Island Sailboats

Explore Island sailboats and the details behind each model. If you are shopping for a Island sailboat, we keep an eye out for Used Island Sailboats.

Model Listings Year Built LOA (ft) Beam (ft) Draft (ft) Disp. (lbs) Hull Designer Rig Keel
Island 327 for sale196031.5 ft10 ft6 ft11,000 lbsMonohullF. S. FordMasthead SloopCenterboard
Island 332 for sale196033.5 ft10.25 ft5.5 ft10,200 lbsMonohullRichard CarlsonMasthead SloopFin
Island 171 for sale197216.75 ft6.5 ft3.5 ft575 lbsMonohullJohann TanzerFractional SloopCenterboard
Island Sharpie 261 for sale198626.25 ft7.92 ft5.83 ft3,700 lbsMonohullBruce KirbyCat KetchCenterboard
Island Class1 for sale192928 ft7 ft4.5 ft7,060 lbsMonohullAlfred MylneFractional SloopLong
Island Sharpie 18198818 ft6.58 ft4 ft1,543 lbsMonohullBruce KirbyCat KetchCenterboard
Island 19198018.67 ft7.58 ft3.75 ft950 lbsMonohullFractional SloopWing
Island One-Design194720.5 ft7.33 ft0800 lbsScowOliver F. Seabrook/Henry SheelFractional SloopCenterboard
Island Sharpie 23198722.75 ft7 ft4.5 ft1,600 lbsMonohullBruce KirbyCat KetchCenterboard
Island 30200630 ft8.45 ft4.8 ft3,126 lbsMonohullRodger MartinCat KetchCenterboard
Island 23193134 ft7 ft4.5 ft5,500 lbsMonohullS. HerreshoffFractional SloopFin
Island OD191139.5 ft9.1 ft5.7 ft0Alfred MylneYawlCenterboard
Island 31192843.5 ft10.58 ft6 ft18,000 lbsMonohullSidney HerreshoffFractional SloopLong

Island sailboats: at least four unrelated lineages, one shared name

"Island" on a used-sailboat listing does not point to a single builder, and it is not the Island Packet or Island Trader lines sold elsewhere on this site. Boats carrying the name sort into at least four separate lineages: a kit-built plywood sharpie family from Connecticut, two Herreshoff-designed one-designs built for Fishers Island, a Long Island daysailer that changed hands from one builder to another, and a scattering of older catalog entries whose builders remain unconfirmed.

Origins and ownership

Bruce Kirby built the first Norwalk Islands Sharpie, a 26-footer, with his friend Tony Widmann for the 1986 sailing season; by 1987, its first year on the market, he had sold more than 200 sets of plans for the smaller NIS 23. Robert Ayliffe of Straydog Boatworks, in Mount Barker, Australia, became the design's Australian distributor that same year, and Kirby eventually handed Straydog the exclusive worldwide rights to sell NIS plans, kits, and accessories.

The Fishers Island Yacht Club formed in 1928, and its early fleet was built by yards including Herreshoff Manufacturing Co., Nevins, and Luders. Herreshoff built both of the Fishers Island one-designs credited here: a Fishers Island 23 example, yard number 1219, went to original owner W.S. Glazier in 1931, while a Fishers Island 31 was still being built as late as 1946.

On Long Island, Ocean Yachts of Patchogue -- a separate company from the shipyards behind this site's Ocean brand page -- built the Islands 17 daysailer from the late 1960s until 1979, when it sold its molds to Arthur Sumner and his son Jonathan, of Amityville. Sumner Boat Works, based at the end of South Bayview Avenue, kept building the same boats with few changes, now under Hart sails, alongside its own Sprite 8 and Mark 25.

The designers

Kirby arrived at the Norwalk Islands Sharpie already carrying design credits for the Laser dinghy, the Olympic Sonar class, and multiple Canadian America's Cup challengers; he named the new boats for the archipelago near his own Connecticut harbor, drawing the hull form from the Connecticut River's late-19th-century oyster sharpies.

