I really think that if you looked at every place you could be in a sailboat between Carrabelle and Pensacola, Destin would be the worst, for access and for costs.
Places I like.
1. Carrabelle - Great little marina on the right as you come up the river. Even has a cruisers lounge area that is really nice to relax in.
2. Apalachicola - Lots of places to stay and tie up, some city owned, but most private. Great little town that easy to walk to and through from a boat.
3. Port St. Joe - Not much to see there, but they have a great marina there that is walking distance to marine hardware store and grocery store, plus a decent bar and grill at the marina.
4. Panama City - Great destination. Two really nice city marinas, plus a million places to anchor. The westernmost city marina is my favorite. Lots of cool stuff withing walking distance and a good store at the marina.
5. Pensacola - Another great destination. Tons of places to anchor. My favorite place is always Little Sabine Bay. There area couple of places to anchor there, but I always take a slip (usually at the Yacht Club, I don't think it's a real yacht club but that's what they call it) and then walk over to all of the really close stuff. You can also head west on the ICW from there and see some really beautiful anchorages all the way to Mobile Bay.
Destin has a horrible inlet, lots of shoals, and the bridge is only 48-49 feet high. A friend of mine let someone borrow his Tartan 34, who tried to sail it under that bridge. It can now be said with authority, that a Tartan 34 will not go under that bridge.
I'm guessing you don't want to just run the ICW from Apalachicola to Mobile Bay, because with your air-draft, you could easily do it. I've done it in the past (can't now with a 62 foot air draft) and it is mostly a pretty fun and scenic trip. You might want to at least do it one way. You could easily anchor out the entire way (on the panhandle, they haven't developed the cruiser hate yet that more southern Florida has and you can anchor anywhere normal navigation regulations allow, just be mindful of tugs and barges coming through, which you will see a lot of).