Life caught up to us in the last part of the year with so many unexpected turns. Matt had a life-impacting injury in September which he fully recovered from. He left for his 2-year mission to Peru just after Christmas. I ended up going on a passage down to Antigua on another boat, and helping to move 2 other friend’s boats. We hauled out Skyward for the Winter. Below are the notable sailing and boat-related experiences for the end of 2023.
Sailing with Family in September and Storm Ophelia
We had a really nice sail with family in September. Nothing out of the ordinary for us, but we appreciated having some wind and time to do this. Storm Ophelia was a very interesting time for me as I was at the marina every day adjusting dock lines. We had some days with tide over the fixed docks. I doubled up several of the lines for added security.
Transporting Tiger Lily a HR46
I was really excited to meet Bob from Tiger Lily finally face to face. We have Instagram’d and emailed back and forth for quite some time about our boats. He invited me to transport Tiger Lily down to Herrington Harbour North for the Winter there. Bob picked me up in his dinghy at Tucker Street Boat Ramp, and we quickly raised the anchor in Weems Creek and headed out for what would be a fun and fast day down to Deale. Bob is very skilled and experienced with his boat, and it shows by how he handles the helm, trims the sails and sets up systems like dock lines. I hope someday I can be that confident in Skyward; I suippose it is a matter of perspective. Going on someone else’s boat and watching them sail is one of the best learning experiences. Bob and Linda will be back in Annapolis and ready for a crossing in the next year or so.
We made a short stop at Herrington Harbour South to top off the diesel tanks. Bob docked the boat like a pro. Coming into HHS, we had some good wind the whole way down. Tiger Lily is almost the opposite of Skyward with electric winches, furlers, and mainsail furler. The speed at which we were able to get Tiger Lily sailing left me speechless, and Bob’s ability to trim the sails with minimal physical input had me thinking about ways to install motors under our winches. We ran into Borealis an HR37 as we entered the HHN area.
Boat Show with Friends
We got the opportunity to meet up with Herco and Elvira from Morgane of Sark. We have been following them on Instagram for a while since they also have a lovely HR46. They would end up Wintering the boat on the hard at Bert Jabins. We decided to make a quick visit to the boat show with them and also give them a tour of Skyward. This was just in time as Rachel had completed most of our new portlight curtains. The HR57 stole my heart, and so we took a lot of pictures of this beauty. You had to be there to see it, but the dinghy dock was so full that people could hardly locate and move their dinghies.
Thanksgiving Day Sail
One of the highlights of the season and year was being able to sail with family on Thanksgiving Day. The winds were low and sea state was calm. We were able to enjoy the afternoon on the Bay after we had an early “dinner”. This turned out to be Skyward’s last sail of the season.




Salty Dawg Rally to Antigua
I’ve posted extensively on this trip. I am planning to head back to Nikitoo to sail from Sint Maarten to Bermuda in May 2024.
Transporting “Aurora” a Morris 36
My good friend, Doug, purchased this nice late 90’s Morris 36 named “Aurora” this Summer in Maine. He moved it down the East Coast during the same week as Storm Ophelia, coincidentally, and he got held up in Atlantic Highlands. He has the boat on Back Creek at Allsop Marina, and he asked if I would help him move it to Oxford for the Winter. We left on a relatively chilly morning and fought a lightening wind situation all day long; amazingly, we sailed almost all the way down the Chesapeake to the Black Walnut Point entering the Choptank River. He let me helm the boat for the first several hours until we hit the Choptank, and I threaded the needle maintaining a broadreach while making our desired bearing.
Winterizing and Haulout
We notified Bert Jabins our intent to haul out for the Winter a bit too late. By September they had already sold out all shore storage spots for sailboats our size (50 ft). They suggested that if we call them in mid-December, they may be able to squeeze us in but that would mean we would have to agree to go back in the water in March. This didn’t seem like a solid plan, so we came to the conclusion that we would stay in the water at the dock all Winter.
We winterized all of the systems through end of November and into December. This all went very smooth as this is now our 3rd time following the process. “Winterizing” the topsides took the majority of our time compared to Winterizing the engineered systems. It just takes a lot of time to drop sails, remove canvas, and take down bits and bobs. I have a written procedure and checklist so that we don’t forget things. We left the engine operable so that we could sail and/or move the boat.
Looking at some long-term Winter weather forecasts got us nervous, so we made the call. The marina was able to haul us out just before Christmas and their annual shutdown. Running up to the scheduled day (Monday, 12/18) we expected a very wet and windy day. We happened to be at the marina on Saturday (12/16), and we unexpectedly ran into Rod. We asked him about our haulout and moving the boat early. He suggested we move the boat THAT DAY and authorized a spot for us to park. The was welcome news to us, so we set to work and put the boat on the Travelift dock with Matt’s help.
Moving the boat on Saturday gave the marina the flexibility to haul us out at their convenience that upcoming week. I was at work watching the Google Earthcam of the marina, and noticed that they started moving the boat. Rachel happened to be at the marina and caught it all on camera while I sat in my office an hour away watching.
The winds were gusting between 20-30 knots that day blowing us off the dock. Rachel said they had 8-10 guys pulling the boat into the Travelift slip. We were again very pleased with the service and team at the marina. Rod is personally involved in the operations side of his business which is a leadership style which we appreciate.
Install the Winter cover
We purchased the North Shore Canvas Winter cover this year. What attracted us is a reference from friends and the company’s responsiveness. They came out and thoroughly measured the boat in November. They shipped the cover to us by mid-December, and we installed it right after we hauled out. We came bck and made a few adjustments and added stand-off blocks for our tie downs. The cover goes down to the toerails and wraps around which you can see in the pictures. It is made with Top Gun which is an acrylic-coated material.
Happy New Year!






















































