We highly recommended this area for shopping, drinks, and restaurants. We had a nice lunch at Daiquiri Deck when visiting. Also, be sure to check out the sports memorabilia shop Stadium Gallery. St. Armands Circle is just below Longboat Key and overall a very cool place to spend some time.
Owen's Fish Camp in downtown Sarasota was our favorite dinner while visiting the area. They offer delicious seafood and an awesome back patio area with live music. They do not take reservations and the wait can be quite long, but they have a grill on the back patio for appetizers while you wait for a table.
Also located in downtown Sarasota, State Street Eating House + Cocktails has a restaurant on the left side of the building and a bar via a separate entry on the right. Although we have not tried the food, the craft cocktails and atmosphere at the bar were top notch.
Since it will be Cinco de Mayo weekend, you may want to drop by this "Mex-eclectic" restaurant right on Main Street, Sarasota. We really liked the nachos and margaritas.
We ran out of time to visit here but hope to check it out eventually! The Ringling, established in 1927, is the official state art museum of Florida. Many Sarasota visitor guides list The Ringling as a must see.
Take a kayak or paddleboard out into the bay mangroves. There are several companies offering rentals and guided tours out of Ted Sperling Nature Park at 190 Taft Drive. We went with Sarasota Paddleboard Company and saw lots of starfish, jellyfish, and seabirds.
The Resort at Longboat Key Club has 45 holes of golf, if you are interested in playing a round or hitting balls. The holes are extremely flat and pretty tight, with a decent amount of water in play.