small dinghy sailboats

10 Best Small Sailboats (Under 20 Feet)

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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Daniel Wade

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

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It’s no accident most of the world’s top professional sailors got their start in small boats. But for those of us that missed the boat learning to sail as a kid, here’s the great news — there’s no age limit on learning to sail! And you don’t need to eye up an F50 foiling catamaran in SailGP to have a good time either. Whether you’re 24 or 40, sailing small boats can provide a much needed escape and open up a whole new world of practical skills, fun on the water and break from work and routine. 

If you're looking to enjoy the tranquillity of cruising on a lake or exploring the coastline, or have your sights set on the vast expanse of the open ocean, mastering the art of a sailing dinghy is a rewarding and affordable way to begin your sailing adventure. But how do you know which is the best boat for you? And where do you try one first? And how much will it cost?

In this article, you’ll get answers to all the FAQs about learning to sail so you can feel confident to give it a go. And we’ll look at the 8 best, most fun small sailboats for you to try!

FAQs: Why can’t I learn on a big boat? What are the benefits of learning in a small boat? Is learning to sail expensive? Where can I try a small boat out first? How much does a small boat cost? Where can I buy a small sailboat? What’s the best small boat for me?

8 Funnest Small Sailboats to Learn to Sail: 1. Optimist 2. Flying Junior (FJ) 3. RS Feva 4. Laser 5. Sunfish 6. 420 7. Wayfarer 8. Hobie Cat

Small boats are better than big boats for learning to sail in

Why can’t I learn on a big boat? 

You can! Plenty of sailors have learned to sail through crewing on bigger keeler boats. But I 100% recommend starting out in sailing dinghies for many reasons:

They’ll teach you more quickly how the boat moves in wind

You’re in control and your own actions and adjustments are immediate and obvious (you’ll learn quicker what went wrong, or right!)

You’ll experience the effects of those in a safe environment, with no major consequences – aside from getting wet!

What are the benefits of learning in a small boat?

Small boats are good for your budget.

Sailing dinghies are an awesome way to give sailing a go without a big investment up front. After all, you want to make sure you enjoy it first right? Smaller boats are much cheaper to buy, maintain and repair, and store.

It’s fun for everyone

Get your family, or a group of mates involved — it’s an awesome way to spend time together mucking about in the water. On a small boat, it’s quick and easy to set up to give it a go and have a great laugh. Small boat sailing’s a pretty fun summer session — and if you’ve got kids doing it with you — that’s the kind of fun experience they’ll remember forever #memories.

You’ll experience tiller steering

A small sailing dinghy has tiller steering — that’s a long lever attached directly to the rudder (as opposed to a steering wheel, which is connected via a mechanical, electrical, or hydraulic system). The benefits of learning to sail with a tiller is that you’ll start to immediately feel if the boat is out of balance, compared to wheel steering which is less intuitive. Your ability to feel the boat responding and keep wind, sail and boat position in balance will be more sensitive learning with a tiller.

You can give racing a go

Sailing small boats may just ignite your competitive spirit with racing regattas! There are many different classes of sail racing offered through most clubs, from dinghy sailing through to keeler races. While many at a high-level do have age class brackets, there are still plenty of options to get involved with at any age. There are plenty of women only sailing events if you’re keen to get involved for the first time . 

Is learning to sail expensive?

Only if you buy a big boat ! Learning to sail doesn’t have to cost a lot. There’s likely a local club nearby that runs affordable adult and family friendly learn to sail classes — either for a one off course fee, or as part of the club membership. Most clubs have an ageing membership and are actively encouraging new people to sail so membership fees are kept as low as possible. They’re especially supportive of the younger generation!

Regarding sailing gear, don’t rush out and buy any expensive sailing gear until you get a feel for sailing, your style of boat, and what the conditions are like for your area. Then you can better choose a wet weather jacket and sailing gear that’s going to suit you. I do recommend you invest in a pair of sailing gloves early on though ( see my top glove picks here )

Where can I try a small boat out first?

Look for a local club with Learn to Sail classes — you’ll be able to get out on the club boats and try those. Most have a fleet of Sunfish (or similar) dinghies to learn to sail and race in. Once you’re comfortable and the sailing bug has bit (it’s catchy and sorry I don’t have the cure) you can look to buy a small boat of your own.

