Best Daysailers, 20 Feet and Up

When it comes to sailboats, what's simple and small is often more beautiful and more fun than a bigger, more complicated boat. Even when price is no object, if your favorite sailing is romping through an afternoon breeze on your local lake or bay, do you need to buy a 50-footer? Here are five of the best takes on daysailers that will get the job done without the need for long slips or massive maintenance budgets.

Harbor 20

For the ultimate kick in the pants, you can’t get much better in a compact package than the prolific Harbor 20.

Designed by Tom Schock in 1997, this versatile boat is evergreen and a true daysailer. Responsive and steady, it’s the best sailing teacher you’ll ever have and even if you sail one poorly, you’ll still get where you’re going.

The rig is deceptively simple, with a traditional mainsail from which you can eek out good sail shape and a self-tacking jib on a Hoyt boom and a roller furler. With tiller steering and all lines led to the forward bulkhead, there are no winches to tend so single-handing is easy—yet four can enjoy sundowners in the spacious cockpit.

Electric propulsion includes a motor that lifts and swivels out of the transom compartment and tucks away when under sail. The bow has plenty of stowage space as well as room for a cooler and batteries. Other than that there’s really nothing much to it, which makes it easy to sail and even easier to put away at the end of the day. Best of all, it only takes about five knots of breeze to get a Harbor 20 moving. That means you’ll be out on the water more often even if just for a quick afternoon respite after work, enjoying the simple joy of sailing as it was meant to be.

Read our review, Boats We Love: The Harbor 20.

Tartan Fantail 26

The Tartan Fantail 26 cockpit is nine feet long, so there’s plenty of room for crew even with the use of a long tiller.

Tartan tapped their longtime designer, Tim Jackett, to design a 26-foot daysailer with striking classic lines but new-world performance. Jackett obliged, drawing a plumb bow with a fine entry and a slight sheer, which all blend together beautifully. But below the waterline, Jackett made sure she would be a contender in club races. Her underbody includes a deep keel with a 1200-pound bulb and a high-aspect-ratio rudder to keep a good grip even when heeling. Combine that with her high-tech lightweight vacuum-infused and balsa-cored construction, and the new Fantail is a beauty above and a beast below.

This sailboat has one sweet and easy ride. Tartan’s signature fractional rig, pocket boom with an integral mainsail cover, and lazyjacks make it easy to manage single-handed. A carbon fiber retractable sprit serves as the attachment point for the asymmetrical spinnaker on a furler. The DS and WE come with a self-tacking jib with a double-ended sheet, while the ST has a traditional headsail. For the racer with big-boat aspirations, a carbon-fiber single-spreader mast and laminate sails are optional.

Watch our Tartan Fantail 26 Video Short Take.

Catalina 275 Sport

If you’re looking for value and performance in an easy-to-manage sailboat, look to the trusted Catalina Yachts brand.

Part of Catalina’s Five Series, the 275 was created by designer Gerry Douglas to sail around the buoys or cruise sweetly on relaxing weekend overnights. This entry-level model includes a hand-laid fiberglass hull, a one-piece resin-infused deck, a five-year warranty and Catalina’s famous “Strike Zone” forward impact bulkhead. The 275 Sport is also trailerable so you can tow it to your favorite cruising grounds—and with a beam of just 8’ 4”, you won’t need a special permit. Gear is small and easy to manage, so the boat inspires confidence for newbies and old salts alike.

The fully battened mainsail has slab reefing, and the self-tacking 90 percent headsail has a traveler mounted just forward of the single-spreader deck-stepped mast. The cockpit is huge and dominates the length of the boat, which is a Catalina trademark. The cushions overlap and cover the center track so you can stretch out in comfort when lounging, and the transom is open for easy boarding from dock, dinghy or the water.

