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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