20 foot sailboats for sale

10 Best Small Sailboats (Under 20 Feet)

Last Updated by

Daniel Wade

December 28, 2023

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

{{boat-info="/boats/hunter-15"}}

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

{{boat-info="/boats/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.

{{boat-info="/boats/hobie-16"}}

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

{{boat-info="/boats/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

{{boat-info="/boats/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.

{{boat-info="/boats/sage-marine-sage-17"}}

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.    

{{boat-info="/boats/laserperformance-laser-sb3"}}

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.

{{boat-info="/boats/fareast-18"}}

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.

{{boat-info="/boats/chuck-paine-paine-14"}}

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.

{{boat-info="/boats/wd-schock-lido-14"}}

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!

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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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Sailboats Under 20 feet

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Herreshoff America Catboat Sailboat

1986 supercat 17 and trailer - t1311746, 1983 22' s2 yach 6.7 grand slam w/ 4hp yamaha and trailer - t1310994, 1980 14' alcort amf sunfish sailboat - t1311665, hobie cat h16, 1969 oday mariner 19' sailboat boat & has trailer, fiberglass sailboat for sale with extra sails, 2.6hp outboard, trailer, + extras, catboat sailboat, 1984 spindrift 17' daysailer sailboat boat & trailer, sail boat for sale used, new old stock: 8’ wooden el toro sailboat w/oars, flotation bags, and dolly., sailboats under 20 feet, hobie wave club tiller assembly (old style), 1977 14' o'day javelin and trailer - t1311874, sailboats under 20 feet provide fun adventure on the sea.

Sailboats are an investment that can provide years of enjoyment for you and your friends. They come in multiple sizes and styles with different configurations of sails and riggings. You can find the exact type of preowned sailboat you need listed for sale on eBay at an affordable price.

Sailboats are classified by their style of sails and rigging and their purpose and use. There are multiple types of sailboats that range in size from small to medium, and these are some of the more common types you will see listed for sale on eBay:

• Catboat - A catboat has a single mast mounted far forward, does not have a jib, and usually has just one sail. However, some catboats have multiple sails attached to the gaff rig.
• Dinghy - This type of small sailboat has an open design and has three or fewer sails. It is mainly used for recreational sailing, training, or for servicing a larger boat. Dinghies are commonly used in youth sailing programs because of their simplicity.
• Sloop - The most common type of modern sailboat is a sloop. This type of sailboat has one mast and two sails, which are typically a Bermuda-rigged mainsail and a headsail. A sloop is efficient at sailing into the wind.
• Cutter - The cutter is similar to a sloop and has a single mast and mainsail that is positioned further aft to make room for a jib and staysail on the head stay and inner forestay.
• Yawl - A yawl has a short mizzen mast astern of the rudderpost for balancing.
• Daysailer - A daysailer or dayboat is a small sailboat that may or may not have sleeping areas. It is larger than a dinghy and can be either monohull or multihull. They often have a small cabin or cuddy to provide minimal shelter.

Most sailboats that are between 15 and 20 feet will have a motor on board, but it will not be used very often. Some marinas require sailboats to use motorized entry instead of sails in the marina, so having a motor is a requirement in those situations. A motor can be useful if it is needed for emergencies.

There are many different companies that make all types of sailboats. These are some of the brands of sailboats under 20 feet you will see often listed for sale on eBay:

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W.D. Schock Boat Builders Presents Harbor 20

Overview of the Harbor 20 Sailboat

The Harbor 20 "The classic modern daysailer"

Classic daysailer meets state of the art marine technology.

The Harbor 20 presents a graceful silhouette, its modern underbody and rig make for a fast and easily-handled contemporary daysailer. The result is a beautiful, cost effective, and easy-to-use boat that will always be in style.

Comfortable Cruising

 The Harbor 20’s accommodating cockpit holds up to eight guests, and no  one needs to sit on the rail to balance the boat, or duck under the boom  when tacking. Deep coamings provide comfortable back support, and two  easily accessible ice chests quickly render your favorite refreshment.  

Natural Club Racer

 A fine entry with firm bilges and a long run aft give the Harbor 20 high  speed potential, high stability and the ability to move smoothly  through choppy water. The rudder is placed well aft, and the 900 lb.  bulb keel keeps the weight low. This keel design gives the boat plenty  of stability without slowing the boat down in light air. The Harbor 20  can be raced competitively either single-handily or with a crew of  two or more. 

Sensible Design, Simplified Sail Control

With incredible stability and loads of conveniences, the Harbor 20 can  be rigged in minutes and sailed solo or with a group. There  is no better opportunity to share sailing excitement with friends and  family – whether they are seasoned sailors or completely inexperienced.  Celebrating over seventy years of boat-building excellence, the Schock  heritage continues with the Harbor 20.  

