We did two round trip deliveries in the late '80s from the Chesapeake to NAs in Newport and LI Sound. I'd start with clean fuel, spare filters, an alternative fuel tank with a spare fuel line. There is no easy way to remove fuel bugs at sea or clear the J/30s the primary fuel line. We pumped fuel from a teakettle while navigating the East River. I'd try to figure out a way to have spare main halyard, even if it were external. The fractional rig means if you lose the primary you risk your life to reach the masthead to replace it. I'd want also want a small storm jib, (possibly rigged to an inner forestay with associated deck gear), and either a trysail or triple reef in the main.
