The conventional wisdom is to leave the USVI in very late April or the first half of May, hoping to avoid the strong cold fronts that blow off the US coast in the spring, and the tropical storms that can form in the early summer. For years, the Cruising Rally Association has sponsored the "Atlantic Cup", in which boats leave Tortola in the first week of May, bound for Bermuda
. After a suitable layover there, with parties, etc. The boats head
out for the Cheasapeake or New England
. I think your chances of having a good passage
are probably best in that timeframe. The route
could vary from St Thomas to Bermuda
and then the Chesapeake, a track that heads NW from St Thomas then curves more north, crossing the Gulf Stream
south of Hatteras, or the route
we took. A friend of mine has done the Gulf Stream
route from south Florida
to the Chesapeake a dozen times with no real issues.
I can relate to you my one and only experience going in that direction. We departed St. Thomas May 1st, 2005, arriving in the Abacos after six days at sea. The winds were moderate and off our starboard quarter until we got to about the Latitude of San Salvador. There the tradewinds petered out, and we experienced a weak cold front with some moderate squalls. No problems.
After a week playing around in the Abacos, we headed north at Moraine Cay and over toward Florida
, where we entered the Gulf Stream opposite Cape Canaveral. It was a great ride north, with SOGs up to 10 kts. I had arranged for weather
from Commanders Weather for the second leg, and they kept us posted daily by email
over my SSB
on an approaching cold front that passed over us just as we reached Cape Hatteras. It was weak, and again, we had no problems at all. It was what you'd call "benign" weather the whole way, and we motor-sailed a fair bit during parts
of it. (I have 85 gallons in tankage and 30 gallons on deck
You can get some bad weather at that time of the year, though. An acquaintance did the same trip a week after we arrived in Virginia, and was hammered in a strong gale off South Carolina, and had to limp into Charleston for repairs
and a rest. In 2002, a friend did that same trip in early May, and was hit by what some called the second "Perfect Storm". A couple of boats were lost
in that one. It's the luck of the draw.
I agree with you that fuel
capacity is a concern for a trip like that. And I'd recommend using a weather routing service--Commanders Weather, Herb Hilgenberg or Chris Parker, for example. Bad weather in the Gulf Stream or at Cape Hatteras is nothing to play around with.