Thanks for all the info! the length is not a big deal and actually 3-5 days would be ideal because I don't have many PTO days. I'm going to look at all of your links and read up more. Starting in Florida would be helpful but if it starts somewhere where the flight is not crazy expensive its do able. The more dives the merrier too but just seeing new places is our main goal. The reason for the $1000 price limit is that I am trying to save up so I can go to Australia next summer while still having a good vacation this summer too. Privacy is not a major issue either.
Thanks again for all the info everyone!
Here's my trip: Dry Tortugas 2015 | The NYC Sea Gypsies
This will let you know a little bit more about the Spree and the Dry Tortugas (they go there frequently).
They leave from Key West, but I usually fly to Miami and take a shuttle because there are no direct flights to Key West from NYC. Airfares are typically less than $300 round trip...!