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40 Best Sailboats

• By Cruising World Editors
• Updated: May 24, 2024

Sailors are certainly passionate about their boats, and if you doubt that bold statement, try posting an article dubbed “ 40 Best Sailboats ” and see what happens.

Barely had the list gone live, when one reader responded, “Where do I begin? So many glaring omissions!” Like scores of others, he listed a number of sailboats and brands that we were too stupid to think of, but unlike some, he did sign off on a somewhat upbeat note: “If it weren’t for the presence of the Bermuda 40 in Cruising World’s list, I wouldn’t even have bothered to vote.”

By vote, he means that he, like hundreds of other readers, took the time to click through to an accompanying page where we asked you to help us reshuffle our alphabetical listing of noteworthy production sailboats so that we could rank them instead by popularity. So we ask you to keep in mind that this list of the best sailboats was created by our readers.

The quest to building this list all began with such a simple question, one that’s probably been posed at one time or another in any bar where sailors meet to raise a glass or two: If you had to pick, what’re the best sailboats ever built?

In no time, a dozen or more from a variety of sailboat manufacturers were on the table and the debate was on. And so, having fun with it, we decided to put the same question to a handful of CW ‘s friends: writers and sailors and designers and builders whose opinions we value. Their favorites poured in and soon an inkling of a list began to take shape. To corral things a bit and avoid going all the way back to Joshua Slocum and his venerable Spray —Hell, to Noah and his infamous Ark —we decided to focus our concentration on production monohull sailboats, which literally opened up the sport to anyone who wanted to get out on the water. And since CW is on the verge or turning 40, we decided that would be a nice round number at which to draw the line and usher in our coming ruby anniversary.

If you enjoy scrolling through this list, which includes all types of sailboats, then perhaps you would also be interested in browsing our list of the Best Cruising Sailboats . Check it out and, of course, feel free to add your favorite boat, too. Here at Cruising World , we like nothing better than talking about boats, and it turns out, so do you.

– LEARN THE NAVIGATION RULES – Know the “Rules of the Road” that govern all boat traffic. Be courteous and never assume other boaters can see you. Safety Tip Provided by the U.S. Coast Guard

40. Moore 24

39. Pearson Vanguard

38. Dufour Arpege 30

37. Alerion Express 28

36. Mason 43/44

35. Jeanneau Sun Odyssey 43DS

34. Nor’Sea 27

33. Freedom 40

32. Beneteau Sense 50

31. Nonsuch 30

30. Swan 44

29. C&C Landfall 38

28. Gulfstar 50

27. Sabre 36

26. Pearson Triton

– CHECK THE FIT – Follow these guidelines to make sure your life jacket looks good, stays comfortable and works when you need it. Safety Tip Provided by the U.S. Coast Guard

25. Islander 36

24. Gozzard 36

23. Bristol 40

22. Tartan 34

21. Morgan Out Island 41

20. Hylas 49

19. Contessa 26

18. Whitby 42

17. Columbia 50

16. Morris 36

15. Hunter 356

13. Beneteau 423

12. Westsail 32

– CHECK THE WEATHER – The weather changes all the time. Always check the forecast and prepare for the worst case. Safety Tip Provided by the U.S. Coast Guard

10. Alberg 30

9. Island Packet 38

8. Passport 40

7. Tayana 37

6. Peterson 44

5. Pacific Seacraft 37

4. Hallberg-Rassy 42

3. Catalina 30

2. Hinckley Bermuda 40

1. Valiant 40

• More: monohull , Sailboats
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Daysailer Review: The Hinckley 42

• By Dennis Caprio
• Updated: October 4, 2007

Hinckley Daysailer 42

Surely that was Merlin at the controls as the Hinckley Daysailer 42 quietly eased away from the float and headed into Somes Sound. Only the faintest hum accompanied our progress, because an electric auxiliary propelled this slim sloop. Although our helmsman, Peter Smith, head of Hinckley ‘s engineering team, seemed an ordinary mortal, the joystick control atop the steering pedestal revealed some pretty special powers: Simply moving the stick forward or backward created thrust, and the farther Smith moved it, the faster we went. Magical.

Only minutes beforehand, I’d been sitting in the conference room on the second floor of Hinckley’s dock house in Southwest Harbor, Maine, admiring the many boats moored in the harbor and chatting with Sandy Spaulding, at the time president of Hinckley Yachts ; Smith; Ed Roberts, vice president of production development and marketing; and John Correa, sales, about why the company decided to build and market this thoroughly upscale daysailer.

The company’s research, Spaulding told me, showed that the sailors who can afford a Hinckley of any size no longer have the time to appreciate all the space and amenities of a cruising boat. Some of those folks have already bought a Picnic Boat, the lovely and wildly successful (300 sold) 36-foot dayboat driven by a single diesel and propelled by a robust high-volume water jet. The company’s single-lever JetStick control had simplified operation and combined with great looks and spirited performance to endear the Picnic Boat to nearly everyone who tried her. In turn, the concept spawned a line of yachts from 29 feet to 55 feet.

