So we decided to go the B&B route.
We made our reservation at the Artist House for Tuesday 03/25. http://www.artisthousekeywest.com/

We'll be in the Eugene Studio Suite.

Tentative plan:
-Leave LBTS around 7:00am
-Cliche or not, drive down in the rental with Buffett's boxed set
-Go straight to El Siboney for lunch
-Check in at the Artist House and get our room situated
-Walk around and soak the environment up, stopping in places that seem interesting, culminating in...
-Sunset at Mallory Square
-Get clean and go to Blue Heaven for dinner
-Do a 1 drink per establishment pub crawl (many of the bars suggested by you all) that ends with us getting to Schooner's Wharf by midnight/12:30 and staying there to watch whoever's playing finish their set.
-Walk/cab back to Artist House for sleep
-Head to Croissants De France to start the day
-Get to the touristy things (Mile Marker 0, Southernmost Point, Hemmingway House)
-Hop in car and stop in Largo on the way back north and go to the state park to snorkel. <img src="http://www.traveltalkonline.com/forums/images/graemlins/toast.gif" alt="" /> <img src="http://www.traveltalkonline.com/forums/images/graemlins/dine.gif" alt="" />