As our time in Annapolis started to run down, we started looking for a good weather window to cross over the Chesapeake to Cambridge, MD where Kim and Jeff’s boat, S/V Pegu Club, was anxiously waiting for them to come get her. The chosen day started out pretty nice as we motored out of the harbor, waving goodbye to Dave (wherever he was…🤣), and looking forward to a great sail to Cambridge.

We were moving along with just the headsail out so I thought it would be a good idea to pull up the mainsail to help us go faster. In order to do this properly, we would need to roll up the headsail, turn into the wind, pull up the mainsail, get it set, then turn back downwind to unfurl the headsail and keep on truckin’. So you know where this is going, right?
As I started to roll up the headsail, it got about halfway rolled and just stop….what the *”#$? Seems like we had this thing called an override on the furling drum. An override is when the line used to perform certain tasks in sail handling (like furling a sail or winching in a sail) travels over itself and becomes basically trapped. Most times, you can transfer the load on the line by tying another line ahead of where the issue is so you are able to work the line as it’s free of any pressure.
Anyways, the headsail is way up at the bow and there’s not a lot of room to work on things up there. We tried for about 15 minutes to free the line but then decided that we needed to go back to port, wave to Dave some more, and fix it out of the wind. As we motored back, I went forward to try and tie up the sail cos it was going to flog itself to death if I didn’t. After I got the sail under control, I laid down on the deck and started working the line on the drum. I guess it was my lucky day cos after a couple of minutes, the line just decided it wanted to free itself. Go figure…🤷.
Smiles came out as we furled the headsail in completely, got the mainsail set, turned back downwind, unfurled the headsail, and continued on our way. See, there’s always something to keep you busy on a sailboat!!

The day progressed under sail as we made our way south and east to the other side of the bay. As we approached the turn to head up the Choptank River, the winds starting to die off and we had to eventually turn the motor on. We motored up the river to the Cambridge Yacht Basin to spend a few days fixing the boat and letting Kim and Jeff get Pegu Club ready to go. I was seriously looking forward to real showers, bathrooms, laundry, supermarkets, and a surface under my feet that didn’t move around all the time!! The only thing that had me a bit anxious was this was also the place where, when we departed, I would be….ALONE!!
Cambridge Yacht Basin, as well as the city of Cambridge, turned out to be very nice places indeed. We spent the few days we were there working on the boats, provisioning, and walking in town. My biggest memory of our time there was that I found the BEST burger I have ever had in my entire existence on this planet!! Yes, it was that good!! If you’re ever in Cambridge MD or just want a great road trip, go to RaR Brewing 504 Poplar St Cambridge MD and get one of their “Chessie Burgers”. I’m definitely stopping there on the trip back north in the Spring!!


The day came for us to keep moving south so early in the morning I backed Infinity out of the slip and headed to the fuel dock to pump out. I chatted with the manager of the CYB as I waited for Pegu Club to cast off her dock lines and then we were on our way. The goal for the day was to get south to an anchorage to ride out a blow that was coming in a few days. This blow turned out to be Tropical Storm Ophelia and it would be my first major weather event of the trip.
Up next… Tropical Storms, Washington DC, and getting wet in Norfolk!!
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