Ellen have you chartered before? I'm moving a boat from Annapolis to Key West starting this weekend. When I get there I can get a feel for what the charter situation looks like and possible itineraries from the locals. The Bahamas are great of course, but like Mike said questionable if/when you can get in. The Chesapeake Bay is a great place to sail, however you wouldn't be swimming and beaching much, When travel opens back up we have Italy and Croatia on our bucket list!