How much does a small boat cost?

Anywhere from $100 to $12,000US depending on the age and type of boat. It’s highly likely you can pick up a used sailboat for a good price, but if you want to spend more (and deck your boat out with the latest high-specs) — you’ll be able to! Remember with costs you will need to factor in the transportation or storage of your boat too. For example, you may need to buy a trailer to transport your small boat, or pay rental to a local marina or yacht club to store this onsite.

Where can I buy a small sailboat?

If you’re looking for a second hand boat, sailing clubs often have small boats available to sell — whether they’re retiring some of their own fleet, or there are members who have upgraded. Keep an eye out on club noticeboards, newsletters or ask around. If you’re in the Learn to Sail classes, you’ll likely meet someone who knows someone who’s got the boat for you!

Alongside my detailed list of the best places to buy a used boat , here are the most popular websites that sell small sailboats:

Boats.com (International) Sailsport Marine (USA) Dinghy Shop (USA) Apollo Duck (UK) Dinghy Mart (UK) Kajiji (Canada) Boat Sales (Australia) Gumtree (Australia) Trademe (New Zealand)

What’s the best small boat for me?

For beginners, selecting the right boat to buy is crucial, as it can make the process of learning more manageable and enjoyable. That’s why I recommend trying a few boats out through a local sailing club first. It’s good to know about the common types of small boats and how they’re different from each other, so now we’ll explore some of the best small boats on which you can learn the ropes and sail with confidence. Note: Sailing dinghies are specifically designed to be sailed by a certain number of crew, and sail at their optimum speed with maximum boat and crew weight ranges (this is more important in racing class rules). For example, adults usually skip the Opti dinghy (usually sailed by under 15’s) and go straight to a bigger size sailboat like the Sunfish or Laser. To guide you on boat size and if you’re looking to sail on your own or with others, I’ve included the length of boat over the water, and indication of number of people and sails onboard.

8 Popular Small Sailboats to Learn to Sail In

Optimist dinghy.

Smallest of the dinghies is the Optimist

Length: 7.67ft / 2.34m Designed for 1 or 2 kids or petite adult, 1 sail

The Optimist dinghy, commonly referred to as the Opti, is a globally recognized sailboat that has introduced countless young sailors to the world of sailing. Its compact size, stability, and simplicity make it an ideal vessel for beginners, especially children. With a single sail and a manageable rigging system, the Opti allows newcomers to grasp the fundamentals of sailing without feeling overwhelmed. Moreover, its buoyant hull design ensures safety, instilling confidence in young sailors as they navigate the basics of wind dynamics and boat control.

2. Flying Junior (FJ)

Fly along in the FJ

Length: 13.22 ft / 4.03m Designed for 2 crew, 2 sails

The Flying Junior , commonly referred to as the FJ, is a robust and agile sailboat designed for both training and competitive sailing. Its sturdy build, stability and responsive rigging system make it an ideal choice for beginners eager to explore the dynamics of wind and water on a more challenging vessel. With a two-person crew, the FJ emphasizes teamwork and communication, fostering a sense of camaraderie and shared responsibility among novice sailors. Its performance-oriented design encourages learners to master the art of sail trim and weight distribution, preparing them for the intricacies of competitive sailing and more advanced boat handling techniques.

Catch sailing fever in the RS Feva

Length: 13.3ft /4.05m Double-handed dinghy for pre-teens and parent / child teams, 3 sails

The RS Feva is a modern sailboat renowned for its user-friendly design and versatility. With a spacious cockpit and a manageable rig, the RS Feva accommodates both single-handed and double-handed sailing, catering to a diverse range of skill levels and preferences. Its responsive nature and forgiving hull promote a comfortable learning experience, allowing novices to focus on refining their sailing techniques without feeling overwhelmed. The RS Feva's emphasis on adaptability and performance makes it a popular choice for sailing schools and families looking to embark on an engaging and rewarding sailing journey together.

