haha! it's essentially a slang phrase that friends may say to each other- "you're such a trip!" meaning "You're crazy!" (crazy in this context meaning funny). Though to be honest it seems like a phrase for generations age 25-35ish. But it may just be me.

I think it derives from the use of the word to mean a reverie induced by hallucinogenic drugs, like LSD. Someone is saying you are amazing. Whether they mean this in a good way or a bad way, context may determine.

when sometimes I make my friends laugh, I always get to hear these words from them... "you're such a trip!"... could it be that I'm too entertaining or they're just too annoyed and fed up with my stories?.. what ever that may be, to me it seems that I am simply capturing their attention and killing boredom. :)

It means you are cool, tho like Randy wrote it is best when you are on drugs.