40 Best Sailboats

We polled our readers to determine the best sailboats of all time.
the 40 best sailboats
Your 40 Best Sailboats stock photo

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.


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moore 24 sailboat

40. Moore 24

Designed by the legendary California sailor and surfer George Olson, the Moore 24 was one of the first ultra-light displacement sailboats, or ULDBs, and launched a whole movement of fast, fun speedsters based loosely out of Santa Cruz. A downwind flyer, some 160 boats were built in a 16-year production run that began in 1972. Moore 24s are still raced hard and often, even in offshore races like the solo Transpac. Courtesy of
pearson vanguard sailboat

39. Pearson Vanguard

With a sloping sheer line and gentle overhangs, the Philip Rhodes-designed Pearson Vanguard was an eye-catching yacht that was also built like the proverbial brick outhouse. In a four-year production run from 1963-1967, some 400 models were built, making it truly on the “vanguard” of the emerging fiberglass production boatbuilding era. stock photo
dufour arpege 30 sailboat

38. Dufour Arpege 30

Long before Beneteau and Jeanneau came to dominate the French import market, Michel Dufour was a key player in the industry, and his 30-foot Arpege was one of his greatest successes. First introduced in 1966, over 1,500 were eventually built, and with a spacious galley, nice sea berths, tremendous forepeak stowage, and other amenities, the boat was certainly ahead of its time. Courtesy of
Alerion Express 28

37. Alerion Express 28

The late California naval architect Carl Schumacher paired a modern underbody with the classic lines of Nathanael Herreshoff’s 1916 beauty, Alerion, to create this simple, fast and beautiful “gentleman’s daysailer.” The Alerion Express was so successful and struck such a chord that it spawned a whole new category of inshore cruisers from builders such as Morris, Hinckley, Friendship and others. stock photo
Mason 43/44 sailboat

36. Mason 43/44

The Mason 43, following its launched in 1978, quickly became a much sought after yacht for both the owner with an eye for traditional lines and the bluewater cruiser seeking a vessel to safely take him across any ocean. Designed by Al Mason and built by Ta Shing in Taiwan for Pacific Asian Enterprises (which went on to build the Nordhaven line of power trawlers), the 43 evolved into the Mason 44 in 1985, with design changes introduced by PAE’s Jeff Leishman. With a cutter rig and full keel with a cut-away forefoot, the Masons performs well under sail and below, the double-berth cabins fore and aft provide lots of comfortable space for the cruising couple or family. stock photo
jeanneau sun odyssey 43ds sailboat

35. Jeanneau Sun Odyssey 43DS

Designed by French naval architect Daniel Andrieu, the 43DS—for deck saloon—was one of the company’s first forays with the concept of adding a raised deck with plenty of windows for interior light and visibility, as well as increased volume and living space. Many other builders threw hats into the DS ring, but on a mass production scale, nobody was as prolific or successful as Jeanneau. Mark Pillsbury
nor'sea 27 sailboat

34. Nor’Sea 27

Small enough to load onto a trailer and drive to the next cruising ground but rugged and seaworthy enough to circle the world on its own hull, the Nor’Sea 27 exemplifies designer Lyle Hess’ notion of affordable boats that can take their owners as far as their dreams might lead them. With its full keel, round stern, lapstrake fiberglass hull, solid bulwarks and extended anchor roller and bow pulpit, the Nor’Sea 27 is a salty looking classic. Still in production today, the builder notes the boat has made at least four circumnavigations and hundreds of ocean crossings. stock photo
freedom 40 sailboat

33. Freedom 40

A former world champion Sunfish sailor turned marketing maven and boat designer, the visionary Garry Hoyt hit pay dirt with his engineless, cat-ketch rigged Freedom 40, which sported a centerboard and un-stayed spars. Hoyt swept all five races in the 1976 running of Antigua Sailing Week with his unique 40-footer, and a whole new brand of offshore cruisers was born. stock photo
beneteau sense 50 sailboat

32. Beneteau Sense 50

With regard to both systems and layout, the newest boat in our list, the Beneteau Sense 50, is also the most innovative and unique. From its Dock & Go docking system, to its single-level floor plan, to its spacious cockpit and interesting overhead arch, this thoroughly modern 50-footer was the first in a whole new series of Sense sailboats that invited sailors and designers to look at monohulls in a fresh light. Click here to read more about the Beneteau Sense 50.
To see more photos of the Beneteau Sense 50, click here.
Billy Black
nonsuch 30 sailboat

31. Nonsuch 30

Built by George Hinterhoeller in Ontario, Canada, unlike most catboats the Nonsuch 30 was rigged with an interesting and useful wishbone boom. But what really separated the 30-footer from other catboats and made it a classic was the thoroughly modern Mark Ellis-designed hull, which incorporated balanced ends, a fin keel and a spade rudder, which gave it surprisingly good upwind ability. Click here to read more about the Nonsuch 30. stock photo
swan 44 sailboat