Designed with simplicity in mind

 The roller-furling headsail and self-tacking club boom will delight your  crew. And when running wing-and-wing, the club boom acts as an  automatic winger, effortlessly holding out the jib. And the control  panel just aft of the mast is centralized convenience at its very best.  Ready to go sail? Simply raise the  main, roll out the jib, and throw off the bow line. When you return to  the dock, just roll the jib back up, stow the main neatly on the boom  using the lazy jacks, and cover the boat and jib with the optional  cockpit cover and jib sock.  

 ll halyards and lines are led below the deck to Harken hardware  mounted on a shelf at the aft edge of the cuddy cabin. Everything  is within easy reach for the skipper and crew.

Specifications & Options

Specifications, electric motor options.

Designed by: Steven W. Schock

Exclusive Builder: WD Schock Corp (USA) 

First Built: 1997

Construction: Fiber Glass

Draft: 3’6”

BALLAST: 900 lbs.

Displacement:1,800 lbs

MAIN: 151 sq. ft.

Jib: 8 sq. ft.

Draft (max): 3.50’

Sail Area/Disp.1: 23.84

Bal./Disp. 50.00 %

Disp./Len. 163.56 

An electric motor is available to push the boat at about five knots and to provide convenient, quiet, and odorless propulsion. The motor, which is permanently mounted on a stainless steel pivot arm, swings out of the aft lazarette and pins onto the starboard gunwale. No wrestling with an outboard and no through-hull fittings! Four hours at maximum speed comes from the two batteries installed forward under the cockpit seats. The 24 volt system can be easily recharged with the in-line three step charger. Just plug it in at the dock.

There are many customize options available, let our representatives help you customize the perfect boat for your needs. Call us today at (951) 277-3377

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Buying a yacht in Russia

Would you like to buy a dream yacht? Will it be a motor or sailing ship? A luxury ocean yacht for sailing long distances or a small model adapted for fishing? The catalog of our company contains a large number of proposals for the sale of yachts in Russia and other countries. We also offer our services in the purchase of yachts in various technical conditions. Thanks to a wide selection of offers, both beginners in yachting and experienced professionals can take advantage of our services - an impressive assortment of vessels successfully combines with a wide range of prices.

You can choose a suitable vessel and buy a yacht in Russia using the capabilities of our company - experienced brokers are employed in 2yachts, ready to confidently and safely guide you through the process of buying or selling a vessel.

Before putting each offer to public access, we carefully check the legal cleanliness of the vessel and study the history of its operation. The managers of the company engaged in this market for a long time and possessing practical knowledge on the operation of yachts in different regions can help you with its purchase and sale.

You can choose a yacht for purchase in Russia , and we will draw up a formal contract, ensure the legal purity of the transaction and consultations on any aspects of owning a ship. At the same time, the confidentiality of your personal information is guaranteed.

If you are looking for a sailing yacht with high driving performance or a motor yacht with excellent controllability, then contacted us at. 2yachts company is a service for selecting the best trading offers from popular world yacht manufacturers. With us you can pick up a yacht that is a combination of unsurpassed quality, functional and efficient equipment and innovative solutions - a vessel that brings maximum pleasure from boat trips.

You can buy a yacht in Sochi or in St. Petersburg in order to be able to get an unforgettable experience of being on the water alone, with a group of friends or surrounded by family members. A walk on a sea yacht is an ideal way to get away from the bustle of the city with its eternal traffic jams and unplanned phone calls to enjoy beaches with azure waters, as well as romantic views and picturesque sunsets. Sea yachts are designed for long-distance travel and have great power, they are also distinguished by good maneuverability and dynamism. We will help you realize your dream, if you feel a craving for adventure and newness - we will choose a yacht with the best value for money.

Factors Affecting Cost

Buying a yacht in Russia is a rather time-consuming and lengthy process that requires the participation of professional yacht brokers. Depending on the condition of the vessel, the year of manufacture, the quality of its equipment, class and size, the acquisition cost can vary greatly. There are several indicators on which the cost of buying a yacht will depend :

• Manufacturer, or shipyard - the most famous manufacturers with expensive products are concentrated mainly in European countries, and the most budget yachts are assembled in shipyards of the countries of Asia and the Middle East;
• Equipment - sometimes the internal filling is made to order, and in some cases it is standard equipment with less power, comfort, speed, etc. In this regard, the cost of ships even from one manufacturer can vary greatly;
• Ship design;
• The age of the yacht.

Also, sailing yachts for sale in Russia cost the buyer less than similar motor lengths, but yachts with a history do not always cost less than recently launched ones. Often, the previous owners are engaged in the modernization of the vessel, installing expensive additional equipment on it or customizing the yacht - in this case, the price for it increases significantly. And sailing yachts often participate in regattas, where they can take prizes and eventually acquire a name - this also leads to a rise in the cost of the vessel.

Note that the cost of a yacht in Russia will be significantly different depending on the length of the vessel. You can always check the final cost of the vessel with a yacht broker, and since this market is very lively, the price can change even during the time during which you pick up a yacht.

You can find out the price of the selected vessel and its technical parameters in our catalog, and you can leave a request for purchase directly on the website, online. To choose a yacht for purchase , you can use the help of our broker for the sale of yachts - our specialists are in collaboration with their colleagues around the world to be able to cover the entire market. Ask our manager your questions to get detailed information on the yacht you are interested in.

We wish you success in conducting transactions on the yacht market!

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