I live here. I can do it pretty much any time you show up.
Figure out when you could do flights and hotel, and then check to make sure we
aren’t all out of town. 
Warning - at some point, the water cools down and you start to use a wetsuit.
-D/a
I also recommend the Key Largo area.
i was going to say the same, I live here so anytime is good for me. Digital: I’m in Key Largo so Plantation/Lauderdale by the Sea are about 1.5 hours north for me. West palm is even further away but I enjoyed shore diving there. Do you ever get down to KL to dive?
Aside from pool dives to get certified, all of my dives have been in wetsuits. I would assume the main issue there would be cost. Is there an impact on visibility? Wildlife?
I’d love to go soon, but I have a lot to arrange finance wise. How early does the water get cold enough to require a wetsuit, approximately? How early does it warm up again?
I really do appreciate the offer and all of the info everyone has offered. I have a few concerns about work right now, and if business takes a bad turn, I might have to wait until next spring, or early summer.
This thread has given me the jones though, so I’m keeping an eye out for good deals.
Another vote for this. I was (I guess still am technically) a PADI divemaster and loved that area. Great park (Pennecamp). I was the VP of my university’s SCUBA club and this was a great trip for college kids without a ton of money. We camped nearby, had great dives, tons of fun, great local food, met tons of people. A commercial diver from the great lakes took a few of us out shrimping at night on his Zodiac (Me, him and two gorgeous college girls). Looking back it may not have been the smartest thing we ever did, but it was entirely innocent, we caught enough for one amazing shrimp cocktail that we shared (I think 8 shrimp total) and have a story to tell 20 years later (we stayed in touch for about 5 years after but lost contact later).
I’ve been diving all over the world and this is still one of my favorites. So many others are where people “with money” go, but this seems to fit my idea of what the early guys who wanted to see what was under the waves had in mind. There is also some really cool fresh water diving in springs/caverns in north central Florida (Swanee river area). Looking a Manatee in the eye just can’t be duplicated.
Yep. Those springs and caves down there are very neat and very enticing.
Now for a PSA. They are also deadly if you are not properly trained and equipped for cave diving. DO NOT go in them if you are not those things. Not even a little. Stay out in the open water part of the springs. The same can also be said for all but the smallest of wrecks.
In the very early days of the internet I sent this sort of PSA to a random guy I ran across on the internet. Never got an email response back. Because he got it too late and busy dieing in a cave instead 
Don’t be that guy.
Thank you Bill. I should have said this. The most scared I’ve ever been in my life as a Divemaster was with a guy I didn’t know (and was asked to check out) who decided to just take off in a cavern. We sat for probably 5 minutes after I finally grabbed his leg to try to figure out which direction was slightly lighter. Luckily we were right. It was supposed to be an easy cavern/spring dive and very quickly turned into an advanced cavern/cave dive. We sent him home the next day.
It is still great diving if you know what you are doing and follow the rules.
Air Tran often has pretty good prices for flights from Milwaukee to different cities in Florida, including Key West.
Cayman Brac is fantastic. The divemasters are very good at ensuring your safety, water is clear, reefs are beautiful, food is delicious, and you are free to just walk into the water from the beach on your own if you want unguided diving. However, the second dive of the morning was usually a free dive with your partner and you were just given a time limit to return to the boat. We discovered that the divemaster hovered high in the water during these dives so he could spot anyone in trouble. People who were practicing buddy breathing found him at their side in moments.
Cozumel was OK but drift diving is stressful(for me anyway) and really requires a guide. Also, every horror story I’ve heard about the bends or some other disaster, happened in Mexico where the diving industry is essentially unregulated. Apparently anybody with a boat can take divers out and often encourage repeat dives without sufficient time to off-gas so they can just get their money and get home.
Key Largo was fine but, mostly, very shallow dives for some reason. Whatever you do, enjoy and feel confident that I am pea green with envy.
That is what we are paid to do. Wonderful days in tropical climates diving in warm waters with beautiful women in Bikinis is just a fringe benefit 
That isn’t actually a bad thing over all. Beautiful things grow where the sun penetrates. I remember most of the dives in that area being around 25-30 feet. The nice thing about Pennecamp being a park is people can’t collect “souvenirs.” Just outside of the park it is much more barren.
I do know that I did one dive outside the park to a wreck that was 90 feet plus.