If it were me..I'd take the earliest ferry and breakfast in STT as suggested..its what we always used to do ..even for a 4 pm flight..I have seen waaaay too much panic at C and I with folks about to miss their plane. As we are now down for months at a time we have started going a day early..take the 10.15 to Red Hook via St John..have a nice lunch at the fish restaurant at the end of the dock overlooking the marina..dinner at "Oceana" of another great Frenchtown restaurant..overnight at Windward Passage..lunch at " Hook Line and Sinker " and on the plane. I would never have done that when I was just down for a couple of weeks but it is a restful way to travel now..especially as we fly to SFO and then drive another 90 mins to Sonoma, Ca.