Happy Island Cottage
Guide · updated July 2026

Where to eat on Anna Maria Island: the owner's short list

Not a directory. These are the five places we send our own guests, the same answer we have been giving in messages for years. All five checked and open as of July 2026.

Which restaurant is best for a beach sunset dinner?

Sandbar Seafood & Spirits, at the north end in the city of Anna Maria. Tables sit right on the beach facing the Gulf, the seafood is the real thing, and at sunset there is no better seat on the island. It is popular for exactly that reason: go early or plan on a wait, and consider a reservation.

Where are the best burgers on Anna Maria Island?

Skinny's Place in Holmes Beach, an open-air burger shack the same family has run since the early 1950s. Cash-friendly, paper-basket, frosted-mug old Florida. Open daily 11 AM to 8 PM. Get the Fatty Burger and onion rings and thank us later.

Where do we get real Italian food near Holmes Beach?

Isola Bella Italian Eatery on Marina Drive, and if you are staying at Happy Island Cottage it is literally around the corner: a two-minute walk. Homemade pasta, small room, open from 5 PM Monday through Saturday, closed Sundays. Reservations are smart in season.

Where should we have breakfast before the beach?

Anna Maria Island Beach Cafe at Manatee Public Beach, Holmes Beach: breakfast from 8 AM daily with the tables basically on the sand. It is the eat-with-your-toes-in-view option, and you are already at the beach when you finish. The trolley stops right there.

What about oysters and seafood off the island?

Anna Maria Oyster Bar on Cortez Road, just over the bridge in Bradenton, is our personal favorite: great oysters, casual, handles big groups without blinking, and easier parking than anything on the island in peak season. Worth the five extra minutes.

Getting to all of these

From our Bradenton Beach duplex units, the Bridge Street restaurant strip is a short walk for whatever the night calls for. Everything in this guide is reachable with the free island trolley (6:00 AM to 10:30 PM daily) or a 5 to 15 minute drive. Groceries: Publix in Holmes Beach.

Staying on the island?

Our three rentals put you a short walk from the sand, with a hungry-guest-tested map of the island included.

See the homes Next: the beach day guide

A local heads-up: the beloved Rod & Reel Pier was damaged by the 2024 hurricanes and is being rebuilt; its restaurant is running from a temporary spot in Holmes Beach meanwhile. We keep this guide honest and current, so if a place changes, this page changes.