Key West
My Lovely wife and I first visited Key West in 1989. We went for my birthday in November. Capt. Tony Tarracino was elected Mayor by 32 votes over incumbent Tom Sawyer ( no relation, but it is that kind of town!). We stayed at the Marriott Casa Marina because I used Marriott points – a lot of Marriott points! We had Margaritas at Capt. Tony’s Saloon: rated 5 out of 10.

Casa Marina was a good walk from the wild side of Duval, but we were young and didn’t mind. We were stopped and bribed with free dinner tickets to attend a Condo-Timeshare sales pitch; which we promptly accepted. The sales pitch did not end happily for the salesman and he literally threw our dinner tickets to me. Not a problem – we were introduced to Louie’s Backyard and have been going back ever since.
Lovely J hadn’t enjoyed the small plane ride from Miami so for our next visit in 1990, we rented a car in Miami and drove to Key West. It was a pleasant enough drive but we have NOT done it again. When the purpose is to get to a place – GET TO THE PLACE QUICKLY!! We sampled Margaritas in all the right (and wrong) places. None rated more than a 7 and that was Jimmy Buffet’s place.
In 1991 we were entertaining a 3 month old son on my birthday so our Key West visits were delayed (with no regrets) until 2015 when we quietly returned without fanfare on a direct flight from Newark, NJ. We stayed here and there and eventually found a place with a porch and a view and big enough for us to invite two friends from Florida (mainland) that we don’t see as often as we’d like. Sun, food, drinks, friends and a porch are all old people need to be happy. BTW, I make my own Margaritas these days (8.5).
Covid and now family issues have put a damper on our Key West visits lately, but I still have a few birthdays left (I’m an optimist!) and Key West with friends is a lovely lovely place.