Hello Randomguy and welcome home (soon) from Iraq. We're glad you are safe.
I haven't been as far as the Dry Tortugas, but just offhand it looks like at least four reasonably long days of sailing from WPB to there, and that's assuming that you have a favorable
wind (which is likely after you make the turn SW somewhere after
Key Largo, 50:50 from WPB up to there), and that the
gulf stream eddies don't slow you down. Overall, I think it's asking a lot. Even WPB to an anchorage in Biscayne Bay is really quite a trip, a minimum of 70 NM, again, you would need a favorable
wind and no
interference from the currents to make it in under 12-14 hours. Having said that you can anchor most places in Biscayne Bay, normally in the lee of the barrier islands, off of Key Biscayne and Elliot Key are common
anchorages, but almost anywhere is OK in light winds. From there you can go out at either Biscayne channel or Angelfish Ck, next place to get back in for an anchorage is either Port Largo or Whale Harbor (both marinas), 50-70 NM depending on where you anchored, or to Rodriguez Key (I personally don't like the holding there). After that it's basically Boot Key or all the way to
Key West, although there are a few
marinas here and there where you can tuck in for the night, and Channel 5. Alternatively, if the weather is/has been good you can
head to the Bahamas from any of those locations, going E is always the tough part (if you want to sail), you usually have a good angle on the wind coming back.
If you want to call me when you are back or during your trip send a PM and I will give you my
phone number. Good luck. Pete