I'd like to get a few $750/night stay. If anyone has insurance for $750/night and needs a room, I'll leave my house!

Following your post! Sounds like you are on my vacation. Just kidding...but exact same dates and itinerary!
My plan is to have all guests test in the US on Wednesday. And bring Emeds to test for the return trip back to the states.

Can we stay with you again, RW? LOL...

I read through the threads about insurance and ultimately decided to buy a policy which for the six of us (immediate family) was just under $300. What got to me in the end was the fear, uncertainty, and doubt (FUD) about interacting with someone in the arrival process who could delay us or stop us from entering whereby we miss our ferry etc. Further, I figured that this was PRIMARY coverage with a lot of features that could, God forbid, become necessary in the event of a family member getting sick or hurt while on this vacation. I am not an insurance expert and I did not get a clear understanding from the policy documents that I skimmed who would have paid the quarantine housing, meals, etc should any of us have been "detained" for a positive test. It was a little more clear that Covid related medical costs would be covered. I think my Anthem BCBS coverage is worldwide and would have paid a portion of my out-of-network costs should they have been incurred, but with my deductible and OON coinsurance I figured that the $300 with primary coverage and all the extras was enough to buy the policy.

The person checking us in for the ferry from USVI to BVI did mention insurance and I said we had it, but I don't think she looked at any details about it in the stack of papers I handed to her. I think I could have shown any card and it would have been accepted. So, I still don't know, thankfully, if quarantine room and board would have been covered by an insurance claim. That would be interesting to know for those of you who are considering buying an extra policy versus relying on your regular medical insurance and the addition of any credit card travel insurance benefits that many have for repatriation etc. From my perspective, the quarantine room and board would likely be the largest extra cost from an unexpected positive Covid test upon arrival or departure.

PRIMARY medical care coverage is a big deal, yes. I generally try to always book that. If it is not primary, there is a chance if you have medical costs, that you have to pay out of pocket and wait for the insurance to reimburse you. For COVID, if you're vaxxed and boosted, the medical costs might not be much. But let's say you have a heart attack or a stroke or whatever, the costs could be astronomical, especially for things like medical evac. Coverage outside the US varies greatly by carrier. Medicare has ZERO coverage out of the country. Our supplement covers 80%, but that 20% not covered could be huge.

For quarantine expenses, St. Maarten has a mandatory insurance policy that everyone must purchase. I would not recommend that the BVI implement that, as the SXM policy is pretty useless, in that it covers only $125 a day for lodging (ONLY--NO coverage for food, which it is required that all food be brought in). I generally buy all my insurance through TTOL sponsor Insure My Trip. They have ratings for which policies they consider to be the best for Covid coverage. It really takes a lot of looking at insurance policies these days, to know what they cover and what they don't. Insure My Trip allows you to compare policies side by side. Insure My Trip link