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What's Up Magazine

Flotilla of Fun

Apr 14, 2014 10:27AM ● By Cate Reynolds
By Beth Rubin

For a reality check on the joys of boat ownership, just ask any captain. Uncooperative marine conditions (wind, tide, and current), extreme weather, and malfunctioning equipment conspire with alarming regularity to dampen many a boat owner’s best-laid plans.

I’d bet a six-pack that during my more than 30 years as a first mate, at least a quarter of the time when we set out for a day or longer, we were forced back prematurely. Sometimes, owing to a dead battery, ailing engine, leaky valve or hose, sick electronics, birds nesting in the boom, or an odor surpassing 10 dead skunks wafting from the bilge, we didn’t even leave the slip.

I’m just saying…if you’re without a boat, your vessel is out of commission, or if you want to try something different, you’re in luck. Living on the Eastern Shore—with water, water everywhere—you have access to multiple ways for exploring the shore’s waterways. If you’re of a certain age, you may recall from the 1950s when Greyhound advertised, “Leave the driving to us.” Well, here’s a chance to enjoy the Bay while leaving the driving to a professional captain.
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“There’s no better way to get a sense of place along the Chesapeake than with an on-the-water experience,” says Chesapeake Bay Maritime Museum Chief Curator Pete Lesher. “And fortunately, the Eastern Shore has an abundance of offerings for visitors and locals alike. Everything from experiencing the life of a Chesapeake waterman aboard a sailing skipjack, to paddling tours on kayaks can be found at various waterfront towns and villages along the Bay.” 

Public Sails

I never tire of a public sail, especially with family or out-of-town visitors in tow. Consider a cruise on the Nathan of Dorchester, celebrating its 20th birthday this July. Built by a dozen volunteers, the Nathan is representative of the 600–800 commercial wooden sailing vessels that dredged oysters from the bay between the mid-19th and mid-20th centuries. The 20-passenger skipjack operates most Saturdays from May through October, departing on two-hour sails from Long Wharf at the end of High Street in Cambridge. When conditions allow, an oyster dredging demonstration is included in the sail. If your time is limited, an hour-long sail runs one or more Sundays a month. The vessel is also available for private charters and special events. While all ages are welcome, kids under 12 must be accompanied by an adult. The cost for the 2-hour sail is $30 for adults, $10 kids 6-12, free for kids through five years. The hour-long sail is half-price. Advance reservations are available online up to midnight preceding the departure day. Otherwise, it’s first come, first served. For more information, go to:
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The schooner Sultana, based in Chestertown and launched in 2001, is a lovingly rendered replica of an 18th century topsail schooner (here, the smallest merchant vessel in the British Royal Navy, way back when Britannia ruled the waves). During 2-hour cruises from late April through early November, passengers are encouraged to hoist the sails, steer with the large wooden tiller, and go below to inspect the crew’s quarters. A highlight for many is firing the guns (“cannons” to landlubbers). Tis quite the spectacle! The price of the cruise is $30 for adults, $15 for kids 5-12. Children under the age of 5 are not permitted onboard. Tickets for weekend sails during the annual reenactment of the Chestertown Tea Party in late May are coveted. During Ecololgy Sails, participants can help pull a sampling net filled with the Bay’s bounty. Music Sails take place a few times a season. Along with education programs during the school year, Sultana offers summer programs for young adults 11 to 14. For more info: or call 410-778-5954.

Peaceful, picturesque Dogwood Harbor, on the Choptank River side of Knapps Narrows on quiet Tilghman Island, is home to the Rebecca T. Ruark. On the National Historic Register, she was built in 1886 and is the oldest working skipjack on the Bay. Captain Wade H. Murphy, Jr., a third-generation waterman and master storyteller, regales visitors with tales of the Bay and an oyster-dredging demo during 2-hour cruises departing up to several times daily depending on wind, waves, and weather. Find out more at; 410-829-3976.

The Chesapeake Bay Maritime Museum also offers many on-the-water programs at its 18-acre waterfront campus in St. Michaels. The Public Sailing programs on select Fridays and Saturdays in the summer months offer visitors the opportunity to get out on the water in one of CBMM’s wooden sailing or rowing skiffs. New this year, on Saturday, May 31st, during CBMM’s annual Maritime Model Expo, the Museum is hosting its first “Floating Fleet Day,” where, for a nominal fee, visitors can take a 30-minute guided boat ride aboard one of the museum’s fleet of historic Chesapeake Bay watercraft, including the 1934 Hooper Island Draketail Martha, the 1912 tug Delaware, and the 1909 crab dredger Old Point, among other smaller craft. The skipjack H.M. Krentz, also docked at CBMM, offers educational sailing tours from April to October, with advanced reservations required. From May to September, several kayak trips are offered, including guided tours of the scenic Miles River with the Midshore Riverkeeper Conservancy, as well as Sultana Projects. Visit or call 410-745-2916 for more information.

Image titlePaddle your own canoe (or kayak)

Opportunities abound for renting small watercraft on the Eastern Shore. Kayaking, in particular, is one of the most pleasurable and stress-free outdoor activities I know of. You’re not competing or being judged on your “form.” You don’t need special equipment (or designer duds). And you don’t need a certificate of expertise to experience the joy of being at one with the water and at eye level with local waterfowl. Here is a sampling of What’s Up’s favorites.

The Chesapeake Bay Environmental Center, the under-appreciated non-profit facility at 600 Discovery Lane in Grasonville, offers canoe and kayak rentals. Here, you can explore, within sight of the Bay Bridge, the area around Marshy Creek, Kent Narrows, and Prospect Bay. This is a prime location for viewing waterfowl and wading birds, the adjacent marsh and shoreline. Boat renters are required to pick up a waiver at the visitor center. The rental price is $15 per vessel per day. (Where else can you find a day’s entertainment for this pittance?) To avoid disappointment, make a reservation at 410-827-6694. The last boats go out at 3 p.m. Note: Paddlers are responsible for checking the local forecast ( Kayaks are not allowed out if heavy winds or thunderstorms are in the forecast. Pack a picnic and field glasses and spend additional time exploring the flora and fauna along the trails and from the observation platforms. For more info, go to or call 410-827-6694.

Three cheers for the St. Michaels Water Trail, a PDF brochure from Talbot County tourism that you can tap into online at Mapped out in living color are four water trails in and around St. Michaels, along with driving directions to launch sites, degree of difficulty for each, information on historic attractions and wildlife viewing along the way, and a list of outfitters in Chestertown, Sherwood, Easton, and Tilghman. Paddles average from two to four hours and are geared to novices and experts—and those of us who fall somewhere in between.
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Image titleOf course, a discussion of paddling Shore waters can’t be had without mention of our national wildlife refuges, both Blackwater and Eastern Neck. Located just 12 miles south of Cambridge, Blackwater National Wildlife Refuge is an ecological jewel with 27,000 acres of mixed habitat, including tidal marsh, ponds, and forest. Blackwater features three paddling trails along which, you might encounter bald eagles, tundra swans, geese, ducks, and a number of endangered species. Similarly, Eastern Neck Wildlife Refuge is a hotspot for migrating and wintering waterfowl. The 2,285-acre island, located south of Rock Hall where the Chester River meets the Bay, has a water trail that circumnavigates the island. A number of outfitters and guides are available near both locations; lists are available at and

“Getting out on the water is a great way to experience this unique region,” says Chesapeake Bay Maritime Museum Vice President of Communications Tracey Munson. We couldn’t agree more and with seemingly endless inlets, bays, rivers, and waterways throughout the Shore, your next adventure is just around the bend.