small wood sailboats

10 Best Small Sailboats (Under 20 Feet)

Best Small Sailboats Under 20 Feet | Life of Sailing

Compact, easy to trailer, simple to rig, easy to maintain and manage, and affordable, the best small boats all have one thing in common: they offer loads of fun while out there on the water.

So whether you're on a budget or just looking for something that can offer ultimate daytime rides without compromising on safety, aesthetic sensibilities, alternate propulsion, and speed, the best small sailboats under 20 feet should be the only way to go.

Let's be brutally honest here; not everyone needs a 30-foot sailboat to go sailing. They come with lots of features such as electronics, entertainment, refrigeration, bunks, a galley, and even a head. But do you really need all these features to go sailing? We don't think so.

All you need to go sailing is a hull, a mast, rudder, and, of course, a sail. And whether you refer to them as daysailers, trailerable sailboats , a weekender sailboat, or pocket cruisers, there's no better way to enjoy the thrills of coastal sailing than on small sailboats.

There are a wide range of small boats measuring less than 20 feet available in the market. These are hot products in the market given that they offer immense thrills out on the sea without the commitment required to cruise on a 30-footer. A small sailboat will not only give you the feel of every breeze but will also give you the chance to instantly sense every change in trim.

In this article, we'll highlight 10 best small sailboats under 20 feet . Most models in this list are time-tested, easy to rig, simple to sail, extremely fun, and perfect either for solo sailing or for sailing with friends and family. So if you've been looking for a list of some of the best small sailboats , you've come to the right place.

So without further ado, let's roll on.

Table of contents

The Marlow-Hunter 15 is not only easy to own since it's one of the most affordable small sailboats but also lots of fun to sail. This is a safe and versatile sailboat for everyone. Whether you're sailing with your family or as a greenhorn, you'll love the Hunter 15 thanks to its raised boom, high freeboard, and sturdy FRP construction.

With high sides, a comfortable wide beam, a contoured self-bailing cockpit, and fiberglass construction, the Hunter 15 is certainly designed with the novice sailor in mind. This is why you can do a lot with this boat without falling out, breaking it, or capsizing. Its contoured self-baiting cockpit will enable you to find a fast exit while its wide beam will keep it steady and stable no matter what jibes or weight shifts happen along the way.

This is a small sailboat that can hold up to four people. It's designed to give you a confident feeling and peace of mind even when sailing with kids. It's easy to trailer, easy to rig, and easy to launch. With a price tag of about $10k, the Hunter 15 is a fun, affordable, and versatile boat that is perfect for both seasoned sailors and novices. It's a low-maintenance sailboat that can be great for teaching kids a thing or two about sailing.

Catalina 16.5

Catalina Yachts are synonymous with bigger boats but they have some great and smaller boats too such as Catalina 16.5. This is one of the best small sailboats that are ideal for family outings given that it has a big and roomy cockpit, as well as a large storage locker. Designed with a hand-laminated fiberglass sloop, the Catalina 16.5 is versatile and is available in two designs: the centerboard model and the keel model.

The centerboard model is designed with a powerful sailplane that remains balanced as a result of the fiberglass centerboard, the stable hull form, and the rudder. It also comes with a tiller extension, adjustable hiking straps, and adjustable overhaul. It's important to note that these are standard equipment in the two models.

As far as the keel model is concerned, this is designed with a high aspect keel as the cast lead and is attached with stainless steel keel bolts, which makes this model perfect for mooring or docking whenever it's not in use. In essence, the centerboard model is perfect if you'll store it in a trailer while the keel model can remain at the dock.

All in all, the Catalina 16.5 is one of the best small sailboats that you can get your hands on for as low as $10,000. This is certainly a great example of exactly what a daysailer should be.

There's no list of small, trailerable, and fun sailboats that can be complete without the inclusion of the classic Hobie 16. This is a durable design that has been around and diligently graced various waters across the globe since its debut way back in 1969 in Southern California. In addition to being durable, the Hobie 16 is trailerable, great for speed, weighs only 320 pounds, great for four people, and more importantly, offers absolute fun.

With a remarkable figure of over 100,000 launched since its debut, it's easy to see that the Hobie 16 is highly popular. Part of this popularity comes from its asymmetric fiberglass-and-foam sandwiched hulls that include kick-up rudders. This is a great feature that allows it to sail up to the beach.

For about $12,000, the Hobie 16 will provide you with endless fun throughout the summer. It's equipped with a spinnaker, trailer, and douse kit. This is a high-speed sailboat that has a large trampoline to offer lots of space not just for your feet but also to hand off the double trapezes.

