First crossing from Chessapeak to Bermuda, any tips?

[nuru05]

So we are going to be doing our first bigger crossing from the Chesapeake to Bermuda in November. We have sailed for the past 2 summers on the great lakes and then came down the Erie and onto the Chesapeake. Our plan is to head over to bermuda and down to the bahamas.

Our boat is a well equipped and maintained Moody 425 with a watermaker, plenty of solar, auto pilot, etc. We also have an EPIRB, starlink, Radar, AID receiving, offshore liferaft, iridium, and hydrovane. So I think we have the basic gear and safety stuff covered. We will have 3 people on board to split up watches.

Our plan is to head out in late October or early November. We figured we would engage Chris Parker to provide weather and departure help and just wait until we have a nice window to take off. Once there we have all the time in the world to explore Bermuda and wait for a nice window down to the Bahamas.

So my questions for all of you who have done this route before are:

If we don't have to be anywhere until next summer is this the best route to take? We are basically going to spend all winter in the Caribbean and then head back up to the Cessapeak for hurricane season. Should we consider going straight down from Bermuda to the BVI's or Puerto Rico? Or are there any other routes that you'd suggest?

what other things should we consider for our departure?

What other advice can you offer?