Thanks for your advice. I don't think we'll take the chance on the DR. A viable idea is the one where we do the ICW ourselves and then only the Bahamas - maybe with the Keys at the end.
However, the problem is that we're only going to rejoin our boat at the END of November. If we leave her in the Chesapeake, that is very late to start a trip South. We could go further South this Summer however, since we do have two months - but how far should we go, given that we have NO experience with hurricanes and will have to leave the boat somewhere at the end of August and fly back to Calgary. If we go further South it should be somewhere from where we could pick up the journey in December as well as somewhere where we can leave her in the care of someone. It should also be a safe area for hurricanes. If you or anyone can help with this problem, we may have the beginnings of a plan!
Thanks for the advice!