Louie's Afterdeck, Key West
This is a great hang out bar that is over the water on the quiet side of the island near the southern most point. It has great views and people anchor nearby and wade over. Was once a hang out for a young Jimmy Buffett and several years ago they even found some old unpaid bar tabs of his. I'm sure he can pay his tab now. It's behind one of the mort expensive resturants on the island but worth the trip.
Dress Code: If during the day, typical Key West attire but because of the resturant at night it might be a bit more formal.