small sailboat for sale near me

• Kayak Parts
• Hobie Kayaks
• Old Town Kayaks
• Other Kayaks
• Hobie Eclipse
• SUP Accessories
• Windsurfing Boards
• Rig Packages
• Masts & Booms
• Parts & Accessories
• Windsurf Foil Boards
• Windsurf Foils
• Wing Boards
• Wing Accessories
• Hats / Gloves / Booties
• Wetsuits / Drysuits / Spraytops
• Trapeze Harnesses
• 231-929-2330

Your Cart is Empty

• $0.00 Subtotal

Taxes and shipping calculated at checkout

• Hobie Cat Parts
• Hiking Sticks
• Mast Floats / Righting
• Wind Indicators
• Battens & Sail Access.
• Hobie Island Parts
• Hobie Bravo Parts
• Hobie Wave Parts
• Hobie 14 Parts
• Hobie 16 Parts
• Hobie Getaway Parts
• Hobie 17 Parts
• Hobie 18 Parts
• LaserPerformance Parts
• Sunfish Parts
• Laser Parts
• Line & Accessories
• Shackles and Pins
• Accessories
• Tools and Maintenance
• Beach Dollies

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!

Related Articles

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.

by this author

Best Sailboats

Most Recent

What Does "Sailing By The Lee" Mean?

October 3, 2023

The Best Sailing Schools And Programs: Reviews & Ratings

September 26, 2023

Important Legal Info

Lifeofsailing.com is a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for sites to earn advertising fees by advertising and linking to Amazon. This site also participates in other affiliate programs and is compensated for referring traffic and business to these companies.

Similar Posts

Affordable Sailboats You Can Build at Home

September 13, 2023

Best Small Sailboats With Standing Headroom

Best Bluewater Sailboats Under $50K

Popular posts.

Best Liveaboard Catamaran Sailboats

Can a Novice Sail Around the World?

Elizabeth O'Malley

June 15, 2022

4 Best Electric Outboard Motors

How Long Did It Take The Vikings To Sail To England?

10 Best Sailboat Brands (And Why)

December 20, 2023

7 Best Places To Liveaboard A Sailboat

Get the best sailing content.

Top Rated Posts

Lifeofsailing.com is a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for sites to earn advertising fees by advertising and linking to Amazon. This site also participates in other affiliate programs and is compensated for referring traffic and business to these companies. (866) 342-SAIL

© 2024 Life of Sailing Email: [email protected] Address: 11816 Inwood Rd #3024 Dallas, TX 75244 Disclaimer Privacy Policy

Featured Sailboat:

Sailboats For Sale

29 listings found.

36 Hunter Vision 1993

Hobie Mirage Tandem Island

• Florida , United States

1972 Luders 36 by Cheoy Lee

Tartan 10 Snowballs Chance

• Connecticut

1975 Bristol 32 Sloop, Keel/CB by Ted Hood (Am’s Cup)

• Massachusetts

Used Yamaha 200 HP 4-Stroke Outboard Motor Engine

• United States

Used Yamaha 115 HP 4-Stroke Outboard Motor Engine

33ft Blue Water Sailboat

Freshwater Only – 1989 Hunter 33.5 Sloop-Rigged Cruiser, Shoal Wing Keel

F&C 44′ Ketch

Reeds Cub Scow – SOLD

Melges C Scow

470 sailboat and trailer

• Pennsylvania

1978 Hunter 30 Cheurbini

Sold – Shallow Draft Cat Ketch 24 Cruiser

1981 Pearson Flyer

Catalina 27 for sale

Hunter 44 DS perfect to live aboard!

• Ohio , United States

Westerly 33

2023 BENETEAU First 24

2023 BENETEAU First 27

2023 BENETEAU First 36

2023 BENETEAU First 44

1978 Mega (C&C) 30

Browse sailboats for sale on sailtrader.

SailTrader is dedicated to providing sailors a marketplace to easily buy and sell sailboats and sails. We are dedicated to offering only sailboats for sale to make it easy to find the right sailboat your looking for.

Find Sailboats For Sale From Anywhere Nationwide

SailTrader is is committed to offering sailboats for sale both locally and nationally. No matter what state your located in, there’s sailboats for sale near you. Popular states for buying and selling sailboats are: Alabama , Alaska , Arizona , Arkansas , California , Colorado , Connecticut , Delaware , Florida , Georgia , Hawaii , Idaho , Illinois , Indiana , Iowa , Kansas , Kentucky , Louisiana , Maine , Maryland , Massachusetts , Michigan , Minnesota , Mississippi , Missouri , Montana , Nebraska , Nevada , New Hampshire , New Jersey , New Mexico , New York , North Carolina , North Dakota , Ohio , Oklahoma , Oregon , Pennsylvania , Rhode Island , South Carolina , South Dakota , Tennessee , Texas , Utah , Vermont , Virginia , Washington , West Virginia , Wisconsin and Wyoming .

• New Sailboats

Find your next new sailboat for sale on SailTrader. Browse a variety of different types of sailboats: keelboats, dinghy’s, catamarans, trimarans and more. Not only will you fins a range of new types of sailboats but you’ll also see a range of brands to choose from like Catalina, Hunter, Beneteau, Jeanneau, Hinckley, J-Boats, Swan and more.

Used Sailboats For Sale

If you’re looking for used sailboats for sale then theirs’s no better place to look then SailTrader. SailTrader is the fastest growing website specifically designed for sailboats. We make it easy to browse through used sailboats for sale to find the right one you’re looking for.

• Cruising Sailboats

Cruising sailboats are the most popular type of sailboat for sale. Today’s sailboat manufacturers offer a range of deck and interior variations giving sailors a lot of options to choose from. Browse through cruising sailboats for sale from: Catalina, Beneteau, Hunter, Jeanneau, Hanse, Custom, Pearson, Morgan, Tartan, Bavaria, Hallberg-Rassy, Grand Soleil and more.

• Racing Sailboats

SailTrader is a reliable source for finding racing sailboats for sale. From boats design just for racing to find a club racer/cruiser, SailTrader has you covered. 

Sell Your Sailboat

SailTrader makes it easy to sell your sailboat online. In a few simple steps, you can list your sailboat on the top marketplace dedicated only to sailing. 

The Sailor’s Marketplace for Sailboats and Sails.

• Used Sailboats

Sell Your Sails

Sails for sail, sail manufacturers.

• North Sails
• Quantum Sails
• Doyle Sails
• UK Sailmakers

Sailing Reviews

• Sailing Line
• Safety Equipment
• Sailing Accesories

As an Amazon Associate SailTrader earns from qualifying purchases.

This website uses cookies to ensure you get the best experience possible.