A storybook town that was once Bermuda's capital, St. George's is also famous as the second English settlement in the New World, after Jamestown. A World Heritage Site, it's a maze of quaint narrow streets with names like Featherbed Alley and Old Maid's Lane (two worth a look are Shinbone Alley and Silk Alley). 

St. George's also played a role in the American Revolution. Bermuda depended on the American Colonies for food, and when the war began, supplies grew dangerously low. Without the approval of the British Bermudian governor, George Washington and Henry Tucker struck a deal: gunpowder for food under the cover of night in Tobacco Bay. King's Square is the best spot for unfolding a map and heading for the sights along the tiny streets and lanes (the Visitors Service Bureau is there, ready to hand over self-guided walking tour brochures and maps). Beckoning beaches include Tobacco Bay, which also happens to be a snorkeling paradise, and Achilles Bay.