OK....got this back from a provider, and don't know what she is referring to. A little help, please?

Besides the obvious definition, I found these two entries in the Urban Dictionary:

sailing  
A Euphemism for smoking marijuana in ithaca.

sailing
Drinking an abundance of Captain Morgan Original Spiced Rum.

It might help to know the context in which the term was used.  She may just have a love of the open water...

if you want to sail it depends on size and is +50...

means what?

What was the context?

'Sailing close to the wind' - chancing your luck, could be that.

It would appear that for an upcharge of $50, you may sail to the Greek Isles - depending upon the size of your ship.

I had never heard of it. Thanks ATL-mgr.... I didn't know it also referred to smoking pot.
(*just when you thought you heard it all*)  *LOL*

Carrie's answer, for some reason, sounded much
more romantic.  kisses ~T

"Easy riding - doing something with out problems"

Possible in referring to the sex act as being unhurried, slow, mmmmmmmmmm..... drawn out and at a pace to drive both involved nuts?

"depends on size and is +50..."
Could she have been talking about Greek ?

with the size of my Dingy , I bet I could get it for $25.

Thank you