Skip to main content

Pocket Cruisers

Six midsize sailboats that offer the necessities –

and some comforts – for short-handed overnighting or weekending


Those of us who become emotionally involved in the recreational boating life usually start off small with a simple vessel and move up in size as our bodies and fortunes grow. Further along in years, however, many return from whence they came and downsize, as physical prowess diminishes and caution replaces daring on the open water.

Over the decades, after rowboats and paddling kayaks and canoes, I started in sailing with a 17-foot centerboarder and moved up to regularly sailing keelboats of 25, 28, 32 and 35 feet. But some 20 years ago I downsized early and bought an older 22-foot pocket cruiser, not because of my age but because I prefer pretty, smaller sailboats that are easier to handle alone and maintain myself.

At the time, this move wasn’t intended to extend my sailing career, but I think it has. Unlike many landlubbers, my preferred form of recreation hasn’t benched me as a couch-potato spectator. As a devoted boater, I am determined to keep active in my sport even if it means giving up something in a trade-off, such as substituting power for sail.

I refuse to become a ballpark groupie or take up golf. If I ever reach a point of no return in being unable to sail solo, I suppose I could always turn to wetting a line. Anchoring or trolling to conserve fuel (and my own energy) might provide even more years on the water, although sitting inactively and staring at it in hopes of shouting, “Fish on!” doesn’t appeal to me.

E.B. White in “The Sea and the Wind That Blows” (“Essays of E.B. White”) pondered the end of sailing as he grew older. “When does a man quit the sea?” he asked. “How dizzy, how bumbling must he be? Does he quit while he’s ahead, or wait till he makes some major mistake, like falling overboard or being flattened by an accidental jibe?”

Not a stretch

Short of disaster, could there be anything worse than being stranded at a dock of the bay, left behind to stew and fume in a folding lounge chair? Just observing the comings and goings of lovely boats from land — as opposed to steering them, enjoying their motion, and keeping them footing along — is too awful a fate to contemplate.

Meanwhile, this spring I focused on other things, such as improving cabin comfort, which never used to be a big priority but is now, especially in a pocket-cruising sailboat. British sailor J.D. (Des) Sleightholme notes in “Pocket Cruising: a New Approach” that the essentials of such a boat are “proper sitting headroom (when leaning back), light and air, dryness, and a carefully thought-out system of stowage. Ideally one might add: a place where one may stand upright to dress and stretch. This latter requirement becomes more and more essential as one grows older.”

I couldn’t agree more. My classic plastic Sailmaster 22 (designed by Sparkman & Stephens and built in Holland in 1962) has a wide double slide-over hatch that opens up more than half the cabin top, giving me said room to “stand upright to dress and stretch.” And I can even steer from there after extending and securing a tiller-mounted extension that reaches to the companionway.

Even yacht designer L. Francis Herreshoff, a grumpy old bachelor, considered a comfortable double berth a necessity. “Most small boats have berths that can’t be slept in unless you are either exhausted or partly drunk,” he wrote, “and few things spoil a happy ship as much as sleeping arrangements that prevent the relaxation of a sound sleep.”

But as I’ve continued to make lists and contrive ways to improve sitting headroom and sleeping arrangements on my boat, I wonder why I didn’t think about those things earlier. If I had it to do over again and was buying new, I’d look at pocket-cruising fiberglass keelboats that meet my requirements of traditional lines, easy single-handing, and already built-in cabin “comforts” (a word I use loosely).

Jack’s starter list

This short wish list of pocket cruisers I like includes sailboats from 24 to 28 feet, except for one gorgeous 30-foot daysailer that simply could not be left out. (The list doesn’t include a catboat, which I have never sailed, but should.) One other requirement was a base price of, say, no more than $70,000.

• The Bridges Point 24, a Joel White-

designed, Maine-built beauty, is near the top of this list. So many of my favorite pocket cruisers, overnighter/daysailers or weekenders seem to be built in Maine that I wonder if there has ever been an ugly Down East sailboat built.

What I like in a cozy cabin are facing settee berths with sitting headroom, a varnished table stowed in an upright position, and a very comfortable and open V-berth with no mast compression post.

