Tuesday, September 22, 2026
Day two of bringing the boat back to the Great Lakes - Tolchester to Chesapeake City
Traveling on a sailboat with the mast down is a pain in the rear and nerve wracking! One is always worried about the mast moving then adding to that it makes walking around the deck quite challenging as we had all kinds of ratchet straps attached to chain plates and deck cleats all over the boat. Meaning there is a lot to trip over and bang your head on. It also means most our cleats were being used to hold the mast down vs being easily available to tie to a dock with. Not to mention the added joy of the boat now being 70ft long with the mast down and hanging 15 ft over the front of the boat and 5ft off the rear. Last time we did this we both said never again. But here we are because we were too cheap to have the mast shipped to our final destination. The scariest part of this trip was going to be the Atlantic leg from Cape May to the Hudson River. We figured that we needed a good 28hr weather window to accomplish that leg. The reality is we expected the journey to be around 18hrs but I like to plan a buffer into our sail plans should something unexpected happen. It appeared we were going to get that desired magic weather window in about three days. So after a few long days of getting the boy dropped off at college, getting the boat provisioned and ready, then a long day on the water heading north in the Chesapeake we decided a short leg was in order and traveled about 20NM from Tolchester, MD to Chesapeake City, MD located in the C&D canal.This turned out to be a great stop. We arrived around 11am, we were the first boat to drop the anchor beating the weekend traffic and were able to head into town just in time for lunch. We were able to visit one of the two museums, walk around the shops a bit, found some ice cream then settled at a B&B with an outdoor bar and live music for a while. We had great weather and it made for a really relaxing day.
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