The 275 does have a cabin with reasonable accommodations for its size. The cabin below includes a compact galley with a sink and one-burner butane stove. An enclosed head has a manual toilet and sink and there are two long berths that double as seats that flank a drop-down table. Another berth is aft, long enough to store lots of gear or boat toys. Under the companionway steps, you’ll find the 15 HP inboard Yanmar diesel that will reach a top speed of seven knots. There’s even a garage space to port, accessible via the cockpit, where you can stow fenders, lines and maybe a gennaker for real downwind fun.

Read our full review, Catalina 275 Sport: Affordable, Easy, Smart, and Fun.

C.W. Hood 32

If you’re all about sailing well and looking good while doing so, the C.W. Hood 32 may be the answer.

This head-turner has classic lines and long overhangs that will demand attention anywhere she goes. A graceful sheer complements a flush deck that recalls the slender racing hulls of years gone by. Classy and responsive, this is the boat you need if you just can’t make peace with modern sailboat design.

Below the waterline, the Hood 32 is a bit of a wolf in sheep’s clothing. A contemporary spade rudder and aft-swept keel with its winged and flattened bulb make her a contender on the beer-can circuit. The folding prop ensures that sailing performance is not hampered, and the boat draws only four feet. The rig is keel-stepped and aluminum or for the aspirational type, it can also be carbon fiber. The tiller and rudder come standard as all carbon. There’s also a choice of wire or rod rigging, and the sail plan includes a self-tacking jib and fully battened main with lazy jacks. A real commitment to the overall aesthetic is the below-deck headsail furler that keeps the topsides clutter-free. The cockpit is large and will easily seat six for a sundowner cruise. Like the true daysailer she is, the Hood 32 has no accommodations below – just lots of stowage space for gear and sails.

Read our full review, C. W. Hood 32: A Classic Daysailer with Modern Advantages.

Corsair Sprint 750 Mark II

For something completely different, how about a multihull daysailer with ripping speeds up to 20 knots? Meet the Corsair Sprint 750 Mark II trimaran, a slippery 24-footer that weighs just 1,800 pounds and folds so it can be trailered (or stored) anywhere.

Based on the previous Corsair 24, the Sprint 750 Mark II draws 5’ 3” with the daggerboard down or just one foot with only the hull. Expanded and ready for sail, the beam is over 17’, but folded the boat is only 8’ 2”. The 34-foot mast is a rotating aluminum wing with synthetic shrouds and stays. Laminate sails with low stretch ensure performance that will make your friends envious and the carbon-reinforced vacuum-infused construction makes this rocket ship light but strong. Tiller steering provides good feedback from the rudder and two Harken winches with four clutches manage most of the lines aboard. A retractable bowsprit holds an optional asymmetrical spinnaker on a top-down furler.

The gray PVC-coated trampolines between the amas and on the bow give the Corsair acreage “on deck,” while the cockpit will accommodate four crew comfortably. There’s not much to the space below because this boat is stripped out for racing. A portable MSD means you can sail all day and a small berth forward will probably be used to store sails and gear. An eight HP outboard is recommended for auxiliary power.

Read our full review, Corsair Sprint 750: Trailerable Sailing Fun.

All these compact designs are meant to remind you of how sailing used to be, before 50-footers became the standard fare at boats shows. Some of these small boats are meant to be crewed and some single-handed. Some are striking as they glide by, others are practical so they can be comfortably handled with minimal hassle. But all are versatile daysailers that are just plain fun—and that’s exactly why small is smart.

Written by: Zuzana Prochazka

Zuzana Prochazka is a writer and photographer who freelances for a dozen boating magazines and websites. A USCG 100 Ton Master, Zuzana has cruised, chartered and skippered flotillas in many parts of the world and serves as a presenter on charter destinations and topics. She is the Chair of the New Product Awards committee, judging innovative boats and gear at NMMA and NMEA shows, and currently serves as immediate past president of Boating Writers International. She contributes to Boats.com and YachtWorld.com, and also blogs regularly on her boat review site, TalkoftheDock.com.