best small day sailboats

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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7 Small Sailboats for Everyday Cruising

• By Cruising World
• Updated: July 29, 2019

Not everyone needs a 30-foot sailboat equipped with bunks, a galley and head to go off cruising. In fact, all we really need is a hull, mast, rudder, and sail. There is nothing better than the thrill of a small sailboat or daysailer slipping through the waters of a lake, bay or even the open ocean.

Whether it’s simplicity to rig, ease of trailering or a manageable size that you’re looking for, these small sailboats are perfect for the cruising enthusiast who wants the thrill of the sea without the commitment of a 30-footer. And some of these sailboats come with cabins. This roundup of the best daysailers goes to show that sometimes big things come in small packages.

Marblehead 22 Daysailer

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.

Catalina 22 Sport

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.

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.

West Wight Potter 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.

Montgomery 17

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.

Catalina 16.5

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.

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.

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11 Best Small Sailboat Brands: How to Choose Your Next Daysailer or Pocket Cruiser

12th oct 2023 by samantha wilson.

Sailing is a relaxing, invigorating pastime that allows you to harness wind and waves in a unique and historic way without requiring a 50-foot yacht to enjoy what’s special about the experience. In fact, small sailboats allow a delightful back-to-basics experience that often gets lost on larger, systems-heavy sailboats.

On a small sailboat you can connect with the sea, feeling the boat move beneath you. The boat is typically easy to rig, simple to sail, and can even be sailed solo. Small sailboats give you the freedom to trailer your or car-top your boat and go anywhere, and they’re perfect for learning the nuances of sailing. There are many excellent brands and models of small sailboat, each with their own appeal, and here we narrow down some of our favorite in the daysailer and pocket cruiser categories under 30 feet. 

Difference Between a Daysailer and a Pocket Cruiser

While there are many different types of sailboat on the market and there is no single definition of either a daysailer or a pocket cruiser, they are used in a particular way, as the names imply. The term daysailer covers a huge array of sailboats, smaller and sometimes larger, and is generally defined as any day boat used for local sailing, with a simple rig, and easy to get underway. A pocket cruiser typically offers a cabin and head, and adequate accommodations for an overnight stay and sometimes longer cruises. Having said that, there is a large overlap between the two in many instances, so the lines may become blurred. 

What Size is a Small Sailboat?

Small is a relative term of course, but in general—and for the purposes of this article—a small sailboat is one that could be sailed by a small crew, often with one or two people aboard. It will have a simple rig and be trailerable, and it might be either a daysailer or pocket-cruiser style vessel as above. Within those categories, there are many models and styles, but when it comes to length we consider a sailboat as small when it’s under 30 feet in overall length. 

The Best Sailboats Under 30 Feet

Pocket cruiser: Beneteau First 27.  The Beneteau First 27 is a modern example of a pocket cruiser, earning Cruising World ’s Boat of the Year award in the Pocket Cruiser category in 2022. With space for up to six people accommodated in a separated bow-cabin and open saloon, it offers families the chance to go farther, explore more, and cruise in comfort. There is a galley with freshwater and a head, adding to the interior home comforts. The sailboat itself is modern, fast, and stable, designed by Sam Manuard, and has been designed to be incredibly safe and almost unsinkable thanks to its three watertight chambers. The handling is also refreshingly intuitive, with a well-designed cockpit, simple deck controls, and double winches allowing it to be sailed solo, by two people, or a small crew. 

Photo credit: Beneteau

Daysailer: Alerion 28.  You’ll certainly turn heads cruising along in an Alerion 28, a daysailer whose forerunner by the same name was designed by Nathanael Herreshoff in 1912 and then updated with a modern underbody for fiberglass production by Carl Schumacher in the late 1980s. This pretty daysailer manages to combine a traditional silhouette and classic feel, with very modern engineering creating an excellent package. Over 470 of these sailboats were built and sold in the past 30 years, making it one of the most popular modern daysailers on the water. With a small cabin and saloon, complete with miniature galley area, it offers respite from the sun or wind and the option for a night aboard. The cockpit offers a beautiful sailing experience, with plenty of space for the whole family. 

Photo credit: Alerion Yachts

The Best Sailboats Under 25 Feet

Pocket cruiser: Cornish Crabber 24.  British manufacturer Cornish Crabber has been producing beautiful, traditional style small sailboats for decades, ensuring they honor their heritage both in the construction style and appearance of their boats. The Cornish Crabber 24 is the most iconic of their range and dates back to the 1980s. It offers a simple yet surprisingly spacious interior layout with cabin, galley, and head, and a good sized cockpit, as well as seating for up to six people. It’s the perfect family sailboat, with clever use of storage as well as just under 5000 pounds of displacement providing stability and easy tacking. Aesthetically the 24 is simply beautiful, with a traditional silhouette (combined with modern engineering), finished in hardwood trims. 

Photo credit: Cornish Crabber

Daysailer: Catalina 22 Capri.  Catalina sailboats need little introduction, and are one of the world’s best-known, most-respected brands building small sailboats. The Catalina 22 Capri (also available in a sport model) is a great example of what Catalina does so well. While we’ve classified it as a daysailer, it could easily cross into the pocket cruiser category, as it offers excellent sailing performance in almost all conditions as well as having a small cabin, galley, and head. Loved for its safety, stability, ease of handling and simple maintenance, it makes for a good first family boat for getting out onto the bay or lake. 

Photo credit: Catalina

The Best Sailboats Under 20 Feet

Pocket cruiser: CapeCutter 19.  This is another model that combines the beauty of the traditional silhouettes with modern-day advancements. The design originates from the classic gaff cutter work boats, but today offers excellent performance—in fact it’s one of the fastest small gaffers in the world. The interior is cleverly spacious, with four berths, two of which convert into a saloon, as well as a simple galley area. With quick rigging, it can be sailed solo, but is also able to accommodate small groups, making it a capable and hugely versatile pocket cruiser. 

Photo credit: Cape Cutter 19

Daysailer: Swallow Yachts’ BayRaider 20.  Classic looks with modern performance are combined in Swallow Yachts’ beautiful BayRaider 20. This is one of the most capable and safest daysailers we’ve seen, but also incredibly versatile thanks to the choices of ballast. Keep the ballast tank empty and it’s light and fast. Fill the tank up and you’ve got a stable and safe boat perfect for beginners and families. While it’s got an eye-catching traditional style, the engineering is modern, with a strong carbon mast and construction. While this is a true daysailer, you can use the optional spray hood and camping accessories to create an overnight adventure. 

Photo credit: Swallow Yachts

The Best Sailboats Under 15 Feet

Pocket Cruiser: NorseBoat 12.5.  Can we truly call the NorseBoat 12.5 a pocket cruiser? Yes we can! The sheer versatility of this excellent little sailboat has convinced us. These beautiful hand-crafted sailboats offer exceptional performance and are described by the manufacturer as ‘the Swiss Army Knives of sailboats’. The traditionally styled 12.5 can be sailed, rowed, and motored. It can be trailered, easily beached, and even used as a camp cruiser, allowing for overnight adventures. There is no end to the fun that can be had with this easy-to-sail and easy-to-handle boat, which makes it a dream to learn in. With positive flotation, lots of clever storage, and a full-size double berth for camp cruising, it really is the perfect mini pocket cruiser. 

Photo credit: NorseBoats

Daysailer: Original Beetle Cat Boat 12: All across the bays of the US east coast cat boats have long been part of the ocean landscape. Able to access shallow rocky coves yet also withstand the strong coastal winds, these traditional New England fishing boats have an iconic shape and gaff-rigged mainsails. Beetle Cat have been producing elegant wooden cat boats for over 100 years – in fact they’ve made and sold over 4,000 boats to date. Their 12 foot Cat Boat 12 is one of their finest models, offering lovely daysailing opportunities. It has a wide beam and centerboard that lifts up, allowing it to access shallow waters, as well as a forward mast and single sail gaff rig in keeping with the traditional cat boats. To sail one of these is to be part of the heritage of New England and Cape Cod, and to honor the ancient art of hand-made boat building. 

