We cruised both coasts of Florida and the Bahamas back in 2002 (and that's getting to be history.) We went in Our Journey, a 36' sailboat and the only boat with a 6' keel west of the Mississippi. Here's what we used:
Maptech Chartbooks. The west coast of Fl, east coast of Fl and the Bahamas. These are great and cheap for paper charts. Needed for planning and backup.
You can download the latest electronic raster or vector charts from the internet and use them on your PC. I had to borrow them from a passer-by in the day, but the PC was invaluable. Now you can use a GPS puck, which is really helpful in navigating the shoal waters of Florida. Really shoal waters. We provided the afternoon's entertainment several times, getting unstuck. Relax, the C-Dory will be a lot easier.
The cruising guides were:
The best local cruising guide was Skipper Bob. Good old Bob is now dead, but the guides have been updated. Great detail knowledge. There's "Marinas Along the Intracostal Waterway" and "Anchorages Along the Intracostal Waterway" AND the "Great Circle Route". They all cover Florida well. We used Anchorages a lot.
Southern Waterway Guide. It goes from Florida to the Mexican border, so you can cruise there. Helpful for marinas, routing, etc.
For Florida's west coast (sorry, left coast) we used A Gunkholer's Cruising Guide to Florida's West Coast. Good local knowledge. For the Bahamas there is The Bahamas Cruising Guide by Mathew Wilson, 2nd ed. Both worked well, but you can wait till you get there and see what's up-to-date.
Now, we also have to find trailer storage. Sometimes the marinas will let you store the truck/trailer where you launch, and other times they're expensive. In the latter case, we've had good luck with a local storage yard. You can find them on the internet and call them to find the best/cheapest one.
And by the way, we used a CQR which is a plough type anchor. There's a lot of soft sand and we dragged a couple of times. Once, overnight, a 1/2 mile. Luck beats skill and we didn't ground. I'd carry a Bruce for those situations. In addition, if you're from the mid-west, get used to tides. At least 3 ft.
When you go to the Bahamas, we found it a lot cheaper to check in at Nassau and then go cruising. Whenever you check in be sure to say "we just got here." We waited overnight and they weren't happy. You'll need a passport. Key West was fun, the Dry Tortugas a blast and we got thrown out of Naples for not having the latest registration on our dinghy.
Looking at your boat pictures, I have one suggestion. If you go to the Bahamas, get a second motor for your C-25. Even if it's a small dinghy motor, you can tie the dinghy alongside the boat and get if moving that way. sometimes there aren't a lot of people in the Bahamas. Sometimes there's too many. Also make sure you got a dinghy if you plan to anchor. Remember, PVC dinghys rot in the south
You're getting this gratuitous advice because Judy's away and the alternative is pulling up the tyle off the kitchen floor.
Boris