I am actually planning on doing the same thing. My plan was to leave at midnight and then drive south, fish all morning/afternoon and head back home. The reports have shifted a bit since the last time you looked at it but I am still planning on going. Not sure if Im going to do surf or bay yet, ill way to see what the surf report looks like tomorrow to make a better decision. Those things change daily.
If your planning on fishing for trout then you won't need your kayak. Just fish the first gut early on with top waters and then move to the second gut as the sun rises. You probably won't need to go further than that.
If you plan on shark fishing then your on your own. In not a fan of sharks non the less fishing for them, too many encounters for me.
High Island is a bit of a haul depending on where your coming from. My preference, if I have the time is to get in at Crystal and access the beach. I then drive up and down till I find action. Birds, bait, etc. If I don't have the time and don't want to mess with the ferry I hit Galveston. Either East Beach or on the west side. The problem is that you can't drive the beach there but you can still drive looking through the houses to find a place to fish.
Im not a fan of Freeport, if I go that far I might as well go to Matagorda and drive the beach again.
Hope this helps and best of luck. Im still waiting for the surf to change again before I fully commit to hitting the beach. If I were fishing for sharks then it doesn't really matter but for trout it does.
"Many go fishing all their lives without knowing it is not the fish they are after."