Sharpen your sailing skills with the Laser

Length: 13.88 ft / 4.23m Designed for 1 crew, 1 sail

There are different Laser designs, however the Laser International is an Olympic class dinghy and widely acclaimed small sailboat known for its versatility and sportier performance. While it may appear more challenging compared to the Optimist and Sunfish, the Laser is an excellent option for individuals seeking a more dynamic sailing experience. Everything you need to know about sailing can be learned on this boat. With its responsive nature and adjustable sail controls, the Laser allows beginners to develop a deeper understanding of sail trim and boat balance. The popularity of the Laser International highlights the versatility of a boat — from learning to sail to getting involved in the racing scene.

Fun in the sun with the Sunfish

Length: 13.9ft / 4.24m Designed for 1 or 2 crew, 1 sail

The Sunfish is a super popular choice for those starting their sailing journey. Its uncomplicated design and ease of handling make it an excellent option for novices who want to develop their skills in a straightforward and stress-free manner. With a single sail and a simple setup, the Sunfish promotes a hands-on approach to sailing, allowing beginners to understand the impact of wind and water currents on the boat's movements. Its stability and responsive nature make it an enjoyable vessel for learning to tack and jibe, two fundamental techniques in sailing.

Any time is a good time for enjoying the 420

Length: 13.9ft / 4.2m Designed for 2 crew, 3 sails

The 420 sailboat is a favoured choice for sailing schools and clubs worldwide, renowned for its balanced design and versatility. With a responsive rig and a moderate sail plan, the 420 offers a smooth transition for beginners progressing from smaller boats to slightly larger vessels. Its two-person configuration fosters teamwork and communication, encouraging novices to develop coordination and cooperation while honing their sailing skills. The 420's manoeuvrability and stability make it an excellent platform for learning advanced techniques, such as trapezing and spinnaker handling, laying a strong foundation for future sailing endeavours. This racing dinghy holds status as a World Sailing International Class .

7. Wayfarer

Start your travels on the sea with the Wayfarer

Length: 16ft / 4.82m Designed for 1-4 crew, 3 sails

The Wayfarer cruising dinghy , built by Hartley Boats is renowned for its sturdy construction and versatile design, stands out as an ideal small sailboat for families and sailing enthusiasts seeking a reliable vessel for both leisurely cruising. It’s the most stable dinghy too! With its spacious cockpit, responsive handling, and adaptable seating arrangements, the Wayfarer offers a stable and predictable sailing experience, accommodating various crew sizes and sailing preferences. Its enduring popularity, strong class association, and supportive community make it a beloved classic in the world of small sailboats, embodying a perfect blend of performance, comfort, and inclusivity for sailors of all levels.

8. Hobie Cat

Start a fun hobby with the Hobbie Cat

Length: 16.7ft / 5.04 m Designed for 1 or two crew, 2 sails

For those drawn to the thrill of catamarans, the Hobie Cat (such as the 16 model) offers an exciting platform for beginners to delve into the world of multihull sailing. With its twin hulls and trampoline design, the Hobie Cat combines stability with speed, providing an exhilarating sailing experience for novices eager to explore the nuances of handling a more complex vessel. While it may require a steeper learning curve compared to traditional monohull boats (it’s harder to tack/change direction upwind), the Hobie Cat rewards learners with its ability to harness the wind and speed across the water. This makes it an enticing option for those seeking an adventurous introduction to sailing! Its asymmetrical hulls eliminate the need for dagger boards and is the perfect beach-launching catamaran. If you’d like to see these in action, here’s a great beginner video series for learning to sail Hobie Cats . 

All of these 8 small boats will give you a fun new sailing experience and help you to understand the relationship between wind dynamics, sail control, and boat balance. I have no doubt you’ll find one here that suits your goals and lifestyle. They’ll all give you an incredible foundation for future sailing in bigger boats.

There is a balance between finding the right boat for you, and not overthinking it. Most importantly, the best small boat is one that you have access to right now! Or the one you can manage yourself and will get you out on the water as soon as possible, learning and having fun.

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Check out our wide selection of small sailboats perfect for beginner family recreational day sailing or serious racing at the highest levels. From the classic Sunfish and Laser to the modern RS Aero and Rocket, we have the right boat for every sailor and the expert advice to make sure you're enjoying every minute on the water.

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