And tiller steering, lifelines, lazyjacks, a one-line reefing system, roller-furling jib, and a deep cockpit with high coamings and maybe “ergonomically contoured” seating. I also prefer an outboard in a well, but I suppose I could live with a small inboard.

The late Joel White designed and had built for his own use the first BP24 with a small, curved Herreshoff-style cabin that formed a point at its forward end, and is practically an extension of the cockpit coamings. More than 70 have been built, almost all of which have a larger box cabin with two small windows on both sides and more elbow room below.

• Garry Hoyt’s Alerion Express 28, another beauty, was designed by the late Carl Schumacher and is built by TPI (Pearson Composites) of Portsmouth, R.I., using its patented SCRIMP system of resin infusion. There isn’t a person on another boat who won’t turn and look as this one slides by effortlessly, often with a lone elder at the tiller. Some 300 are sailing.

Usually Awlgripped in a traditional dark color, the Alerion Express has New England written all over it. The comfortable cockpit with high, angled, varnished coamings seats six, with a mainsheet dead-ending in the middle of the cockpit on a barney post. (I would prefer the mainsheet on a traveler behind the tiller.)

Down below, the cabin is fine for a compromising couple overnighting, weekending or even coastal cruising because of a wide, full settee berth to port and a V-berth forward. On both sides of a single seat to starboard is a sink and galley. I’d rather have that seat extended forward to make a double and use a bucket for a sink.

The Alerion 28 also has a patented, self-tending Hoyt jib boom that becomes a built-in whisker pole when sailing off the wind. The jib has roller furling, and the mainsail has lazyjacks and single-line reefing handled from the cockpit.

• The Great Harbor 26, designed by Bill Cook and built by Hank Hinckley (he has built four) in Maine, is trailerable with a lifting keel with a minimum draft of 2 feet, but is also available with a fixed feel. Traditional in looks and performance and with an inboard diesel, it has facing settee berths and an “enclosed” portable head in a V-berth cabin. The cabin layout is semicustom, and owners are “encouraged to actively participate in the boat’s final layout,” says Hinckley, who built hull No. 1 for himself.

Two main berths with lockers at the forward ends are standard. The sole is teak and holly, and the interior of the hull is lined with hardwood sheathing. A padded backrest insert board provides sitting headroom, and a portable cooler with teak top doubles as a companionway step.

• The Dark Harbor 20 designed by S&S is a skinny, full-keel, one-design racer with a beam of only 6 feet, 8 inches and an LOA of 30 feet with long overhangs. Says designer Robert Perry: “Show me the sailor who wouldn’t want this beauty sitting at his dock, and I’ll show you a sailor dead to the beauty of yacht design.”

This classic dates to a 1934 S&S design, and of the 21 that were built, all but one are sailing today. This first fiberglass DH20 was completed by Shaw Yacht of Thomaston, Maine.

In the literature there is nothing said of the cabin layout, but a drawing depicts what appears to be two facing benches that might be considered places to sit (or even sleep) in a pinch with thick foam bunk cushions. It meets almost none of my demands below deck, but I just couldn’t leave it out because it’s so lovely.

• Eastsail Yachts’ New Moon 25 Coastal Cruiser, designed by Eliot Spalding, is a traditional full-keel cruiser with a high, boxy cabin and pronounced sheer and transom-hung rudder. Eastsail also offers the Offshore 25, the same hull but with a cutter rig and a short bowsprit. Both boats claim standing headroom and have the same beam (8 feet, 6 inches) and draft (3 feet, 8 inches). But the offshore version has more room below and more sail area (400 square feet, compared with 355 square feet). An outboard is an option.

Yacht designer Robert Perry calls it a “true full-keel design where there is no distinction between the forefoot and the keel. It’s a vintage shape, [and] the sheer spring is pronounced, but I like it. … I would prefer a full-width V-berth with the head tucked under the aft end of it [rather than enclosed] … but a nice big berth can be a concern.”

According to product literature, “the owner specifies the rig, interior design, wood to be used, type of head, number of berths, water tankage, etc., depending upon the type of sailing planned.”

