The best way to arrive to Annapolis, Maryland, is from the water. You’ll pass everything from tankers to kayaks in the Chesapeake Bay. And as you near town, the elegant buildings and dome of the U.S. Naval Academy will come into sight. We docked at the Annapolis Yacht Club, where sailing races are held every Wednesday. (You can stand on the pedestrian Spa Creek bridge for a great view of the finish line.) For a short period, Annapolis actually served as the nation’s capital in 1783, and many historic colonial buildings remain. (Think Boston on a much smaller scale.) The Historic Annapolis Foundation offers walking tours with a guide or self-guided digital-audio tours so you can go at your own pace.

Thanks to the many delicious snacking spots, you can take refreshment breaks along the way. For example, after stopping at the City Dock area (where there's a statue honoring Alex Haley and commemorating the docking of Kunta Kinte slave ship), you can inhale a delicious crepe at Sofi’s and then dash off to the U.S. Naval Academy for a tour. Don’t miss the crypt of Revolutionary war hero John Paul Jones--he's the guy who uttered the famous slogans “We have not yet begun to fight” and “Never give up the ship.” Other don't-misses: the model midshipman’s room or Bancroft Hall, one of the largest dormitories in the world (with a rifle range in the basement).