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My Chesapeake Story: Doug Oeller

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My Chesapeake Story

My Chesapeake Story: Doug Oeller

June 22, 2026 | #MyChesapeakeStory

CBMM members become a part of the Chesapeake story and join our mission. We hope that you visit often throughout the year, explore all that we have to offer across our 18-acre waterfront campus, and discover how this special place is shaping the legacy of the Bay and its cultural heritage through exploration and preservation. Share your My Chesapeake Story with us by emailing havefun@cbmm.org and use #MyChesapeakeStory on Facebook, Instagram, and Threads to share what CBMM and our mission mean to you as well as photos of those special moments on our campus.

Amid air horns, drifting bubbles, and the cheers of more than a dozen friends, Capt. Doug Oeller guided Tidings into a slip at the Chesapeake Bay Maritime Museum’s Members-Only Marina on a sun-splashed afternoon last month. 

For Oeller, the scene marked the end of an epic journey on his 19-foot sailboat, and CBMM was the perfect spot to reach the finish line of his circumnavigation of the lower 48 states and roughly 4,800 miles on the water. 

“I treasure this place,” Oeller said, shortly after stepping onto the dock. “I thought it would be a wonderful place to host a party for my friends. Here I am—happy and proud and tired.”

 

Oeller has been a CBMM member for more than 20 years and a faithful participant in October’s Mid-Atlantic Small Craft Festival just as long.  

The Germantown, Md., resident has used the Members-Only Marina as a favorite stop while cruising the Chesapeake Bay with family and friends, and more recently, he’s volunteered as a delivery captain with CBMM’s Charity Boat Donation Program. 

“I just think it’s a great, great resource for the community and for small boaters,” Oeller said. 

Upon reaching retirement after a career in veterinary medicine, Oeller was ready for adventure. He contemplated the Great Loop before setting his sights even higher. 

“I just came up with a Greater Loop,” Oeller said with a smile. 

Doug Oeller and his wife Meg pose in front of a map of his journey.

Doug Oeller and his wife Meg pose in front of a map of his journey in the Van Lennep Auditorium.

After years of planning, Oeller set sail into the Bay from Kent Island in May 2018 and headed north. Since then, he’s spent at least two to three months each year (except for an 18-month break during the COVID-19 pandemic) aboard Tidings, a 1998 Cornish Shrimper 19 Mark II.

From Maine, Oeller trailered the sailboat across the country with stops at Lake Champlain and all five Great Lakes. He traversed the West Coast, including a summer spent cruising the scenic San Juan Islands and visits to ports in Oregon and California, before driving to Texas. From there, he cruised the Gulf of Mexico, around Florida, and back up the East Coast.

The memorable moments included a near-disaster navigating the locks of the Brazos River in Texas and a postcard-perfect day off Florida’s coast, with dolphins flanking the boat as he sailed alongside his wife, Meg.

Along the way, he navigated the challenges of journeying in a small boat without the comforts of home. During one particularly sunbaked stretch, he steered with one hand and held a golf umbrella with the other, improvising relief from the relentless heat.  

“Hopefully, it shows that you don’t need a large cruising yacht to go out and have adventures,” Oeller said.

Last month, Doug Oeller (right) completed his circumnavigation of the lower 48 states at CBMM.

Last month, Doug Oeller (right) completed his circumnavigation of the lower 48 states aboard Tidings at CBMM.

Even while pursuing that adventure, Oeller remained connected to CBMM. Between legs of the voyage, he returned to volunteer with the Charity Boat Donation Program and reconnect with friends at the Mid-Atlantic Small Craft Festival for a weekend of messing about and swapping tales from the water. 

Many of the small-craft enthusiasts joined Oeller along the way. He planned for a largely solo journey, but he was delighted when one sailor after another volunteered to spend a week as his crewmate. 

“It’s been fun,” Oeller said. “With no distractions, you really get to know people. You get close pretty quick when you’re together like that 24 hours a day.” 

Those relationships were evident from the crowd gathered at CBMM’s docks to celebrate the completion of his journey with a party in the Van Lennep Auditorium. 

Starting out, Oeller kept an open mind about what he might find navigating so many new places and harbors. After sailing thousands of miles around the nation, he’s finished the extraordinary journey with an even greater appreciation for the Bay. 

“I really like this part of the Chesapeake Bay,” Oeller said. “I’ll be coming here as long as I’m able.”