Been quite a few years, but have run the Harvest Moon many times in the past. If you choose your weather window well then its an easy sail.
Biggest gottchas are lots of commercial
traffic around major channels and on parts
of the ICW
patch obstacles. I've sailed past unlit large pipe stands a few times...a bit unerving to sail close past a subsantial section of pipe sticking out of the water
in the dark. Stay well clear of any oil patch installations as there can be unlit hazards close by them.
The seas usually get a little irregular after you round Matagorda sea bouy (at least the times I have).
Port A entrance is easy and well marked.
Have gone bump in a few places on the ICW which were not charted as shallow, but I expect those change often. Once after a barge had to do some aggressive maneuvering ahead of us...I think they pilled up silt. Dowload latest Local Notice to Mariners for NAV aid stauts etc right before you go.
There are some long straight stretches on the ICW where the next mark is so far away it can be hard to spot. Good binocs are handy to have. When running the ICW, dont just fixate on the next mark ahead, look behind you periodically to check the position of the last mark you passed....to confirm you are still in the channel.
at the helm
? All important around big traffic and in the oil patch. In addition to monitoring 16, scan local VTC and working channels so you have an idea of what the commercial traffic around you is doing?
Heavily commecialized section of coast line so the good old Coast Pilot is a good reference. Lots of it wont apply to a recreation vessel, but often some good tid bits in there.
These days I assume you can maintain internet
connectivity for all or most of this route
, which could come in handy.