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The Draw
• Caribbean-style island getaways within driving distance of Miami
• Some of the best protected marine reserves in the U.S.
• A party-hearty atmosphere with an escape route, via plantation-style inns and far-flung island daytrips
The Scene
More than 400 islands make up the 150-mile-long Florida Keys, which trail off the continent on their way to the Caribbean. The more easily accessible Upper and Middle Keys attract the weekend crowds, which drift in to deluxe hot spots like longtime celeb-magnet Cheeca Lodge as well as Hawk's Cay, which sits on its own 60-acre island. Make the commitment to the Lower Keys to find more environmentally protected turf filled with turtles, fish, deer, and hundreds of bird species. And let's not forget that anomaly at the end of the line: Key West (aka "The Conch Republic"), with its anything-goes vibe tempered by a mellow-as-molasses tropical atmosphere.
To Be Seen
• The Overseas Highway. The three-hour drive from Miami to Key West is a must-do road, passing over 159 miles of oceans and islands on its way to The Conch Republic.
• Spiegel Grove shipwreck. In 2002, the U.S. Navy sunk this 510-foot vessel near Dixie Shoals in Key Largo, making it the largest craft ever intentionally sunk to create an artificial reef. Most of the ship is easily accessible at depths from 50 to 85 feet.
• Fort Jefferson. On Garden Key in the undeveloped Dry Tortugas (70 miles west of Key West) stands a huge, six-sided 19th-century fortress that acted as an Alcatraz-type prison in the 1800s. Take a day trip to this impressive, eerie fort that looks like it's floating above the Atlantic.
• Hemingway House, Key West. Stroll through Papa's residence, filled with his furniture, typewriters, photos and cats; more than 60 of them roam the place (many with extra toes), descendants of Ernest's own six-toed feline.
• Key West National Wildlife Refuge. This 200,000-acre preserve (most of it made up of ocean) was established in 1908 and remains one of Florida's premier unspoiled underwater attractions.
For The VIP
• Charter a tall ship schooner. Key West is home to two of the finest examples of traditional tall ships: the 80-foot Schooner Liberty and the 125-foot Liberty Clipper. Take either boat out on a fully crewed banquet under the stars or a champagne sunset sail, all to yourself.
• Jules Undersea Lodge. In Key Largo, this one-of-a-kind exclusive accommodation requires you to scuba dive (no training required) into a furnished two-bedroom underwater apartment, with hot showers, TV, DVD player, phone and fully stocked kitchen.
• Stay in a tropical estate. Avoid being cooped up in a hotel or B&B by renting an entire classic plantation-style home or oceanfront deluxe cottage through one of the area's real estate agencies.
Overrated
Key lime pie. You'd think every restaurant would have a drop-dead version of this classic dessert, but most taste like rip-offs made to round out the menu. The bona fide thing can be found at the very local Seven Mile Grill on Marathon Key.
Underrated
The Waterfront Playhouse, Key West. At $30 a ticket, you can catch surprisingly first-rate productions, thanks to the island's talented arts community. You may even catch part-time island resident Kelly McGillis on stage.
Don't Miss
Little Palm Island. This private-isle resort with just 30 bungalows was once one of Harry Truman's favorite hangouts. But you don't have to stay here to enjoy its privileged atmosphere: Make a reservation at the restaurant (with tables directly atop the beach), and a private shuttle boat will pick you up from Little Torch Key.
When To Go
High season can last from December all the way to spring vacations in April, and summer is becoming a second high season (the Keys are much cooler and breezier than mainland Florida). For the thinnest crowds, go in late spring or fall -- just watch out for fall hurricanes and weekend traffic on the Overseas Highway.
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