If the
weather is iffy, you can hop north up the coast to Clearwater or Tarpon Springs and then go across to
Panama City or Pensacola depending on the weather window. If you go into
Panama City there are good
marinas just inside to the west is Baypoint Marina. With a 44 , I think your
mast will exceed 49 feet, so you will have to go back outside to Pensacola. Palafox is a nice marina in downtown Pensacola and the Big
lagoon just inside and to the west is a nice anchorage. You can
motor to Mobile in the GICW with no worries about your
mast height from Pensacola, or you could make it 2 days and stop off at the Wharf or Lulu's for the night. In Mobile Bay, watch the chart and stay away from the shallows and spoil areas and go through where cuts are marked on th chart. Of course, you could go direct to Mobile Bay from SW
Florida if you have a good weather window. We sailed to Punta Gorda going out at Pensacola in a
Cabo Rico 38 and it took just under 4 days. It's a great trip,if the weather is right!