Nice trip report.
Love your style.....rent a beach chair and troll the beaches. Great idea for the busy season.
As for Packing..from a sloppy mans perspective..I find that I really only use a few pair of shorts and 2 bathing suits. Lots of tees and cpl dress shirts and slacks. Biggest hassle is the shorts for working out/ running in the AM. I only bring a few. The sneakers I always bring down and throw out and buy new pair when I get home. That usually gets me through 2 weeks with a cpl laundry washes.