I would go early. Much earlier. Before Hurricane season. Then, Go well south.
Possibly April or May to Bermuda. June is Hurricane season, insurance
may be an issue.
Hurricanes can be avoided. Much easier than N Atlantic depressions.
Early season Hurricanes tend to be further South, less severe, don’t usually achieve named status until they are approaching the Caribbean.
Or if you want to go later. just don’t bother with Bermuda stick to coast. I have no idea how your mast
fits in with the ICW
. Even if you have to go outside a few times, it’s likely a more pleasant trip.
Going via Bermuda late in the year. You will have to deal with the N ATlantic. Then heading S from Bermuda you still have it for a while.
Then you won’t.
You’ve got a fair old ways to go with advers, little or no wind
till you get far enough South to catch a fair wind
Can you motor
through it. Yes. If you have the fuel
From my perspective a late season trip in November is just asking for a rough time. Later gets worse.
Yes it can be done. Wait for the right window. Expect some Nasty weather maybe not to Nasty but moderately nasty. get to Bermuda and wait for the right weather to head
Best route. Rather than trying to go from Bermuda South. Go east in spring. Enjoy the Azores
. I’ve never been there just seen them from a distance. Then via Portugal
then Cross to Caribbean with the ARC
A hell of a lot further. Less risk of crap weather, and your boat taking a beating.
It’s a long way. Or a very long way with some nice stops.
Or enjoy the Maritimes in the Spring and Cross to the Uk France
etc then head south to join the ARC
Of course it also depends on where you have been before and what you want to see. Other than the Sea.
If I really wanted to go via Bermuda then head south skipping going east.
I would go in the Spring, I would head right down to the Southern Windwards. For the Main part of Hurricane Season.
I would still consider early part of Hurricane Season a reasonable risk. If you have good means of getting a weather chart. Know the warning signs,
Of course this is probably contrary to most advice. Just what I would consider.