Given your lack of offshore experience I would suggest you do the traditional coastal route where you can use the ICW and take short coastal hops in good weather outside. A lot depends on your TIME to do the trip. If it is rather unlimited.
1. Go down through the East River and the Jersey shore...stopping at Atlantic Highlands, Manasquan Inlet, Atlantic City and Cape May.
2. Go up the Delaware Bay and to the C&D canal to the Chesapeake Bay
3. Enter the ICW at Norfolk and work your way down to Florida. The Okeechobee canal is closed so you will have to go around southern florida to the keys and then up the west coast.
I would allow 2 months for the complete trip but it probably could be done in 5-6 weeks with good weather and really pushing.
A captain would want to take another crew member beside yourself and head offshore to save time. Probably heading to Bermuda first and then down and probably taking around 10 days.
Maps/Guides: Maptech Chartbooks, Mid-Atlantic and Southern ICW guides, Skipper Bob's GUIDE TO ICW anchorages, Doyles Guide to SE US Inlets.
Going offshore you'll need a
life raft and
EPIRB and jacklines and
harnesses at a minimum and you may wish to rent or buy a sat phone for emergency long distance communication. Obviously...the boat, sails and
rig and engine need to be in top shape for going offshore with spares for
repairs of critical items underway.
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