Why you might roll your eyes:
Maryland’s capital is a popular day trip from Washington, but also easy to disdain as a place of overpriced antiques shops and other tourist traps.
Why you’ll love it:
The small city isn’t really for landlubbers; it’s a boater’s mecca best seen from the water. In fact, you can learn to sail in one weekend at one of the country’s best sailing academies, the Annapolis Sailing School. No interest in doing the work? Sit back and enjoy the Chesapeake Bay on the schooner Woodwind. A two-hour sunset sail ($44) is a spectacular way to see the historic city, as the setting sun casts a golden glow over the white dome of the State House.