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Best Things To Do in Key West

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Indoors or out, Key West will keep you busy. Key West separates the Atlantic Ocean from the Gulf of Mexico, but it looks and feels like the Caribbean. Water sports, fishing, diving, parasailing, boating, reign supreme during the day, followed by eating, drinking and serious partying after sundown. Key West has long been the destination of serious anglers intent on world records. With so many fishing opportunities, however, even novices can enjoy a good measure of rod-bending fun on even a half-day trip. Snorkeling is great, but scuba is better, stay submerged longer and really appreciate the wrecks and reefs. Although the Florida Keys boasts the only living coral barrier reef in the United States, the most notable dive of late is the wreck of the Vandenberg. For such a flyspeck of an island, it’s amazing how many activities are available: fishing, diving, water sports, sightseeing, sunbathing, surfing, dining, shopping and enough bars to handle an impressive per capita consumption of alcohol.

Fury Water Adventures

Neighborhood: Old Town
If you’ve never parasailed, it’s time to fly. Get yourself strapped in, whisked off your feet and settle back for an awesome glimpse of Key West that most others never see. You head out into the harbor on a fast boat; when it’s time to fly, the crew hooks you up to a large parachute, then slowly picks up speed to inflate the ’chute until it lifts you off the deck. Pretty soon, your head is even with the top of the Key West lighthouse. It’s safe, so don’t worry about falling, and besides, even if you do, it’s a blue splash, not red. Other activities offered include snorkeling, kayaking, rock climbing and even water trampoline.

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Harry S. Truman Little White House

Neighborhood: Old Town
Of all the presidents who have visited Key West, the one who kept coming back was Harry Truman, the haberdasher from Missouri. He didn't just vacation here, he loved the city. A former command post for the Navy, it became Truman's vacation headquarters immediately after World War II and it served as his Winter White House for the balance of his presidency.  

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Sunny Days Catamarans

Neighborhood: Old Town
A great option is feeling your hair flowing in the wind sailing aboard a high-speed catamaran to Fort Jefferson in the Dry Tortugas. The massive 19th-century brick fort was used to imprison the conspirators who helped John Wilkes Booth assassinate President Abraham Lincoln. It’s 70 miles from Key West, and its remoteness means there are fewer impacts on the coral by divers and a greater variety of sea life on view.

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Ernest Hemingway Home and Museum

Neighborhood: Old Town
Serving as Hemingway’s home base from 1928 until 1940, Papa loved this hard-drinking, hard-fishing town and the town loved him. He would write all morning in his secluded office above the pool room behind the main residence, the area walled off and only his famed six-toed cats allowed to roam the small property. The afternoon was reserved for fishing or guzzling booze at gin joints like Sloppy Joe’s. Hemingway wrote "The Snows of Kilimanjaro" and other works while in Key West. The house is worth visiting, particularly tiptoeing up the steps to peer into the office where Hemingway’s desk, chair, typewriter and wall ornaments are supposedly just as he left them. Plants and trees shade the back yard and you’ll encounter a graveyard of past generations of his beloved cats. The visit’s worthwhile for about half an hour, after that it’s boring.

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Subtropic Dive Center

Neighborhood: New Town
Get wet and go deep on any of the three daily trips to wrecks or reefs, including a night dive. We prefer to dive first thing in the morning because the water is usually calmer. A lot depends on water clarity, and it’s wise to call and ask about that in the morning before you head for the boat. The newest popular dive site is the Vandenberg, a World War II-era troop carrier later converted to track nuclear missiles. Subtropic does a daily 8AM trip to the Vandenberg.

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Conch Tour Train

Neighborhood: Old Town
A simple and breezy way to learn about the history of Key West’s Old Town is to hop aboard the Conch Train. The drivers tend to be amusing, no matter how many times they repeat the same old lines. It begins at the Front Street Depot where you can wait in the adjacent schlocky gift shop until your train is ready to roll. You can get off and on, but you could miss some of the insights about the history of various guesthouses and attractions. Since the train is open-sided, skip this tour if it’s really hot or looks like rain because the full tour runs 90 minutes.

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Custom House Museum

Neighborhood: Old Town
Long known simply as “the big red brick building,” the latest use of this towering former mansion is all about art and history. Built in 1891, the building has served as a post office, courthouse and government center. It also spent many years sitting empty and boarded up. The Key West Art & Historical Society changed all that with a massive restoration project and it’s now chock full of interesting things. View paintings of old Key West and portraits of famous characters in the city’s history, and saunter through exhibition rooms that touch on topics such as Hemingway’s adventurous life, pirate lore and the very location where the U.S. agreed to declare war on Spain after the sinking of the USS Maine.

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Captain Mike Weinhofer

Neighborhood: New Town
Weinhofer is a veteran charter boat captain and skilled with everything from bonefish to billfish. It’s not likely you’ll bat zero with Captain Weinhofer behind the wheel. On the reef and wrecks it’s all about snapper, grouper and cobia, while offshore the limelight belongs to marlin, sailfish, swordfish, wahoo, blackfin tuna and the like. Inshore quarry range from tarpon to permit.

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Key West Butterfly Conservatory

Neighborhood: Old Town
Don’t ask us why anyone would come to Key West to view butterflies, but evidently a lot of people enjoy this attraction. And they’ve got birds, too. OK, if small things that fly float your boat, you’ll like this quiet conservatory with many species of the insects flitting here and there. For dyed-in-the-wool entomologists, you can learn all about their breeding habits and lifestyles.

