Key West (Photo:Stockdonkey/Shutterstock)
4.5 / 5.0
Cruise Critic Editor Rating

By Gwen Filosa
Cruise Critic Contributor

Port of Key West

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.

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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.

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.

Port Facilities

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.

Good to Know

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.

Getting Around

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.

Currency & Best Way to Get Money

Currency is the U.S. dollar, and ATMs are readily available.

Language

English is spoken in Key West.

Food and Drink

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)

Shopping

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)

Best Cocktail

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.