Beetle Cat official website

Photo credit: Beetle Cat

The Best Small Sailboats for Beginners

When it comes to learning to sail, it’s important to have a boat that is easy to handle. There’s no quicker way to put yourself or your family off sailing than to start off with a boat that is either too big or too complicated. When choosing your first boat we recommend the following characteristics:

• Small: The benefits of starting off with a small boat are many, as we’ve seen above. They’re easier to control as well as to moor, and they react more quickly to steering and sails. They can be trailered and launched easily, and the loads generated are much lower than on bigger, heavier boats.
• Easy to sail: You want a boat that is stable and forgiving of mistakes, doesn’t capsize easily, and isn’t too overpowered in a stronger breeze. Keep things simple and learn as you go.
• Simple sail configuration: Choosing a boat that can be rigged by one person in a few minutes, and easily sailed solo, makes it easier to take along inexperienced crews. With regards to the rig, all you need are a halyard to hoist the mainsail and a sheet to control the mainsail.
• Tiller steering: We recommend boats with tiller steering over wheel steering when starting out. The tiller allows you to get a real feel for the boat and how the rudder works as it moves through the water. 

For more information on choosing the best beginner sailboat check out our full guide. There are many popular brands of beginner boats including Sunfish, Laser, and Hunter Marlow. Some of our favorites include;

Hobie 16: The classic Hobie catamaran has been a well-loved beginner sailboat for years, and the Hobie 16 started life back in 1969. Since then they’ve made and sold over a staggering 100,000 of the 16s. It has twin fiberglass and foam hulls, a large trampoline, and a pull-up rudder so it can be sailed straight onto the beach. The basic package comes with an easy to handle main and jib with plenty of extras available too such as a spinnaker and trailer. The Hobie 16 promises a great learning experience and lots of fun in a very nifty and inexpensive package. 

Photo credit: Hobie

Paine 14: You’ll immediately fall in love with sailing when you step into a beautiful Paine 14. Made from seamless epoxy cold-molded wood, the P-14 is simply beautiful and offers the classic sailing experience with the design and innovation of a more modern hull and rig. Two people will be able to enjoy getting out on the water together and learning the ropes. The Paine 14 has a lead ballast keel that accounts for nearly half her weight, giving her the feel of a much larger boat, but is still trailerable and easy to manage offering the best of both worlds.

Photo credit: Chuck Paine

High-Performance Small Sailboats

Small sailboats generally become high performers if they are light, have a lot of sail area, or they have more than one hull. More recently, some of have been designed with foiling surfaces, as well. For the purposes of this article, we’d like to close by pointing out one model that is super fast and has versatile pocket-cruising capabilities.

Corsair 880 trimaran : The Corsair 880 trimaran is the grandchild of the company’s F27, a model that launched the popularity of trailerable leisure trimarans about 40 years ago. The 880 has taken the model to new heights and exemplifies the incredible space benefits you can achieve in a 29-foot sailboat. We’re talking an aft cabin, room to sleep 5 people, an enclosed head, and standing headroom in the galley and main saloon. It brings many of the opportunities that a much larger yacht plus the ability to cruise in extremely shallow water. Whether you want to cruise to the Bahamas or enjoy a high-adrenaline race, the Corsair 880 offers incredible performance and unlimited adventures in a truly pocket size. 

Photo credit: Corsair

Written By: Samantha Wilson

Samantha Wilson has spent her entire life on and around boats, from tiny sailing dinghies all the way up to superyachts. She writes for many boating and yachting publications, top charter agencies, and some of the largest travel businesses in the industry, combining her knowledge and passion of boating, travel and writing to create topical, useful and engaging content.

More from: Samantha Wilson

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8 Best Daysailers Under 21 Feet – Buying Guide

SAFFIER SE 33 UD

It’s a sunny day, and you want to take a spin around the harbor. What better way to do that than launching a daysailer?

