Have chartered out of Pensacola for five years until purchasing my present boat two years ago. Great place to have a boat; you can sail the bays, sounds, ICW, and the Gulf when conditions are good. Lots of places for weekend sails with related anchorages & marinas.
Hope this helps:
Bottom paint: might as well apply now. Ablative paint is good, use highest Cu content &
two coats. Compound & Wax topsides of hull.
Zincs: Replace shaft zinc if it is more than 1/2 consumed or you will paying a diver shortly
Mast: Typical inspection & maintenance. Clean,lube, & retape VHF & light fittings
Replace anchor & steaming light bulbs if they are older. Inspect shrouds, tangs,
spreaders, turnbuckles, etc. If you are really energetic, wash & wax the mast.
Shipping: Use a reputable carrier that obtains all highway permits & has insurance that
will cover your boat in the event of total loss. Also, I advise either removing the
shrouds completely from the mast, coiling, and placing in the bottom of the trailer
or wrap & tape shrouds in bubble wrap first and then shrink wrap the halyards &
bubble wrapped shrouds to the mast. If you allow shrouds to remain on mast
and only shrink wrap, the vibration from the truck & trailer will chafe the
anodized finish on the mast. Happened to me on my shipment. The trucker
warned me when he picked up the boat; however, the yard had already packed
the mast and shortage of time was a factor.
Taxes: Unfortunately, you will be required to register & pay taxes on the value of your
boat & it is going to be a lot more than $130. Checked on that a couple of years
ago. You have about 6 month grace period. After that, the boat will have to be
registered and taxes paid. Call the Florida boat registration dept that is part of
Florida wildlife & fisheries division for factual info. And, yes they do check for
proper registration on the water & in the marinas and do enforce with penalties.
Marinas: Downtown marinas are Palafox Marina, Bahia Mar on Bayou Chico (in town),
as well as two others across from Bahia Mar on Bayou Chico off Pensacola Bay.
On Pensacola Beach, there is Sabine marina & Innerlight marina (on Santa Rosa
Sound)
I plan on moving the boat to Pensacola eventually. I really like the place, the lifestyle, food, and the sailing is great. Definitely agree that a reverse cycle air conditioner/heating system is a priority for the summer and winter too. The Florida panhandle is not similar to southern Florida. There are a lot of cold days & nights from December thru February; however, it warms quickly a day or two after the passage of cold fronts. Good Luck, I think that you will like it.