Spanish Town is a little tight for a big cat but not hard to negotiate. I wouldn't stay over night as it tends to be hot. What breeze there is comes across the Valley which warms it at night and it is broadside to the slips. AC is almost mandatory. I would consider a run to Liverick for the night. A lot will be closed in late September but a few places will be opening about halfway through your sail.
Bring light weight rain gear because, with the ENSO in transition, it looks like the first part of October may be a bit wetter than usual this year.
-------------------- Travel is fatal to prejudice, bigotry, and narrow-mindedness, and many of our people need it sorely on these accounts. - Mark Twain