Learn to Sail
The Washington Sailing Marina near Reagan National Airport and the Mariner Sailing School in Alexandria make becoming a skipper convenient and fun. Both feature weekend learn-to-sail programs and weeknight classes for adults. In no time, you’ll know how to rig a boat, navigate, tack, and jibe on a Sunfish or Flying Scot sailboat. One word of advice: Couples should not share a boat when learning to sail. Kids’ camps are offered through August. Adult basic weekend class $320 and up at the Washington Sailing Marina (703-548-9027), $400 at Mariner Sailing School (703-768-0018). 5 to 9 miles.
M (Moderate Difficulty) / 
Kid-Friendly / $$$ ($76 and up per person)
Set Sail on a Schooner
On the Sultana, a replica of a pre-Revolutionary War schooner, you’ll feel transported back in time. The ship usually departs from Chestertown, a historic Maryland town considered one of America’s best-preserved Colonial seaports. While aboard, you can enjoy cool breezes, take in views of the bucolic Chester River shoreline, or join the crew as it raises the sails and fires the cannon. Two-hour weekend public sails cost $30 for adults, $15 for ages 5 through 12; reservations recommended; 410-778-5954. 80 miles.
E (Easy Difficulty) / 
Great for Groups / Kid-Friendly / $ ($35 or less per person)
Sail a Skipjack
A skipjack is like a time machine, transporting passengers back to an era when these sail-powered boats ruled the bay. Now the remaining fleet mainly hauls tourists (oystering only in winter), including two Talbot County boats: Wade H. Murphy Jr.’s 1886 Rebecca T. Ruark (adults $30, under age 12 $15; 410-829-3976) and Ed Farley’s 1955 H.M. Krentz (adults $44, ages 12 and under $22; 800-979-3370). Both colorful captains pepper two-hour tours with bay lore—and even let you hoist the sails and dredge for oysters like in the good old days. 82 to 95 miles.
E (Easy Difficulty) / Kid-Friendly / $-$$ ($35-$76 per person)
