To establish themselves as winter sets in
If your boat is located anywhere North of the Chesapeake Bay, you will most likely want to consider heading out to Bermuda where you can sail due south on the easterlies that begin to establish themselves as winter sets in. This makes for a good shakedown leg, plus a stop in Bermuda is always nice. Crossing the gulf stream is one of the only real hurdles of this part of the trip, so choosing the right moment to set out is critical. Plan to arrive on the west side of the stream during fine weather. Whether you plan to stop in Bermuda or not, the island which is 450 nautical miles offshore, should be considered a port of refuge in the event a storm develops or worse, if a late season hurricane fires up. Make sure you have a very good understanding of the navigational and entry procedures for St. Georges Harbor which is located on the eastern end of the island.
If the idea of being offshore for up to eight or nine days doesn’t really inspire you, my best advice is to sail down the coast to Florida, hop across to the Bahamas and island hop all the way down to the Virgin Islands. Make sure you provision for a least a two week trip. You will have at least two to three days from Norfolk to Miami, then 1500 miles between Miami and the BVI. I made this trip on a 75 foot catamaran several years ago and the biggest problem I had was getting around Cape Hatteras where the Gulf Stream kisses the coast and can cause havoc for the unprepared. An alternative to running this gauntlet is using the Intracoastal Waterway which you can pick up in Norfolk and pop out to the southwest of the Cape and head straight to Charleston or Miami from there. There is access to several inlets if conditions become difficult along the way.
For anyone considering beelining it to the BVI from anywhere on the East Coast other than Newport, I wouldn’t recommend it. You will experience wind on the nose for almost the entire trip causing you to burn through a lot of fuel, be uncomfortable most of the way, and wish you had used the Bahamas route. Which is the way I recommend you do it.
The only times I’ve ever really enjoyed this trip was starting out of Fort Lauderdale and making for Exuma Bank. Be sure to arrive at the northwest entry area, just to the north of Nassau, as close to 10 a.m. as possible so that you can cross the 40 miles or so bank in good sun. This will allow you to see the coral heads until you get to the other side. If you arrive there too late, don’t try to cross it. Go as far as you can, find a safe spot to anchor and wait until the next day. It feels a bit strange anchoring in the middle of nowhere, but you will have no problem finding 15-ft. depths and plenty of sand.