18 Small Sailboats for the Weekender

Whether you want to cruise to your next destination at 55 mph or are striving for simplicity, this fleet of trailerable sailboats and pocket cruisers will fit your needs and budget.

By Mark Pillsbury
Updated: April 18, 2019

In order to go cruising, most of us require a sailboat with a head, a galley, and bunks. The boat, likely a 30-footer and more often a 40-footer, will have electronics for navigation and entertainment, refrigeration if the trip is longer than a coastal hop, an engine for light wind, and, depending on our appetites for food and fun, perhaps a genset to power our toys and appliances.

To go sailing, however, all we really need is a hull, mast, rudder, and sail. To experience the pure joy of sheeting in and scooting off across a lake, bay, or even the open ocean, there’s nothing better than a small sailboat. You can literally reach out and touch the water as it flows past. You instantly feel every puff of breeze and sense every change in trim.

Some of the boats in this list are new designs, others are time-tested models from small sailboat manufacturers, but every one is easy to rig, simple to sail, and looks like a whole lot of fun either for a solo outing on a breezy afternoon or to keep family and friends entertained throughout your entire sailing season. This list is made up of all types of sailboats, and if you're looking for a list of some of the best small sailboats for beginners, you'll find exactly that here.

Any one of these boats could be labeled as a trailerable sailboat, daysailer, or even a weekender sailboat. Enjoy browsing!

Marblehead 22 Daysailer

Marblehead 22 Daysailer

If you have an eye for elegant lines and your heart goes pitter-patter over just the right amount of overhang beneath a counter transom, the Marblehead 22 daysailer, designed by Doug Zurn and built by Samoset Boatworks in Boothbay, Maine, will definitely raise your pulse. Traditional-looking above the waterline and modern beneath, the cold-molded hull sports a deep bulb keel and a Hall Spars carbon-fiber mast with a wishbone rig and square-top main. The 11-foot-9-inch cockpit can seat a crowd, and a small cuddy forward will let you stow your friends’ gear for the day. www.samosetboatworks.comMarblehead
Catalina 22 Sport

Catalina 22 Sport

Many a harbor plays host to an active fleet of Catalina 22s, a boat that’s been a popular weekender over the years, given its basic amenities and retractable keel, which allows it to be easily trailered. Recently, the company introduced the Catalina 22 Sport, an updated design that can compete with the older 22s. The boat features a retractable lead keel; a cabin that can sleep four, with a forward hatch for ventilation; and a fractional rig with a mainsail and a roller-furling jib. Lifelines, a swim ladder, and an engine are options, as are cloth cushions; vinyl cushions are standard. The large cockpit will seat a crowd or let a mom-and-pop crew stretch out and enjoy their sail. www.catalinayachts.comCatalina
Hunter 22

Hunter 22

With its large, open-transom cockpit and sloop rig, the Hunter 22 makes a comfortable daysailer for family and friends. But with its cuddy cabin, twin bunks, optional electrical system, opening screened ports, and portable toilet, a parent and child or a couple could comfortably slip away for an overnight or weekend. Add in the optional performance package, which includes an asymmetric spinnaker, a pole, and a mainsheet traveler, and you could be off to the races. The boat features a laminated fiberglass hull and deck, molded-in nonskid, and a hydraulic lifting centerboard. Mount a small outboard on the stern bracket, and you’re set to go. www.huntermarine.comHunter
BayRaider from Swallow Boats

BayRaider from Swallow Boats

Easy to rig and trailer, the BayRaider from England's Swallow Boats is a relative newcomer to the small-boat market in the United States. Nearly all of its 19 feet 9 inches is open cockpit, though a spray hood can be added to keep the forward sections dry. The BayRaider is ketch-rigged with a gunter-style mainmast. The topmast and mizzen are both carbon-fiber, which is an option for the mainmast as well. The BayRaider can be sailed with a dry hull in lighter conditions or with 300 pounds of water ballast to increase its stability. With the centerboard and hinged rudder raised, the boat can maneuver in even the thinnest water.
$28,900, (904) 234-8779, www.swallowboats.comBayRaider
West Wight Potter P 19

West Wight Potter P 19

With berths for four and a workable galley featuring a cooler, a sink, and a stove, West Wight Potter has packed a lot into its 19-foot-long P 19. First launched in 1971, this is a line of boats that’s attracted a true following among trailer-sailors. The P 19’s fully retractable keel means that you can pull up just about anywhere and go exploring. Closed-cell foam fore and aft makes the boat unsinkable, and thanks to its hard chine, the boat is reportedly quite stable under way. www.westwightpotter.comWest Wight
NorseBoat 17.5

