Did the SDR to BVI's in 16. They have a "tentative" departure date but are very strong on go when you feel its right. Think my year the departures were spread out over 3 or 4 weeks. No problem from the organizers standpoint. This is a real offshore trip and you will probably get hit with at least one weather front. Much different than the HaHa (have done 5 or 6 of those). One way or the other you need to be ready for it.
They have upped the price
requirements. I have SSB
and InReach which was fine then but now they also require email
capablity. If you already have that no problem, but I don't and didn't want to spend the $ for a one time use. Did the trip from Norfolk to BVI's at the same time and chatted with several of the Rally boats while enroute.
Went to the Keys and Bahamas from Chesapeake last year. My insurance
only requires that I be north of St. Mary's until Nov 1 so I could leave the Chesapeake earlier. Advantage of leaving earlier is you won't be freezing in the Chesapeake in October. I'm from So. California
so not used to those temps.
If going to the Bahamas I definetly say go down the coast. There are lots of great stops and you can do all day trips except for one overnight getting around Hatteras. Event that is not too bad if you start from Virginia Beach.
One big difference of east vs. west coasts is weather. On the east coast
it changes every few days so if a calendar is not an issue you can always be reaching or running, regardless of whether you're going north or south.
One note on the Bahamas, they are pretty cool in the winter months. I would suggest heading to the Exumas
or even further south early then working north.