In 2014, I built a 17-foot “Northeaster Dory” from Chesapeake Light Craft. When I first started building the dory, the idea was just to have a simple daysailer to putz around my home waters in eastern Long Island Sound, within sight of the New York City skyline. While I was building it over the winter, the armchair sailor in me got inspired by a video of a young couple beach-cruising in Maine in their Northeaster Dory. (Search for “the Boatymoon” on YouTube to see this wonderful video). It brought back fond but vague memories of sailing in Maine with my grandfather as a kid in the 1970s. So after having sailed my dory for only a few weekend day outings, I and an unsuspecting and probably too-trusting buddy did our first cruise in Maine with it. The dory, a very lightweight, modernized version of the traditional Swampscott Dory, is great in relatively calm waters and it rows as well as it sails, with the added advantage that if you drop the mast you can have two people tandem rowing and knock off the miles at a good clip. We were out for 5 days and sailed and rowed (well, it was an incredibly windless week so we mostly rowed) about 65 nautical miles including a circumnavigation of Deer Isle with stops at Isle Au Haut and Swans Island.
However, dory cruising was by necessity beach cruising. You had to find a place to camp ashore each night, as the dory is neither stable enough or big enough for even one person to bivouac in afloat. We spent each night on a different island of the Maine Island Trail – one of the most incredible gems on Earth, and within a day’s drive of New York. Each night we had our own campsite (and usually a AW whole gorgeous island) to ourselves. It was wonderful, but you had to find a MITA site for each night.
After two 5-day cruises in Maine in 2014 and 2015, I was completely hooked on this sort of adventuring. But I decided I needed a boat that was a bit larger, more stable and seaworthy, and that would allow me and a friend to sleep aboard. That would open up a lot more cruising possibilities in Maine, and maybe even the opportunity for some weekend overnights on Long Island Sound, where beach cruising is impossible because just about every meter of shoreline is privately owned. I even entertained fantasies of dropping my anchor 50 yards off the private beach of some Greenwich hedge fund Gazillionaire and squatting on his waterfront view in my little poor man’s yacht with the boat tent pitched, expecting a squad of private security thugs to appear in a powerboat and tell me to move on or be arrested or worse… (Well, I digress, and I haven’t actually tried that last part yet.)
I toyed with the idea of building an Iain Oughtred Caledonia Yawl, and spent many winter evenings watching and re-watching every installment of Geoff Kerr’s fantastic “Building the Caledonia Yawl” video series on Off Center Harbor. A gorgeous, seaworthy and traditional boat. But one of my must-have requirements was the ability to singlehandedly haul my boat up onto the floating dock at my yacht club, since I didn’t want to deal with a boat on a mooring, and to be able to move the boat on a beach with just two people. The Caledonia Yawl and even its svelter cousin the Sooty Tern were just too big for that.
I saw a profile of Clint Chase’s Calendar Islands Yawl in WoodenBoat’s “Small Boats” magazine and was intrigued. He designed the boat to be optimized for open-boat camp-cruising along the rocky and crenellated coast of Maine, and named the design for the supposedly 365 islands in Casco Bay, Maine. It seemed the right combination of size, rig, build complexity, and camp-ability that I was looking for. After endless comparisons of specs of designs by Vivier, Oughtred, and others I decided the CIY was for me. In December of 2016 I called Clint and ordered up a kit.