We left Maryland Yacht Club in Pasadena, MD at 0900 on 6/19/2026 headed for Cuttyhunk, MA.
| Leg | Start | Destination | Distance, nm | Duration, hrs |
|---|---|---|---|---|
| 1 | Maryland Yacht Club, Pasadena, MD | Cuttyhunk, MA | 352 | 49 |
The weirdest part of this timing is that the original trip plan didn’t have us leaving until 6/20/2026. For whatever reason, I started telling the weather router that we were departing on 6/19/2026. I was confused with all of the personal calendar items that week and thought we were leaving on a Friday. I had what my kids would say is a “hardware glitch”.
Basically, we got to Cuttyhunk one day too early, and so we had to adjust almost the entire trip with reservations in Dockwa. That was a little embarrassing to be in the middle of the ocean with my wife realizing I had made a mistake like that. Fortunately, our weather routing (both from MWXC as well as PredictWind, Windy, and Grib files) showed a favorable weather forecast for the whole trip. We didn’t anticipate any squalls or challenging weather on the route we had planned.
We left MYC and headed straight up the Chesapeake Bay for the C&D Canal. As we slipped the lines, it wasn’t long before we were passing Whorton Creek, Still Pond, and Betterton. I noticed the current was favorable with our direction of travel. And that’s when it hit me that we were all messed up on our departure day and time. We knew that we would be going against current through the C&D Canal. We just kind of pushed forward, and I took pictures of my favorite sights that we see along that part of the Bay with some beautiful homes, green lawns, and a winery.
Through the C&D Canal, I was fascinated with the blue paint color of the bridge we went under. It just seemed more blue than I remembered. We also crossed paths with a tug and barge which was actually coming from Pennsylvania headed to my chemical plant in Curtis Bay. This was not possible in late January due to the snow and ice pack in the Canal.
Then we punched out into the Delaware Bay where the current was really strong pushing us down the Bay. The wind was also working in our favor and whipping up waves and spray as seen in this stationary light with dozens of birds on it.
We rounded Cape May, NJ and began a 2 night stint on a rhumb line to Cuttyhunk, MA. The wind was gentle and directly behind us almost the whole way across the ocean. Several miles away from shore, the water turned clear and deep blue. I put up a pole and tried to sail wing-on-wing, but that did not last long with the sails flapping.
We had no crab pots, fish traps or lobster traps the entire trip except in the middle of the ocean. We came within 100 ft of this marker but we were 25 nautical miles off shore in 200+ ft of water. This was definitely unexpected, and we couldn’t help think what would have happened if we hit this at night with little visibility.
We had a downwind trip the entire way once we exited the Delaware Bay with 4-6 ft swells behind and abeam which made the trip a little rolly. That didn’t matter, because we were having a decent time watching the sun and the water, and we felt very safe aboard Skyward. The picture on the left is a sunset and the picture on the right is a sunrise from the East.
We started our approach to Cuttyhunk which is an island first occupied in 1602 making it the first English settlement in New England. As we approached the island, the water turned a beautiful green color and the sun was bright in our eyes. We had to shout “Land Ho!” at the first sight of land, which fell mostly on deaf ears.
The entrance to Cuttyhunk was one of the narrowest we’ve ever navigated, but we followed a couple of other boats into the cut. After we realized the mistake of departure planning, and we began changing all of our reservations…I was excited to change the reservation at Cuttyhunk to be on the inside rather than the outside. And boy were we lucky to have been on the inside, because the wind was pretty stiff the next evening even on the inside.
When we got into the mooring field, we realized that we were among a couple dozen boats from the Betheny Yacht Clulb, which is where my friend is from on Astra – a Hallberg-Rassy 48.
We did the trip in 49 hours. That is because we motored way too fast at 2800-3000 rpm. Our mechanic said to run high RPM to try and troubleshoot our engine issues. The idea is that we would run higher RPM which the engine likes and which would blow out any remaining coke in the exhaust line. That caused us to burn 70 gallons of diesel when it should have only been 50 gallons. Because of the wind direction, the entire port side of the boat was coked up with soot, and we breathed that unburnt diesel air the whole way. This however helped us determine that the cause of our exhaust smoke is most likely due to incomplete combustion related to a blocked exhaust system. More on that in the future. The engine ran very reliably, and we had no worries.
We did have two incredible surprises on this trip, 1) We had limited or no fog the entire way up, and 2) we had no fishing vessels near us!