30. Swan 44

A strong, robust cruising boat built for high-seas, blue water adventures, the Swan 44 was designed by Sparkman & Stephens, and the yacht’s well-known Finnish manufacturers, Nautor Swan, produced 76 boats in a production run that lasted from 1972-1975. With her understated profile and standard teak decks, many sailors consider the 44 the prettiest Swan of them all. Larry Moran, Chicago
C&C landfall 38 sailboat

29. C&C Landfall 38

With a tall rig, relatively light displacement (15,000 pounds), and available in either a deep fin (5’ 8”) or shallow draft (4’ 11”) configurations, the C&C Landfall 38 was a strong yet sleek sloop with outstanding sailing characteristics. Along with her 48-foot sister ship, the Landfall series bolstered C&C’s reputation as a builder of fast, versatile, high-performance cruisers. stock photo
gulfstar 50 sailboat

28. Gulfstar 50

Gulfstar Yachts, founded in Florida in 1970 by Vince Lazzara, a pioneer in fiberglass production boatbuilding, turned out a full line of roomy, affordable cruising sailboats, but arguably the best was the Gulfstar 50, introduced in 1975 and continuing in production until 1980. Its center cockpit design allows for an enormous aft owners stateroom, and because it was initially conceived for charter, it has proved a comfortable sailboat for families over the years. The boat remains a popular choice for liveaboards or those seeking an island escape. stock photo
sabre 36 sailboat

27. Sabre 36

The successor to a popular 38-footer, the Sabre 36 sports good-looking contemporary lines combining a sweet low profile and a striking reverse transom. A lively sailboat with a good turn of speed, the thoroughly modern sloop employed a Hall spar and rod-rigging, and was available with a fixed, 6’ 4” fin keel or a keel-centerboard that drew 4’ 2” with the board up and a deep 7’ 8” with the board down. stock photo
pearson triton sailboat

26. Pearson Triton

A vintage Carl Alberg creation with narrow beam, long overhangs, a large mainsail and small fore-triangle, the 28’ 6” Pearson Triton was designed to the influential CCA (Cruising Club of America) rule. Cousins Clint and Everett Pearson introduced the boat to commercial and critical acclaim at the 1959 New York Boat Show, which it took by storm. Before its production run was through in 1967, more than 700 Tritons were built. stock photo

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islander 36 sailboat

25. Islander 36

After the success of his maxi race boat, Windward Passage, designer Alan Gurney was one of the hottest names in the business when he was commissioned by Southern California’s Islander Yachts to draw a new 36-footer. The Islander 36 is emblematic of an era when boatbuilding thrived in California, and also represents one of the earliest and best dual-purpose “racer/cruisers.” Courtesy of Sailboats Northeast,
gozzard 36 sailboat

24. Gozzard 36

With its clipper bow, teak wheel, low-aspect cutter rig and detailed interior, the Canadian-built Gozzard 36 is one of the saltiest mid-sized cruisers from a sailing-mad country that produced scores of them. Built in the mid-1980s, the 36-footer looks like something from an altogether different era, and they still pop up in many a distant anchorage today. stock photo
bristol 40 sailboat

23. Bristol 40

No list of the best in cruising boat designs would be complete without an example of the great Ted Hood’s vast body of work, and the Bristol 40 gets our nod for numerous reasons. With her prominent overhangs, sweet sheer line, low freeboard, undistorted hull shape and narrow beam, this iconic 40-footer set high marks for seaworthiness and style. Courtesy of
tartan 34 sailboat

22. Tartan 34

Following the success of a Sparkman & Stephens-designed 27-footer, and a Ted Hood-designed 37-footer, the Ohio-based builders Douglass & McLeod returned to S & S for the third, 34-foot addition to the burgeoning Tartan line. Like her sisterships, the Tartan 34 was commissioned as a “high performance, offshore cruising-racing boat.” The handsome lines of this keel-centerboard craft have withstood the test of time. stock photo
morgan out island 41 sailboat

21. Morgan Out Island 41

Designed and built, at least originally, by the legendary Charley Morgan, the Morgan Out Island 41 was a success on multiple fronts: The shoal-draft cruiser was one of the first center cockpit boats, it played a pivotal role in the growth of the burgeoning bareboat charter trade, and it helped transform and streamline the business and methods of production boatbuilding. During a 20-year production run that began in 1971, over 1,100 OI 41’s were launched. Courtesy of
hylas 49 sailboat

