I would start with a good cup of coffee and a real breakfast. I'd make a sign out of some cardboard, grab a couple folding chairs, and hang out at dog beach for a few hours, reading and enjoying the morning. Then I'd take my sign and chairs and head to someplace nice for lunch, maybe to have a cuban from a food truck. Then I'd be off to Duval with my folding chair and sign and hang out there for a while. If I could, I'd set up right in front of the curry mansion museum. After a few hours there, I'd move down to the southernmost marker and hang out there with my chairs and sign. And as the night started to fall, I'd walk along duval and whitehead, listening to music from the various bars, and stopping when I found one to my liking.