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Sunset Watersports

Neighborhood: New Town
Generally it’s better to leave the navigating to someone with local knowledge, but if you’re an old hand behind the console, these folks will rent you a boat. It’ll come with GPS, a fish finder, VHF radio, bait and tackle and coolers for the catch or drinks. Or venture to one of the best reefs in the Keys: colorful Looe Key, scene of the 1744 wreck of the British warship HMS Looe and several other ships. The reef is within the marine sanctuary; no fishing equals lots of fish on the reef. 

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Key West Aquarium

Neighborhood: Old Town
If you haven’t seen enough strange creatures walking past on Duval Street, check out the Key West Aquarium. It’s small and a bit antiquated, but if you can look past that you’ll find a homey charm to this attraction. Built in 1934, it features shark and turtle feedings, narrated mini-tours, a Touch Tank and exhibits showing moray eels, parrotfish and scores of other species.

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Key West Shipwreck Museum

Neighborhood: Old Town
Life’s a wreck, and then you find one. That was the motto of salvagers in times when wind power wasn’t enough to keep sailing vessels upright in a storm. “Wreckers” profited from others’ misfortunes; when a sailing ship ran up on one of the numerous area reefs or was driven ashore by storms, they salvaged the cargoes and sold them. This industry made Key West the richest city in Florida until advancements in marine power and navigation made shipwrecks less common. Climb the 65-foot observation tower and pretend you’ve spotted a merchant vessel offshore laden with goodies. If you hope the hull breaks open on a reef or it gets pushed ashore by a gale, you’re a wrecker at heart. There are lots of cool artifacts and exhibits, as well as a nice presentation on how the salvaging industry worked.

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Key West Resort Golf Course

Neighborhood: New Town
OK, this isn’t Pebble Beach or Augusta National, but it’s a surprisingly sporty layout when you consider the scarcity of dry land. Claiming to be the “Southernmost Golf Course” in the United States, it’s an 18-hole, par 70 layout designed by Rees Jones. They do rent clubs and you probably won’t play the course more than once, so leave the bag at home.

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Mallory Square

Neighborhood: Old Town
Even if you’re in Key West only one night, make sure to take in the scene on Mallory Square: There are jugglers, wire walkers, guys made up like robots, magicians, fakirs and singers all performing for visitors as the sun sinks slowly over the harbor. Our favorite is Jeep and his dog Cleo, with Jeep strumming a guitar and rasping out ballads while Cleo gently bites down on dollar bills extended by tourists and drops them into a bucket, corny but endearing. Amid the junk souvenir stands are local artisans selling their own handcrafted knickknacks. It’s certainly a remarkable sunset celebration.

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Audubon House and Tropical Gardens of Key West

Neighborhood: Old Town
You can pretty much count on any place where John James Audubon may have tossed his bags ending up a tourist attraction. Key West is no exception, although this is actually the former home of a wrecker named Captain John Geiger. When Audubon visited the area in 1832, he made a number of drawings, and one of these was of a white-crowned pigeon that purportedly included a tree in Geiger’s front yard. True or not, the property is beautiful, replete with an herb garden, orchids, bromeliads and a nursery said to be a faithful re-creation of an 1840s garden. Take the audio tour and note the historic home furnishings.

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Mel Fisher Maritime Heritage Museum

Neighborhood: Old Town
Who hasn’t thought about finding sunken treasure? This place tells the story of one man who did. Mel Fisher, a former chicken farmer, said to hell with the hens one day and set his sights on finding Spanish galleons. Fisher hit pay dirt off Key West in 1985, when his crews found the mother lode of the Nuestra Senora de Atocha. The galleon had been lost in a hurricane in 1622 while sailing from the Americas to Spain loaded with silver ingots, silver and gold coins, emeralds and other artifacts worth an estimated $450 million. The precious cargo salvaged from the Atocha and another ship of the 1622 treasure fleet, the Santa Margarita, fill this museum. The gift shop seems over-priced, but then any authentic gold escudos or silver reales from wrecks more than 400 years old don’t figure to be cheap. In the summer of 2010, two guys found an easier way to recover sunken treasure when they lifted a nearly 5 pound gold bar out of its “touch” case in the museum and walked out with it. Street value? About $550,000.

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Old Town Trolley Tours

Neighborhood: Old Town
If you want a similar tour to the Conch Train but would rather bump along in something a bit larger, try Old Town Trolley Tours. We like the train better just because it’s a bit funkier, but the trolley also hits over 100 points of interest in its 90-minute loop and you can hop on and off all day. If you’re intending to see a lot of town, at $29 a day, the Trolley is cheaper than a cab for getting around as long as you’re not in a hurry, you can wait as long as 30 minutes for the next trolley to show up.

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Fort East Martello Museum & Gallery

Neighborhood: New Town
This is our favorite museum in Key West and we never get tired of visiting it. With 8-foot-thick walls, this Civil War-era fortress never saw action. It has an absolutely fascinating collection of historic artifacts, historical records and military memorabilia relating to Key West. Even if you’re not all that interested in the city’s evolution, history and art buffs will enjoy the variety of exhibits and the folk art from noted regional artists, including some modern sculptures made from recycled machine parts.

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Sebago Watersports

Neighborhood: Old Town
Sebago offers a Key West champagne sunset cruise with complimentary beer, wine and champagne. Looking back toward the island from a mile or two out at sea, the buildings reflect bright red, matching the Rumrunner in your glass. It really doesn’t get any better than this. Sebago’s website offers a web cam with updated views of the city and attractions.

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Captain Damon Santelli

Neighborhood: New Town
We recently did a half-day trip with Captain Santelli, running 17 miles into the Gulf until he located good bottom structure with his depth sounder. After anchoring, out went bags of chum and he ladled more of it from a bucket. In minutes we engaged chunky yellowtail snapper, snagging enough for our small party of five for dinner. What a fun trip, and especially all the insights by the skipper on techniques. This guy’s really smooth and will put you on the hotspots.

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