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Key West Overview
Key West, the southernmost city in the continental U.S., is the largest and most vibrant of a chain of tiny islands called the Florida Keys that are scattered, like a string of pearls, south of Miami. Closer to Cuba than to Miami (with respective distances of 90 and 150 miles), Key West, dubbed the "Conch Republic," is a very popular destination on Western Caribbean itineraries -- and is easily one of the funkiest and wackiest ports of call in all of cruising.
Key West earned its conch moniker in 1982, when residents of this free-spirited place tried to secede from the U.S. after Border Patrol, in an effort to catch smugglers and illegal aliens, created a roadblock at Key Largo. The roadblock was a disaster for tourism. As such, the island's then-mayor declared war on America -- and then required more than $1 million in foreign aid. No funds were forthcoming and Key West backtracked.
Key West was first settled in the 1820s and considered America's richest city per capita in 1886. It is compact (about the size of New York's Central Park), laidback and kitschy-cute, filled to the brim with gingerbread cottages, Victorian mansions with widow's walks, sidewalk cafes, T-shirt shops galore, colorful and moderately famous local characters, and plenty of historical richness along winding white-picket-fenced streets. It may be hard, initially, to appreciate Key West's charm, particularly for cruise travelers who disembark at the confluence of ticky-tacky tourist shops on Lower Duval Street. But it's an easy place to explore -- and walking (or cycling) through smaller side streets will reveal quite a lovely city.
Famous residents include Ernest Hemingway (you can visit his house-cum-museum, where he wrote novels in the 1930s, and visit his favorite pubs-cum-tourist attractions). You can also walk in the footsteps of President Truman, who lived on Front Street. The actress Kelly McGillis has long owned a restaurant here.
Key West famously appeals to all types of folks, and especially is a magnet for artists and hippies as well as cruise ships. It's a colorful and magical visit any time of year, so put on your most colorful flip-flops, get out your sunglasses, slap on the sunscreen and start humming Jimmy Buffet's "Margaritaville."
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Other Western Caribbean Cruise Ports:
Belize City • Costa Maya • Cozumel • Falmouth • Galveston • Grand Cayman • Havana • Key West • Mobile • Montego Bay • New Orleans • Ocho Rios • Playa del Carmen (Calica) • Progreso • Roatan • Tampa
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Best Cocktail
Sip a rum runner, the drink of the Keys, at Sloppy Joe's, Ernest Hemingway's favorite bar. For a "mojito" (rum, lime, mint), head to the Cuban restaurant El Meson de Pepe.
Best Souvenir
A bottle of key lime juice or frozen key lime pie wedge dipped in chocolate 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)
Language
English is spoken.
Currency & Best Way to Get Money
The currency is the U.S. dollar, and ATM's are readily available.
Where You're Docked
Cruise ships usually dock at either Pier B, near the Truman Annex, or the Navy (Outer) Mole, near Fort Zachary Taylor. If docked at the latter, a tourist trolley shuttles you off the base. There is also a smaller dock at Mallory Square.
Hanging Around
As an island (a "key" in local lingo) that is just two miles long by four miles wide, almost everything is near the dock -- including shopping, dining, barhopping, scuba diving and beach bumming. Mallory Square, on the waterfront near the docks, has restaurants, shops and public restrooms.
Getting Around
Easy as key lime pie! Consider Duval Street the main thoroughfare. Most of the most popular bars, T-shirt shops and art galleries can be found from the 200 block to the end near Mallory Square. Although there is an open container law in Key West (no consumption of alcohol on public streets) it isn't regularly enforced, especially along the 100 and 200 blocks of Duval.
Bikes and mopeds are the most popular modes of transportation, for both locals and visitors. We rented a perfectly reliable bike dockside (paying a small premium for the convenience; a fully refundable deposit or cruise key card was required). Reliable shops to rent from are the A and M Rentals (523 Truman Street; 305-294-4556) and Tropical Rentals (1300 Duval Street; 305-294-8136).
"Conch Cruisers" are another popular mode of transportation. These slow-moving electric vehicles operate on marine batteries, so think golf cart. Available in hard top or soft top, rent them for two, four or more passengers. They're rentable in increments of two hours. A reliable shop for renting is Key West Cruisers (500 Truman Ave.; 305-294-4724 or 888-800-8802). Deposits are required.
For first-timers, the Old Town Trolley Tours and the Conch Tour Train offer on-and-off all-day transportation (and throw in audio-recorded info as well).
Pedicabs are available and generally charge per minute. Perfect Pedicab on Duval Street is one of the more popular companies.
Watch Out For
Sunburn and mosquitoes. The sun at latitude 24 is quite intense, and the tropical mosquito bite has been known to transmit dengue fever. Take your own bite out of crime (although Key West has a low crime rate) by keeping an eye on your personal items so as not to be a victim of theft.
