May or June is generally a good time to do that passage
. As donradcliffe
said, there's a possibility of seeing some bad weather in May.
I did the passage
from St Thomas to the Bahamas
, then up around Hatteras to the Chesapeake in May 2005, and had no weather issues whatsoever. A friend did it a week later in a 70 footer. He got hammered off South Carolina and limped into Charleston for repairs
. Another friend was hove to for three days off Georgia
, taking knock-downs while maintaining hourly comms via sat phone
with the Coast Guard until it abated. He limped into Wiynah Bay, SC, with a shredded main and dicey engine
. Three other yachts were lost
and some crew died off Hatteras in that storm (May, 2002). I don't mean to spook you, because the bad storms are the exception in May, and you'll likely have a great sail, but it doesn't hurt to be prepared.
If you're not up on weather forecasting you might want to consider engaging a weather routing service
to give you an initial forecast
and then daily updates via SSB email
or by sat phone
. The risky zone is usually from off the Georgia
coast and north. You can ride the Gulf Stream
and gain 3 knots or so, but watch the weather because the Stream intensifies whatever comes off the coast.