Careful planning and an open mind combine to create a surprisingly upscale experience in touristy Key West. By Lisa Rogak
Key West is one of AmericaÂ’s most popular destinations, but given the cruise ship traffic and hordes of tourists here, those in 
search of high-end travel experiences might think theyÂ’re few and far between in The Conch Republic and steer clear of it entirely. And that would be a huge mistake.
It may take a little digging to seek out high-end Key West, but itÂ’s there and itÂ’s worth the legwork. In fact, even the more plebeian pursuits arenÂ’t to be missed.
Anglers will find themselves in heaven here, thanks to the wealth of fishing tournaments that go on in late spring into early summer. Dolphin fish, a.k.a. mahi-mahi or dorado, is the catch of choice, and whether you participate or watch, you’ll be richly rewarded. On Memorial Day weekend, the Yamaha Dolphin Masters Invitational starts off the season, followed by the Key West Gator Club Dolphin Derby in late June. The Conch Republic Ladies’ Dolphin Tournament wraps it up over Independence Day.
Key West has had an admittedly checkered past from its early days as a Spanish outpost, and today, a healthy dose of bohemia and eccentricity is still part of the mix. Happily, for an island that measures only eight square miles, this place packs more activity than most Caribbean islands 10 times its size. The island is also a draw for celebrities: Jimmy Buffett and authors Judy Blume and Meg Cabot own real estate on the island, and actress Kelly McGillis runs KellyÂ’s Caribbean Bar, Grill & Brewery on Whitehead Street.
You’ll find entertainment on every street in Key West, but to get the true feel of this quirky island, visitors need only spend an afternoon wandering the streets away from the crowds and tacky souvenir shops of Duval Street. Head down Whitehead Street and veer off into the tiny side streets—given girls’ names like Amelia and Petronia—where the homes of former sea captains sit alongside mansions with ornate Victorian touches. Or take a bike ride around the perimeter along North and South Roosevelt Boulevard, stopping every so often to admire the view of the Gulf and stick your toes in the sand. keywestchamber.org.
The Essentials Key West
1 Where to Stay Wake up to a stellar view of the water in a Gulf-front king room at the Hyatt Key West Resort and Spa. The hotel is close enough to all the major attractions, yet is tucked away just enough to avoid the hustle and bustle. keywest.hyatt.com; 601 Front Street; 305-809-1234.
2 Where to Eat Locals and visitors alike praise Blue Heaven for the atmosphere, the drinks, and, above all, the food, which remains true to the funky Caribbean vibe of Key West. The Jamaican Jerk Chicken is a favorite. blueheavenkw.homestead.com; 729 Thomas Street;Â 305-296-8666.
3 What To Do A day-long seaplane trip to Dry Tortugas National Park provides a glimpse of the Florida Keys that few people see, from shipwrecks to a private island that Tennessee Williams occasionally visited. Key West Seaplane Charters: keywestseaplanecharters.com, 305-293-9300. The Ernest Hemingway Home and Museum is a registered historic landmark and remains home to descendants of the six-toed cats that kept Papa company when he lived and wrote here. hemingwayhome.com; 907 Whitehead Street.