We pre-cleared customs for the Newport to Bermuda race. I highly recommend doing the same. We will still need passports on the boat, partly so we can return.

I'd definitely be concerned with a 2 day weather window, that will be tough to manage. We could wait a year for the right window! Lots of other details with liability and insurance (blah blah IMO but this is lawyer-centric 21st century america). I highly doubt you could get event insurance for that race, I know my boat insurance runs out 25 miles offshore but I'm skeptical you absolutely cannot get insurance offshore. Will it be worth it $$ wise? Maybe not.