Sailing

Don't have a lot of advice, took my ASA classes down in Ft. Lauderdale, and some of the cool places we stopped was no name key, Boca Chita Key and at our furthest point south we stopped/ate at Gilberts resort. It was a decent meal/stop.

Boca Chita

If you plan on staying inside until Ft. Lauderdale, be prepared for what I call "The Land of 10,000 Bridges." If you head south past the Lake Worth Inlet, you'll hit a stretch of bascule bridges that will try your patience. Some of them are on request, but many are on a schedule. If you can't make 6 - 6.5kts SOG (small inlets can affect you along the way with current), you will often miss openings and spend even more time waiting around. Make sure you have a list of the bridge names so that you can call them for openings. Personally, I will never go this route if the weather is at all cooperative. To futher complicate things, it can be tough finding an anchroage if you want to stop.

When you say "outside" regarding Lauderdale to Seven Mile, do you mean outside the reef? There's really no reason to do that, you'll have nothing but adverse current from the gulf stream slowing you down on the east side of the reef. I'd recommend going "inside" down Hawk's Channel. When you head back north, if the sea state is good (i.e. the wind is not out of the north), then go outside and pick up some free speed from the stream pushing you north.