An Insider's Guide to Key West, Florida

Discover the island's eccentric personality on a "Duval Crawl" along Key West's main street, visiting Duval Street's many iconic bars and souvenir shops. Or wander quiet roads to admire stately homes draped with flowering plants — or charmingly dilapidated ones marked by funky front porch decor like an old bathtub transformed into a fish-filled aquarium.

You can also experience the island's personality on the hop-on-hop-off Conch Tour Train. Since 1958, it has shuttled visitors past island attractions like the Historic Seaport, former U.S. President Harry Truman's Little White House and treasure hunter Mel Fisher's Maritime Museum, while guides explain how each contributed to the island's colorful history.

After dark, test your courage on a Ghosts and Gravestones trolley tour, which delves into the island's haunted lore. The 1½-hour journey explores Key West's chilling past, including a visit with the allegedly cursed and demonic toy, Robert the Doll, as well as a trip to the African Slave Cemetery.

Built in the mid-19th century to defend the southeastern USA's coastline, Fort Zachary Taylor played an important role during the U.S. Civil War and the Spanish-American War. Today it’s part of a state park. After taking a guided tour, head to Truman Beach, one of Key West's nicest stretches of sand, which offers places to swim, sunbathe and picnic.

Pay your respects to one of Key West’s most famous residents, the lauded writer Ernest Hemingway, at the Ernest Hemingway Home and Museum. Take a guided tour to learn more about "Papa's" legacy on the island and see the desk where he often wrote.

Only in Key West is Mother Nature's daily grand finale — the sunset — celebrated with so much fanfare. Head to Mallory Square, which overlooks the water, an hour before sunset to watch jugglers, fire eaters and musicians perform until the sun dips below the horizon. Listen closely. At the exact moment the sun sets, someone blows a conch shell like a horn and the crowd erupts in applause.

You can also visit the southernmost point in the continental USA. Walk to the tip of the island and take a photograph next to the concrete buoy that marks the spot.

Key West's drinking culture is a force to be reckoned with, and there is no shortage of bars. Party with other travelers and listen to live music at island mainstay Sloppy Joe's, or rub elbows with locals at the Green Parrot, a laid-back bar with twinkling green ceiling lights, cheap beer and walls covered in local memorabilia. For more tropical drinks, grab a mojito or margarita on the porch at Caroline's Cafe. Santiago's Bodega serves inventive tapas-style plates. Plan to indulge in a decadent brunch at Blue Heaven, where diners sit in a lush courtyard as Key West's infamous roosters wander past.

Turn up the adrenaline a notch on a Fury Water Adventures tour. The outdoor outfitter offers snorkeling, parasailing, as well as jet ski and kayaking trips around the island's coral reefs and mangrove forests.

From Miami, it's easiest to rent a car and drive about 260 kilometers down U.S. Route 1 to Key West. After exiting Miami's urban landscape, you'll drive through the Keys' major islands and over the Seven Mile Bridge, surrounded by sparkling turquoise water. Along the way, stop for a fresh seafood lunch and slice of tart Key lime pie (a Florida Keys classic) at Keys Fisheries Market & Marina, located on Marathon Key. Shuttles and buses from Miami to Key West are available.

Charming inns dot Key West’s streets. The Lighthouse Hotel sits across from the Hemingway house and is a one-block walk from Duval Street. It offers intimate, bungalow-style rooms and poolside breakfast.