Hi, there. We've been busy cleaning the boat to get our shivering bodies further south, so I just looked in.
If you're new to the ICW, I'd suggest you read up about the navigation marks and bridge heights, etc. in the Cruisers Wiki before you head out. Atlantic Intracoastal Waterway
Going North, one keeps Green to Starboard, Red to Port. And things get confusing when the ICW crosses a harbor entrance and you're switching between ICW marks and other waterway navigation marks. The entry in the Wiki has illustrations. The AICW page also gives schedule and times for bridges. Note that the Julia Tuttle Causeway Bridge in Miami is a fixed bridge with 56' clearance! No choice but to got outside here. As you will see, there are a lot of bridges to wait for in Florida. Once past Florida and Georgia, the number of bridges is more reasonable, but lots of inlets will have shoaling, and it changes from season to season. Florida is marking the clearance on some of their bridges lower than the 65' controlling height of previous years (supposedly because a boat damaged its mast because a clearance was not correct - and the fellow sued Florida.
It's not easy trying to make time on the ICW. Though the controlling depth is supposed to be 7 feet, shoaling is always a problem in the Carolinas, and the Georgia ICW is a twisting, turning, shallow maze. Tides in GA run about 6 feet, so you need to watch them as you make your way there. Low tide can be sticky going.
The ICW can be quite pretty, but it is slow.
Do keep a watch behind you as well as ahead. By June most of the big sportfishing boats should already be north so you might luckily not have big wakes to contend with, but beware. You'll also want to do most of your traveling during weekdays, leaving the weekends to the local weekend boaters - some parts of the waterway are insanely crowded on weekends, and the drivers of those little powerboats don't understand "no wake".
I'm lobbying to bring Watermelon north for this summer, but we'll probably do the majority offshore.
Oh! Be sure you take back bearings as you travel up the ICW. some of the channels are quite narrow and it's very easy to get out of the channel. Where shoaling is most prevalent the marks will be floating marks, not permanent, so keep a close eye out in those places.
You'll meet a lot of nice people along the way, so it can be a very pleasant trip.
What are you going to use for charts and navigation?