Hey Tim
I think Tuesday and Wed. are going to be good, as Raul said.
I don't care how tuff you are, Mr. Cape Cod, you will probably need a wetsuit on Wed!
As far as I know, most areas around here are very safe. The beaches in St. Pete are safe, for sure.
Can you ride on Tuesday? If so, you might be able to do a downwinder. That's always a treat.
If not, if it is NW, they are plenty of spots for your wife and baby to hang out in while you ride along St. Pete beach.
They can watch you ride and not have to be freezing right on the beach, or be on the beach and take a break.
Keep in touch with us in the "Let's Ride" section (this section), we can narrow down a place to ride and hook up with some locals for you.
It shouldn't be hard, we haven't had wind for a while, so I suspect at least 15 (maybe more like 40) riders will be out on Tuesday.
Wednesday looks flat out over the top. When Accuweather is saying gusts to 45, we have some issues.