Siesta Key itself isn't too adventurous. Pretty tourist friendly. Siesta Key Oyster Bar is a fun time, you can do Yelp "wait in line" feature to essentially make reservations. Flavio's Brick Oven Pizza & Bar Siesta Key has great pizza and good Italian. There is a crepe place for breakfast/lunch that is fun. If you want to venture off the island I HIGHLY recommend Lovely Square in Gulf Gate for an EXCELLENT breakfast. Gulf Gate Mall itself is a neat place to check out (not on a sunday) Napule Sarasota nearby also has FABULOUS food. Back to Siesta Key - avoid the overly obvious tourist traps like Daquiri Deck! Honestly, SK is fun, but for food you are better off looking elsewhere. Sarasota and Saint Armands Key are better for dinner.