I've been from Lauderdale to Key West, up and back a few times, Hawk Channel and Bayside, in and out. This gives you weather and sea state options, which are good to have. Hang in Miami for some high end on water life with the big boys. If you haven't been through the Keys by water, I'd recommend you go for it.
There are numerous stops along the way from resorts, restaurants, marinas to cruiser hangouts, like The Dockside, Boot Key Harbor, Marathon. If you SCUBA or fish, you'll be in your element. Key West is a destination itself and a run to the Dry Tortugas Nat'l Park, about 100 miles west, gets you into the 'wilds'.
Brings back some great memories...
Aye.