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Tricky Waters: Eastern Shore of the Chesapeake

When I was 11, my Dad, his buddies and I sailed Wind Dancer, his C&C 37, from Long Island Sound to Chesapeake Bay. It was my second offshore passage.

Oh, the places you’ll go!”

When Dr. Seuss wrote these words, he must have had cruisers on his mind. Rare is the cruiser who doesn’t dream of sailing over the horizon, of exploring remote areas. Distance breeds confidence, confidence breeds a taste for adventure, and few vehicles are better equipped to deliver one into the heart of the unknown than a sailboat. 

In the United States and Canada alone, cruisers can find enough challenging cruising grounds to fill a lifetime—places where the scream of an eagle, the spout of an orca or the call of a lonely loon will be the soundtrack to your days afloat. These places aren’t for greenhorns; they beckon to experienced cruisers and demand preparation and judgment. And while they vary greatly in terms of latitude and remoteness, each of these destinations harbors rewards both subtle and extravagant for those bold enough to look for them. 

Read about Pacific Northwest: Vancouver Island

West Side of the Florida Keys

Mid-Atlantic Coast: Eastern Shore of the Chesapeake

When I was 11, my Dad, his buddies and I sailed Wind Dancer, his C&C 37, from Long Island Sound to Chesapeake Bay. It was my second offshore passage. My memories of Smith Island, located in Virginia on the eastern side of the lower Chesapeake, are still vivid. Here we visited a generations-old fishing community where an archaic English dialect was still actively spoken, and where time seemed to have stopped. Once you break in with the locals, we learned, you connect with some kind-hearted souls. 

Like all worthy cruising grounds, the Eastern Shore is not without its challenges. “The biggest problem is finding a safe anchorage,” says Ed Gatewood, a longtime Chesapeake cruiser. “Few creeks are navigable for vessels with [more] than three feet of draft, and some that are deep enough get shallow quickly—a sailboat can’t get far enough inside for protection from wind-driven waves in the prevailing southwesterly summer winds, which means being ready to pull up anchor in the middle of the night.” Still, Gatewood says he loves cruising there using his hook and suggests that Kiptopeke Beach (20 miles from Norfolk) offers reasonable holding and protection, thanks to the scuttled concrete McCloskey ships that were installed as a breakwater in 1948. 

The Chesapeake can be thought of as three distinct areas—the lower bay, the middle bay and the upper bay. The lower bay boasts deeper soundings and access to Norfolk, Hampton and Virginia Beach, but with the aforementioned tricky anchorages. The middle bay offers a myriad of protected harbors and attractions, including Solomons, St. Michaels and Oxford. In the upper bay, Gatewood recommends Wharton Creek, Still Pond and the Sassafras River for their safe harbors and freshwater swimming, while the views from Georgetown Yacht Basin on the Sassafras are excellent.

I have clear memories of monitoring Wind Dancer’s anchor, but a clearer memory involves watching my Dad navigate with Loran. This often necessitated posting a bowman to scan for oyster mounds and sandbars. My job was to monitor the depth sounder. While we stayed afloat, we saw other sailboats go aground. Fortunately, they de-augured themselves by using crew on the rail, coupled with some throttle work, a time-honored technique.

 According to Kirk Adams, another longtime Chesapeake cruiser, cell service is patchy throughout the eastern shore. WiFi is available at most marinas, but signals are weak, necessitating trips ashore. Adams reports that marina amenities, like showers, laundry, fuel and water, are usually excellent, but that most pump-out stations are inconveniently situated. Also, both Gatewood and Adams point to the importance of being fully provisioned, as many grocery stores on the eastern shores are a bit “lacking” in gastronomic options.

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