We are set up in Apalachicola and heading to Tampa Bay. I need input on the weather patterns to look for for a smooth(ish) crossing. Right now the seas are 4 foot and people are saying it was a miserable crossing coming here.
Plus any advice or tips would be greatly appreciated.
I've not sailed that stretch of the Gulf personally, but lived on Tampa Bay eleven years and sailed much in Fall and Winter. Heading southeast in the eastern Gulf--wait for a NE to E wind which usually follows the passage of a cold front. Probably will have two, to perhaps three, days before the wind finally veers to SE. But, a good fair wind, and low seas (if close offshore) usually follow a front. (Keep an eye on depths.) Typically strong NE at first, 20 to 25 kt; diminishing 15 to 20 kt, then 10 to 15 kt late on the 2nd, or on the 3rd, day. If you tire of the wild ride, duck in at Clearwater and sail the ICW into Tampa Bay.

There's a
small protected harbor earlier at Dunedin, but you cannot gain the ICW there.
An alternative is to wait until the fairly mild SE wind sets up two or three days after a cold front passes (and is usually present anytime between fronts), and then "motor sail" down to Tampa in typically mild seas. Would NOT recommend trying it on an
approaching cold front; wind veering SW to NW to N--usually very strong & gusty, can be stormy out of SW early, plus much rain as front passes; steep wind chop ("washing machine" conditions), and COLD!!

Most locals head for a place to hunker with an approaching cold front (unless RACING!?!

).