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Re: BVI to Annapolis
The offshore route from the BVI to Annapolis can be dangerous. Especially in April, early May. Cold fronts coming of the US East cost can be very unpredictable causing extremely rough conditions as waves pile up against the eddies east of the gulf stream. Weather forecasts in this area are good for about 3 days which is not always enough. It took us 8 days on a 55 foot sloop with a hull speed of 10+ knots. We sat for 1 day of that 8 mid ocean waiting for some weather to clear. We also had 240 gallons of diesel so motoring was never a problem.
First off, you need good communications. A SSB is a must for this trip. A sat phone is a definite plus. Radar helps especially in skirting passing squalls and when traveling from the lower Chesapeake to Hampton Roads. Those military vessels and car carriers can be downright frightening at night. Since you will be out of the range of CG helos for most of the trip an offshore liferaft would be prudent.
We used Southbound 2 (Herb Hilgenberg) for our weather routing. He is excellent and has tons of experience. Additionally we downloaded real time gribs and forecasts through our sat phone which overlayed on our Maxsea charting software.
Bottom line is that it can be a pleasant trip if everything goes right and you get a good weather window. The problem is that you are mid ocean and you have no bail out options if the weather changes from your 5 day forecast. Because of the gulf stream and it's meanders and eddies, the waves in this area can be very steep and confused. We got caught out in a 3 day gale. Our bailout option was Bermuda which we chose not to take because it would have only reduced our exposure to the storm for a day and we would not have arrived in daylight causing further delay. 25 foot breaking waves with the sporadic 40 degree off angle wave thrown in. I'm not sure a catamaran would be the right pick if you encounter that.
If it were me I would island hop up to the Bahamas then cross over to Florida and wait for the right timing to to take the up elevator to the Chesapeake. Lots more relaxed and could be a fun trip.