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BY MARC LEEPSON

There’s no place like Key West, Florida. The nation’s southernmost city, Key West sits at Mile Zero of U.S. Route 1 about 160 miles southwest of Miami—and about 90 miles north of Havana. It’s a city of some 25,000 residents that attracts hundreds of thousands of tourists each year. The visitors come to soak up the year-round tropical Caribbean-like climate and the famously laissez-faire, good-time life-style embodied in Jimmy Buffett’s Margaritaville.

Key West also is a military town. The first American naval base was established in 1823 (two years after Spain ceded Florida to the United States) to defend the city from the pirates who roamed the Caribbean. The battleship U.S.S. Maine sailed from Key West in 1898 to Havana, where it sank, propelling the United States into the Spanish-American War. The first naval air station was built in 1917 during World War I. By the early 1960s, the city was known as a Navy town, albeit it with a good sprinkling of hippies.

Key West today has many hotels, guesthouses, and B&Bs. Expect rates north of $500 per night at the fancy four-star waterfront hotels during the high season, but more moderately priced lodging at most B&Bs and guesthouses, many of them old Victorian edifices nestled on quiet streets.

If you are retired military, a bargain can be had at the Navy Lodge, located inside the Naval Air Station Key West on Boca Chica Key, a few miles north of Old Town Key West. You can get a large, clean, no-frills room there for well under $100 per night. DOD also has some vacation rentals, RV parks, and marinas available to retired veterans and to 100 percent-disabled veterans. For a listing, go to www.dodlodging.net

The Air Station is the home of the Navy’s Tactical Combat Training System, a Top Gun pilots training base. Boca Chica also has several other military tenants, including the Army’s Special Forces Underwater Training School. The base is not open to the public. However, if you served at Boca Chica, special tours can be arranged. Call the base’s Public Affairs Office at 305-293-2425 at least six weeks before your visit. Anyone can get a good view of the Top Gun pilots in action by parking outside the base.

Four HAWK missile batteries were deployed in and around Key West at the start of the Cuban Missile Crisis in 1962; they remained until 1979. Visitors today, however, can only get fleeting glimpses of the once-bustling batteries.

FOOD & DRINK

There’s no shortage of restaurants and bars in Key West—in fact, the city is famous for them. Most of the bars clustered along Duval Street, the main drag, draw a mix of locals and tourists. The bars, not surprisingly, tend to be loud, busy, and very informal. The most popular drinking establishments include Sloppy Joe’s, Hog’s Breath Saloon, the Green Parrot, Capt. Tony’s Saloon, and the Rum Barrel.

As with the hotels, you can dine fancy, plain, or in between. There are hundreds of eateries to choose from, many of which offer outdoor dining. Although fresh seafood is the big attraction, Key West offers a variety of cuisines, including many ethnic restaurants. The Thai Island Restaurant & Sushi Bar, for example, offers moderately priced Thai food (and sushi) with a picture-postcard view of the harbor from its upstairs deck.

At Hogfish Bar & Grill on Stock Island, the atmosphere is just short of rowdy; alcohol flows freely; staff and patrons alike wear shorts and flip flops; and there’s plenty of good bar food.

You could venture even farther off the beaten tourist path to nearby Geiger Key Marina, a simple, open-air eatery on the water facing Saddlehill Key, just down the road from Capt. Jeff’s Key West fishing charter boat operation. You sit at picnic tables and dine on short-order breakfast, lunch, dinner, and Sunday brunch food. They’re known for fish sandwiches, including fried hogfish, mahi-mahi, and yellowtail. As with nearly every other Key West eatery, Geiger Key has a bar. 

There’s no shortage of opportunities to charter a boat to check out Key West’s shallow water flats and the crystal blue waters beyond the city’s barrier coral reef—the only living-coral barrier reef in the U.S.—to do some deep-sea fishing. You’ll find bonefish, tarpon, Spanish mackerel, and barracuda along shore; grouper and snapper around the reefs; and dolphin fish, billfish, tuna, and wahoo offshore.

Or you can take a dolphin watch tour, rent jet skis, go parasailing, sit back and relax on a glass-bottom boat tour, or take a leisurely sunset cruise.

It’s all but mandatory for visitors to descend every evening on bustling Mallory Square to take in Key West sunsets. Nearby is the Little White House, where President Truman spent many winter days. You can get a discounted ticket by ordering ahead of time online.

The understated Key West-Florida Keys Historical Military Memorial is composed of ten concrete pedestals arranged in a semicircle behind a large flag pole. It is dedicated to members of the armed forces from Key West’s Monroe County who died in service from World War II through today. Nearby is the 54-acre Fort Zachary Taylor Historic State Park. During the Civil War it was headquarters for the Navy’s East Gulf blockade squadron. Guided tours are available every day at noon; admission to the park—which also includes a popular beach and café— is $6 per vehicle.

Not far from Fort Taylor is Key West’s other Civil War-era structure, Fort East Martello, which the Union Army began building in 1862 with a tower to help guard against an attack by the Confederate Navy. After the war ended the unfinished fort was abandoned. In 1950, the Key West Art & Historical Society restored the fort to its 1860s appearance. Admission for seniors is $8.

For more information on visiting Key West, go to www.fla-keys.com