These sailboats are traditionally smaller than a cruise ship or yacht, but considerably bigger than kayaks , catamarans, inflatable dinghies , and other smaller boats. Owning an open sailboat shouldn’t cost you an arm and a leg, but expect to spend some top dollar.

Here are 8 best daysailers that are 21 feet or under.

CATALINA 16.5

Let’s kick things off with the Catalina 16.5 sailboat. It might come as a surprise to find a Catalina boat listed among the best daysailers under 20 feet because the name is more known for bigger cruiser yachts. But there are a whole lot of small boats built by Catalina, too.

The Catalina 16.5 is one of the most versatile hand-laminated fiberglass sloops from this designer and can be purchased with the option of a 4-feet 5-inch shoal-draft keel or a centerboard that draws 5-inch with the board up.

Consider choosing the lead-keel option if you want to park it on a mooring or at the dock. It is built to remain stable in such conditions. On the flip side, getting the centerboard version is most suitable if you want to store the boat on a trailer.

Catalina builds all their boats with a self-bailing cockpit, and the 16.5 is no different. It comes with a huge self-bailing cockpit. There is a waterproof hatch and a stowage space forward of the boat. The boat also comes with standard hiking straps and a tiller extension if you want to step on to the side deck for some spray in your face and good visibility forward.

You can get out on the water with around ten grand or more. Check out current listings for Catalina 16.5 .

 Boats  →

Teaching your kids or anyone to sail requires a low-maintenance and very steady boat. This is where the Hunter 15 shines. It is a perfect knockabout sailboat that can take a lot of rough beating without breaking, thanks to its high freeboard and fiberglass construction.

The boat has a wide beam that ensures she’s steady no matter what. Crew-weight shifts or sudden crazy jibes that may happen along the way won’t do a thing to this boat. And even the most fearful and unsteady learner won’t fall out of it. It will take a tremendous effort to capsize this beautiful boat, making it one of the best daysailers any daysailer (or intending daysailer) would want to have.

But stability and durability are not the only pluses for the Hunter 15. It has a self-bailing cockpit that allows any water that gets into the boat to exit quickly. There is room enough to comfortably accommodate up to four people.

Getting a durable and high-performance sailboat that will cruise smoothly on the water is one thing; finding convenient storage is an entirely different ballgame. Thankfully, you don’t have to spend extra cash when it comes to this boat. The sailboat can fit into your garage while sitting on a trailer. And here’s another good thing with Hunter 15; you don’t have to worry about varnishing wood afterward.

But perhaps the best part of the Hunter 15 is that it is a very affordable boat. Although sailboats don’t come cheap, you don’t have to break the bank to own one of the beauties.

Prices for a new one range from around $10k, and you can find used ones for less. Check out the listings of Hunter 15 and other equally excellent models of the Hunter sailboat.

Ready for some painless daysailing? Renowned designer, Chuck Paine, has something classy and beautiful for you. The Paine 14 (obviously named after the designer) is a trailerable sailboat with exceptional performance and purposely styled after the traditional Herresholf 12 1/2 boat, except for its size. Paine 14 is a lot smaller in all aspects, which accounts for its considerable lightness.

It is fitted with a modern spade rudder and fin keel, giving the boat more agility and speed as she sails. And even with a lead-ballast keel almost her total weight, this sweet, small vessel maintains stability at top speed.

But why is a boat with an old-time appeal be listed among the best daysailers? Simple. It is a blend of the classic old and modern performance. Indeed, it is constructed from cold-molded wood with varnished gunnels and transom, but don’t be fooled by that century-old look.

Chuck Paine worked some modern magic into this cute beauty with the inclusion of a carbon mast and an extremely easy way to attach sails to it. Setting up sail is quick and simple, and you can get it done and over with in only a couple of minutes.

The boat can be gaff-rigged, or you can use a Marconi rig. Got a standard car? That’s all you need to trailer this light sailboat, and you are good to go.

Check here for Paine 14 listings .

