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When a girl gets on her knees and blows on your balls so hard they swing like a mast of a sail boat.
Last night my girlfriend got on her knees to suck my cock and instead she blew on my nuts..sail boating.
by titsmcgee555 November 12, 2010
When a girl's breasts are insufficient in size for motorboating, hence the next lowest denomination of aquatic transportation is used.
Andrew: Why didn't you motorboat her last night?
Corey: She had little A cups, I tried...
Andrew: You sailboating son of a bitch
by gack513 January 05, 2011
the act of pressing you nose against a flat chested woman and just blowing
Did you motorboat sarah's friend last night? Nope, just went sail boating, there where no boobs!
by Touge_Drifter September 19, 2012
The acting of rocking a mans member (aka sailboat) back and forth inside a womans vagina (aka cum-boat), this process is refered to as surfing her seas, after which the man finishes within her, this process is refered to as "unloading cargo"

*all aspects must be followed to be considered sailboating
Friend 1: "Dude, what'd you do last night?"
Friend 2: "Not much, just some sailboating."
Friend 1: "Idiot! Think she'll get pregnant?"
Friend 2: "I dont care, not my bitch."
by Gary Flongtard December 07, 2011
Much classier than motorboating. To gently blow on a woman's nipples.
Nothing puts Amanda in the mood like sailboating.
by BarrettAll November 27, 2011
Blowing on boobs.
I went to motorboat my girl last night but I was laughing so hard that I just blew on them instead...sail boating!
by Letsgeauxmunging2night November 14, 2009
A three-some consisting of two girls and a guy. The guy lays on his back while one girls rides him and the other sits on his face. The two girls face each other holdings hands, creating a triangle or "Sail".

The same thing as Eiffel tower but for 2 girls, 1 guy.
ddannnggggg! Dina and Snooks really know how to go sailboating!!
by Sailboatking August 11, 2011