NSB looks like a very tight inlet if the weather is not cooperating. i don't think it will be a fun experience if it is blowing 20-25 knots out of the East when you get there. There appears to be no margin for error.
What are you using for self steering? That is the question that we singlehanders always ask.
Primarily myself and the tiller along with an egg timer. I also have practiced sailing using bungee cords and sail trim to hold a course. Lastly i have a tiller lock which holds the tiller on course long enough for me to tinker with the jib or do something else.
this is why i have planned the trip in no more than 12a hour runs with me possibly leaving out of st augastine at night to make new smyrna before dark the next day. My average cruising speed should be around 4.5 knots with dinghy in tow.
If merrits on the wy why not! Yea the keys sound like a fun time.. plus its something new. I just hope there is ample spear fishing.