That's why you won't find a better place to kite surf," says Paul Menta, founder of The Kite House kite surfing school. "We'll get you up and flying by the end of the week."
Kite boarding, or kite surfing, is one of the fastest growing watersports in the country. In most places, students spend several days learning how to fly a kite on land before they try their luck with a board in open water.
"We have so many great spots to teach in shallow water, so we can accelerate the process," Menta says. "We can teach in a day or two what most schools take to do in a week."
Menta has added a new sport to his arsenal of fun: stand-up paddle boards. These oversized surf boards are propelled by a kayak paddle. "There is no learning curve," he says. "You just get up and go."
Stand-up paddle boarding, or paddle surfing as it is sometimes called, has proven so popular that Menta has had to increase the size of his fleet just to meet demand. "It's crazy," he says. "People love it."
For more information on planning your own outdoors getaway to Key West, call 1-800-FLA-KEYS (352-5397) or visit www.fla-keys.com/keywest.