Cruising the Chesapeake: A Bay Sailor Returns Home

Cruising the Chesapeake was like icing on the cake.

My Uncle George kindled my love of sailing. George taught me to race on his Ericson 37 that he kept at the Maryland Yacht Club. My family often joined him for excursions on the Chesapeake Bay, visiting popular destinations such as Solomons Island, St. Michaels, and Crisfield.

My love for all things related to water began at an early age. I recall having to be dragged out kicking and screaming from the backyard pool. It was one of those above-ground pools, probably 20 feet across. Not large by any means, but I loved to spend my summers swimmingly. Learning to swim on summer trips to Ocean City, MD, at an early age also taught me to respect and love the ocean.

Sunset on Coxes Bay
Sunset on Coxes Bay.

A tribute sail to the man who introduced her to sailing on the Chesapeake.

Today, as I write this, I have returned to the Chesapeake to cruise these same spots on my boat, Sweet Escape, a Leopard 40 catamaran. I know that George would be proud that I have made my life about sailing, spending seven years thus far, as a full-time cruiser. It’s been nearly 50 years since I sailed or raced in the Bay, and it’s wonderful to be back exploring with my husband, Jann, on our boat.

Having spent the past two years sailing the Bahamas and Eastern Caribbean, it was time to head north, to Annapolis, for so many reasons. Number one: to cruise the Bay and visit those places that held a special place in my mind and in my heart. You could say it was a tribute sail, to my late Uncle George.

smiling group of people at Cascia Winery near the Chesapeake Bay
The author making friends at Cascia Winery in Stevensville, MD. 

We sailed all the way up to my hometown of Baltimore to see my cousins and take my cousin Lynn, a Bay racer, for a sail. She brought some of her racing crew along for the day. We had a blast. It was the first time that any of them had sailed on a cat. Jann gave anyone who wanted time on the helm. We didn’t have a lot of wind, but we raised all the sails and used what we got. It was the first time in almost two years that we had seven guests onboard for a sail.

I’ve come full circle. I can look back and see how these waters are indelibly etched into my psyche. Now that we’ve come to the end of our two-year plan, we will offer our boat up for sale. She is our last boat. She has been a wonderful home, taking us safely anywhere we decided to go. Cruising the Chesapeake was like icing on the cake and a perfect place to retire from the cruising life.

by Nancy Birnbaum