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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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The Home of the Flicka 20 Sailboat

Heritage Series

The 208CC is loaded with premium features and thoughtful design elements. — PowerBoat Television

The 208CC has redefined what a 20-foot fishing boat can do.

Tackle the toughest conditions, dive the reefs, or cruise the harbor. The 208CC features an expansive cockpit and a large walk-in console with a portable head. Gunwale rod racks, rod holders and several options for livewells maximize every inch of usable space in this center console.

208CC Virtual Tour

208cc specifications, features & options gallery.

Additional info, if available, will be shown here.

Standard Features

• PermaGrid® Fiberglass Stringer System
• Limited Lifetime Structural Hull Warranty
• NMMA, ABYC & CE Certified
• Self Bailing Non-Skid Decks
• NO WOOD All Composite Construction
• Closed-Cell Foam Flotation
• Variable Deadrise Deep V Hull
• High Density Composite Transom
• White Gelcoat Hull Color
• Welded Stainless 316L Steel Console Grab Rail
• 8″ Stainless Steel Cleats (6)
• Stainless Steel Bow and Stern Eyes (3)
• Welded 316L Stainless Steel 1″ Split Bow Rail
• Folding Recessed Telescoping Transom Ladder
• Walk-Thru Transom Door w/ Stainless Steel Latch
• Stainless Steel Drink Holders on Console (2)
• Stainless Steel Drink Holders on Bow Platform (2)
• Heavy Duty White Rubrail w/ Black Insert
• Powdercoated Aluminum T-Top with Electronics Box, Rod Holders (4), & LED Spreader Lights (2)
• 3/8″ Clear Acrylic Windshield
• Walk-in Console (5’2″ head-room)
• Stainless Steel Steering Wheel
• Hydraulic Seastar® Steering w/ Tilt Helm
• Ritchie Compass
• Console Mounted Porta-Potti
• Stainless Steel Cockpit Toe Rails (2)
• Raw Water Washdown Outlet
• Fresh Water Shower w/ 6 Gallon Tank
• Radar Plate for T-Top or Hardtop
• Canvas T-Top w/ Rod Holders (4) & LED Spreader Lights (2)
• LED Navigation Lights
• LED Cockpit/Livewell Lighting
• 1250 GPH Auto/Manual Bilge Pump (1)
• Console Switch Panel with waterproof switches, circuit breakers & 12V Outlet
• Battery Selector Switch & Wiring for Dual Batteries
• Waterproof Electrical Connectors & Tin Plated Copper Wiring
• Heavy-Duty Marine Grade UV Resistant Vinyl Upholstery
• Powdercoated Aluminum Leaning Post w/ 72QT Cooler
• Folding Aluminum Seat on Front of Console w/Backrest
• Stainless Steel Folding/Removable Stern Seat w/Backrest
• 20 Gallon Transom Baitwell
• Insulated Bow Storage/Fishbox w/ Overboard Drain
• Stainless Steel Gunwale Mounted Rod Holders (4)
• Under Gunwale Rod Racks
• Stainless Steel Anchor Roller w/ Hawse Pipe & Anchor Hook
• Bow Anchor Locker with Overboard Drain

White Yamaha F150 Four Stroke w/ Stainless Steel Prop, Fuel/Water Separator, Group 24 Battery & Box (2), Digital Tach (w/ Engine Trim, Hours, Trip & Warning Lights), Digital Speedo (w/ Fuel Level, Trip, Time, Volts & Low Fuel/Volt Alarms)

Optional Features

Hullside Color Dark w/ White Bottom

• COLORS: Stars & Stripes Blue

Hullside Color Light w/ White Bottom

• COLORS: Pewter, Ice Blue, Sea Foam Green
• Console Cover – Black, Grey, Navy, Toast
• Sun Top w/ SS Bows & Hardware
• Instrument Box for T-Top
• 15′ Silver Radial Outriggers for T-Top
• 3-Sided Enclosure for T-Top
• Console/Helm Seat Cover

Single Yamaha F200XSA2 Digital Electronic Steering, White

• Garmin EchoMap Plus 94sv with GT54 Transducer
• Fusion Stero RA55 with JL Audio 6.5″ M3 Speakers (2)
• Additional, Speakers (2), JL Audio M3 6.5″
• Trolling Motor/Power Pole Pre-Rig Move Starboard Forward Cleat (2) Battery Trays
• Battery Charger Package w/ 115V Power Inlet (2 Bank)

Performance

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Leisure Owners Association

Dedicated to supporting owners of Leisure yachts around the world

With its long waterline and generous beam, the Leisure 20 is a superbly balanced four-berth family cruiser that can be sailed just about anywhere comfortably and safely.

Leisure 20 sailing

Aimed at the European market because the restriction on many inland waterways for “recreational” craft was 20 ft, the ’20’ is surprisingly roomy for its size. The hull was drafted by German designer Horst E. Glacier while the deck was designed by Brian Meerloo, thus starting with the more modern style from the beginning. For both serious offshore cruising and inshore pottering, it’s the ideal trailer-sailer, subsequently giving you a virtually unlimited choice of horizons.

Under sail the Leisure 20 is extremely stable, vice-free and fast, performing well under all types of conditions.

The spars are in aluminium alloy. Originally gold, the spars of later boats are black or silver. All standing rigging and rigging screws are stainless steel. Halyards are internal.

Under power it will cruise happily and economically with a five to seven horsepower outboard, being very manoeuvrable whether going ahead or astern.

Fin and twin keels are of cast iron, the latter being of high aspect ratio hydrofoil section. The centre board version has a galvanised mild steel plate, housed in a cast iron stub tube. Rudder and skeg are moulded GRP with steel framework and stainless steel fittings. A teak rubbing strake is standard and moulded non-slip areas on deck are designed to ensure safety.

Leisure 20 beating

Accommodation

The cockpit is deep and wide and features a outboard motor well in the stern, with the cover providing an additional seat or table.

The accommodation includes four sensibly sized cushioned berths with ample stowage space, finished in teak timbers and veneers with a full galley, including cooker and sink, fitted on the starboard side. Headroom is 1.62 m (5 ft 4 in) in the cabin, with two large coach-roof windows on each side and a translucent fore-hatch. As a result, it is particularly light and airy.

Specification Detail

Leisure 20 brochure, performance.

Leisure yachts (apart from the Leisure 17) are seldom raced. The only racing handicap information we have are PY (Portsmouth Yardstick), SY (Secondary Yardstick) various Recorded Numbers (RN) and Club Numbers (CN) as shown below. For cruising boats, The RYA has updated the Portsmouth Yardstick scheme with the National Handicap for Cruisers (NHC). More up to date information may be obtainable from the RYA NHC site and the Byron  web site.

The only yardstick information we have are various Club Numbers (CN) and Recorded Numbers (RN) as follows:

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