I visit this part of Florida at least annually for my work in College Advancement. A new co-worker had never been there, so my husband and I showed her our favorite places.
For great food and wonderful service, visit Tim and his staff at the Old Salty Dog on Siesta Key. This long-time favorite of local and visitor alike was expanded and remodeled in the last year. Ask Tim "When are the Reds playing?" (and say Tom sent you).
A walk on the softest sand in North America at Siesta Beach is a must. White as snow. Great place to watch a sunset or see fourth of July fireworks.
Food and roots music to die for at the Packing House is a required stop. Near I75 and Fruitville Road, this hole-in-the-wall has amazing seafood and cajun influenced dishes.
Other sunset spots - a trip would not be complete without a detour down to Venice Beach and a Rum Runner at Sharky's. Follow this with a dinner (and the next day's lunch and dinner) at Luna's for homemade Italian (located off SR41). Take an afternoon to shop with the wealthy at St. Armand's Square, over the causeway from downtown Sarasota. Wander Lido Beach just a few steps away and go shell-hunting.
One of the simplest things we did with my new co-worker was drive the Keys from Bradenton to St. Armands. You see the scene change from funky Bradenton Beach to the tall trees and no buildings on Coquino Beach (at state park and favorite quite sunset view), through the wealth and manicured lawns of Longboat Key. This soothing drive is best done before the mass exodus of the daytime beach goers.
We love the pace of life and the beautiful Gulf of Mexico here. And if you are an arts/theatre fan, no better place in Florida to combine all of it!