One of Hawaii's most interesting historic towns, the former Hawaiian capital also has a rich Yankee whaling history. In the 1800s, Lahaina was the center of the global whaling trade and its beautiful Historic District is a National Historical Landmark.

Grand Cayman's splashier side is the real draw. Offering a host of experiences, from petting attention- and food-seeking stingrays at Stingray City to exploring jaw-dropping drop-offs and dive sites, Grand Cayman is a watery wonderland.

With its ultramodern skyline, it's easy to forget that Dubai, part of the United Arab Emirates, was once a small town of Bedouin traders.

Where else are Ernest Hemingway and Jimmy Buffett equally revered? Key West is a sunny, fun destination with enough sights to keep you busy when you're not snorkeling, parasailing or catching some rays.