We are on a mooring ball here in Boot Key Harbor, waiting to cross to the Bahamas. We left Kemah, Texas on November 15. We travelled the ICW from Galveston to Pensacola. You will get used to the barge traffic quickly, and it's no big deal, really.
You can check our blog, and go back to the beginning post. On the map, it shows every stop that we made. I used Active Captain to plan our trip, as well as some advice from a friend from Texas, who was about 2 weeks ahead of us. Where is the Light Switch? | sailing away with R & B
All but one travel day after Pensacola was offshore, coastal cruising. Our airdraft is 50', and bridges determined that we go outside. We were able to do the ditch from Port St. Joe to Apalachacola, a nice short day travelling on a beautiful stretch.
If you want to get farther south, you'll have an overnight crossing from Apalachacola (or Carrabelle) to Tarpon Springs, or Clearwater Beach. It's going to be at least 145 nm, depending where you leave from, and your chosen destination.
Once in Clearwater, you can resume ICW travel to Ft. Meyer's Beach. From there, it's outside again, except a short trip inside from Marco Island to Ten Thousand Islands if you are shallow draft (4').
Go for it! It's a great trip with much to see.