A 1981 Walter Simmons

Here’s another sweet Craigslist find: a 1981 Walter Simmons Design Vintage Classic wooden sailboat, in seemingly excellent condition. Built by Maine boatbuilder Walter Simmons, each of these classic Lincolnville Salmon Wherries require over 300 hours in construction. Made from cedar planks that have been copper riveted on bent white oak frames with mahogany trim, they’re lovely little boats, and this one is a fine example at an easy price.

This is a traditional sprit-sail sloop rig with dacron sail, bronze belaying pins, main sheet cleats, bronze oar locks, two rowing stations, (4) 9 ft oars, mahogany rudder, oak tiller, oak center board, and bronze anchor. The price includes her trailer. She’s been stored indoors and sailed in freshwater in Texas, Louisiana, and Arkansas.

Developed for the Atlantic Salmon fishery in the late 1700s or early 1800s, Lincolnville Wherries are ideally suited for working in surf and on and off the shore.

They were never moored, and like the boat in the photo (a 14 footer), their plank keels enabled to stand upright when beached, making launching and landing a whole lot easier, and protecting the planking from abrasion.

As far as we have been able to determine, we have built more of these wherries than any of the old-timers, and now we’re fast approaching that age group ourselves. We built our first one in 1973, and 40-odd wherries later, we can say without hesitation that the Lincolnville Wherry is one of the finest small craft afloat…not to mention one of the prettiest to be found anywhere

Our boats are centerboarders. The original boats used rock ballast, and the last of the Salmon fishermen in town allowed as how some ingenious souls used sheep as moveable ballast when they sailed over to the islands. Why? Sheep are afraid of the water, so when the boat heels under sail they climb to windward…just where ballast is wanted. We can’t verify that because there are no photos and no one left to ask, but you’ll have to agree that it makes a good yarn.

Duck Trap Woodworking

Listed for $6800 in Hutto Texas.

Rosewest Cape Cod

We’re in love. The new Cape Cod from Rosewest is a stunningly beautiful open cockpit 24 foot daysailer that hits all of the right notes for us. Evoking traditional European pilot cutters from the 19th century, with their long overhanging stern and bluff bow, we could stare at her lines all day long.

Classic in concept, but thoroughly modern in design and construction, one of her most striking features is the spacious cockpit, able to seat 8 people comfortably. Sporting an elegant, u-shaped bench, there is still plenty of room for captain and first mate to attend to the sailing, while guests can relax in leisure. A smart little cocktail table is designed to be easily deployed for entertaining said guests. This boat is designed for all types of fun.

Other nice features include an easily deployed swim ladder, a freshwater deck shower, and even a little cozy cabin hidden under a large deck hatch for nap time.

The Cape Cod is an extremely versatile boat, with a long centerboard and deep kick-up rudder, allowing her to be brought right up to shore. She has an easily handled blade jib (self-tacking version optional) and a retractable bowsprit that accommodates light air sails.

All in all, this Cape Cod is one of our favorite daysailers to come out in quite a while. Starting at around $100K.

Robert Perry 36′ Custom Daysailer

Daysailers don’t often come to mind when thinking of Robert Perry designs. Known worldwide for essentially inventing the performance cruiser, this daysailer – the Boomer – benefits from his vast knowledge of hull form and sailing ease. Designed to be sailed FAST either singlehanded or with small crew, she’s in ready to race condition.

Built in 2007, this boat is composite construction with carbon mast and boom. She has a built-in bowsprit to fly the asymmetrical spinnaker with a top down furler included. She comes with a full array of Raymarine ST60 instrumentation and autopilot.

Built for speed but accommodating of crew comfort, she comes with a chemical head and refrigeration. Her cockpit is generous and comfortable, with twin helms and plenty of room for crew on race day.

She is listed in Seattle for $99,500.

1947 Rhodes Daysailer

Douce Amie, this lovely little Rhodes daysailer, was originally built in 1947, number 524, at the Brigham Shipyard in Greenport Long Island. Most of Douce Amie’s life was spent sailing the shores of Connecticut and New York, only recently did the boat find it’s way to Maine. She received an extensive restoration at Old Lyme Marina during the winter of 1999/2000. Restoration included repowering with a reconditioned Yanmar 1gm 10, new fuel tank, batteries and electrical. Onboard electronics include an Icom VHF, Garmin small chart plotter, and she comes with a road ready Triad trailer.

Her sails were new in 2000 and include a mainsail, large and smaller jib set on a fractional rig. She has a Harken roller furler making her sails very simple to set and furl.

She has been most recently owned by a talented woodworker who has kept the boat up nicely and in ready to sail condition.

The boat is offered with a road ready Triad trailer. In Maine, listed for $27K.

Hazel – An ultra-elegant daysailer from G&B

We had to admit to ourselves recently that the primary reason we find ourselves visiting the Gannon and Benjamin website so frequently isn’t just to gaze upon their beautiful hand-built boats, but it’s to pretend for a moment that we actually ARE Gannon and Benjamin. The photos of their shop on Martha’s Vineyard, and the days they spend laboring over their craft are as appealing as their final products.