Spaulding reckons that the Daysailer 42 will strike a similar chord with dedicated sailors and spawn a line of elegant sailing yachts. Hinckley turned to Bruce King for the design, an easy decision considering the stunning results of their prior collaborations. The design brief called for classic lines and lively performance; a special concern was ease of casting off, handling under way, and putting the boat to bed after the day’s sail. King contributed the artistry, Smith and his engineering/design staff lovingly filled in the many details.

Love at first sight will go a long way toward choosing buyers for the Hinckley Daysailer 42, because she is a glass slipper among hiking boots. Narrow for her LOA to reduce wetted-surface area and maintain the spirit of early 20th century designs, she extends her stem upward from the waterline like the arm of a prima ballerina performing “Swan Lake”. In profile, the curve of the stem recalls that of N.G. Herreshoff’s Buzzards Bay 25. The counter stern echoes the arc of the stem, providing a delightful aesthetic balance to the yacht’s profile. Seen from either after quarter, the delicate tumblehome in the stern will interrupt your breathing. Painted nonskid on the decks gives the feel and look of the painted canvas common in the days of construction in wood. The substantial bulwarks should discourage owners from requesting lifelines, further reinforcing the classic theme.

Classicism usually equals restraint, except in the grand gestures-and the DS42’s seemingly excessive crescent-shape rocker profile certainly qualifies. Sacrificing a significant chunk of waterline length is worth such an elegant overhang. The other compromise-if you hope to provide comfortable sitting headroom in the accommodations and a low profile in the trunk cabin and topsides-is a deep canoe body amidships. The deep underbody of the DS42 and the wave-making resistance it creates limits her top speed. Will anyone care? I’ll wager not, at least among the seriously interested buyers, because the DS42 is all about the pleasure of hassle-free sailing-of slowing one’s frenetic life for an hour or two (or more) of sailing in peace when the mood strikes. Truth is, the mood will strike more often than not. One look at the Daysailer 42 will set a sensitive sailor’s fingers tingling with the feel of the wheel between them.

Hydraulically powered, sail-handling gear makes the DS42 a genuine solo machine. Pressing a button hoisted the mainsail from its Leisure Furl boom. Pressing another button unfurled the non-overlapping jib. A row of six buttons, three each side of the steering-wheel well, control the main sheet via a substantial hydraulic ram, tucked under the side deck on the port side of the cockpit. Each button wears a guard to prevent the helmsman from accidentally trimming or easing the main as he moves around. A reasonably dexterous big toe can open each of the guards; if shod you’ll need a hand to open them. Hinckley could have chosen only three buttons and placed them on the centerline, but having three each side places them a most convenient reach away, whether you’re helming from the high side or low. One of the buttons eases the main, one of them trims it, and the third provides a high-speed trim, which is great for quick jibes.

Main hoisted, we bore off a bit to let the wind fill the jib as Correa fingered the button that controls the primary winch on the starboard side. We selected a port tack in a true wind of 10 knots, and Smith motioned me to the helm. The Daysailer 42 gracefully heeled to the wind and accelerated to her hull speed. Oh my, the steering was superb, about as creamy and accurate as you’re likely to find in any yacht. Befitting her style, the 42 likes gentle inputs from the wheel. Although the lifting keel (a stainless steel fin with a lead bulb at the tip) has limited the depth of the rudder to about four feet, well-chosen sections and surface help the helmsman keep the yacht in her groove.

Narrow sailing yachts generally behave very well in all conditions, and the DS42 is no exception. A narrow hull maintains fair waterlines as it heels, which balances the yacht and discourages unpleasant steering characteristics. Their minimal wetted-surface area also makes them ghost well in light air. Combine this light-air ability with a responsive helm, and you can forget about the auxiliary until the wind stops altogether or you have to battle a current to get to your destination.

Belowdecks, the accommodations are tight by the standards of a 42-foot cruising yacht , but well in keeping with the Daysailer 42’s role as daysailer/overnighter. Once you’re seated on one of the settees, though, the saloon grows to a cozy sanctuary. I’d be perfectly content to spend a few nights aboard the 42, cooking on a two-burner propane camp stove, lounging in the huge cockpit or snuggled into the V-berth with a book and a single-malt Scotch. Yes, the trunk that houses the lifting keel intrudes on the saloon, but this hardly matters. I predict that its presence will become one more thing to fall in love with aboard the DS42, a truly captivating personality under sail.

Contact: Hinckley Yachts, (207) 244-5531; www.hinckleyyachts.com .

_ Read more about Hinckley yachts._

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