Posted: Feb 19, 2019 - 10:23 AM
If your boat can handle shallows (ie, no daggerboards or daggerboards & case that you don't mind light groundings and the boat can sail reasonably well with them up, kick up rudders, etc), it'll be easy.
Looking at the map (didn't know Flamingo!) , ICW won't be of help :-/ and you'll be going against the prevailing winds (ESE). If logistics allow, I'd do the reverse route, kick back in a broad reach.
I sail biscayne bay mostly so might be off.