Spent last week at Sunset Harbor in Key West. Stayed in our unit and all was fine. Masks are required in the main building for check in but no where else. Restrictions at the pool were limited to allowing only 26 in the pool at a time, but we never even got close to that amount. Most restaurants were opened and required masks to go inside and were ok to remove once you were at your table. If you needed to move around the restaurant, you needed a mask. Same restrictions as in NY. LaTeDa dining appeared the same as most seats are already outside, Blackfin was limited inside dining but has an outdoor patio and was fine. Half Shell, Latitudes, Conch Republic, all seemed fine. Wahlburgers has opened there and we tried it, inside dining. Seemed fine. Eaton Street Seafood still serves the best lobster rolls and we kayaked out of Hurricane Hole because Geiger Key kayaking was closed the day we went up. Fort Zachary Taylor beach was beautiful although I should have brought water shoes to make it over the coral to the water. Next time!
The only time I felt uncomfortable was on Duval on weekend nights as the crowd was loud, drunk and unmasked. We stayed away and were fine. No bars as they seemed risky (and not our thing anyway so no loss there).
Instead of flying this year from NY, we drove. Took about 32 hours down, longer home. Not sure I would do that again.....The benefit to the drive was we drove our Tesla and the ride was great. Lots of superchargers all the way, last one in Marathon. And the Hyatt parking is in the Margaritaville garage, which had EV charging available for free. So that was a great find.
Almost cancelled this trip, but after cancelling everything else this year we decided to go and I was glad we did.