Wife's family have a condo at Harbor Point in Truman Annex and we would go every year... one of those special places.
As mentioned must hits-
-Blue Heaven Breakfast
-El Siboney is a good spot
-Great afternoon booze spot is Schooner Wharf- decent mahi sammich
-Touristy but Sloppy Joe's is great
-Also touristy but Hogs Breath has a must have mahi sammich and imo, the best Rum Runner.
-Also like Kelly's for a great outdoor setting and Bagatelles for a nice dinner on Duval
-Pepes is a good joint for breakfast as well.
On the way down or if you go up the keys to fish be sure to check out, in this order, these joints-
The best seafood I've had, period. Crusted grouper is insane.
WHARF BAR AND GRILL
The Square Grouper on Cudjoe key is great.