Don't Miss
 Your best bet for a great island overview is hopping on and off the open-air Conch Tour Train. Buy the tickets onboard or at Mallory Square, where it departs. It also leaves from the Welcome Center on North Roosevelt Boulevard. Daily 9 a.m. - 4:30 p.m. If the weather is iffy, take the covered Old Town Trolley Tours. The trolley also departs from Mallory Square.
You can't visit Key West and not stop in at the Ernest Hemmingway Home and Museum. A tour will take you inside his book-filled writing studio, past the old typewriter where he wrote "Farewell to Arms" and out to the swimming pool (the first one in Key West). You'll also see some 60 well-cared-for felines, descendants of the many cats that lazed on Hemingway's lap while he wrote, that now roam throughout the property. Daily 9 a.m. – 5 p.m. (907 Whitehead Street; 305-294-1575)
Cross the street and climb the nearly 90 steps to the top of the Lighthouse and Keepers Quarters Museum for jaw-dropping views. Daily 9:30 a.m. - 5 p.m. (907 Whitehead Street; 305-294-0012)
Shopping! There's no need to advise you on souvenir shops (they are everywhere and easy to find) but for more discerning discoveries, there are numerous art galleries, fun boutiques and craft emporiums. Our favorites? Besame Mucho (315 Petronia Street) is a fabulous female feel-good boutique, with Kiehl's products, exotic handbags and funky housewares. Key West Aloe (540 Greene Street) has locally made goodies. Key West Hand Print Fabrics (Greene and Simonton Streets) offers tropical wear -- we also love the not-as-local Lilly Pulitzer.
Named for the painter and bird expert, James Audubon, the Key West Audubon House and Tropical Gardens is a lovely stop. It's a chance to see some rare Audubon prints, too. The gardens are spectacular. Daily 9:30 a.m. - 5 p.m. (205 Whitehead Street; 305-294-2116)
Stroll the two-mile Harborwalk, which runs from Front to Grinnell streets. It's filled with cute shops and such -- and the passing ships and schooners make for pretty views.
The oldest attraction on the island is the Key West Aquarium. It's worth seeing just for the lovely sea horses. They offer free guided tours at 11 a.m., 1 p.m., 3 p.m. and 4 p.m., which get you up close for some shark, barracuda and stingray feedings. Daily 10 a.m. - 6 p.m. (1 Whitehead Street; 305-296-2051)
At the Key West Butterfly and Nature Conservatory there's an amazing greenhouse with some 1,500 butterflies. Daily 9 a.m. – 5 p.m. (1316 Duval Street; 305-293-9258)
The Truman Little White House Key West Home and History Museum was originally built as officer's quarters for those stationed at the Navy Station. President Truman used it for working vacations, as did Eisenhower and Kennedy. Daily 9 a.m. - 4:30 p.m. (111 Front Street; 305-294-9911)
Tip: If you are really serious about sightseeing, you can purchase a Key West Passport. It includes the Conch Train or Old Town Trolley, the aquarium, the Hemingway Home and Museum, the Shipwreck Historeum, the Little White House as well as some shopping discounts. For more information, visit Trusted Tours and Attractions.
Check out Editor's Picks: Offbeat Key West for more sightseeing recommendations.
Been There, Done That
Culinary aficionados really shouldn't miss a tasting experience at Peppers of Key West (602 Greene Street). 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 (you'll have to bring your own, though).
At the Mel Fisher Maritime Museum you can view treasures salvaged from the 17th-century Spanish galleon "Nuestra Senora de Atocha," shipwrecked in the waters off of Key West. Weekdays 8:30 a.m. – 5 p.m. Weekends 9:30 a.m. – 5 p.m. (200 Greene Street; 305-294-2633)
It's not Pere Lachaise in Paris, but it's way more fun. Visit the Key West Cemetery for hilarious 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 or take a 90-minute guided tour that starts at the main entrance on Tuesday and Thursdays at 9:30 a.m. Daily dawn to dusk. (Margaret and Angela streets)
If you don't want to dive yourself, sail 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 Furycat Catamaran Glass Bottom Boat cruises at noon, 2 p.m. and 4 p.m., with sunset cruises at 4:30 p.m. (2 Duval Street; 800-994-8898)
Book a seat with Island Airplane Tours for a seat-of-your-pants, 15-minute ride in an open-cockpit 1940 Waco biplane. You swoop over just about everything on the island. If you're game for something a bit more spine-tingly, take a ride in the S2-B aerobatic plane for figure eights, loops and rolls. Key West Airport.
For a look at nearly two centuries of black history in Key West, visit the Lofton B. Sands African-Bahamian Museum. Daily 10 a.m. – 6 p.m. (324 Truman Avenue; 305-295-7337)
Beaches
Best Party Beach: Smathers Beach off South Roosevelt Boulevard. The water's shallow so it's good for little kids, too. There are food concessions, restrooms, equipment rentals including chairs and umbrellas, and excellent water sport rentals.
