We wanted to take my dad somewhere on the boat, and although it wasn’t Fathers Day, we wanted to celebrate having him around. We decided St. Michaels was a great location as we are familiar with it and we could get a discounted dock at the Chesapeake Maritime Museum.
We mostly motor-sailed into St. Michaels on Friday during the day. Nothing but a boring droning of the engine in the background. My son, Matt, wanted to go to get experience sailing because he wanted to get a job this summer at a sailing camp. We got to St. Michaels and tied up at the dock with great help from Josh the dockmaster.


We walked around the Museum then around town. We chose to eat at Foxy’s which was meh. I took some pictures of the boat from the other side of the inlet seeking the perfect shot.




We awoke the next morning to a loud creeking noise. Rachel thought we were grinding the rub rail up against the dock. I jumped out of bed and ran outside to see that the tide was very high, and the dock line was tied very low on the pole and it was stretching a bit too much. Rachel followed me shortly afterwards and paddle boarded around the inlet. I couldn’t help but watch at the sunrise.


After about an hour, everyone was on deck and with the paddleboard safely tied down, we slipped the lines hoping for some wind. We had virtually no wind through the entire transit out the Eastern Bay, so it was a leisurely motor sail back towards the Bay. My dad and I shared a seat on the cockpit gunwale and soaked in the sun and the sounds of the water breaking on the bow.
As soon as we got out into the Chesapeake Bay headed for Annapolis very slowly under sail, we discovered that the Annapolis to Newport Race was sailing right through our path. The start of the race just began and the boats were screaming towards us with their spinnakers flying. You can see from the YB Races app where the race boats were and where Skyward was.
I have only seen sailboat races on TV before, so this was a bit of an adventure. There were suddenly boats all around us with spinnakers and crews hanging out on the decks. We were in awe of the spectacle and we also had to control the boat. It was so exciting that we even got the kids out of the cabin and off their phones for a few minutes. To be fair, Matt was already on deck with us.
Admidst this excitement, I turned on Facebook Live for the first time and had a bit of fun with the family.
We tried tacking back and forth to find wind along the Western shore of Kent Island. There was nothing there, and we were making very little headway towards Annapolis. One of the boats which I cannot recall the name of was approaching us quickly with their yellow spinnaker flying, and we decided to slow and allow them to cross our bow. Unexpectedly, they stopped and took down their spinnaker which caused us to veer dangerously to shallows on the Western shore of Kent Island. We had to turn on the motor for a few seconds to tack and get out of there. Frustrating!
After watching the majority of the boats pass us on port, we got onto a starboard tack and rode it across the Bay. The wind kicked up from the Northeast and we hurredly cranked out the Genoa. Blowing 15-18 knots we achieved a maximum SOG of 8.04 knots.
That was thrilling to say the least. My dad had no idea how excited we were and how perfect those conditions were for what we were trying to accomplish. OK, maybe he had an idea, because I kept yelling it loudly from the aft deck as I trimmed the sails ever so slightly.
We didn’t quite get the main fully raised and the genoa couldn’t be trimmed better as the backstay adjuster wasn’t installed — so the forestay was at a dockside setting which is loose.
I can say that the rigging was tested very well on this trip. We ended up neck-and-neck with that Jeanneau; not too bad for a boat that is 2x heavier. Happy Fathers Day!