20. Hylas 49

An evolution of the original Sparkman & Stephens-designed Hylas 47, the Hylas 49 took some very good ideas and made them even better. A collaborative effort between Hylas’s Dick Jachney and a Hylas owner named Tony Seibert, the 49, built in Taiwan by Queen Long Marine, had a lengthier hull (thanks to a sugar scoop transom), a redesigned deck, and a revamped interior with three dedicated staterooms. Like its predecessor, it was built for blue water. Courtesy of Hylas Yachts
contessa 26 sailboat

19. Contessa 26

No list of noteworthy bluewater sailboats would be complete without mention of the thoroughly capable and seaworthy Contessa 26. The diminutive cruiser was designed by David Sadler, built by J.J. Taylor & Sons of Toronto, Canada and a few other builders, and made forever famous by then 18-year-old Tania Aebi, who completed her solo circumnavigation aboard Varuna at the age of 21. What more can we say? Click here to read a full review of the Contessa 26. stock photo
Whitby 42 sailboat

18. Whitby 42

A husky, voluminous 42-footer that nicely addressed the sometimes conflicting requirements of long-distance voyaging and long-term living aboard, the ketch-rigged Whitby 42 has been a fixture in far-flung anchorages since it was first launched in 1942. Originally built in Canada with a long, fixed keel, in later years a centerboard version was introduced and named the Brewer 12.8. Read a review of the Whitby 42. Courtesy of East Coast Yacht Sales
Columbia 50 sailboat

17. Columbia 50

When first launched in 1966, the Columbia 50, by a large margin, was the biggest production cruising boat on the market. With moderate displacement and a very distinctive profile—particularly the long flush deck forward, combined with graceful overhangs and a unique but familiar cabin house—the Bill Tripp design was also available as a kit boat in the early 1970s. stock photo
morris 36 sailboat

16. Morris 36

The fourth and largest collaboration between builder Tom Morris and designer Chuck Paine—following the lovely trio of Frances, Leigh and Annie—the Morris 36 featured a powerful masthead double-spreader rig available as a cutter or sloop. At the launch, _CW’_s Dan Spurr wrote, “Chuck and Tom are quite the team when it comes to designing and building distinctive, quality cruising boats. Their latest lady is in keeping with the Maine boatbuilding traditions to which they are both loyal.” Click here to read more about the Morris 36. stock photo
hunter 356 sailboat

15. Hunter 356

Florida yacht designer Glenn Henderson was well known for his slick, spare, very competitive race boats before he took a job with Hunter Marine as chief in-house designer in 2000. The Hunter 356 was one of his first efforts, and was notable for its fine sailing qualities, combining shoal draft with a stiff, stable platform. Our Boat of the Year panel liked it so much they named the boat the Best Production Cruiser Under $200K for 2001. Billy Black
cal 40 sailboat

14. Cal 40

Designed by Bill Lapworth and built by Jensen Marine in Costa Mesa, California, the Cal 40 was nothing less than revolutionary, and displaced a mere 15,000 pounds, unheard of when first launched in 1964. The boat was a winner in the marketplace and on the racecourse, taking first and second in the 1965 Transpac from Los Angeles to Honolulu, and following that up a year later with a victory in the 1966 Newport-Bermuda Race. stock photo
beneteau 423 sailboat

13. Beneteau 423

With a company like Beneteau, which has produced dozens of models and thousands of boats, it’s hard to single out any particular vessel. But we like the 423 for many reasons that showcase the builder’s best qualities. Designed by Groupe Finot, the boat was quick and nimble, but not at the expense of a well-thought-out, comfortable interior. It also came in at under $200K, and like so many of her sister ships, offered a lot of value for the buck. Click here to read a full review of the Beneteau 423. Courtesy of
westsail 32 sailboat

12. Westsail 32

An upgraded version of the old Colin Archer-style turn-of-the-century pilot boat, despite a derogatory nickname (not a particularly speedy vessel, some jokers refer to it as the “Wet Snail”), the double-ended Westsail 32, of which over 800 were built, sailed countless sailors over distant horizons. The boat’s popularity peaked after it appeared on the cover of Time magazine in 1973 as an ideal vessel for chucking it all and heading to the islands. stock photo
CSY 44 sailboat

11. CSY 44

Originally conceived as a bareboat charter vessel, the CSY 44 was a ruggedly built mid-cockpit cutter also available in a pilothouse version. But the hefty lay-up schedule, moderate sail area and full hull sections made it as appealing to cruising traditionalists as it was to the charter fleet. The boat was available ready to cruise or in a kit version, which broadened its appeal. Click here to read more about the CSY 44. stock photo

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Alberg 30 sailboat

10. Alberg 30

There are home runs and then there are home runs. The Alberg 30, originally designed as a club racer by Carl Alberg in the early days of fiberglass, proved over time to be a grand slam for a designer who had more than his fair share of hits, and for Whitby Boat Works, which built more than 750 of the boats over a quarter century run that stretched from 1961 to 1984. With a full keel, low freeboard, long overhangs and low-aspect rig, it’s a boat whose looks harken back to the age of wood. But solid fiberglass construction techniques ensured a longevity that’s spanned several decades of changing tastes in boat design. Courtesy of The Alberg 30 Association
island packet 38 sailboat