Best Beach for Quiet Time: Rest Beach near the White Street Pier. It's only about 300 feet long -- but you'll avoid the crowds, albeit with less amenities. Restrooms are walking distance away.
Best Gay-Friendly Beach: Higgs Beach at the end of Reynolds Street. It's got chairs and snorkel equipment rentals, tennis courts, volleyball courts, a large playground (Astro Park), restaurant, outdoor showers -- and a handful of gazebos for shade.
Best Beach with Culture: Fort Zachary Taylor Beach at the end of Southard Street. There's the historical fort and a Civil War Museum. It has picnic tables and grills, bathrooms, showers and lots of shade.
Lunching
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. Daily 11:30 a.m. – 10:30 p.m. (700 Waddell Avenue; 305-294-1061)
Another lovely place to lunch is La Te Da. It may 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. Daily 8:30 a.m. – 3 p.m., 6 -11 p.m. (1125 Duval Street; 305-296-6706)
For ultra-casual fare in an ultra-funky setting, BO's Fish Wagon is named after owner Buddy Owen. He started out selling his famous fish sandwiches from a wagon on Duval Street before building this, er, shack (the wagon's in the middle). Order the fried grouper and don't miss his key lime mayo. Daily 11 a.m.(or so) – 9 p.m.(or so) (William and Caroline streets; 305-294-9272)
For Cuban cuisine, El Meson de Pepe is convenient (right off of Mallory Square) and atmospheric. Drinks, tapas, soups, salads and more, try the ropa vieja (shredded beef and tomatoes). Daily from 8 a.m. (410 Wall Street; 305-295-2620)
A & B Lobster House has been around for more than 50 years, serving up platters of the freshest lobster. Reservations highly recommended. They also have a pretty cool cigar bar, Berlin's. Daily 11 a.m. - 11 p.m. (700 Front Street; 305-294-5880)
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! Monday - Saturday 8 a.m. – 3 p.m. and 5 – 10(ish) p.m., Sunday brunch 8 a.m. - 2 p.m., dinner 5 p.m. – 10(ish) p.m. (729 Thomas Street; 305-296-8666)
Mangoes, with its prime on-Duval location, is Key West's best restaurant -- for people watching. The food's good, too. Try to snare a table in the front courtyard. Daily noon – 11(or so) p.m. (700 Duval Street; 305-292-4606)
Award-winning Camille's has the best hand-pulled chicken salad. Daily 8 a.m. - 10 p.m. (1202 Simonton Street; 305-296-4811)
Pepe's Cafe and Steakhouse opened in 1909 and has been going strong ever since. Great burgers, omelets and excellent barbecued chicken inside or outside on a deck. Daily 7:30 a.m. - 10 p.m. (806 Caroline Street; 305-294-7192)
Santiago's Bodega is an outstanding choice for a low-key communal lunch of salads (the Avocado Pear salad is tasty), tapas (seasoned grouper, spanakopita) and Sangria. Santiago's Bodega is worth the hike (about 10 blocks from the pier). The place is small, so advance reservations are recommended. Daily 11 a.m. - 10 p.m. (207 Petronia Street; 305-296-7691)
Staying in Touch
Coffee Plantation offers espresso drinks, baked goods, sandwiches and free Wi-Fi with purchase in a Caribbean atmosphere. (713 Caroline Street; 305-295-9808)
McDonald's provides free Wi-Fi. (3704 N Roosevelt Blvd.; 305-296-5800)
Miami Subs is fast food in paradise. Menu of Philly Cheese Steaks, chicken wings, pizza, burgers, subs, wraps and salads. Also serves breakfast sandwiches. (1800 N Roosevelt Blvd.; 305-294-0001)
Shore Excursions
Lloyd's Tropical Bike Tour is a two-hour cycling ride with a personal guide who reveals all as you pedal along back streets. Taste exotic fruit, tour private gardens, meet locals. Plus, Key West is really flat, so cycling is easy. Call for reservations and details. (Truman Ave. and Simonton St.; 305-294-1882)
Catamaran Echo has private charters for up to 16 people. You can choose to sail to an island sandbar for a picnic, swim with dolphins, snorkel, learn to hunt lobster, have a sailing lesson or simply take in the sunset. Normal departure times are 9 a.m. and 1:30 p.m. (Harborwalk at the end of Margaret Street; 305-292-5044)
Parasailing here is fabulous -- you fly for four to six minutes at about 400 feet. Sunset Watersports has two locations -- Key West Beach Water Park at Smathers Beach or All Day Watersports Adventure at Key West Bight -- and you can choose to parasail by yourself, with one friend or even two. The 9 and 10 a.m. sails from Key West Bight are discounted. (305-296-2554)
For More Information
On the Web: www.fla-keys.com
Cruise Critic Message Boards: Key West
The Independent Traveler: Florida Exchange & Caribbean Exchange
-- Updated by Jodi Thompson, Cruise Critic contributor.
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