Both Fishers Island one-designs were designed by A. Sydney Herreshoff. The club's own fleet history distinguishes the Fishers Island One Design from the Herreshoff 23-foot Class -- the Fishers Island 23 -- as two separate boats, alongside the Fishers Island Sound 31, the Luders 16, the Rhodes 27, the Bullseye, and the International One Design; they should not be treated as the same design under two names.

The Islands 17's design credit is less straightforward: a former Sumner Boat Works employee's restoration account describes it as basically a copy of the Tanzer 16, with a slanted transom giving it extra length -- built in the style of a Johann Tanzer design rather than as an original Tanzer commission.

Construction through the eras

Norwalk Islands Sharpies are simple, hard-chined boats built of marine-grade plywood sheathed in fiberglass and sealed inside and out with marine epoxy, carried on free-standing, tapered aluminum masts -- construction chosen to keep them easy to build, especially from a kit. Kirby's original 26-foot prototype carried 1,400 pounds of lead ballast, cast in bars two feet long, bolted and faired into the bottom; after sailing that prototype, he increased its sail area to 340 square feet. Per an October 2010 update from Straydog Boatworks, the Mk2 kits were being laser-cut in Australia, the UK, and New Zealand.

Lines and generations

The Norwalk Islands Sharpie family spans roughly 18 to 43 feet, including 23, 26, 29, 31, and 35-foot sizes alongside the smallest and largest. The Fishers Island one-designs come in two sizes, the 23 and the 31. The Ocean Yachts/Sumner Boat Works line ran smaller still: the Sprite 8, the Islands (later Sumner Islands) 12, 15, 17, and 19, and the Mark 25. Catalog records also list a handful of further one-off designs -- an 1911 "OD," possibly the Alfred Mylne-designed Belfast Lough Island Class, a 1947 "One-Design," possibly Henry Scheel's Sea Island One-Design, and further single entries from 1929, 1960, and 2006 -- unconfirmed leads rather than established history.

Who Island is for

A buyer after a self-built, trailerable plywood cruiser wants the Norwalk Islands Sharpie, in whatever size suits; one after a wood one-design classic with real racing pedigree wants the Fishers Island 23 or 31; and one after a small, simple fiberglass daysailer wants the Ocean Yachts/Sumner Boat Works line. All three deserve to be shopped as what they are, not as one "Island" brand.

Frequently asked questions

01Is Island a single sailboat manufacturer?+
No. Boats carrying the name sort into at least four unrelated lineages: the kit-built Norwalk Islands Sharpies designed by Bruce Kirby, two Herreshoff-designed one-designs built for Fishers Island, a Long Island daysailer that passed from Ocean Yachts to Sumner Boat Works, and a handful of older catalog entries with no confirmed link to any of the three. None of them is connected to the separately sold Island Packet or Island Trader brands.
02Who designed the Norwalk Islands Sharpies, and where does the name come from?+
Bruce Kirby (1929-2021), already known for the Laser dinghy, the Olympic Sonar class, and multiple Canadian America's Cup challenges, designed the Norwalk Islands Sharpie fleet after the Connecticut River's late-19th-century oyster sharpies. He named the boats for the archipelago near the Connecticut harbor where he lived.
03Was the Islands 17 designed by Johann Tanzer?+
No. A first-person restoration account of the boat describes it as basically a copy of the Tanzer 16, with a slanted transom that gave it added length -- built in the style of a Johann Tanzer design rather than as an original Tanzer commission.
04Are the Fishers Island One Design and the Herreshoff 23-foot Class the same boat?+
No, they were two distinct designs. A history of the Fishers Island Yacht Club, founded in 1928, lists the Fishers Island One Design and the Herreshoff 23-foot Class as separate boats in the same club fleet, alongside the Fishers Island Sound 31, the Luders 16, the Rhodes 27, the Bullseye, and the International One Design.
05Who built the Sumner Islands 12, 15, 17, and 19?+
Sumner Boat Works, run by Arthur and Jonathan Sumner out of Amityville, New York, on South Bayview Avenue. The Sumners bought the molds from Ocean Yachts of Patchogue around 1979 and continued building the same line with few changes, using Hart sails, alongside their own Sprite 8 and Mark 25.