One reason we decided not to take the Great Loop (north to the Erie barge canals, through the Great Lakes, down the Mississippi then the gulf coast then the east coast) was because unstepping the mast and its electrical wiring is such a pain.
From NY to Florida, we traversed something like 160 bridges! About half were fixed bridges of 65-feet, (our mast is 41-feet above the waterline), but the rest were draw bridges of one kind or another. Generally, we would call the bridge tender on the VHF radio and they would open for us. Many of those bridges had restrictions and would only open at certain times, (often on the hour and half hour), which required some planning and waiting. It wasn't really difficult but it often meant we'd have to wait for the next opening as Pelagic can only travel at 5-6 knots. There were dozens of bridges south of Ft. Lauderdale making that leg a bit slow.
Our bigger concern was the depth of the water. Pelagic draws 4-feet and because of shoaling and lack of maintenance, the ICW has some notorious shallows that require vigilance. The Aqua Map app displays the most recent sonar scans of the bottom and that was helpful to steer around the dangerous spots.
In South Carolina, we went through the Socastee Bridge around 10:00 am heading north. About an hour later, a terrible accident occurred when a young man driving across had a seizure and crashed off the bridge killing him and closing the bridge for several days. Other boaters we knew were stuck south of the bridge for days until it re-opened. Quite a sad story.
Much of the ICW is in open waters that traverse bays, rivers and sounds. The rest is made of of creeks, canals and cuts. It's all well-charted and well-marked but it still requires careful attention to navigation.