Delmarva Circumnavigation

Trip dates: 
Saturday, June 13, 2026 to Wednesday, June 17, 2026
Trip length: 
5 days
Type of watercraft: 
Sail
  • Sunrise on the Magothy
  • Sandy Point Shoal Light, the start of our adventure
  • A brief stop in Chesapeake City
  • in the C&D Canal
  • Posing with Michael in Delaware Bay
  • At the helm under the Bay Bridge
  • Nearing the finish

What started as a January email and a loose idea finally came together into the most significant sailing trip I've undertaken. A continuous circumnavigation of Delmarva, following the route of the Cape St. Claire YC "Great Ocean Race", on Eighth Deadly Sin, a well-loved J/35 and my twin brother Michael's primary racing ride. The trip was envisioned as a warm-up round for a possible Annapolis to Newport campaign next year. The boat has been undergoing improvements all spring to get ready for the trip, and we had to put some time in on day 1 to get her ready to go. After dinner and a little nap, we got underway at about 4:30am. We sailed south out of the Magothy to Sandy Point light, the official GOR starting point. From there, we enjoyed light to moderate reaching conditions up the Bay all morning as we sorted out shifts and got ready to run the boat continuously. 

We made the C&D canal at about 4pm, and with an evening full of nasty weather on the horizon we stopped at Scheafer's Canal House for dinner and to seek refuge for the storm. After a lovely meal on the veranda and a little sightseeing, the storm finally rolled in around 9pm. We battened down the hatches and tucked in for the night, with plans to get going after the weather cleared. Between the storms and significant adverse current, we finally got going early the next morning. We enjoyed moderately heavy air from the north for a deep reach out of the Delaware River, turning heavy by the time we made Delaware Bay. By late afternoon I was on shift, and steered the boat around Cape Henlopen and into the Atlantic. Unfortunately, I did get a little seasick from the heat and the rollers, but was fine again after a couple hours. We enjoyed a delicious sloppy joe dinner, and I laid down for a nap off shift.

A couple hours later, the up shift called us on deck to deal with a mainsail reef, which we later shook out. I did as a result get to see a great sunset off Ocean City. The graveyard shift was uneventful, and by the time I was up the next morning we were down to Chincoteague.

The following day was met with pleasant conditions for the rest of our 150mi ocean hop, and we made the entrance to the Bay around dinnertime. Another great meal, and our great sailing conditions continued into the evening as we took the sunset shift and enjoyed a wonderful red sky sailing through Hampton Roads. 

After our next rest, we were back up for the early morning shift up the Bay to Smith Point and into the mouth of the Potomac. The shift was largely uneventful, and I was definitely starting to feel the effects of several days of little sleep and continuous sailing. Shortly before sunrise, clouds built and we realized we would encounter a squall arond Point Lookout. We struck the jib and got ready to sail with the main alone, but as the storm intensified and threatened 60kt gusts we called some off-watch crew up to strike the main and motored south as fast as possible. We didn't outrun the storm, but thankfully it just ended up bringing torrential rain and no meaningful wind or lightning. We kept motoring north for a while as the storm took all our pressure.

My next shift began north of Cove Point, and ended up being the last of the trip. The breeze filled from behind, granting us a spectacular day of fast downwind sailing, easily making 8kts on average straight up the Bay. We sailed under the Bay Bridge in the late afternoon, and reached our official finish point at Baltimore Harbor light around 5:30pm. We rounded and beat back into the Magothy under heavy conditions, and realized we'd be back just in time for the MRSA Wednesday night race. We dug out the class flags and came screaming in just in time to cross the start with the other racers. We got a great start, and led the fleet to the first mark, before retiring and heading in.

The trip was overall a success, and was a great experience to check off my sailing bucket list, and learn a ton about offshore sailing and more extended passagemaking. Definitely one for the books!