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Key West Overview
Key West, the southernmost city in the continental U.S., is the last in a chain of tiny tropical islands -- the Florida Keys -- scattered off the mainland. Dubbed the "Conch Republic," Key West is a very popular destination on Western Caribbean itineraries -- and is easily one of the funkiest and fascinating ports of call in all of cruising.
Key West, where natives are lovingly called "Conchs," and the high school football team goes by the "Fighting Conchs," earned its "Conch Republic" nickname in April 1982, when a band of locals declared secession from the U.S. in protest of the U.S. Border Patrol placing a roadblock just north of the top of the Keys.
While federal agents were trying to stymie drug smugglers, Keys residents decried the roadblock as a tourism disaster as well as disrespectful to its people. But Key West's mayor and his supporters failed to sway a federal court in Miami to lift the roadblock. Soon after, he read a proclamation at Mallory Square declaring the Keys no longer a part of the U.S. and demanding $1 million in foreign aid.
The move to secede was short-lived but remains a point of pride for Key Westers, who still fly the blue "Conch Republic" flag in the subtropical heat and ocean breezes. Key West was first settled in 1822 and by 1886 had become America's richest city per capita. Compact, cozy and adorable, the city's Old Town neighborhood is filled with cottages with gingerbread-topped porches, Victorian compounds, sidewalk cafes, cigar stands and T-shirt shops. Residential throughout, every sign, window and awning in Old Town must pass scrutiny of the city-appointed Historic Architectural Review Commission.
Key West cruise ship passengers, who number some 820,000 a year among the island's 3 million visitors, disembark at Mallory Square, a Navy pier near the Westin Resort. But the island city is a breeze to explore by walking, bike, scooter or even pedicab. Famous residents have included Pulitzer Prize-winner Ernest Hemingway, whose home on Simonton Street is now a museum where six-toed cats roam the grounds, pool and living quarters. Key West was also a home away from home for President Harry Truman, whose one-time respite from Washington, D.C., is the "Little White House," a museum by the waterfront.
Art galleries, Cuban coffee, fine dining and overstuffed sandwiches all abound in Key West. Locals will serve you fresh coconut water by drilling a straw hole into one of the green fruits that come from the island's palm trees.
The city famously appeals to all types of folks, and attracts artists, hipsters, foodies and beach bums along with cruise ships. Locals love to repeat the line about never knowing if the guy beside you at the bar in flip flops and a tank top is a millionaire or a former merchant marine -- or both. Rich retirees rub elbows here with those who work two and three jobs to be able to call Key West home.
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Other Eastern Caribbean Cruise Ports:
Antigua • Castaway Cay • CocoCay • Freeport • Grand Turk • Great Stirrup Cay • Half Moon Cay • Jost Van Dyke • Key West • La Romana (Casa de Campo) • Labadee • Nassau • Nevis • Princess Cays • Samana and Cayo Levantado • San Juan • Santo Domingo • St. Croix • St. John (U.S.V.I.) • St. Kitts • St. Maarten • St. Martin • St. Thomas • Tortola • Virgin Gorda
Sip a rum runner, the drink of the Keys, at Sloppy Joe's, Ernest Hemingway's favorite bar. For a mojito, which smoothly mixes rum and mint, head to the Cuban restaurant El Meson de Pepe.
A traditional Key Lime pie, with a luscious tang and flaky crust, or a single piece dipped in chocolate and frozen on a stick shipped to a friend's home or yours, from Kermit's Key West Key Lime Shoppe. (200 Elizabeth Street; 305-296-0806)
English is spoken in Key West.
Currency & Best Way to Get Money
Currency is the U.S. dollar, and ATMs are readily available.
Where You're Docked
Cruise ships usually dock at either Pier B, near the Truman Annex, or the Navy-owned Outer Mole pier, near Fort Zachary Taylor State Park. If docked at the latter, a tourist trolley shuttles you off the base into town. There is also a smaller dock at Mallory Square.
Key West is an island, or Key, that is just two miles long by four miles wide, so all the essentials are near the docks -- bars, restaurants, shopping, scuba diving and beach-going. Mallory Square, on the waterfront near the docks, has restaurants, shops and public restrooms.
