I'm trying to picture what's "more casual" than shorts, sandals, and print-splashed or t-shirts at a place that's pretty much outdoors with ping long tables and chickens sharing the floor space.
@8893 — On my visit, 3 nights staying in a beautiful home in The Meadows neighborhood a 5 minute walk from the Historic District (and beater biking everywhere else) was ideal. If driving to & from the Keys, I'd suggest a 4th night closer to Miami, rather than stressing about possible traffic-delays, which was part of our last day. We did get conch fritters at divey Alabama Jacks in Key Largo.
As to Freedom Fest, I had a men's group cohort who - after his wife died and his youngest went off to college - decided to be who he'd come to know he was during his decades as a Flushing pharmacist who raised a family in a split level home and n the Five Towns. One of his first adventures was a trip to Key West. During the Halloween Parade, he stuck his face into the local TV news camera and mouthed, "HI, MOM" with great gusto. Back on the mainland, he stopped in to see his dear, aging mother in Pompano Beach. Within minutes of his arrival, she calmly said, "You know, I saw you on television the other night." All of his wondering about how he'd come out to her with his big & scary secret news disappeared in an instant.