Anna Maria Island is a barrier island north of Longboat Key. Anna Maria is a charming small town at the north end of the island with an “old Florida” feel. With no high rises, unlike Longboat Key to the south, you find small homes, old hotels, beach restaurants, a beautiful boat harbor and an historic pier. I recommend:
Waterfront Restaurant, 111 S. Bay Blvd.: This restaurant comes highly recommended by locals for its great food.
Sandbar Restaurant: A great spot to meet with friends for sunset on the beach. 100 Spring Ave. in Anna Maria. It is popular, so make sure to go early.
Ginny’s and Jane E’s Cafe & Coastal Store is also popular with locals. It is a service station turned café and homewares shop on the island’s north end. It is a great breakfast spot. 9807 Gulf Dr.
I just read about Rod & Reel Pier, a local’s favorite since 1947 that is at the end of a pier on the water. Their grouper sandwiches are supposed to be great!
My local friends also recommend Isola Bella Italian Eatery for great Italian specialties. 5904 Marina Drive, Holmes Beach. Where I ate with them, The Sign of the Mermaid, has closed and is now the The Porch Restaurant. Located in a newly renovated, historic cottage from 1913, it is an upscale restaurant featuring steaks and seafood. It is the concept from the owners of Ginny’s and Jane E’s. 9707 Gulf Dr.
If you want to stay on the island, the Waterline Villas & Marina, an Autograph Collection Hotel, is a good option for rooms or vacation rentals. 5325 Marina Dr, Holmes Beach