Hey everyone, you may have heard of it, may have even tried it, though this is mainly for those who don’t know and may like it. Day sailing.

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A daysailer, day sailer, or dayboat is a small sailboat with or without sleeping accommodations but which is larger than a dinghy. Dayboats can be monohull or multihull, and are typically trailer-able. Many dayboats have a small cabin or “cuddy” for storage and to provide shelter, or for sleeping in, but which is not always large enough to stand erect in. Dayboats’ greater stability also distinguishes them from dinghies and are generally sailed more like a small yacht than a dinghy. For example, although crew weight may well be shifted to increase performance, this is not crucial to stability, as it is in a dinghy. The distinction between keelboats and day sailers is not always clear. Generally, a keelboat is a large boat (over 27 feet (8.2m) and usually not trailer-able) used for longer trips, whereas daysailers, as the name implies, are used for trips less than 48 hours, and often only a single day.

Basically, it is a small sailboat used for sailing in the day.

Whatever their design, all good little boats have one thing in common: they’re tons of fun.

Categories of Day Sailers

Traditional under 20 foot


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Modern Classics



Family boat/Trainers

Why is day sailing fun?

Athletic, good for keeping in shape

Close to the water, exhilarating

Builds skill set that allows you to sail any boat properly and even competitively

There are tons of dinghy/day sailing regattas, and rentals are available in many places for fun day sailing!

Many Day Sailers are for going out during the day and a lot of them are for racing.

Some of the best day sailers under 20 ft that can be raced also

The term daysailer is a tricky one, because any sailboat can head out of the harbor for a daytime sail, even those equipped to cruise overnight or for longer periods. Yet when your sailboat is shorter than 20 feet, you’ll usually find it’s easier to get underway, easier to handle under sail, and cheaper to buy and maintain. If that sounds like good value to you, take a look at our list of some of the best true daysailers we know of.

Hunter 15


If you’re looking for an affordable, new, low-maintenance knockabout for teaching your kids to sail, the Marlow-Hunter 15 may be your best bet. With fiberglass construction and high freeboard, you can do a lot to this boat without capsizing, breaking it or falling out of it.

The 15’s self-bailing cockpit means that shipped water can find a fast exit, and the wide beam will keep her steady no matter what crazy jibes or crew-weight shifts happen along the way. Up to four can sail together and at the end of the day, you can store it on a trailer in your garage

Catalina 16.5

Catalina Yachts may be known for their larger cruising boats, but they build plenty of small ones, too. The Catalina 16.5 is a hand-laminated fiberglass sloop that’s one of their most versatile and can be purchased with a choice of centerboard (draws 5” with the board up) or a shoal-draft keel (4’5”). Buy the centerboard version if you need to store on a trailer; the lead-keel version has the stability to remain parked at the dock or on a mooring.

Like all boats built by Catalina, this 16’4” boat has a huge self-bailing cockpit. Forward, there’s stowage space and a waterproof hatch. Standard equipment includes hiking straps and a tiller extension, so you can get out on the side deck for good visibility forward and a bit of spray in your face.


For exercise and adrenaline rush in a breeze, or just plain smooth sailing in lighter winds, the 13’ 10” Laser dinghy is a great choice for one or two adults. That’s assuming you’re OK with the fact that the fiberglass boat’s light weight and powerful sail makes it easy to capsize—as well as recover.

The Laser is raced as an international sailing class; competition ranges from Olympic sailing championships to simple club races. However, most of the 200,000 boats that have been built over the years are simply sailed for fun, in part because the 1969 design has a single sail, a two-part mast, daggerboard and kick-up rudder that make it relatively easy to store, transport and launch.

Hobie 16

Another long-lasting design with a great turn of speed and space for four on its trampoline is the Hobie 16 beach catamaran. More than 100,000 of these have been launched since 1969 when they made their debut in Southern California. The Hobie 16 is trailerable, can carry a crew of four, and weighs only 320 pounds.

Sage 17

Designed by Jerry Montgomery in 2009, the Sage 17 is a stable little go-anywhere sloop.Solid no matter where you stand, the boat has a carbon-fiber deck, cabin roof, and transom, with balsa core in the horizontal deck areas. All of that is mated to a faux-lapstrake fiberglass hull made with vinylester resin. The result, according to her designer, is a 1,300-pound boat that is lighter and faster than his ‘70s design, the very popular Montgomery 17.

NorseBoat 17.5


Here’s something completely different—a boat that bills itself as the “Swiss Army Knife of Boats” because you can sail it or row it. With traditional styling, the NorseBoat 17.5 is a performance boat whether human or wind-powered that features two rowing stations and lots of room to stow stuff.

The mast and sails are an option, although it would hard to daysail without them. New boats are offered with sailplans featuring a fully battened mainsail set either on an unusual curved gaff or a rigid headboard. The mast is free-standing and made of carbon fiber, and you can also set the optional furling headsail from the sprit. For maximum ease of use, you can trailer the boat and store it in your garage.

FarEast 18

Built in China, the FarEast 18 is a 19-foot Simonis Voogd design that emphasizes high speed with low maintenance at a relatively modest price. It carries a square-top fully battened mainsail and a sprit-flown asymmetrical spinnaker. A kick in the pants for buoy racing, this daysailer can compete with six crew, but will also sleep three below if you decide to stay out overnight.

Paine 14

If you want a classic beauty with up-to-date performance, look at the Paine 14, named for its well-known designer, Chuck Paine, and styled purposely after the century-old Herreshoff 12 1/2, e. The Paine 14 is scaled down—about 10 percent smaller in all dimensions—and lighter. With a modern fin keel and spade rudder, she’ll sail faster and be more agile, yet she maintains stability with a lead-ballast keel close to half her overall weight.

Built of cold-molded wood/WEST epoxy, the Paine 14 looks like a boat your dad might’ve sailed as a kid. With varnished gunnels and transom, this boat has old-time appeal. But Paine gave her modern features including a carbon mast and a new way to attach sails so the boat is ready to sail in minutes. The Paine 14 may be rigged with either a gaff or Marconi rig and can be trailered behind a standard car.

Lido 14

Most sailors learned to sail in a daysailer, the small boat has seating for six but can be singlehanded and even raced short-handed. Two hundred boats were ordered the first year the model was launched, and 40 years later, approximately 6,300 Lido 14s had been built. Today, although new boats are no longer available, you can easily find used boats for sale, a very active owner’s association and lots of one-design racing in different parts of the country.

Super Snark


Sea Skimmer

Sunchaser I and II

If you want to go fast and be close to water, it is a blast! For more ideas look no further than Olympic Sailing races in the Olympics. Which the way these guys are already preparing for sailing in Tokyo in 2020!

Their events:

Men’s events:


    470: two-person dinghy

    49er: two-person high performance skiff

    Finn: one-person heavyweight dinghy

    Laser: one-person dinghy

    Nacra 17 (mixed): multihull

    RS:X: sail board


Women’s Events:


    470: two-person dinghy

    49erFX: two-person high performance skiff

    Laser Radial: one-person dinghy

    Nacra 17 (mixed): multihull

    RS:X: sail board

Give it a try if you haven’t, we are sure you will enjoy it!

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