NorseBoat 17.5

Designed for rowing and sailing (a motor mount is optional), the Canadian-built NorseBoat 17.5—one of which was spotted by a CW editor making its way through the Northwest Passage with a two-man crew—features an open cockpit, a carbon-fiber mast, and a curved-gaff rig, with an optional furling headsail set on a sprit. The lapstrake hull is fiberglass; the interior is ply and epoxy. The boat comes standard with two rowing stations and one set of 9-foot oars. The boat is designed with positive flotation and offers good load-carrying capacity, which you could put to use if you added the available canvas work and camping tent. NorseBoats offers a smaller sibling, the 12.5, as well; both are available in kit form.
$19,000, (902) 659-2790, www.norseboat.comNorseBoat
Montgomery 17

Montgomery 17

Billed as a trailerable pocket cruiser, the Montgomery 17 is a stout-looking sloop designed by Lyle Hess and built out of fiberglass in Ontario, California, by Montgomery Boats. With a keel and centerboard, the boat draws just under 2 feet with the board up and can be easily beached when you’re gunkholing. In the cuddy cabin you’ll find sitting headroom, a pair of bunks, a portable toilet, optional shore and DC power, and an impressive amount of storage space. The deck-stepped mast can be easily raised using a four-part tackle. The builder reports taking his own boat on trips across the Golfo de California and on visits to California’s coastal islands. Montgomery makes 15-foot and 23-foot models, as well. www.montgomeryboats.comMontgomery
CW Hood 32 Daysailer small sailboat
With long overhangs and shiny brightwork, the CW Hood 32 is on the larger end of the daysailer spectrum. Designers Chris Hood and Ben Stoddard made a conscious decision to forego a cabin and head in favor of an open cockpit big enough to bring 4 or 5 friends or family out for an afternoon on the water. The CW Hood 32 is sleek and graceful through the water and quick enough to do some racing, but keeps things simple with a self-tacking jib and controls that can be lead back to a single-handed skipper. A top-furling asymmetrical, electric sail drive and Torqeedo outboard are all optional. cwhoodyachts.comWalter Cooper
Sun Cat from Com-Pac

Sun Cat from Com-Pac

Shallow U.S. East Coast bays and rock-strewn coasts have long been graced by cat boats, whose large, gaff-rigged mainsails proved simple and powerful both on the wind and, better yet, when reaching and running. The 17-foot-4-inch Sun Cat, built by Com-Pac Yachts, updates the classic wooden cat with its fiberglass hull and deck and the easy-to-step Mastender Rigging System, which incorporates a hinged tabernacle to make stepping the mast a one-person job. Belowdecks, the twin 6-foot-5-inch berths and many other features and amenities make this cat a willing weekender.
$19,800, (727) 443-4408, www.com-pacyachts.comSun Cat
Catalina 16.5

Catalina 16.5

The Catalina 16.5 sits right in the middle of Catalina Yachts’ line of small sailboats, which range from the 12.5 to the 22 Capri and Sport, and it comes in both an easy-to-trailer centerboard model and a shoal-draft fixed-keel configuration. With the fiberglass board up, the 17-foot-2-inch boat draws just 5 inches of water; with the board down, the 4-foot-5-inch draft suggests good windward performance. Hull and deck are hand-laminated fiberglass. The roomy cockpit is self-bailing, and the bow harbors a good-sized storage area with a waterproof hatch. www.catalinayachts.com Catalina
Hobie 16

Hobie 16

No roundup of small, trailerable, and fun sailboats would be complete without a mention of the venerable Hobie 16, which made its debut in Southern California way back in 1969. The company has introduced many other multihulls since, but more than 100,000 of the 16s have been launched, a remarkable figure. The Hobie’s asymmetric fiberglass-and-foam hulls eliminate the need for daggerboards, and with its kick-up rudders, the 16 can be sailed right up to the beach. Its large trampoline offers lots of space to move about or a good place to plant one’s feet when hanging off the double trapezes with a hull flying. The boat comes with a main and a jib; a spinnaker, douse kit, trailer, and beach dolly are optional features. www.hobiecat.comHobie
Hunter 15

Hunter 15

Novice sailors or old salts looking for simplicity could both enjoy sailing the Hunter 15. With a fiberglass hull and deck and foam flotation, the boat is sturdily built. The ample freeboard and wide beam provide stability under way, and the heavy-duty rubrail and kick-up rudder mean that you won't have to worry when the dock looms or the going grows shallow. Both the 15 and its slightly larger 18-foot sibling come standard with roller-furling jibs.
$6,900/$9,500 (boat-show prices for the 15 and 18 includes trailers), (386) 462-3077, www.huntermarine.comHunter
Super Snark

