If you are going to limit your cruising range to the ICW, why not consider a power boat? You will be motoring most of the time in the ICW. If you do choose sail, look for something with shallow draft, roller furling for those times when you will be motorsailing or sailing, and good ventilation with screened opening ports. You might want to consider where you would store two anchors, since current conditions in limited anchoring space often demands two.
The Catalina 28 MKII is a great boat. My wife and I have sailed ours all over New England and have lived aboard for weeks at a time. There is plenty of room for two anchors as the last writer mentioned. We have an autoprop on ours which gives plenty of power with low fuel consumption. with a wing keel the boat should be great in the ICW. We are in the process of trading ours now, we are moving up to a Tartan 37, but I would highly recommend the boat.