A common saying in the boating world is that the two happiest days in a man’s life are when he buys a boat (especially a yacht) and when he sells it. When a person buys a boat or a yacht, the buyer is often unaware of the costs of that boat or yacht—hence, the second happiest day is when he sells it.
 
The “two happiest days” saying originally applied (cited in print from the first half of the 19th century) to being married and to holding political office. The “yacht” version has been cited in print since at least 1931. The “two happiest days” saying also has been applied to buying cars, collectibles and to many other events.
 
Other sayings about boat ownership include “A boat is a hole in the water into which you pour money” and “BOAT: Break Out Another Thousand (dollars).”
 
“The two happiest days in a time traveler’s life: The day they complete their time machine and the day they stop themselves from completing their time machine” is a related joke.
   
     
10 January 1823, Village Register and Norfolk County Advertiser (Dedham, MA), pg. 1, col. 2:       
Hipponax.—The two happiest days you pass with a wife, are, the day on which you marry, and the day on which death walks with her.
 
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The Lives of the Lords Chancellors and Keepers of the Great Seal of England:
From the earliest times till the reign of King George IV
By Baron John Campbell
Philadelphia, PA: Blanchard and Lea
1851
Pg. 452:
IT is said that the two happiest days of a man’s life are the day when he accepts a high office, and the day when he resigns it; and there can be no doubt that with Sir Thomas More the resignation day was by far the more delightful.
 
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History of the life of Arthur, Duke of Wellington
Volume 3
By G. R. Gleig
London: Longman, Green, Longman, and Roberts
1860
Pg. 398:
It is an old saying, that the two happiest days in a public man’s career, are that in which for the first time he accedes to office, and that on which he retires from it.
 
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July 1897, The Gentleman’s Magazine, pg. 8:
“THE two happiest days in the life of a politician,” once remarked a leading statesman, “are those upon which he enters office and leaves it.”
   
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The Autobiography of Martin Van Buren
By Martin Van Buren
Edited by John Clement Fitzpatrick
Washington, DC: U.S. Government Printing Office
1920
Pg. 448:
Whatever hopes they may indulge that their cases will prove an exception to the general rule they will find, in the end, their own experience truly described by Mr. Jefferson when he said that the two happiest days of his life were those of his entrance upon his office and of his surrender of it.
     
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The American Magazine
Volume 112
November 1931
Pg. 120:
I had a yacht once, but— like the musician who “played with Sousa once” — only once! That was enough! Looking back, I sometimes think the two best days of my life were the day I bought that boat and the day I got rid of it.
 
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September 1940, The Rotarian, “Thank God for a Dull Life” by Channing Pollock, pg. 15, col. 2:
Most of us want what we haven’t, but having it is like having a yacht, of which someone observed that the two happiest days are that on which you buy it and that on which you sell it.
 
Time magazine
Letters, Jun. 8, 1959
Monday, Jun. 08, 1959
Sir:
The two happiest days of a man’s life—the day he bought the boat and the day he sold the boat.
LESLIE D. MAURER San Antonio
 
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The Complete Book of Boating:
An owner’s guide to design, construction, piloting, operation, and maintenance
By Ernest A. Zadig
Englewood Cliffs, NJ: Prentice-Hall
1976
Pg. 580:
It goes: “The two happiest days in a boatman’s life are the day he buys his boat and the day he sells it.”
     
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Esquire: the magazine for men
Volume 102
1984
Pg. 264:
“The two happiest days in a boat owner’s life are the day he buys his boat and the day he sells it, ” Ryder says from behind his desk. “Owning a boat is a headache. That’s why the average boat is used only about two days a month.”
   
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The World’s Wasted Wealth 2:
Save Our Wealth, Save Our Environment
By J. W. Smith
Cambria, CA: Institute for Economic Democracy
1994
Pg. 280:
A friend told me, “The two happiest days of my life were the day I bought that boat and the day I sold it.”
     
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The Wolf of Wall Street
By Jordan Belfort
New York, NY: Bantam Books
2007
Pg. 217:
My crooked accountant, Dennis Gaito, had begged me not to— reciting the age-old axiom: “The two happiest days for a boat owner are the day he buys his boat and the day he sells his boat!”
 
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The Military Millionaire:
A Financial Lifestyle Guide for Service Members and Their Families
By Ken Heaney
Trafford On Demand Pub.
2010
Pg. 38:
They say the two happiest days for the boat owner are the day he buys the boat and the day he sells it!