Montgomery 17

Popularly known as the M-17, The Montgomery 17 was designed by Lyle C. Hess in conjunction with Jerry Montgomery in Ontario, California for Montgomery Boats. Designed either with keel or centerboard models, the M-17 is more stable than most boats of her size. This boat is small enough to be trailered but also capable of doing moderate offshore passages.

This small sailboat is designed with a masthead and toe rail that can fit most foresails. It also has enough space for two thanks to its cuddly cabin, which offers a sitting headroom, a portable toilet, a pair of bunks, a DC power, and optional shore, and a proper amount of storage. That's not all; you can easily raise the deck-stepped mast using a four-part tackle.

In terms of performance, the M-17 is one of the giant-killers out there. This is a small sailboat that will excel in the extremes and make its way past larger boats such as the Catalina 22. It glides along beautifully and is a dog in light air, though it won't sail against a 25-knot wind, which can be frustrating. Other than that, the Montgomery 17 is a great small sailboat that can be yours for about $14,000.

Norseboat 17.5

As a versatile daysailer, Norseboat 17.5 follows a simple concept of seaworthiness and high-performance. This small sailboat perfectly combines both contemporary construction and traditional aesthetics. Imagine a sailboat that calls itself the "Swiss Army Knife of Boats!" Well, this is a boat that can sail and row equally well.

Whether you're stepping down from a larger cruiser or stepping up from a sea kayak, the unique Norseboat 17.5 is balanced, attractive, and salty. It has curvaceous wishbone gaff, it is saucy, and has a stubby bow-sprit that makes it attractive to the eyes. In addition to her beauty, the Norseboat 17.5 offers an energy-pinching challenge, is self-sufficient, and offers more than what you're used to.

This is a small, lightweight, low-maintenance sailboat that offers a ticket to both sailing and rowing adventures all at the same time. At about 400 pounds, it's very portable and highly convenient. Its mainsails may look small but you'll be surprised at how the boat is responsive to it. With a $12,500 price tag, this is a good small sailboat that offers you the versatility to either row or sail.

If you've been looking for a pocket cruiser that inspires confidence, especially in shoal water, look no further than the Sage 17. Designed by Jerry Montgomery in 2009, the Sage 17 is stable and should heel to 10 degrees while stiffening up. And because you want to feel secure while sailing, stability is an integral feature of the Sage 17.

This is a sailboat that will remain solid and stable no matter which part of the boat you stand on. Its cabin roof and the balsa-cored carbon-fiber deck are so strong that the mast doesn't require any form of compression post. The self-draining cockpit is long enough and capable of sleeping at 6 feet 6 inches.

The Sage 17 may be expensive at $25k but is a true sea warrior that's worth look at. This is a boat that will not only serve you right but will also turn heads at the marina.

Having been chosen as the overall boat of the year for 2008 by the Sailing World Magazine, the Laser SB3 is one of the coolest boats you'll ever encounter. When sailing upwind, this boat will lock into the groove while its absolute simplicity is legendary. In terms of downwind sailing, having this boat will be a dream come true while it remains incredibly stable even at extraordinary speed.

Since its debut in 2004, the Laser SB3 has surged in terms of popularity thanks to the fact that it's designed to put all the controls at your fingertips. In addition to a lightweight mast, its T- bulb keel can be hauled and launched painlessly. For about $18,000, the Laser SB3 ushers you into the world of sports sailing and what it feels to own and use a sports boat.

As a manufacturer, Fareast is a Chinese boat manufacturer that has been around for less than two decades. But even with that, the Fareast 18 remains a very capable cruiser-racer that will take your sailing to the next level. In addition to its good looks, this boat comes with a retractable keel with ballast bulb, a powerful rig, and an enclosed cabin.

Its narrow design with a closed stern may be rare in sailboats of this size, but that's not a problem for the Fareast 18. This design not only emphasizes speed but also makes it a lot easier to maintain this boat. Perfect for about 6 people, this boat punches above its weight. It's, however, designed to be rigged and launched by one person.

This is a relatively affordable boat. It's agile, safe, well-thought-out, well built, and very sporty.

If you're in the market looking for a small sailboat that offers contemporary performance with classic beauty, the Paine 14 should be your ideal option. Named after its famous designer, Chuck Paine, this boat is intentionally designed after the classic Herreshoff 12.5 both in terms of dimensions and features.

