The east coast can be ugly that time of year. Plus you would be going against the Gulf stream with frequent northers. I would expect that to be a cold miserable bumpy ride.
The intercoastal is always a possibility, except the mast height on the Benny 49? 64Ft (most bridges I saw on the latest bridge list I downloaded are now 65ft, with 1 56ft, and possibly a few that are still under construction).
The draft at 7 ft should be OK, Barges travel most of the ICW, but I have heard of shallows, and have scraped and run aground with less draft than that in areas that, "in theory", have much more depth.
I wouldn't feel real confident in taking a boat that big across the Ocheechobee right now, I have heard of low water, and not well maintained channels, (maybe a local can give up to date info?).
That leaves the big ocean route. NS to Burmuda then to the keys and around to St peter, leaves a whole lot of wide open vulnerability to storms, but is the least complicated route.
But then you probably knew all this already.
I plan that any wave with an ascociated low will probably develop at any time, giving 3 -5 day window in between the waves. That still leaves you mid- ocean with a storm over the horizon, and rough seas.
How flexible is delivery time? A few weeks can make a big difference, but the winter storms are no picnic either.
ICW may be your best bet, with a few offshore hops to avoid the less well maintained areas. That leaves you with one short circle around the keys that can be planned to coincide in between two tropical waves.
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