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.

About Key West


All of the city's famous attractions, shops, restaurants and bars are within walking distance


The city's Duval Street can get rowdy, especially at night and during spring break and holidays

Bottom Line

Key West is a diverse city that will make you forget you're in Florida

Find a Cruise to the Eastern Caribbean

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.

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.

Currency & Best Way to Get Money

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


English is spoken in Key West.


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.

Key West Awards

Cruisers’ Choice Destination Awards

2017 Top-Rated US & Canada Destinations
2016 Top-Rated US & Canada Destinations