Sights in Town
Most of Key West’s attractions, historical and otherwise, are found in Old Town, the original part of the island. Old Town’s main tourist artery is the shop- and bar-heavy Duval Street, and navigating by foot is the chosen course for most. You can also pick up the pace by renting a bike, scooter or buggy.
Tourists often begin their stay in Key West by heading to the buoy marking the Southernmost Point in the Continental U.S. (at the corner of South Street and Whitehead Street). The buoy would be accurate if someone kicked it a few hundred yards onto the adjacent Naval installation, which isn’t open to the public. Still, photo ops at the disingenuous buoy are popular.
Just before dusk on a clear night, join the droves descending waterside to Mallory Square, where you can watch escape artists, fast-footed dance men, shopping cart eaters or other performance artists before witnessing one of Key West’s spectacular sunsets, a fiery Caribbean pink that subsumes everything in view.
Formerly a post office, court house and government center, the Key West Art & Historical Society at the Custom House features such oddities as Hemingway’s bloodstained WWI uniform and an informative pirate display. Exhibits reveal the city’s history through paintings — like famous Key West residents in portrait and a collection of wood reliefs depicting Old Key West street scenes by Mario Sanchez. Revolving exhibits range from whimsical sculptures to bank artifacts.
If you lecture friends, “Always do sober what you said you’d do drunk. That will teach you to keep your mouth shut,” you’ll want to visit the Ernest Hemingway Home and Museum, where the Nobel Prize-winning author of “A Farewell to Arms” and “The Sun Also Rises” lived and penned terse, no-nonsense prose for more than 10 years. Learn about the legend himself, wander the grounds and croon a high-pitched “hello” to one or several of the 40 to 50 resident cats, descendents of the original feline occupants.
Hemingway isn’t the only famous American with a Key West residence-turned-museum. President Harry Truman first visited the island in 1946, using a late 19th-century home both as his winter White House and for vacations during his (almost) two terms. After that the house would be known as the Little White House. Guided tours tackle the politics of the Cold War and Key West’s naval history. There’s also a botanical garden on the grounds.
Key West’s maritime history is on display at the kitschy Key West Shipwreck Treasures Museum, comprising earnest presentations by actors in period pirate garb, video features and a climb up the “lookout tower.”
Go to a saloon for a cocktail any time of day and a touch of historic Key West. The most popular, Sloppy Joe’s, circa 1933, was allegedly frequented by Hemingway and has the memorabilia and annual Hemingway look-alike contest to “prove it.” Another popular option is Captain Tony’s Saloon. The owners claim it was their place (then known as “Sloppy Joe’s” bar) where Hemingway slowly imprinted a deep groove into his favorite bar stool. They’ve got the stool to prove it. Many of Key West’s watering holes feature live music on weekend nights at very least.
Running from mid through late October, Fantasy Fest is Key West’s twisted answer to Mardi Gras, featuring street parties, costume balls and a surreal float parade during which a Conch King and Queen are crowned. There are few rules and often fewer clothes. It’s legal to carry alcohol in public — in a paper or plastic cup — and visitors, many decked out in seizure-inducing costumes or little more than body paint, take full advantage. Highlights from past ribaldry include a mock virgin sacrifice to a giant rooster.
James Audubon and Winslow Homer were inspired by Key West’s seascapes and wildlife, other artists by the rollicking Old Town street scenes. Visitors enamored of colorful, island-themed art may want to do nothing but wander in and out of Key West’s more than 50 art galleries.
While it lacks the modern feel of aquariums in places like Baltimore and San Diego, the Key West Aquarium, one of the oldest tourist attractions in the town, has no issue with charm. Small and breezy, the aquarium is home to tropical fish, eels and barracuda, as well as a nice touch tank with starfish, turtles and nurse sharks. Families will enjoy the kid-friendly demonstrations and multiple daily shark feedings.
You may be underwhelmed when you reach the small Key West Butterfly & Nature Conservatory, but once inside the hot, humid display room, you’ll be surrounded by hundreds of colorful exotic butterflies, plus birds and tropical flowering plants (for added flavor). This is a great attraction for kids.
Fort Zachary Taylor State Park showcases an impressive mid-18th-century fortress. There are in-depth guided tours available, on which you’ll learn about difficulties in construction (yellow fever) and the fort’s unique role in the Civil War (smartly seized and controlled early on by Union forces). And while most locals probably would not recommend Key West’s public beaches — they’re small, crowded, rocky and sometimes a trifle dirty — the cleanest and sandiest can be found at Fort Zachary Taylor.
Some may mock, but hopping on an Old Town Trolley or the even more lambasted Conch Tour Train provides casual transportation (with commentary) to Key West’s greatest hits, never mind the embarrassing-looking choo choo you’re on.
Out of Town
Don’t miss a visit to the island of Bahia Honda, a state park offering a superb natural beach (you’ll quickly get used to the strong seaweed smell), great fishing and snorkeling, kayaking, rare plant spotting, and hiking. Head up to the old Bahia Honda Bridge, part of the iconic Overseas Highway, for a phenomenal view of the island and its surroundings. There is a gift shop selling hot food, but the park also has grills where you can cook your own grub.
Wherever you are, keep an eye out for the elusive Key deer, a miniature member of the species whose height averages just 24 to 32 inches — and it swims, too. If you want to significantly up the chance that you’ll spot the tiny creature, head north to Big Pine Key’s National Key Deer Refuge, which has thousands of acres of protected pine forest, wetland and marshes. Also keep an eye out for the Lower Keys marsh rabbit and silver rice rat, two endangered species whose habitats have been threatened by human development.
There’s no better way to get off the island for the day than to get out on the open ocean. You can charter a boat or get on one of the local fishing vessels for a taste of deep sea or coastal angling (try Easy Day Charters). If you’re looking for an especially active excursion, complete with numerous wildlife encounters, consider an eco-tour by schooner or kayak; Danger Charters‘ day sails are a top pick, while Blue Planet Kayak rents equipment and earns praise for its eco-tours. Sunset sails are also available through most charter companies.
Day trips to the lonely Dry Tortugas National Park and Fort Jefferson, some 70 miles west of Key West — accessible via ferry, charter boat or pricey but unforgettable seaplane — set the scene for unparalleled underwater adventures and a most fascinating history lesson. The isolated fort was originally set up to defend navigation into the Gulf of Mexico. Try Key West Seaplane Adventures if you opt for the plane or Yankee Freedom for the more leisurely ferry trip over.
If you’re coming or going to Key West from the north, as most who visit Key West do, stop at the Islamorada Fish Company and get a grouper sandwich or some alligator bites at the expansive indoor/outdoor waterside restaurant. Located at Mile Marker 83, the complex also features a huge store where you can pick up a fishing rod or some lower Keys paraphernalia.
–written by Dan Askin