Getaway Guide: Summer Boat Rides On The Chesapeake

August 15, 2013 8:00 AM

(credit: Jay Lloyd)

Reporting Jay Lloyd

Herman Melville’s Ishmael chose to go voyaging when it was a damp, drizzly November in his soul. For the rest of us, the shoreline beckons during these lazy days of summer, when relaxing hours on boats provide the body with a cooling bay breeze and the mind is lulled by the tranquility of protected waters. The best place to find these rejuvenating boat rides in and around happening harbors is on the nearby Chesapeake Bay. Here are a few favorites. – Jay Lloyd

(credit: Jay Lloyd)

(credit: Jay Lloyd)


80 Compromise St.
Annapolis, MD 21401

Casting off aboard a sleek schooner powered by the wind onto the broad Chesapeake Bay is a rare experience. To sail from Annapolis is to follow in the wake of American Naval heroes. Woodwind and Woodwind II, a pair of 74-foot schooners, sail from “Ego Alley” on the Annapolis waterfront within sight of the U.S. Naval Academy. Two-hour cruises take you on a passage from the mouth of the Severn River to the bay, and then they follow the wind. The boats leave their dock next to the Marriott Hotel four times a day, and sunset cruises are the most popular. On your return, step from boat to Pusser’s Rum Bar and relive the cruise. Adults pay $39 on weekdays and $42 for weekend and sunset cruises. Kids under $12 sign on for $27. There are also discounts for seniors. Check cruise schedules and rates here.

Buccaneering is the way to go for kids on an Annapolis family getaway. Pirate Adventures provides cruises complete with pirate garb, yarns and swashbuckling hijinx. The colorful square rigger sails from Annapolis City Dock. Join the crew at:

(credit: Jay Lloyd)

(credit: Jay Lloyd)


Sharp Street Pier
Rock Hall, MD 21661

Captain Mark Einstein turns the Chesapeake Bay into a chunk of the Caribbean. From the moment you cast off from Rock Hall, Maryland on the fabled eastern shore of the bay, reggae music is in the air, margaritas are poured, sails are set and “Crab Imperial” is cruising past the jetty into open water. The Captain and First Mate Suzanne carry only six passengers, so there’s plenty of room to pick a prime location on deck or take the helm and get the feel on motion under sail. Sunset cruises are spectacular and echo to the roar of the Crab Imperial’s cannon. Yes — there is a fine brass cannon aboard, just in case those Pirates of the Chesapeake get a bit too close! Hour-and-a-half cruises are $30 a head.

(credit: Jay Lloyd)

(credit: Jay Lloyd)


Baltimore, MD 21202

Baltimore, the magnetic Inner Harbor and historic Fort McHenry are joined at the hip with American nautical history and adventure, and a true Baltimore getaway should include time on the water. One option is the Spirit of Baltimore, a compact cruise ship that cruises the Inner Harbor and the Patapsco River serving up well prepared buffets washed down by a favorite tipple. If you’re familiar with the Spirit of Philadelphia, you’ll be ready for a relaxing voyage from an iconic harbor. Cruises cost $18 to $45. There’s a fleet of three boats including “Seadog,” which offers the thrill of “go-fast” action.

One very reasonable way of getting around the Baltimore waterfront and touring from Inner Harbor to Fort McHenry is by water taxi. It makes all the key stops, while offering riders great views of Baltimore’s skyline and major attractions. An all-day ticket for unlimited rides is $10 for adults, $5 for children. Buy tickets on-line at or at Harborplace.

(credit: Jay Lloyd)

(credit: Jay Lloyd)


301 N. Talbot Street
St. Michaels, MD 21663

St. Michael’s is considered one of the most picturesque and pristine towns on the Chesapeake Bay. The Miles River and its web of creeks and streams provide some of the most secluded and sought after anchorages on the Eastern Shore. You can get an eye-filling view of the harbor and the magnificent waterfront estates and mansions from the decks of the cruising ferry “Patriot.” It sails from its slip near the Maritime Museum twice a day on weekdays and four times daily on weekends. Special evening cruises — alive with music, food and grog — are also on tap. Scan the schedule and fares at:

Bon voyage!

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