To make your money go the farthest, I would suggest Islamorada FL. Spend two days on a charter ($1,000 per day incl. tips), then spend the remaining on the party boats or even some inshore flats/mangrove fishing. The charter will get you on the big fish, the party boats will get you on the grouper and other cool reef fish, inshore will get you on Permit.

A party boat trip is only about $60 per person + tip for about 6 hours. It's a very good deal! One boat down there offered the usual

I spent an entire week down there, and it was awesome! We rented a house down there that had it's own dock/pier that we fished in the evenings...we would drop a chum block a few hours before dark off the end and caught grunts, mangrove snapper, puffer fish, and even small sharks. That in itself was pretty cool! Sunup to sundown we were fishing!