Great sailing Joe! I knew that wind out of the West was going to help you. The weather is good for the next few days so make a run for it! I wish I was doing the same, I may have to sail an Amtrak that way.
Key West is always too much for my wife. Too busy too crowded too stressful. She likes Islamorada better. I remember the boats in Isamorada decorated with Christmas lights and we stood on the beach and drank fruity rum drinks and danced to the band and yelled - Happy New Year as the fiireworks went off..Myself - I think Key West is wonderful and charming and if it is too crowded around Christmas time well that just shows you its the best place to be. You probably already know its shallow there and other here know far more about it than me, I did rent a sailboat in the Keys and from what I could tell winter is the flat season with less wind but its still pretty good. Fishing is very good. For local flavor check out the Conchscooter blog. http://conchscooter.blogspot.com/