I vaca in Islamorada for at least a week every year. I can help with food and booze.
Islamorada fish company is good for sunset diner and drinks(also they have a good fish market), morada bay for drinks at sunset, lorieli's for any meal,drinks the bar opens for breakfast(cheap),Islamorada bakery for breakfast, while at robbies feeding the fish you must eat at the hungry tarpon

have a great time