Cruising World: 40 Best Sailboats

Cruising World polled their readers to determine the best sailboats of all time.

Check out the article to read more and learn how these were chosen.

Sailboat

Valiant 40

1973 • 39′ 11″ / 12.2 m
Sailboat

Hinckley Bermuda 40-1

1959 • 40′ 8″ / 12.4 m
Sailboat

Catalina 30

1976 • 29′ 11″ / 9.1 m
Sailboat

Hallberg-Rassy 42 (Enderlein)

1980 • 42′ 3″ / 12.9 m
Sailboat

Pacific Seacraft 37

1980 • 36′ 10″ / 11.3 m
Sailboat

Kelly-Peterson 44

1976 • 43′ 9″ / 13.4 m
Sailboat

Tayana 37

1976 • 41′ 11″ / 12.8 m
Sailboat

Passport 40

1980 • 39′ 5″ / 12 m
Sailboat

Island Packet 38

1986 • 37′ 11″ / 11.6 m
Sailboat

Alberg 30

1962 • 30′ 3″ / 9.2 m
Sailboat

CSY 44 (Mid-Cockpit)

1977 • 43′ 11″ / 13.4 m
Sailboat

Westsail 32

1971 • 39′ 11″ / 12.2 m
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Sailboat

Beneteau 423

2002 • 43′ 1″ / 13.2 m
Sailboat

Cal 40

1963 • 39′ 4″ / 12 m
Sailboat

Hunter 356

2000 • 34′ 6″ / 10.5 m
No photo available
Sailboat

Morris 36 Justine

1983 • 36′ 3″ / 11.1 m
Sailboat

Columbia 50

1965 • 50′ 0″ / 15.2 m
Sailboat

Whitby 42

1972 • 41′ 11″ / 12.8 m
Sailboat

Contessa 26

1965 • 25′ 5″ / 7.8 m
Sailboat

Hylas 49

1992 • 48′ 10″ / 14.9 m
Sailboat

Morgan Out Island 41

1971 • 41′ 2″ / 12.6 m
Sailboat

Tartan 34 C

1968 • 34′ 4″ / 10.5 m
Sailboat

Bristol 40

1965 • 40′ 2″ / 12.3 m
No photo available
Sailboat

Gozzard 36

1985 • 35′ 11″ / 11 m
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Sailboat

Islander 36

1971 • 36′ 1″ / 11 m
Sailboat

Pearson Triton

1958 • 28′ 3″ / 8.6 m
Sailboat

Sabre 36

1985 • 35′ 11″ / 11 m
Sailboat

Gulfstar 50

1975 • 50′ 0″ / 15.2 m
Sailboat

C&C Landfall 38

1979 • 37′ 6″ / 11.5 m
Sailboat

Swan 44 (S&S)

1972 • 43′ 11″ / 13.4 m
Sailboat

Nonsuch 30

1978 • 30′ 3″ / 9.2 m
Sailboat

Beneteau Sense 50

2010 • 49′ 1″ / 15 m
Sailboat

Freedom 40 CC

1976 • 39′ 11″ / 12.2 m
Sailboat

Nor'sea 27

1976 • 27′ 8″ / 8.5 m
Sailboat

Jeanneau Sun Odyssey 43 DS

1994 • 42′ 1″ / 12.8 m
Sailboat

Mason 43

1978 • 43′ 9″ / 13.4 m
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Sailboat

Mason 44

1985 • 43′ 11″ / 13.4 m
Sailboat

Alerion Express 28

1990 • 28′ 2″ / 8.6 m
Sailboat

Dufour Arpege 30

1966 • 29′ 11″ / 9.1 m
Sailboat

Pearson Vanguard 33

1963 • 32′ 6″ / 9.9 m
Sailboat

Moore 24

1972 • 23′ 9″ / 7.2 m
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For Sale