 Chuckpaine  →

If you want a sailboat that will get your adrenaline pumping and bring out the competitive sailor in you, perhaps you should take a look at the Laser .

The 13-feet 10-inch Laser boat is not included on the list of the best daysailers for nothing. It is raced both as club races and as an international sailing category, featuring in world-class competitions, including the Olympic sailing championships.

However, you don’t have to take part in a competition to enjoy sailing this boat. And you definitely don’t need it for exercising. The Laser is a great choice even if you simply want to enjoy plain smooth sailing just for fun.

The Laser boat has an incredibly lightweight build with fiberglass and a powerful sail. It is an excellent choice for a single cruiser and works well for two adults, too. Be warned, though. It can easily capsize because it is lightweight, but it will also recover just as fast, too!

The boat is easy to transport, launch, and store, thanks to its kick-up rudder. Laser Performance built this model to have a single sail, two-part mast design, with a daggerboard.

This sailboat is very affordable. Prices start from $7k for new boats, and you can find used ones for far less than that. Check here for Laser boat listings .

You can’t go wrong with a design that has been in existence for over five decades and with more than one hundred thousand boats launched since it debuted in Southern California. The Hobie 16 is a long-lasting design that has stood the test of time and attracts quite a following.

This sailboat weighs only 320 pounds, so it is conveniently trailerable. It has ample room to accommodate a crew of four without straining it. The hulks are built from asymmetric fiberglass sandwich and come with kick-up rudders. This gives you the option of sailing all the way to the beach.

The Hobie 16 is designed to have great speed, thanks to its abundant high-speed gear. But that’s not all. It is also equipped with a spinnaker, a trailer, and a douse kit. The main and jib offer a wide sail area of more than 200 square feet.

Both adults and kids will enjoy having lots of fun in this spacious sailboat, especially in the summer. Little wonder it is one of the very best daysailers available on the market.

The Hobie 16 is a high-performance boat with starting prices for new ones in the $12K range. You can find used ones at a little less. But if you want a simpler, smaller, and more affordable option, take a look at the Hobie Cat Wave . It is not a high-performance design, but it offers loads of fun, too. It comes with roto-molded hulls and fitted with a boomless mainsail. This smaller version costs almost half the price of the 16’s, which is a pretty good bargain.

NORSEBOAT 17.5

Looking for one of the best daysailers that will stand out from any crowd? The Norseboat 17.5 might just be the perfect sailboat for you. Dubbed as the “Swiss Army Knife of Boats,” this one-of-a-kind sailboat can be sailed or rowed.

But wouldn’t it take a lot of effort to row this boat? No. Not with the boat’s sheer. The fiberglass hull has lots of sheer – a deliberate and apt design to make rowing easy-breezy. So, even if there’s no wind, you can still have fun rowing while getting some exercise in the process. And if the wind is strong enough, you can relax and let the jib and mainsail do their thing.

The Norseboat 17.5 is the perfect choice for daysailers searching for a high-performance boat that comes with beautiful traditional lines. But even if you are a sea kayaker who is looking to move up, or a cruising sailor seeking to downsize a bit, you’ll find this legendary pedigree to be a good fit for you.

Some of its features include a fully battened mainsail, pivoting carbon mast, shallow draft, furling headsail, and a signature curved headboard. The lightweight boat comes with two rowing stations and performs excellently well, whether wind-powered or rowed. Plus, it has plenty of room to stow stuff.

The boat’s light weight makes transportation easy. All you need is a mid-sized car, and you can easily tow it. Storage is equally hassle-free, as the sailboat can fit into any standard garage.

Check out the current listings for Norseboat 17.5 .

 Norseboat  →

Traditional daysailers are small sailboats that you can take for a quick spin around the harbor. They lack accommodation primarily because they are not designed for spending the night (it’s even in the name!). But all that has changed over the years, and that distinction is almost non-existent with modern designs such as the Fareast 18 .

The boat is a Simonis Voogd design with incredibly high performance, high speed, low maintenance, and comes at a comparatively affordable price. The mainsail has a fully battened square-top and an asymmetrical spinnaker. This is an excellent choice for buoy racing with enough room for a crew of six to compete.