Super Snark

Under various owners, the Snark brand of sailboats, now built by Meyers Boat Co., has been around since the early 1970s. The Super Snark, at 11 feet, is a simple, easily car-topped daysailer that's fit out with a lateen rig and sail. Billed as unsinkable, the five boats in the company's line are built with E.P.S. foam, with the external hull and deck vacuum-formed to the core using an A.B.S. polymer. The Super Snark weighs in at 50 pounds, and with a payload capacity of 310 pounds, the boat can carry two.
$970, (800) 247-6275, www.meyersboat.comSuper Snark
Norseboat 21.5

Norseboat 21.5

Built in Canada, the NorseBoat 21.5 is a rugged looking craft that comes in a couple of configurations: one with an open cockpit and small doghouse, and another with a smaller cockpit and cabin that houses a double berth for two adults and optional quarter berths for the kids. Both carry NorseBoat's distinctive looking carbon fiber gaff-rigged mast with main and jib (a sprit-set drifter is optional), and come with a ballasted stub keel and centerboard. Because of its lightweight design, the boat can be rowed and is easily trailered.
$36,000 (starting), 902-659-2790, www.norseboat.comNorseboat
Flying Scot

Flying Scot

Talk about time-tested, the 19-foot Flying Scot has been in production since 1957 and remains a popular design today. Sloop rigged, with a conventional spinnaker for downwind work, the boat is an easily sailed family boat as well as a competitive racer, with over 130 racing fleets across the U.S. Its roomy cockpit can seat six to eight, though the boat is often sailed by a pair or solo. Hull and deck are a fiberglass and balsa core sandwich. With the centerboard up, the boat draws only eight inches. Though intended to be a daysailer, owners have rigged boom tents and berths for overnight trips, and one adventurous Scot sailor cruised his along inland waterways from Philadelphia to New Orleans.
$17,300 (includes trailer), 800-864-7208, www.flyingscot.comFlying Scot
RS Venture

RS Venture

Known primarily for its line of racing dinghys, RS Sailing also builds the 16-foot, 4-inch Venture, which it describes as a cruising and training dinghy. The Venture features a large, self-draining cockpit that will accommodate a family or pack of kids. A furling jib and mainsail with slab reefing come standard with the boat; a gennaker and trapeze kit are options, as is an outboard motor mount and transom swim ladder. The deck and hull are laid up in a fiberglass and Coremat sandwich. The Venture's designed to be both a good performer under sail, but also stable, making it a good boat for those learning the sport.
$14,900, 203-259-7808, www.rssailing.comRS Sailing
Topaz Taz

Topaz Taz

Topper makes a range of mono- and multihull rotomolded boats, but the model that caught one editor's eye at Strictly Sail Chicago was the Topaz Taz. At 9 feet, 8 inches LOA and weighing in at 88 pounds, the Taz is not going to take the whole crowd out for the day. But, with the optional mainsail and jib package (main alone is for a single child), the Taz can carry two or three kids or an adult and one child, and would make a fun escape pod when tied behind the big boat and towed to some scenic harbor. The hull features Topper's Trilam construction, a plastic and foam sandwich that creates a boat that's stiff, light, and durable, and shouldn't mind being dragged up on the beach when it's time for a break.
$2,900 (includes main and jib), 410-286-1960, www.topazsailboats.comTopaz
WindRider WRTango

WindRider WRTango

WRTango, a fast, sturdy, 10-foot trimaran that's easy to sail, is the newest portable craft from WindRider International. It joins a line that includes the WR16 and WR17 trimarans. The Tango features forward-facing seating, foot-pedal steering, and a low center of gravity that mimics the sensation of sitting in a kayak. It weighs 125 pounds (including the outriggers and carbon-fiber mast), is extremely stable, and has single-sheet sail control. The six-inch draft and kick-up rudder make it great for beaching, while the hull and outriggers are made of rotomolded polyethylene, so it can withstand running into docks and being dragged over rocks.
$3,000, 612-338-2170, www.windrider.comWindRider

Latest

Sailing Totem: Cruising, the Ultimate Pandemic Prep
The Wonder of an Offshore Sail
Tartan Yachts has a New Owner
Video Chats with Steve Colgate
Off Watch: Bye-Bye Boat
Off Watch: A Disappearing Town Along the Northwest Passage
Five Questions for Franck Bauguil, VP of Yacht Ownership and Product Development for The Moorings, Sunsail and Leopard Catamarans
Off Watch: Ashes to Sea
Dates Announced for the 50th Annual Newport International Boat Show