You could make a short trip around to Apalachicola and Carabelle. Then take the jump to Clearwater. That shortens the sail across the Gulf plus leaves you a little closer to shore if weather
does change on you.
Once to Clearwater, it's an incredible beach. But then go around to St. Pete and it's entirely different and still very nice. From there it's simply a matter of time and how far you want to go. Bradenton and Sarasota
. Bradenton Beach, Longboat Key, Siesta Key. If you want a city your wife will adore, but your wallet might not, then on down to Venice. It is one of the nicest, prettiest cities there is. Beyond that, we love Sanibel, Fort Myers
and Charlotte Harbor
areas. But I'm thinking to keep the trip pleasant, Venice would be the furthest you'd want to try and it may even be a bit too much.
You can have a blast in the Clearwater to Sarasota
corridor. Plus the contrast before and after of Apalachicola and Carabelle areas. Just covering those areas you will have found something for everyone.