Depends on your schedule.
Daylight cruising might be:
Stadium - Pumpkin Key - Rodriquez Key - Boot Key - Key West
Beware at Boot Key, you have to enter thru Sister Creek and it's shallow so you may want to wait for high tide.
Key West your options are plenty, anchor, mooring
ball, or marina. IIRC, Key West Bight Marina is $2/ft/night in the summer. They have 3 catamaran
slips or parallel on the A dock (don't accept the end of D dock), make an advanced reservation.
Key West to St. Pete direct is your call. Long passages are no problem with enough crew, but can be downright dangerous sleep deprived. Again, this depends on your schedule.
A daylight only enjoy-the-sights passage
Key West - Marco Island - Ft. Myers Beach (Moss Marina or Diversified or anchor outside or at Punta Rassa) - inside to Useppa or Pelican Bay - inside or outside to Sarasota
- outside to St. Pete (you can't make it under the bridge at Sarasota).