Best check the forecasts and pilot charts
. I have done the NE to Bermuda trip many times and have had all sorts of weather
from dead calm for days and days to full in gales in the stream. Try to log on with Herb at SouthboundII and use his advice
.. he's pretty damn good for this run. There are usually a whole slew of yachts heading down from NE stopping at Bermuda on the way to the Caribbean
The fall run in late fall usually has strong winds from the north west or north east as I recall
. Last year it was pretty brutal and lots of boats sustained damage.
You may be able to find a mooring
in St Georges, but the Bermudians don't cotton to people hanging around their island. Best check out their regs on leaving a yacht for 6 months.