A bay-and-beach itinerary makes the history slide down easily. On a stroll along historic Annapolis' cobblestone streets lined with 18th-century buildings, it's easy for kids to imagine bewigged merchants hurrying to their shops. Mid-shipmen in dress whites marching in lockstep add to the allure of U.S. Naval Academy tour. Sailing on the Chesapeake Bay is fun, and gets you in touch with the essence of the city. Then hug the coast as you head north to Baltimore to explore the eye-catching exhibits at the Inner Harbor museums before dropping down to southern Delaware for swimming, kayaking, fishing, and sand castle building along 25 miles of ocean and bay shoreline that stretches from Lewes to Fenwick Island near the Maryland line.

Day 1-2: Annapolis, MD
Sailing's been a passion in Annapolis ever since it was established in 1649. Located where the Chesapeake Bay meets the Severn River, the city functioned as a busy customs port before the Revolutionary War. Ships unloaded spices and ceramics from China; rum, sugar, and coffee from the West Indies; and slaves from Africa and the West Indies. Alex Haley's ancestor Kunta Kinte, as chronicled in Roots, was sold into slavery in Annapolis after coming to the New World in chains aboard the Lord Ligonier, which anchored in the harbor on September 29, 1767. To peek into this region's storied past, stroll by the City Dock to see the Kunta Kinte-Alex Haley Memorial, a bronze sculpture of the Pulitzer prize-winning author reading to three children.

Walking is the best way to see old Annapolis, whose 1,500 restored historic buildings are the largest concentration of 18th-century architecture in the United States. The U.S. Naval Academy (410.263.6933; www.usna.edu), established in 1845, anchors the city's east side. Visit the chapel to view the elaborate stained-glass windows, including one designed by Tiffany, and see the crypt of naval hero John Paul Jones. It's common to spot midshipmen in their dress whites moving briskly along Main Street. Stop for lunch at Chick & Ruth's Delly (410.269.6737; www.chickandruths.com) on Main Street, an Annapolis institution since 1965 and a favorite eatery for politicians and other locals. Then head to the Maryland State House (410.974.3400; www.mdarchives.state.md.us/msa/homepage/html/statehse.html). Built in 1772 it's the oldest state capitol in continuous operation in the country.

You can't go to Annapolis without getting out on the water. The Woodwind (410.263.7837; www.schoonerwoodwind.com), a 74-foot schooner, sails two-hour scenic cruises in the bay. Those with tykes, meanwhile, should consider a cruise on the Sea Gypsy. Even before the young buccaneers board the ship, Pirate Adventures on the Chesapeake (410.263.0002; www.chesapeakepirates.com) morph them into pirates by painting on tattoos and getting them to don vests and bandanas. On the voyage, kids read treasure maps and defend the ship with water canons. For the opposite sensation, join Annapolis By Boat's (443.994.2424; www.annapolisbyboat.com) Captain Rick Brown, who takes up to six passengers for outings on a 30-foot Express Cruiser. Along with lighthouse and sunset cruises, consider the two-hour Wednesday Night Race, which puts you in the middle of Annapolis weekly challenge.

Afterwards, follow the competitors to the Boatyard Bar & Grill (410.216.6206; www.boatyardbarandgrill.com) in Eastport, just across Spa Creek from historic Annapolis. While your kids enjoy the burgers, crab cakes, and salads, you can down oysters with a Dark & Stormy (dark rum with ginger beer) and watch a video of the race.

Overnight at the nearby Washington DC/Capitol KOA (410.923.2771; www.capitolkoa.com). Located 15 miles northwest of Annapolis, the 50-acre facility has a pool and offers tent and RV sites as well as cabins.