1973 Morgan Out Island 41 SL cover photo 1973 Morgan Out Island 41 SL cover photo
Clearwater, FL, US
1973 Morgan Out Island 41 SL
$20,750 USD
1986 Whitby Boat Works 42 cover photo 1986 Whitby Boat Works 42 cover photo
Port Washington, WI, US
1986 Whitby Boat Works 42
$98,900 USD
1986 Hallberg Rassy MK1 cover photo 1986 Hallberg Rassy MK1 cover photo
Bocas del Toro Province, Boca del Drago, PA
1986 Hallberg Rassy MK1
$300,000 USD
1981 Valiant Yachts 40 Pilothouse cover photo 1981 Valiant Yachts 40 Pilothouse cover photo
Port Aransas, TX, US
1981 Valiant Yachts 40 Pilothouse
$80,000 USD
1983 Hinterhoeller Nonsuch Classic cover photo 1983 Hinterhoeller Nonsuch Classic cover photo
Kittery, ME, US
1983 Hinterhoeller Nonsuch Classic
$34,000 USD
1978 Catalina 30 cover photo 1978 Catalina 30 cover photo
Oakland, CA, US
1978 Catalina 30
$15,000 USD
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1986 Whitby Boat Works 42 cover photo 1986 Whitby Boat Works 42 cover photo
Port Washington, WI, US
1986 Whitby Boat Works 42
$98,900 USD
1972 Whitby Whitby 42 cover photo 1972 Whitby Whitby 42 cover photo
Annapolis, MD, US
1972 Whitby Whitby 42
$5,000 USD
1977 Islander 36 cover photo 1977 Islander 36 cover photo
Marina del Rey, CA, US
1977 Islander 36
$25,850 USD
1979 Islander Islander 36 tall rig deep keel cover photo 1979 Islander Islander 36 tall rig deep keel cover photo
Muskegon, MI, US
1979 Islander Islander 36 tall rig deep keel
$24,900 USD
1986 Whitby Boat Works 42 cover photo 1986 Whitby Boat Works 42 cover photo
Fredonia, WI, US
1986 Whitby Boat Works 42
$98,900 USD
1976 Kelly Peterson KP 44 cover photo 1976 Kelly Peterson KP 44 cover photo
Jalisco, MX
1976 Kelly Peterson KP 44
$125,000 USD
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1980 Morgan Out Island 41 cover photo 1980 Morgan Out Island 41 cover photo
Fort Lauderdale, FL, US
1980 Morgan Out Island 41
$74,900 USD
1992 Pacific Seacraft Crealock 37 Cutter Rig cover photo 1992 Pacific Seacraft Crealock 37 Cutter Rig cover photo
United States
1992 Pacific Seacraft Crealock 37 Cutter Rig
$139,000 USD
1991 Island Packet 38 cover photo 1991 Island Packet 38 cover photo
Lombok, West Nusa Tenggara, ID
1991 Island Packet 38
$97,000 USD
1962 Pearson Triton cover photo 1962 Pearson Triton cover photo
San Francisco, CA, US
1962 Pearson Triton
$12,000 USD
1989 Gozzard Gozzard 36 AC cover photo 1989 Gozzard Gozzard 36 AC cover photo
Staten Island, NY, US
1989 Gozzard Gozzard 36 AC
$130,000 USD
1972 Morgan Out Island 413 CC cover photo 1972 Morgan Out Island 413 CC cover photo
St. Catharines, ON, CA
1972 Morgan Out Island 413 CC
$66,800 CAD
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1972 Morgan Out Island 413 CC cover photo 1972 Morgan Out Island 413 CC cover photo
St. Catharines, ON, CA
1972 Morgan Out Island 413 CC
$66,800 CAD
1977 Morgan Out Island 41 cover photo 1977 Morgan Out Island 41 cover photo
Charleston, SC, US
1977 Morgan Out Island 41
$37,000 USD
1983 Islander 36 cover photo 1983 Islander 36 cover photo
Long Beach, CA, US
1983 Islander 36
$24,900 USD
1990 Island Packet 38 cover photo 1990 Island Packet 38 cover photo
British Virgin Islands
1990 Island Packet 38
$129,000 USD
1981 Catalina 30 Tall Rig cover photo 1981 Catalina 30 Tall Rig cover photo
Sandusky, OH, US
1981 Catalina 30 Tall Rig
$17,900 USD
1968 Whitby Boat Works Alberg 30 cover photo 1968 Whitby Boat Works Alberg 30 cover photo
St. Marys, GA, US
1968 Whitby Boat Works Alberg 30
$38,500 USD
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