This is a lightweight design that brings forth modern fin keel and spade rudder, which makes it agile, stable, and faster. The Paine 14 is built using cold-molded wood or west epoxy. It has varnished gunnels and transoms to give it an old-time charm. To make it somehow modern, this boat is designed with a carbon mast and a modern way to attach sails so that it's ready to sail in minutes.

You can rest easy knowing that the Paine 14 will not only serve you well but will turn heads while out there.

Many sailors will attest that their first sailing outing was in a Lido 14. This is a classic sailboat that has been around for over four decades and still proves to be a perfect match to modern small boats, especially for those still learning the ropes of sailing.

With seating for six people, the Lido 14 can be perfect for solo sailing , single-handed sailing, or if you're planning for shorthanded sailing. While new Lido 14 boats are no longer available, go for a functional used Lido 14 and you'll never regret this decision. It will serve you well and your kids will probably fall in love with sailing if Lido 14 becomes their main vessel during weekends or long summer holidays.

Bottom Line

There you have it; these are some of the best small sailboats you can go for. While there are endless small sailboats in the market, the above-described sailboat will serve you right and make you enjoy the wind.

Choose the perfect sailboat, invest in it, and go out there and have some good fun!

Daniel Wade

I've personally had thousands of questions about sailing and sailboats over the years. As I learn and experience sailing, and the community, I share the answers that work and make sense to me, here on Life of Sailing.

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20 Best Small Sailboats for the Weekender

By Mark Pillsbury
Updated: May 24, 2024

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 – we’re talking sailboats under 25 feet. 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 popular boats could be labeled as a trailerable sailboat, daysailer, or even a weekender sailboat. And while most would be labeled as a one or two person sailboat, some could comfortably fit three or even four people.

– CHECK THE WEATHER – The weather changes all the time. Always check the forecast and prepare for the worst case. Safety Tip Provided by the U.S. Coast Guard

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. samosetboatworks.com

Catalina 22 Sport

Many a harbor plays host to an active fleet of Catalina 22s, one of the most popular small sailboats 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. It’s clear why the Catalina 22 is one of the best sailboats under 25 feet. catalinayachts.com

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. marlow-hunter.com

Not sure whether you want to race, cruise or just go out for an afternoon sail? Since 1958, sailors have been having a ball aboard the Uffa Fox/George O’Day-designed Daysailer. Fox, who in the 1950s was on the cutting edge of planning-dinghy design, collaborated with Fall River, Massachusetts boatbuilder O’Day Corp. to build the 16-foot Daysailer, a boat that features a slippery hull and a small cuddy cabin that covers the boat roughly from the mast forward. Thousands of Daysailers were built by various builders, and they can be found used for quite affordable prices. There are active racing fleets around the US, and new Daysailers are still in production today, built by Cape Cod Ship Building. capecodshipbuilding.com

BayRaider from Swallow Boats

Easy to rig and trailer, the BayRaider from England’s Swallow Yachts 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, swallowyachts.com

Big fun can come in small packages, especially if your vessel of choice happens to be the 12 ½-foot Beetle Cat. Designed by John Beetle and first built in 1921, the wooden shallow draft sailboat is still in production today in Wareham, Massachusetts at the Beetle Boat Shop. With a draft of just 2 feet, the boat is well-suited for shallow bays, but equally at home in open coastal waters. The single gaff-rigged sail provides plenty of power in light air and can be quickly reefed down to handle a blow. In a word, sailing a Beetle Cat is fun. beetlecat.com

– LEARN THE NAVIGATION RULES – Know the “Rules of the Road” that govern all boat traffic. Be courteous and never assume other boaters can see you. Safety Tip Provided by the U.S. Coast Guard

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. westwightpotter.com

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, norseboat.com

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. If you’re in search of a small sailboat with a cabin, the Montgomery 17 has to be on your wish list.

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. The CW Hood 32 makes for a great small family sailboat. cwhoodyachts.com

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. If you want a personal sailboat ideal for solo sailing, the Sun Can is a great choice. 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, com-pacyachts.com

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. catalinayachts.com

No roundup of best small sailboats (trailerable and fun too) 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. hobiecat.com

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, marlow-hunter.com

– CHECK THE FIT – Follow these guidelines to make sure your life jacket looks good, stays comfortable and works when you need it. Safety Tip Provided by the U.S. Coast Guard

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, meyersboat.com

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, norseboat.com

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.

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, rssailing.com

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, topazsailboats.com

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, windrider.com