[RickFLM4]

Drive from South Beach to Key West will be 3-4 hours FYI, but there are also flights there from Miami. Starts getting nice here in October so should be a good time to visit. If it will be near Halloween Key West will be mobbed with people for Fantasy Fest.

I haven't been in quite a while but prefer the chains like Westin or Hyatt in Key West. Small island so everything is within reach but you'll probably want to stay somewhere walking distance to Duval. Other than drinking and riding around on a scooter (preferably not at the same time) and maybe a couple of touristy things, there isn't a ton to do in Key West IMO. However it is a place to visit at least once to check out the character of the place.

Have never stayed in the Clevelander but they have a nice outside bar. Or at least they did 20 years ago when I was probably last there.

I'm guessing but expect getting to Cuba may be easier from Miami than Key West. Maybe Key West has some prop jets.