Jeez, you guys are getting me jealous. We just had our first frost up here in RI yesterday. Hawai'i is definitely on my bucket list, but the Keys are a perfectly acceptable substitute until I can get there (even if I can't hunt the deer on Big Pine). Southwest gets me to Ft Lauderdale cheap, and once you get past Miami the car ride is fantastic. Nothing beats being able to wade out hundreds of feet from shore on Bahia Honda, still be in knee-deep water, and sight cast to fish cruising the flats.
The Keys are great! I had friends live down there for years and I went to visit them at least twice a year, sometimes for a month + long stays. So many great fishing spots and like you said, you can wade out hundreds of feet or just take out a kayak. I haven't been down there in about 7-8 years, as most of my friends have left the Keys. As for Hawaii, if you ever make plans to visit, I would be happy to share our condo in Kihei, Maui (which is directly across from Kam II beach). We rent it out when we are not there and would give you and all other AHA members our friends and family discount ($60/nt April - Nov).