It's a snap in Key West. Consider Duval Street the main thoroughfare. Popular bars, T-shirt and souvenir shops and art galleries line both sides of the street and can be found from the 200 block to the end near Mallory Square. Although there is an open-container law in Key West prohibiting alcohol on public streets, it isn't largely enforced on visitors along the 100 and 200 blocks of Duval.
Bikes, scooters and flip-flops are the most popular modes of transportation, for both locals and visitors. Key West is really flat, so cycling is easy. Bike rentals typically require a refundable deposit or cruise key card. A and M Rentals (523 Truman Avenue; 305-294-4556) and Tropical Rentals (1300 Duval Street; 305-294-8136) are reliable shops.
"Conch Cruisers," slow-moving electric vehicles that resemble golf carts, are also available for rent. They can hold two to six passengers and can be rented in two-hour increments. A reliable shop is Key West Cruisers (500 Truman Avenue; 305-294-4724). Deposits are required. For first-timers, the Old Town Trolley Tours offers hop-on, hop-off, all-day transport, while the Conch Tour Train features a personal tour guide driving you through Old Town while pointing out the sights and historic markers. Pedicabs are available and generally charge per minute. Perfect Pedicab on Whitehead Street is a popular company.
Watch Out For
Sunburn, thirst and vacation-induced absent-mindedness. The sun is quite intense and very deceiving. Liberally apply sunblock to avoid a subtropical burn.
Water bottles aren't an accessory in the Keys, they're a necessity. Take a moment to hydrate before heading out under the island's blue skies and cotton candy-spun clouds. South Florida mantra: The best parking spot isn't the one closest to your destination; it's the one in the shade.
Also, the Key West Police Department reports are filled with lost-and-found property reports from visitors. Keep an eye on your belongings while you're downing a rum drink or frosty brew, or while singing along with the whole bar to a Jimmy Buffett or Kenney Chesney classic.
One of Key West's treasures and one of the easiest stops to make is the Ernest Hemingway Home and Museum. Walk through the Spanish-styled home built in 1851 and out to the swimming pool (the first one in Key West). The preserved estate features about 40 extremely well-cared for, free-roaming cats, descendants of the six-toed felines that lazed on Hemingway's lap while he wrote. Tour guides know each cat by name. (907 Whitehead Street; 305-294-1136; open 9 a.m. to 5 p.m. daily)
Across the street from Hemingway's old digs and 88 steps up a circular iron stairway is the top of the Lighthouse and Keeper's Quarters Museum, offering spectacular views of the island. Opened in 1848, the lighthouse became known for having a woman as its first keeper -- unheard of in the 19th century. The U.S. Coast Guard decommissioned it in 1969. (938 Whitehead Street; 305-294-0012; open daily 9:30 a.m. to 4:30 p.m.)
Souvenir shops are plentiful downtown, serving up conch shells, T-shirts, cigars, watercolor paintings and the must-have Mile 0 magnets (U.S. Route 1 has its southern terminus in Key West), shot glasses and bumper stickers. For more discerning keepsakes, Key West offers art galleries of various prices and genres and feel-good boutiques and shops: Besame Mucho (315 Petronia Street) is a fabulous store, with an apothecary and housewares like Moroccan tea glasses. Key West Aloe (416 Greene Street) features locally made goodies. Key West Hammock Company (717 Duval Street) is a hammock haven. The not-so-local favorites include dressmaker Lilly Pulitzer (600 Front Street) and the Tervis Store (431 Front Street) selling insulated tumblers.
Named for the painter and bird expert James Audubon, the Audubon House and Tropical Gardens is a nonprofit opened in 1960 by a Key West native. The gardens are lovely, and in addition to tours, a gift shop and gallery offer a host of Audubon prints. (205 Whitehead Street; 305-294-2116; open daily 9:30 a.m. to 5 p.m.)
Stroll the two-mile Harbor Walk, which runs from Front to Grinnell streets at the city-owned historic seaport. Shops and restaurants line the harbor, which is home to schooners, catamarans and other sightseeing vessels.
A reliable attraction on the island is the Key West Aquarium, worth seeing for its "Touch Tank," where visitors may hold sea stars, conchs, giant hermit crabs and horseshoe crabs. Tours and feedings start at 11 a.m., 1 p.m., 3 p.m. and 4:30 p.m., and often include close-up feedings of sharks. (1 Whitehead Street; 305-296-2051; open daily 10 a.m. to 6 p.m.)
