I've done this trip a couple of times, although I started the
offshore part in the Chesapeake. I usually use Chris, as I've got an
SSB on board. While the usual
route is to make as much easting as possible, I've never made it to Bermuda on those runs, I was always too far west to make it worthwhile.
I just participated in the Newport-Bermuda
race and got to visit Bermuda for the first time. It is very nice, sort of like a balmy Switzerland with prices to match. Unless you really want to visit it might be best to sail on by.
I think if you tell Chris your trip parameters (maximum waves/winds, preferences regarding Bermuda, etc.) then he has the experience and expertise to give you an optimal route.