We present Hazel as evidence. The Hazel 18 is a plank-on-frame daysailer originally designed by Nat Benjamin and hand-built at the G&B shop. She is designed and built for simplicity of use – easy to rig, easy to sail, easy to love.



Her sheerstakes, broadstrakes, and garboards are of wana, a South American species that is extraordinarily dense, providing extra strength. They offer this model in both a marconi and gaff-rigged sail plan.

We hope to visit their boat yard sometime soon for a closer look at what they do. But for now, we love their vision:

“Getting all the details right, not cutting corners, and using the best materials are what build longevity into a boat,” says Ross. But Nat and Ross want it clearly understood that they do not consider their business an “artistic endeavor,” if this means turning out little gems of boats that no one can afford. If every wooden boat has to be an expensive boat, there wouldn’t be many of them around. We take pride in getting all of our work done in a reasonable period of time and at a good price.”

See Hazel and many other lovely little boats at Gannon and Benjamin. 



A stunning Herreshoff Watch Hill 15

Jeanne is a replica of a 1922 Herreshoff Watch Hill 15, built by Artisan Boatworks in 2011. Her construction is wood and epoxy composite planking over steam bent frames with a laminated backbone. She features a 2 KW electric pod drive with folding propeller and is described as in “as new” condition.

The seller describes the boat as a thrilling sailor – fast, stiff and responsive, with a “slippery” hull that leaves no wake at hull speed. She just looks beautiful underway, that’s for sure.


The original Watch Hill’s were designed by Nathanael Herreshoff in 1922 and are a Marconi-rigged version of the legendary Buzzards Bay 15 class, designed in 1899. There were 3 variations of the “15-Footer” built, and all were keel-centerboard sloops with cedar planking on bent oak frames. The original design, the Buzzards Bay 15, has a 15 foot waterline, 24’6” LOA, a 2’3” draft with the board up, and a gaff rig. The second design, the Newport 15 only varies in its draft, which is 6” deeper. And in 1923, 11 Watch Hill 15’s were delivered to the Watch Hill Yacht Club. These boats drew 2’3”, and had a few minor modifications to the trim and freeboard, with a pointed coaming and slightly higher sheer aft.



Jeanne looks absolutely perfect in her color ways and is elegant in her simplicity. She comes equipped with a 2011 galvanized Triad trailer and sail covers. Located in Westport, CT.

Find Jeanne here on Yachtworld.


A Hinckley-maintained M29

Designed by Sparkman & Stephens, the Morris M29 is one of the relatively contemporary daysailers that aim to capture the golden era of sailboat beauty in a fully-modern form. This particular sweetpea, Sprint, has been gracing the waters of Newport, RI since her owner built her in 2010. Used only seasonally, and maintained by Hinckley Yachts, she’s clearly been kept in excellent condition.

The M29 with tiller steering is designed to be crewed by a single person or raced by a crew of 2 or 3. Sail handling has been engineered for simplicity, reliability and ease of use. All control lines, sheets, and halyards have been led either below deck or along the cabin top within easy reach of the helmsman, keeping the side decks clear and safe.



One compelling feature is actually one that’s missing – no winches! Sheet loads are reduced naturally by “clever engineering”, leaving the cockpit clutter free. Features such as the flush-mounted jib furler create a clean, efficient sail plan to optimize speed and performance while accentuating the M29’s natural beauty.

Weight management was apparently a top design priority, as is evident by the 100% resin infusion construction, carbon mast and rudder. Not to be confused with the floating condo type, the elegant yet spare accommodations below keep things simple and to the point – this boat is for sailing.

Sprint appears to be perfectly maintained and comes equipped with Raymarine instruments for depth, speed and wind, and Raymarine radio and compass.


The M29 is a delicious combination of classic lines and modern engineering, and Swift appears to be an ideal example. In Newport, RI at an asking price of $150k, visit the Hinckley website for details.

A Typhoon Senior in NC

Here’s a lovely example of one of our very favorite little daysailers, the Cape Dory Typhoon Senior. The Typhoon Senior, is, you guessed it, the larger sibling to the classic Typhoon and was built between 1984 and 1987, with a total run of only 57. Like the Typhoon, The Senior was designed by the legendary Carl Alberg. Like many of the Cape Dory’s Alberg designed, the 22 foot Typhoon Senior has a full-keel and is known for being ruggedly built and easy to sail in heavy weather, with a ballast of 1,700 pounds.



Like other Cape Dory’s, she features just the right amount of teak – enough to make you swoon but not enough to kill you when it’s maintenance time – and bronze fittings throughout.

One of our favorite things about the Senior is the built-in motor well that keeps the outboard (none included with the sail of this boat) out of eyesight but within a natural and easy reach to the pilot at the helm.

This example comes with two sets of North Sails, one new. Full interior and cockpit cushions, depth sounder and compass, and a dual battery set up.



Owner claims her to be in excellent condition, with a smooth and blister-free bottom and from the few photos provided she certainly seems like she’s ready to go.

Located in Southport, North Carolina at 11K.

See more at the lively and very helpful Cape Dory owners site.