• The Landing School’s 26 Weekender falls more into the overnighter/daysailer category. Its lovely lines are by Ken Rusinek, a school instructor inspired by the lines of Nathanael Herreshoff’s original Alerion, with its short, rounded cabin house. It’s a cold-molded hull with a fin keel and powered by a small inboard diesel.

“Since the primary intent is daysailing,” states the literature, “the low-profile cabin can provide shelter or an overnight’s respite. A properly sized V-berth, a head, small galley, and two comfortable seats make the cabin comfortably cozy.”

The cockpit of the LS26 is 8 feet long with wide seats and high backrests, giving the feeling of sailing in, rather than on, a boat. Nineteen have been built, but the school now is focusing on building the Arundel 27 powerboat, although it may start up the LS26 again.

Just a start

That’s my starter list, which is by no means complete. Even with all my nit-picking demands and restrictions, forgive me for not including other pocket-cruising, keelboat gems out there, some of which are probably being built somewhere in Maine by mom-and-pop yards, even in wood. I’ll conclude with one more E.B. White respite, from the same essay, and return to his wise reflections on dealing with the challenge of continuing to sail small boats as he grew older:

“I liked to sail alone. The sea was the same as a girl to me — I did not want anyone else along. … I was always in trouble and always returned, seeking more trouble. Sailing became a compulsion: there lay the boat, swinging to her mooring, there blew the wind; I had no choice but to go.

“With me, I cannot not sail. Yet I know well enough that I have lost touch with the wind and, in fact, do not like the wind anymore. … There is a great question in my mind whether a man who is against wind should longer try to sail a boat. But this is an intellectual response — the old yearning is still in me, belonging to the past, to youth, and so I am torn between past and present, a common disease of later life.”

But White could not, at the time, bring himself to sell the boat and face not having it there waiting for him every summer day on his mooring in Maine.

“There will lie the sloop, there will blow the wind, once more I will get under way. And as I reach across to the red nun off the Torry Islands, dodging the trap buoys and toggles, the shags gathered on the ledge will note my passage. ‘There goes the old boy again,’ they will say. ‘One more rounding of his little Horn, one more conquest of his Roaring Forties.’

“And with the tiller in my hand, I’ll feel again the wind imparting life to a boat [and] will smell again the old menace, the one that imparts life to me.”

Put power in your pocket


The power pocket cruiser offers a fertile field for the independent designer. Necessarily small and simple, the vessel still presents design challenges, as it must be roomy, economical and seaworthy, says naval architect Karl Stambaugh. Ease of construction also is desirable, in case someone should want to build the little cruiser themselves. And, of course, it has to look good.

Stambaugh, 50, founder of Chesapeake Marine Design of Severna Park, Md., has balanced the power pocket cruiser elements nicely in his Redwing 26. It’s an outboard-powered boat for two, built of plywood and with a traditional look. “This is a boat designed to camp aboard, to explore the creeks and coves,” says Stambaugh. “And it’s an affordable, trailerable package.”

Stambaugh’s design for the 26-footer (8-foot, 6-inch beam) is an evolution of designer/author/historian Howard Chapelle’s drawings of an 18-foot camping skiff. And the Redwing 26 shares the profile, small trunk cabin and engine well of the older boat, as well as the flat bottom.

“The hull is based on a skiff or sharpie, with a touch of dory thrown in,” says Stambaugh. “It’s a slender form with a fine entry to break the chop.” The bottom is rockered fore and aft to ease its motion in choppy waters, but it’s essentially straight, side to side.

Stambaugh added more flare to the sides, like a dory’s, which increased interior space. And the naturally shoal draft of the sharpie shape is further enhanced by the use of an outboard. The flat bottom means you can nose the boat into shore or up to the beach — an important quality in a backwater pocket cruiser, he says.

The Spartan layout is more a blank canvas than something etched in stone. In other words, says Stambaugh, the amount of extras in the interior is up to the owner. He designed the layout with a V-berth forward, a portable head in an enclosed compartment just aft to port, and a minimal galley to starboard, with room for a two-burner stove, sink and refrigerator or icebox — all pretty traditional. The pilothouse dinette, with benches and a table between, can convert to a sleeping berth. Stambaugh also found room for a true interior helm station with wheel, dash and chart table — vital in a pocket cruiser.