While you typically will not spend the night in a daysailer, there’s nothing wrong with taking a short break below deck. The boat can comfortably sleep up to three just in case you decide to spend the night on the water.

Fareast 18 design features a foam-core hull/vacuum-infused fiberglass, a carbon-structured contemporary bulb keel, and vacuum-infused foils. This high-tech boat is small enough to be rigged and launched by a single sailor.

Even with only one foot of water, this boat will float with the keel retracted and the rudder off. And it is quite easy to trailer this boat.

Check for the current price of new Fareast 18 boats .

 Fareast  →

If you are in the market for a top-class daysailer, you might as well take a look at the Saffier Se 33 UD . Hennevanger brothers, the designers, threw in a lot of know-how and investment to bring this dream boat to reality. The production facility shows in the vacuum-infused build and quality finish of the boat.

Saffier has a collection of models that range between 21 feet and 37 feet, with each boat thoroughly tested to ensure seaworthiness. Considering the size of these boats, one will naturally assume they will be difficult to sail. But that’s not the case with these boats. Even the largest models can be sailed single-handedly and quite easily.

The Se 33 UD was launched in 2014 and done a sporty design. It sails smoothly in all weather conditions, thanks to its solid sprayhood. The sailboat features a practical self-draining cockpit to expel any water that gets into the boat. Included in the cockpit are a folding transform and two-meter benches. The boat is spacious enough for a crew of four, and you can even take a quick nap below.

This top-class boat is an excellent choice if you have deep pockets. Starting prices are in the range of $150k for new boats. You can also check out the new Se 27 model if you want something that is serious fun. The new models can clock up to 20 knots.

For more on pricing, you can check out listings on these boats.

How to Choose the Best Daysailers – Buying Guide

With well over a hundred different daysailers on the market, it can be daunting to pick just one. Here’s what to look for when deciding on which open sailboat to buy for yourself or family use.

Ease of Sail

How a boat behaves when the wind blows up can make it easy or difficult to sail. A lot of modern sailboats are incredibly fast and are great for racing, but can be quite tricky to handle.

You want to look for an open boat that is tamer and stable. This is the perfect choice for a family day sailing boat, especially if you want to encourage kids to learn to sail. Look for a boat that is heavy enough to remain stable regardless of the crew’s acrobatics. It should be easy to rig, launch, and sail, even by a single person.

Reliability

While it is okay to take proper care of your boat, it is equally important to choose a boat that is easy to maintain. Go for boats with hulls designed to a beating without breaking down. Pay attention to the sails, too. Select one with tough sails that won’t easily blow out of shape after just one season of sailing.

Choose a Daysailer with Safety Features

Whether you will be sailing alone or with your family, safety should come first. Pick a boat that can cope with trouble in any condition or weather, and both on rivers or open waters. Look for a sailboat with positive foam floatation. Even if the hull gets filled with water or is punctured, the boat shouldn’t sink.

But because you cannot completely rule out manufacturing errors, even the best daysailers with safety designs can still capsize. However, you should look out for one with a “self-rescue” feature. In other words, choose a boat that rides very high even when it capsizes, so that the weight of her crew will quickly get her to recover without external help.

High Performance

Safety and stability are great, but that shouldn’t translate to a dull boat. You want a sailboat that provides safety as much as it offers some level of fun and exciting challenge even with your family on board.

Ample Space

Daysailers are typically small sailboats, but they should provide enough room to suit your purpose. Whether you want to sail with your family or a few friends, choose a boat that can comfortably accommodate the entire crew.

While not a requirement, a few modern designs include overnight abilities. Consider choosing these types if you spend a lot of time in the open water, even if you are primarily using an open daysailer. You never know when you will be tempted to spend the night cruising in the open water.

About Chris

Outdoors, I’m in my element, especially in the water. I know the importance of being geared up for anything. I do the deep digital dive, researching gear, boats and knowhow and love keeping my readership at the helm of their passions.

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