My first encounter with this elegant little (ex-catboat) sloop came as a phone call from Frank O’Brien whose sister, Marjorie, has owned GYPSY for over half the boat’s century-plus life. The O’Briens asked if I’d look over her design—and, via photos, the boat herself—to help them evaluate her historical significance. “Sure, I’d be glad to,” I answered, so they then sent copies of the drawings and specifications that were used back in the winter of 1900-01 to build her, and a handful of contemporary photographs. After studying these documents I became totally enamored of this simple but sensible craft.

Her design is from the board of B.B. Crowninshield (1867-1948), a prolific and technically trained naval archi-tect with an unusually good eye. The variety of designs he turned out boggles the mind and includes the 1901 AMERICA’s Cup candidate INDEPENDENCE; the seven-masted schooner THOMAS V. LAWSON a year later; the 210′, 1,348-ton wooden cargo schooner HESPER of 1917 that, along with her near sister LUTHER LITTLE, dominated the Wiscasset, Maine, waterfront for 50 years; several Gloucester fishing schooners; and a great many smaller wooden yachts such as the well-known and much-loved Dark Harbor 17 Y2-footers. It’s high time for a major article or even a book about B.B. Crowninshield and his designs.

Although GYPSY is one of the smallest Crowninshield designs, she received the office’s standard treatment, resulting in more than the usual share of technical attention -with eight pages of written specifications, a set of detailed drawings with offsets, and a page of particulars that lists esoteric performance-predicting ratios, such as sail-area-to-wetted-surface, displacement-to-LWL, and the boat’s rating under the then-in-vogue Seawanhaka Rule. (This “length-and-sail-area” rule favored a short waterline, long ends, and a scow-like hull shape.)

Four boats were built to design No. 149, all of them launched in 1901 from A.C. Howland’s shop in Monument Beach on Cape Cod, which later, under the Reuben Bigelow name, built the famous racing schooner NINA. Of the four little caboats, only GYPSY-thought to have been WITCH originally—remains. 

There’s a lot to like about the design, but most of all I admire this boat’s simplicity and good looks. At 22′, she’s a craft that could be set up and planked in a garage-turned-workshop. The 2 1/2″ oak keel timber, about 21′ in length and 9″ wide at its widest point amidships, would be the most difficult timber to obtain. It’s a fairly sophisticated piece to shape and install as well, but not beyond what an average woodworker could turn out. As I understand the drawings, the keel is to be gradually tapered in thickness as well as width toward the bow and stern. There’s a hook scarf forward where the stem attaches, eight notches amidships each side for the frame ends in way of the centerboard trunk, and an abrupt step down to 2 ” in thickness where the skeg begins. Although the bend in this sprung keel timber is an easy one, the spec-ifications call for steaming to make the piece more lim-ber when pushed down over the molds. (This hull would doubtless be set up upside down and turned upright after planking.)

As to her looks and layout, a level platform makes it easy to move around in the cockpit and extends under the foredeck for out-of-the-bilgewater storage. The mahogany horseshoe-shaped seats harmonize with the oval coaming which, in turn, complements the boat overall. A balanced, non-fouling rudder (shown on the drawing, but now missing from GYPSY), protected by the skeg, won’t foul lobstering gear, and a generous bilge area beneath the platform gives space for inside ballast (if you choose to carry it; GYPSY sails with none) and keeps your feet out of the bilgewater. There’s an outside-ballast option for builders and sailors who prefer it, and, unlike the plumb ends of the usual catboat, this one has generous overhangs for a racy look and for more speed and stability under sail. GYPSY, in fact, carries 40% of her overall length as overhangs that don’t touch the water until she heels!

If building new, I’d be inclined to use sheet plywood rather than pine for the deck, in which case the diago-nal straps and lodging knees could be dispensed with. (GYPSY herself now has such a deck along with several other repairs and modifications.) Either Dynel or canvas laid in epoxy would make a virtually bulletproof sheathing over the plywood. As for the rig, you could leave it as shown, or do what the O’Briens have done, which is to give her a longer mast (moved aft so it’s just ahead of the coaming) and turn her into a marconi sloop with a shorter boom and permanent backstay. They also have added a short bowsprit and from the end of it carry a roller-furling, masthead jib so she’ll fly along in light weather carrying about 10% more sail than the gaff rig’s 311 sq. ft. For bigger winds, they use a smaller, boomed and self-tending headsail (set farther aft near the stem-head) that runs about three-quarters of the way up the mast and cuts the total area to somewhat less than the full gaff-headed sail. With this small jib and a reef in the main, the boat is set up for comfort and safety in the notorious afternoon sou’westers of Buzzards Bay, where GYPSY sails.

And sail she does! Despite the age of the boat and her owners, who are both in their seventies, GYPSY still sees a lot of use. Frank admits she’s wet at times, but he swears by her ability. Because of her beam and hard bilges, he points out, she’s a boat that sails on her bottom, not on her side, making her unusually comfortable. With over 50 years’ experience with this design in all kinds of conditions, his should be reliable testimony.

I expect we’ll see some new Crowninshield 149s show up on WoodenBoat’s Launchings pages before long. She’s too fine a boat to ignore; but if you build her, make sure you rout-in the sheer-enhancing cove shown on the sail plan, and carefully carve the scrolls that go with it.