The Harry S. Truman Little White House was originally built as officers' quarters for those stationed at the local Navy Station. In 1946, President Truman made it a winter respite for working vacations, as did Presidents Eisenhower and Kennedy in later years. Today, it's a living history museum and meeting place for government leaders. (111 Front Street; 305-294-9911; open daily 9 a.m. to 4:30 p.m.)
If you are serious about sightseeing, you can purchase a Key West Island Passport. It includes the Conch Train or Old Town Trolley, the aquarium, the Hemingway Home and Museum, the Shipwreck Treasure Museum, the Little White House as well as some shopping discounts.
Been There, Done That
Culinary aficionados really shouldn't miss a tasting experience at Peppers of Key West. Hop on a stool at the tasting bar and check out a wide range of sauces. Quirky owners Tom and Mike recommend your tasting be accompanied by mouth-cooling beer, which can be purchased at several bars a few steps away. (602 Greene Street)
The Mel Fisher Maritime Museum showcases treasures salvaged from the 17th-century Spanish galleon "Nuestra Senora de Atocha," shipwrecked in the waters off of Key West. (200 Greene Street; 305-294-2633; open 8:30 a.m. to 5 p.m. weekdays, 9:30 a.m. to 5 p.m. weekends)
History lovers will enjoy the Key West Cemetery for offbeat headstone inscriptions such as "I Told You I Was Sick" and "At Least I Know Where He's Sleeping Tonight." You can browse on your own with the provided self-guided tour maps. (701 Passover Lane; 305-292-8177; open dusk to dawn daily)
If you don't want to dive, check out the waters while sailing along on a huge glass-bottomed catamaran. The reef that surrounds the city is the only living coral reef in North America and is chock-full of exotic fish, including spiny lobsters and snapper. The Fury Catamaran Glass Bottom Boat cruises at noon, 2 p.m. and 4 p.m., with sunset cruises at 4:30 p.m. (Departs at the end of Duval Street, between Ocean Key Resort and Pier House Resort; 877-994-8898)
One of Key West's most treasured historic landmarks, the San Carlos Institute was founded in 1871 by Cuban exiles as a center for education and civic pride. Today, it's a museum, library, art gallery, theater and a site for community college classes. (516 Duval Street; 305-294-3887)
Best Party Beach: Smathers Beach, off South Roosevelt Boulevard, features shallow water, so it's good for little kids, too. There are food concessions and restrooms. Equipment rentals include chairs, umbrellas, kayaks, windsurf boards and other water sports.
Best for Quiet Time: Rest Beach near the White Street Pier, at about 300 feet long, is a locals' favorite. So is the pedestrian and bicycle-only fishing pier, where glorious sunset-viewing and people-watching are free gifts of the island. Amenities are few, but restrooms are just down the road at Higgs Beach.
Best Gay-Friendly Beach: Higgs Beach at the end of Reynolds Street offers chairs and snorkel equipment rentals, tennis courts, volleyball courts, kids playgrounds on both sides of the road, a beachside restaurant, outdoor showers and a spacious dog park -- with separate space for little dogs -- across from the beach.
Best for Snorkeling: Fort Zachary Taylor State Park's beach at the end of Southard Street requires a daily entrance fee. The beach offers sparkling blue and green waters, a snack bar, snorkel and chair rentals, shady picnic areas with grills and tables, and the best public restrooms and showers on the island. There is also the historic fort and a Civil War Museum.
