The best of boating in the bay

creative director

II’m not from the Chesapeake. I come from the landlocked Midwest; Duluth was my “beach town”. But I was lucky enough to grow up in a lakeside cabin where I spent the summers driving speedboats, pulling water skiers and sailing in one-design races on a small lake in Iowa. I loved the playground by the lake as a child, but I dreamed of one day being on a large body of water – a place where boats did not slip away, avoiding accidents and collisions while zooming in a tight circle.

So the first time I walked the cobblestones of Annapolis, with a view of the Chesapeake Bay from the top of Main Street (“Were there really cities like this in the United States? !”), I was moved to settle there. My husband and I were in Annapolis to buy a boat, a sailboat, to live. It was a far-fetched idea, but as newlyweds we had little to lose, and no idea what we were about to learn. Did I know that our Panda 38 would have fifteen push-ups? Fifteen! Have I ever heard of a pulsation damper? Or a turbine? I thought setting sails, mooring and sailing was all you needed to know when living on a sailboat. I was totally wrong!

After 33 years of boat ownership on the Chesapeake, I have come to know many people like us who went into buying a boat without knowing much about boat mechanics. But our Chesapeake community comes to the rescue. There are few places in the world where boaters have all the resources at their fingertips to learn all aspects of powerboating and sailing. From boat rental clubs, where you can get your sea legs on before you embark on a purchase, to diesel mechanics, electricians, riggers and seamanship schools, our bay is teeming with nautical experiences. There’s no easier place to learn the ropes (or lines) of boating than the Chesapeake Bay.

From Hoopers Island photo credit: Kate Fritzinger

Nor is there a better place to explore and navigate. Our scenic bay is shallow yet gentle and forgiving. The many anchorages are protected, peaceful and generally have good anchorage. Waterfowl are abundant; the fishing is great. But that’s not all On the golden pond. Summer squalls can come with a fury, batter you and leave you with torn sails and missing dinghies. Small craft should heed NOAA weather warnings; it can be life or death. The Chesapeake Bay Class offers all boaters a comprehensive education.

However, owning a boat does not come without its own set of infuriating challenges. There will be mechanical and electrical issues that will make you curse the day you bought your boat. The cost of marine repairs is usually well outside your expected budget. DIY patches are in places where you can barely fit in, let alone turn a socket wrench. But after a few years of courage, you realize that your boating knowledge has increased exponentially. Every new trick you learn from your engine mechanic, your diver, your boat broker, has built a boating knowledge you never thought you would acquire. And moor your boat? Well, you have that as motor memory.

So do not hesitate to lock yourself in this dream of owning a boat. Be patient. Learn from all Chesapeake boaters who are knowledgeable and helpful; there are as many as there are beautiful coves and harbors to explore.

Hampton Harbor


Annapolis, Maryland and Hampton, Virginia.

Annapolis is known as the “Sailing Capital of America” ​​not only because of the year-round series of races for boats large and small, sponsored by several different yacht clubs, but also because it acts the capital of Maryland. Oh, so there are all the bars too. And of course, it’s the home of the original sailboat in the water show that has brought sailors from around the world to City Dock every October for over 50 years.

Hampton has plenty to offer sailors and boaters who cruise the southern Chesapeake Bay, from gracious yacht clubs to marinas and resort-like restaurants embracing Tidewater traditions. Summer is regatta season on the Hampton River, home to many sailing schools. Attractions include the Fort Monroe National Monument and Old Point Comfort Lighthouse to the Virginia Air and Space Science Center. Hampton has a multitude of boat ramps and kayak launches that provide access to its many beaches and natural areas where wildlife abounds.

Herrington Harbor South


Ports of Herrington North and South, Anne Arundel County, MD

These two family-friendly marinas on Herring Bay in southern Anne Arundel County deserve kudos on many levels, from their manicured grounds to country club amenities like pools, saunas, formal and informal dining options, without forgetting nearly 600 protected, deep swimming pools. water slides with direct access to the open Chesapeake Bay. The on-site Yacht Center is considered one of the most comprehensive boat repair and maintenance centers on the East Coast.

Riverwalk Landing Piers, Yorktown, Virginia.

The Riverwalk Landing Piers provide a dock for passing boaters close to all of the town’s many restaurants and shops, outdoor concerts and festivals. Concrete floating docks provide 1,200 linear feet of trash. A second pier located behind the Riverwalk restaurant provides additional mooring. Mooring balls are also available. Facilities include electricity, water and sewage disposal, plus a private shower and toilet. Readers appreciate the establishment’s “Clean Marina” status.



Leo Wardrup Memorial, Cape Charles, Virginia.

For nearly 20 years, the Leo Wardrup Memorial Cape Charles Cup has offered a weekend “a cruising event for serious racers and a racing event for serious cruisers”. Sponsored by the Broad Bay Sailing Association, the regatta is named for veteran sailor Leo Wardrup, who died in 2014. Rolling starts of various classes are launched in mid-August from Little Creek Marina in Norfolk and sail approximately 16 miles to across the Chesapeake Bay. at Cape Charles on the southern tip of Virginia’s east coast.


Triple Crown of Charity Sailing, Annapolis, Md.

The Triple Crown of Charity Sailing, sponsored by Weems and Plath, was established in 2018 to recognize the best sailor and fundraiser for the CRAB Cup, Leukemia Cup and Hospice Cup races. The skipper with the highest score in all three races and the highest fundraising wins a “Guardian’s Trophy”, while the permanent trophy is displayed at the Market House in downtown Annapolis. Proceeds benefit the Hospice of the Chesapeake, the Leukemia & Lymphoma Society and the Chesapeake Area Accessible Boating Program.

About Patricia Kilgore

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