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.



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.



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.



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.



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.



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.



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.


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.