New and Used Daysailer Sailboats for Sale

Daysailer sailboats are small boats that can be used for small spins around the harbor, or even those inching up to around 40ft in length. With a wide range of sizes, you’re sure to find the right daysailer boats for sale for you below.

Search for a Daysailer Sailboat

Find New and Used Daysailer Sailboats for Sale

Sort By:


Best Daysailer Sailboat Brands and Builders

Daysailer Sailboat Buying Guide

What is a Daysailer Sailboat?

A daysailer sailboat – or sometimes a day boat – usually refers to a smaller sailing vessel that may have no sleeping accommodation, in the strictest interpretation of the word. But some daysailers have these accommodations, so the definition may not be quite so set in stone. There is also some debate on what size really deserves the daysailer designation, with some classifying a daysailer as larger than a dinghy (perhaps under 20 feet), but the larger size range seems to have some gray areas, with the LOA nudging up to 40 feet plus. Some of the more traditional, small boat daysailers are trailer-able and easily rigged and sometimes sailed single handedly. These sailboats may not have engines and may make use of outboard engines for power and use a single rudder or spade rudder system. A daysailer can also be a multihull and there are many boat design options to suit your particular taste. Some smaller versions are easily handled single-handedly.

What are Daysailer Sailboat Made Of (Construction Material/Hull Design)?

A daysailer sailboat can be built from many materials, including wood, vacuum infused fiberglass, metals, and even some with carbon masts. Most sailboat designs have displacement hulls, but it’s the keel that could make all the difference on how you use your daysailer sailboat. The keel usually counterbalances the force of the wind, and there are a few configurations for sailing vessels. If your daysailer is trailer-able, it would most likely have a moveable keel – either a daggerboard, centerboard, or lifting keel – that raises into the boat to enable easy trailer transportation. Some daysailers have fixed keels and remain in the water.

Certain pocket cruiser boats for sale may come equipped with a fully battened mainsail and those on fin keel boats may have a spade rudder making it easier to navigate (but more prone to damage from floating debris). Popular day sailing boats include the Catalina 275 Sport, the Hobie 16, the Hunter 15 model, the Norseboat 17.5 and the Paine 14 class. As you can see, most of these pocket cruisers are under the 20ft mark and make for fun days spent cruising around the harbor.

Why Should You Buy a Daysailer?

You should buy a daysailer sailboat if you have a love of solo sailing, being out on the water, or racing. A daysailer may offer the opportunity to get out with a minimum of fuss and time since operating a small boat – so you get to spend more time sailing and less time getting the boat prepped. A smaller daysailer can be great for racing and can be a fun and easy way to learn the intricacies of sailing while enjoying short daysailing. A larger daysailer with a few more amenities will allow you to spend your weekends on the water instead of simply short spins around the harbor.

And simply because they are not as large as other sailboats, doesn’t mean you can’t customize them or make a few upgrades! With options for carbon masts, fully battened mainsails, spade rudders and vacuum infused materials, your small daysailer can still turn heads when you cut across the water!

What is the Difference Between a Dinghy and a Daysailer?

The main difference between a dinghy and daysailer comes down to size. A dinghy is usually under around 20ft at the maximum, with daysailers sometimes stretching out to nearly double that size. Dinghy sailboats will never have cabins onboard, or even sheltered areas, whereas daysailers can sometimes have a cockpit below.

How Much Does a Daysailer Cost?

  • The exact cost of daysailer boats for sale will depend on a few things:
  • Age – Are you buying a new a Catalina 275 Sport model, or an older Norseboat 17.5, for example.
  • Condition – How has the boat aged, and does it need any work? Is it built of a long-lasting vacuum infused fiberglass, or of more vulnerable wood?
  • Builder – There are many fantastic builders and models to choose from – from the Paine 14 to the Hunter 15 and Hobie 16 models, each brand will come with certain pros and cons, with a price tag to follow.
  • Length – Larger models tend to cost more, although this isn’t always the case.
  • Boat design – Does the boat design set it apart for racing? Or offer more space and greater sail area?

While the price tag will vary, most daysailers will cap out around the $50,000 mark. Of course, if you have very high-tech sails or equipment, like carbon masts, a fully battened mainsail or vacuum infused resins, the costs could be greater.

What are Good Daysailer Brands?

With many enjoying day sailing or a pocket cruiser to spin around the harbor, or simply want a small boat to sail single handedly, there are a number of reputable daysailer brands to choose from: