Oh dear, m'dear, the reality of a lottery win doesn't quite show in your plan...
What about starting in the Bahamas or Bermuda, then jetting over to Hawaii, then back to St. Tropez or Caan? Then back to the Caribbean where we find us a nice little island of our own to purchase...and fix up...and retire to!
Now, those are the plans of a lottery winner!!
Oh yes, NOT to worry m'dear! We can certainly add that to our plan BUT we want to hit the all the coasts of the United States before we move OCONUS. We'll island hop and pick out our vacation and home spots later.
How that sounds like quite a “trip”.