It's not uncommon for folks in 20-22' boats to run from SE Florida to the Bahamas. Yes, they pick their days. In other conditions, a 54' Bertram will have a rough trip.
As far as the Keys are concerned, getting around in a smaller boat is always easier. On top of that, finding a quality public boat ramp in the Keys can be a challenge, so a small boats have many more options. If you trailer in the Keys, make sure your trailer is completely functional to include the brakes and lights -- the Monore County Sheriff will gladly write you a ticket if they aren't.
Just remember, when going to the Keys, you're leaving the US, so a passport is required for everyone. Opps, I meant the Bahamas .
PB