9. Island Packet 38

Though it’s difficult to single out any particular Bob Johnson-designed Island Packet, the 38 is especially notable as it was the company’s first “big” boat, introduced in 1986, after 26-, 31- and 27-foot models. With its full-foil keel, reasonable draft, and versatile cutter rig, the IP 38 incorporated many of the features that personify the popular and much admired brand. stock photo
passport 40 sailboat

8. Passport 40

Introducing its Bob Perry-designed performance cruiser in 1980, the builder of the Passport 40 boldly predicted it “will go in the records as the ‘perfect’ liveaboard’s boat.” Though such records aren’t actually kept, a production run of 148 sloops over the next 11 years, attests to the success of the concept. A fine boat to sail, the Passport 40 is spacious below and benefits from the fine craftsmanship and materials available from the better Taiwanese yards of the era. Its layout—with head and shower in the forepeak and large Pullman berth forward of the comfortable main cabin and huge galley—is both practical and appealing. Interest in used Passport 40s remains strong today. Read a review of the Passport 40. stock photo
tayana 37 sailboat

7. Tayana 37

One of the most successful semi-custom cruising boats ever, and one representative of the scores of yachts produced in the Far East, the Tayana 37 was designed by Bob Perry in 1975, in many ways in response to the tremendous success of the Westsail 32. Nearly 600 models were sold, and they are still a familiar presence in distant harbors the world over. Courtesy of
peterson 44 sailboat

6. Peterson 44

Check the world’s great cruising routes in any given season and chances are good you’ll spot a shorthanded couple aboard a Peterson 44 sailing comfortably and confidently toward the next harbor. Originally designed for Jack Kelly Yachts by Doug Peterson, the KP44, as it’s sometimes known, is a fine example of a late ’70s-early ’80s moderate displacement, long fin keel, center cockpit sailboat, with roomy accommodations below and good sailing performance in any sort of breeze and seaway. Read a review of the Peterson 44. Ann Hoffner
pacific seacraft 37 sailboat

5. Pacific Seacraft 37

In the 1970s and ’80s Pacific Seacraft earned a dedicated following for its bluewater-capable, rock-solid cruising sailboats. When it added the W.I.B. Crealock 37 to its line up in 1980, it only enhanced its place in the market. Unlike most sailboats, which are designed for a particular owner or builder, Crealock said he simply drew the lines of the 37 for someone who wanted to go anywhere with speed, safety and comfort. The 37 incorporates a modern underbody with a canoe stern and several rig choices, including yawl and cutter configurations. Over the years, the PS 37 came to exemplify the performance cruiser in this size range. stock photo
hallberg-rassy 42 sailboat

4. Hallberg-Rassy 42

Though Hallberg-Rassy is well-known for two 42-footers—one designed by Olle Enderlein in 1980, and a second by German Frers in 1991—for this round-up we’re choosing the Enderlein version, which enjoyed an 11-year production run during which 255 hulls were built. Many of these HR 42s, which were available as sloops or ketches and featured clean, flush decks, were veterans of round-the-world voyages, and a used one in good shape is more than capable of another circumnavigation today. Click here to read more about the Hallberg-Rassy 42. Courtesy of Hallberg-Rassy
catalina 30 sailboat

3. Catalina 30

We’d wager that it would be a challenge to find a harbor of any size in America without a Catalina 30 hanging either on a mooring or berthed in a slip. In an age when Americans wanted to go sailing and could afford to do so, this modest-sized sloop launched voyaging dreams by the thousands. Literally. The 30 came in Mark I, II, and III versions and had the longest production run—1975 to 2006—ever. More than 6,500 hulls were launched by the California builder of the same name. Courtesy of
hinckley bermuda 40 sailboat

2. Hinckley Bermuda 40

With its low freeboard, sweeping overhangs, yawl rig, and seemingly perfect proportions, the Bill Tripp-designed Hinckley Bermuda 40, produced in Maine by one of America’s greatest Builders, might just define elegance afloat. Production began in 1959 and continued into the 1990s with a few changes, primarily to rig and centerboard, over the years. Courtesy of Hinckley Yachts
valiant 40 sailboat

1. Valiant 40

Few if any contemporary yacht designers have as broad and varied a body of work as the prolific Bob Perry, but his celebrated Valiant 40 is certainly the most popular of them all. Perry’s double-ender, with its signature canoe stern, has a salty profile, but it’s the split appendage fin-keel and skeg-rudder combination that made it one of the first true “performance cruisers.” Read a review of the Valiant 40. stock photo