For an elegant yet casual culinary experience with a fabulous atmosphere that feels miles away from the craziness of Duval Street, Louie's Backyard is a longtime locals' favorite. Sit on the outdoor deck, right on the Atlantic and shaded by lush sea hibiscus trees. It's the only restaurant in Key West where you can hear the sound of the waves breaking on the beach. (700 Waddell Avenue; 305-294-1061; open 11:30 a.m. to 10:30 p.m. daily)
Another lovely place to lunch is La Te Da. It might be better known for its female impersonator cabaret shows at night, but the restaurant's outdoor tables, set in a garden and around a pool, are a peaceful haven. (1125 Duval Street; 305-296-6706; open 8:30 a.m. to 3 p.m. and 6 p.m. to 11 p.m. daily)
For ultracasual fare in an ultra-funky setting, B.O.'s Fish Wagon is named after owner Buddy Owen, who started out selling his famous fish sandwiches from a wagon. The eatery supplies Key Westers with freshly fried fish sandwiches, including grouper, and a signature Key Lime mayonnaise. (William and Caroline streets; 305-294-9272; open 11 a.m. to 9 p.m. daily)
For Cuban cuisine, El Meson de Pepe is convenient (right off of Mallory Square) and atmospheric. It offers drinks, tapas, soups, salads and more; try the ropa vieja (shredded beef and tomatoes). (410 Wall Street; 305-295-2620; open from 8 a.m. daily)
A & B Lobster House has been around for more than 50 years, serving up platters of the freshest Florida spiny lobster. They also have a cushy upstairs cigar bar, Berlin's. (700 Front Street; 305-294-5880; open 11 a.m. to 11 p.m. daily, reservations highly recommended)
At Blue Heaven try the tasty tortillas filled with black beans, brown basmati rice, melted cheese and sour cream topped off with a dollop of fresh avocado. You can add jerk chicken or pan-seared fish. If they've got lobster Benedict on the Sunday menu, order it! (729 Thomas Street; 305-296-8666; open 8 a.m. to 3 p.m. and 5 p.m. to 10 p.m. Monday to Saturday, 8 a.m. to 2 p.m. for brunch and 5 p.m. to 10 p.m. for dinner on Sunday)
Mangoes, with its prime Duval Street location, is one of Key West's best restaurant for people watching -- as well as enjoying the Florida-Caribbean infused salads and entrees. Its front courtyard offers great tables. (700 Duval Street; 305-292-4606; open noon to 11 p.m. daily)
Award-winning Camille's has the best hand-pulled chicken salad and serves breakfast anytime. (1202 Simonton Street; 305-296-4811; open 8 a.m. to 10 p.m. daily)
Pepe's Cafe and Steakhouse opened in 1909 and has been going strong ever since. Great burgers, omelets and excellent barbecued chicken fill the menu. Oysters are a specialty, as is the outside covered patio. Homemade desserts are a must. (806 Caroline Street; 305-294-7192; open 7:30 a.m. to 10 p.m. daily)
Santiago's Bodega is an out-of-the-way locals' favorite in historic Bahama Village, but then again, nothing is too far in tiny Key West. Tapas, salads and sangria have made this small dining spot famous. Seating is limited, so advance reservations are recommended. (207 Petronia Street; 305-296-7691; open 11 a.m. to 10 p.m. daily)
Staying in Touch
Coffee Plantation offers espresso drinks, baked goods, sandwiches and free Wi-Fi with purchase in a comfy, low-key atmosphere. (713 Caroline Street; 305-295-9808)
McDonald's provides free Wi-Fi. (3704 N. Roosevelt Boulevard; 305-296-5800)
Best for Thrill-Seekers: Parasailing in Key West is fabulous -- and most excursions allow you to soar for four to six minutes at about 400 feet, either by yourself or with a friend. Usually, you won't even get wet (unless the operator decides to have fun and dip your feet). Keep in mind: Most excursions won't run in windy weather.
Best for Spirit-Lovers: As with any historic city, Key West has its share of ghost stories and cemetery walks. On the haunted walking tours offered by most cruise lines, you'll walk past the 19th-century wooden houses of Old Town and learn about Robert the Doll, an eerie plaything that now lives in a Civil War fort that once served as quarantine barracks for soldiers suffering from yellow fever.
Best for Garden-Lovers: Key West's streets are full of distinctive plantation architecture, but many visitors don't realize the tropical beauty that's often hidden behind the stately wooden doors. Cruise ship walking tours take people to properties on the National Register of Historic Places, including the home of Francis Watlington, Curry Mansion -- a home created by Florida's first millionaire -- and Audubon House, filled with European antiques and original "Birds of America" engravings.
For More Information
On the Web: Florida Keys website
Cruise Critic Message Boards: Key West
IndependentTraveler.com: Florida Travel Guide
--Updated by Gwen Filosa, Cruise Critic contributor