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Sailing the Seas of Cheese 

The phrase "Sailing the Seas of Cheese" means that the speaker is experiencing great personal change. The Seas of Cheese is an album made by "Primus" in 1991. The album's title is referenced throughout the album, and referenced in many albums after this ones release.
David: "Hey Lauren! We miss you back home! How's Chicago treating you?"
Lauren: "David. David I'm not good. I'm Sailing the Seas of Cheese right now..."
David: "What? Oh Lauren what happened? Are you-"
Lauren: "I had to drop out of school Dave. Mark left me a-and, I have to dance to pay the bills and..."
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smooth sailing 

easy going, an unbumpy ride into the future.
"I've finally got that out of the way". "Well, now it's smooth sailing from here"
smooth sailing by shortanstuff February 6, 2009

abbey sailing team 

A well-rounded, lively group of elite seamen who are unafraid to face the elements of Bristol Harbor. Sailing is the favorite past time, only of course behind frisbee. We're more than a cult than anything. There is always so much room for activities! We're sweaty not cause we were watching Cops, we were fcking shit up! Exceptional in sailing, however not in driving the mini buses, these sailors will make your wetsuits wetter and your drysuits...well they'll get wet anyway. We always try to abide rule #69.3 section b- "Never screw your crew". But since the rules are more like guidelines..something is usually blowing out there other than the wind....
What can you say, we're the best ASS out there: Abbey Sailing Squadron
kid 1: Hey are you part of the abbey sailing team ?
kid 2: yeah its fantastic!

midget sailing 

The sexual act that involves a small person.

If a man inserts his fully-stiffed penis into small person's anus/vagina, he can start to rotate the small person around his penis, thus imitating the act of turning the sailboard wheel - giving him an unique grinding sensual pleasure.

Rotation can be also invoked by slapping the small person really really hard.
Man and his wife fighting: "You bitch, if you were a midget, I'd slap your ugly face so hard, I would be midget sailing till next Tuesday!"
midget sailing by doublerainbowomg September 7, 2010
The fine art of getting really wet, really cold, going nowhere really fast, while spending large amounts of money
Sailing owns, though
Sailing by jackts9999 May 4, 2009

Pussy Sailing 

a term that means looking for girls/pussies.
looking for wiling girls to have sex.
"Man, It's been a rough week."
"Yes, we should go pussy sailing."
"Indeed"

Sailing on the Pumpkin Tide 

Refers to becoming drunk while alone in order to enhance one's creative process. Probably originated in the webcomic Problem Slueth.
Person 1: Can you come over tonight?
Person 2: No, I've had some ideas rolling around so tonight is going to be for sailing on the pumpkin tide.