Food
I like the Rod and Reel Restaurant on the pier down the block better than City Pier. I have had two bad experiences at City Pier (service and food). At R&R, the fish special sandwich is always perfectly cooked, fresh and a huge portion. My sons love the chicken fingers which are the largest I have ever seen.
Another great spot is Capalbos on Cortez off the island. They have a very inexpensive pizza buffet that includes salad and homemade soups. They also offer two for one drinks. The pizza is delicious and they offer quite a number of different variations! Go early as it gets packed!
For a special night, try the Chart House in Longboat Key. The food, service and views are wonderful.
For ice cream, we have tried all of the places on the island. My kids say Olaf's (down the road from Gulf Stream) is the best!