An Insider’s Guide to Key West

Few cities in the southern latitudes offer as much fun and variety.

October 4, 2007

Over the years, I have visited Key West more times than I can remember. Still, given the opportunity to wander its streets, I am reminded it would take a lifetime to complete the experience. Key West is a unique destination. Its “Old Town” is not a theme park-style model of the past; it is a living, breathing town-a refreshingly laid-back novelty in today’s busy world.

In terms of U.S. geography, Key West is at the end of the line-the last stop on southbound U.S. Highway 1 and 154 miles from Miami. Barely 4 miles long and 1 mile wide, it was relatively isolated until 1912, when Henry Flagler completed his railroad. When the railway was disabled by the 1935 Labor Day hurricane, its remains were converted to a roadbed, now known as the “Overseas Highway.” The Calusa Indians came before Flagler, chased by the Seminoles. Legend has it the battle that followed was so violent that when the Spanish explorers arrived they named the Key “Cayo Hueso” (Island of Bones). The English somehow molded the name into Key West.

Since then, the island has served as a melting pot for a variety of cultures and lifestyles. Cubans, Bahamians and those escaping persecution and prosecution are all a part of the matrix. Fantasy Fest in October celebrates this diversity and is something like Mardi Gras unplugged. If you have an ounce of intolerance, time your visit accordingly. Conch Republic Independence Day in April celebrates the date the Keys symbolically declared the obvious. Key West also hosts conventional gatherings, including powerboat and sailboat races, art festivals and fishing tournaments. Dockage is always dear (winter and summer), so plan ahead.


Key West has had its highs and lows as a center for treasure prospecting, cigar manufacturing, sponging and just about anything else that could make a buck. These days, the good times are back, driven by tourists who arrive by land and sea. Duval Street is the bloodline of Old Town and is rife with bars, bistros, art galleries and T-shirt shops. While Duval is loud and amusing, I have always found the most pleasure wandering the small side streets that feed it. The surprisingly quiet neighborhoods are composed of a patchwork of gingerbread-trimmed homes and small businesses built mostly from the exotic hardwoods scavenged from sailing ships that found the reef. Some of these structures are lovingly restored and others are not, but all have their place in the city’s colorful history.

As the last stop on the line, Key West has been a receptacle for a diverse collection of characters. Jimmy Buffett is the most recent popular artist to find inspiration in the city, but Ernest Hemingway and Tennessee Williams were residents long before “Margaritaville” was penned. John Audubon too had a home in Key West, and President Harry S. Truman annexed a portion of the U.S. Navy base for “The Little White House.”

All have left their mark. Hemingway’s home is open for tours, as is the Audubon House and the Little White House. Buffett’s songs are sung in virtually every bar, and those who can’t get enough can pay homage to the entertainer in greenbacks at his restaurant, Margaritaville Cafe. Another favorite, Kelly’s Caribbean Bar, Grill and Brewery, is a tribute to early commercial aviation and resides in the original home of Pan American Airways.


The list of bars of note in Key West is too long to document. Sloppy Joe’s, Hemmingway’s legendary haunt, should not be missed, especially during the Hemingway Days festival, when gray-bearded look-alikes sing the praises of Pappa (I’ve been tempted). Captain Tony’s, the original Sloppy Joe’s, is also well seasoned. I have heard some of the best (loud) music in Key West at the Hog’s Breath Saloon. Try El Meson de Pepe for a touch of Cuban food and culture. The Rooftop Café, for fine dining outdoors above the busy street, is one of my favorites, as is Antonia’s for absolutely terrific Italian food.

Finding Key West by boat is not particularly challenging. Skippers, however, must remember to avoid interacting with the bottom, as sea grasses and coral are protected in the Florida Keys National Marine Sanctuary, in which Key West resides. From the eastern coast of Florida, you can choose Hawk Channel (inside the reef) or run offshore of the reef-the choice is dependent on your vessel’s draft and the sea conditions. If you depart from the western coast of Florida, Key West is a straight shot across the Gulf of Mexico.

There are a number of excellent marinas with direct access to the old town. Most are well protected in the Key West Bight. Galleon Resort & Marina has berths for vessels up to 150 feet. Resort amenities include a swimming pool, a private beach and a tiki bar. Galleon’s floating docks are ideal for smaller (under 60 feet) boats. A&B Marina has berths for vessels up to 130 feet. Dining at the A&B Lobster House, which opened in 1947, is worthwhile.


The Key West Bight Marina, in the Key West Historic Seaport, has berths for vessels up to 150 feet. While it’s a few steps farther from Duval Street, the area has its own flavor, which is distinctly nautical and at most times lively. Turtle Kraals Restaurant & Bar, for example, is located on the site of Key West’s first sea turtle cannery, which opened in 1849. Another option in this area is Conch Harbor Marina.

Boats too large for the Bight will find the upscale docks of the Hilton Resort & Marina fitting. I am particularly fond of this marina, though you must tolerate the tidal surge. Offering a view of the sunset (when a cruise ship is not in the way), the marina is surrounded by shops and is a stone’s throw from Duval Street and Mallory Square. The latter is a spiritual center of sorts, where locals, inspired by the sunset, display an odd assortment of talents from cat taming to juggling. For those staying ashore, the Hilton Resort & Marina offers first-class amenities with suites overlooking the marina. The Ocean Key Resort and the Pier House Resort and Caribbean Spa are also nearby.

While you can rent everything from a bicycle to a biplane to tour Key West, the best way to see the area is on foot. While it might seem corny, if you have never visited the city, a ride on the Couch Train is an excellent way to establish your bearings. The Key West Lighthouse and Keeper’s Quarters Museum and the Shipwreck Historeum Museum will please the kids. The Key West Aquarium, built to attract tourists during the Great Depression, remains a popular draw.


Key West is, of course, surrounded by water, and backcountry and offshore fishing and eco-tours are popular, as are diving and snorkeling the reef. Charters are available through most of the area’s marinas.

There are few cities so small that offer so much.


The Galleon Resort & Marina, (305) 292-1292; A&B Marina, (305) 294-2535; Key West Bight Marina, (305) 296-3838;


Hilton Resort & Marina, (305) 292-4375; Conch Harbor Marina, (305) 294-2933; Hilton Resort & Marina, (305) 294-4000; Ocean Key Resort, (305) 296-7701; Pier House Resort and Caribbean Spa, (305) 296-4600; Wyndham Casa Marina Resort, (305) 296-5000;


A&B Lobster House, (305) 294-5880. Antonia’s, (305) 294-6565. Louie’s Backyard, (305) 294-1061. Pisces, (305) 294-7100. Rooftop Café, (305) 294-2042. El Meson de Pepe, (305) 295-2620. Turtle Kraals Restaurant & Bar, (305) 294-2640. Hot Tin Roof, (305) 296-7701, ext. 7057. Kelly’s Caribbean Bar, Grill and Brewery, (305) 293-8484. Bagatelle Restaurant, (305) 296-6609.


Conch Train, (305) 294-5161. Ghost Tours, (305) 294-9255; Key West Golf Club, (305) 294-5232; Shipwreck Historeum Museum, (305) 292-8990; Harry S. Truman Little White House, (305) 294-9911; Key West Aquarium, (305) 296-2051; Mel Fisher Maritime Museum, (305) 294-2633; Hemingway Home & Museum, (305) 294-1136; Key West Butterfly & Nature Conservatory, (305) 296-2988; Audubon House and Tropical Gardens, (305) 294-2116; Key West Lighthouse & Keeper’s Quarters Museum, (305) 294-0012;


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