“To me, the minimum layout means standing headroom in the pilothouse, the comfort of a V-berth, the convenience of a small galley, and an enclosed head,” says Stambaugh. “Beyond that, it becomes up to the owner.” There’s no shower in the Redwing 26, for instance, but one could be included, he says. The electrical system is meant to run lights and nav gear only, but there’s room for additional battery boxes and an inverter.

The Redwing 26 is economical when it comes to performance. Stambaugh says the ideal power plant is a 30-hp 4-stroke outboard, which gives the boat a consistent, trawler-like cruising performance. With the engine placed in a sound-proofed engine box aft, the Redwing 26 should be a silent runner.

“I put it there not only for quiet, but to move some of the weight forward for better balance,” says Stambaugh. “The stern has plenty of buoyancy, so it can take [the engine weight].”

There’s also an inboard version of the Redwing, with the engine box placed amidships and the prop projecting through a protective skeg. Cruising speed for both versions would be 7 to 9 mph.

The boat’s traditional look — part sharpie, part Chesapeake Bay deadrise, part dory, says the designer — belies its basic plywood construction. The Redwing 26 has a nice sheer, a doughty plumb stem, and a cambered pilothouse roof — proof that a plywood boat doesn’t have to be boxy. “The aesthetics,” Stambaugh says, “are in the design.”

The Redwing 26 can be built using plywood-on-frame or the stitch-and-glue method. The hull, deck, superstructure are all of 1/2-inch sheet plywood, and Stambaugh estimates it would cost about $12,000 to build the basic version.

The pocket cruiser is the culmination of a design series (18, 21, 23 and eventually the Redwing 26) that Stambaugh began more than a decade ago, after seeing Chapelle’s camping skiff. Stambaugh admits the boat — and the concept — isn’t for everyone. “You have to be content to go slow,” he says, “to take the time to see where you’re going, to enjoy a leisurely pace. Also, it’s not an offshore cruiser, although it’s a pretty seaworthy boat.”

But it is economical and eye-pleasing, ready for the backwaters where its namesake, the red-wing blackbird, reigns. Says Stambaugh: “The Redwing 26 can be a long-distance inland cruiser, capable of lengthy stays on the waterways and rivers, and the miles and miles of coastline in ‘small-boat country.’ ”

Chesapeake Marine Design, Severna Park, Md. Phone: (800) 376-3152.


• “Essays of E.B. White,” HarperPerennial, a division of HarperCollins Publishers, New York N.Y.

• Bridges Point 24 — SAIL AREA: 278 square feet DISPLACEMENT: 3,944 pounds BASE PRICE: $39,000. Bridges Point Boatyard, Brooklin, Maine. Phone: (207) 359-2713.

• Alerion Express 28 — SAIL AREA: 352 square feet DISPLACEMENT: 5,700 pounds BASE PRICE: $57,000. Newport R&D, Portsmouth, R.I. Phone: (401) 683-9450.

• Great Harbor 26 — SAIL AREA: 303 square feet DISPLACEMENT: 3,625 pounds BASE PRICE: $70,000. Great Harbor Yachts, Southwest Harbor, Maine. Phone: (207) 244-7607.

• Dark Harbor 20 — SAIL AREA: 357 square feet DISPLACEMENT: 5,200 pounds BASE PRICE: $54,500. Shaw Yacht, Thomaston, Maine. Phone: (207) 594-5035, Sparkman & Stephens, New York, N.Y. Phone: (212) 661-6170.

• New Moon 25 — SAIL AREA: 355 square feet, DISPLACEMENT: 6,700 pounds BASE PRICE: $60,000. Eastsail Yachts, Bow N.H. Phone: (603) 224-6579.

• Landing School 26 Weekender — SAIL AREA: 302 square feet, DISPLACEMENT: 4,630 pounds BASE PRICE: $76,000. The Landing School, Kennebunkport, Maine. Phone: (207) 985-7976.