Unique Things to Do on Anna Maria Island

1. Ride the free trolley from one end of the island to the other

The island trolley runs the length of Gulf Drive, from Coquina Beach at the southern end up to the north end, and it does not cost anything. Not a token fare. Nothing. It is operated by the county as public transport and it is the reason parking on this island is survivable at all.

Riding it end to end, with the windows open, is a genuinely pleasant forty minutes and the best possible orientation on your first afternoon. You will see where the beaches are, where the two business districts are, and how small the whole thing actually is.

• Stops run frequently along Gulf Drive in both directions. The county publishes the current route map and timetable.
• It runs from early morning until late in the evening, seven days a week.
• It is the right answer on a Saturday, when the beach lots are full by ten.
• If you want to take a bike aboard, check whether the trolley you are boarding has a rack on the front.

2. Walk out to Bean Point for the sunset

The northern tip of the island, where the Gulf of Mexico meets Tampa Bay. There is no parking lot, no restroom, no lifeguard and no sign making a fuss about it. You leave the bike or the cart at a residential street end and walk in through the sea oats, and then the beach opens out and there are almost no people on it.

Two bodies of water meeting means the shelling here is the best on the island and the current is the strongest. Come to look rather than to swim, take a light for the walk back, and keep the noise down on the way through the neighborhood.

3. Spend an evening on Bridge Street

Two blocks in Bradenton Beach running from the Gulf to the bay, and the closest thing the island has to a main street. Low buildings, live music spilling out of doorways, and the particular quality of an evening where everyone walked or rode there.

The Historic Bridge Street Pier at the bay end was badly damaged in the 2024 storms and is being rebuilt, so check before you plan on walking out over the water. The street itself is fully open and busy.

4. Wait for dolphins at the Coquina boat ramp

On the bay side at the south end of the island, across Gulf Drive from Coquina Beach, there is a boat ramp beside a channel. Dolphins work it regularly, and unlike almost everywhere else you might see them, you can stand on solid ground fifteen feet away with a coffee.

Early morning and the hour before sunset are best. While you are there, cross to Leffis Key, the small preserve immediately beside it, and take the shell path up to the lookout over Sarasota Bay. It is about a twenty-minute walk and hardly anyone staying on the island knows it exists.

5. Cross the bridge to Cortez

Over the Cortez Bridge on the mainland side sits one of the last working commercial fishing villages on this coast. Not a themed one. An actual one, settled in the 1880s by families who came down from the North Carolina Outer Banks, still listed on the National Register of Historic Places, still full of wooden bungalows with boats in the yards and nets on the docks.

Fish houses sell what came in that morning, and the whole village takes about two square miles. It is the single best half-hour drive off the island, and it is a car trip: the bridges are posted above the speed a low-speed vehicle may use, so the cart stays home. The details are in the Anna Maria golf cart guide.

A note on the piers

Anna Maria Island had three landmark piers and the 2024 hurricanes took all three out of service: the Anna Maria City Pier at the north end, the Rod and Reel Pier near it, and the Historic Bridge Street Pier in Bradenton Beach. Each is on its own rebuilding path and the timelines have moved more than once. Any guide that tells you to go walk out on one is working from old information, so check the city's own page before you build an evening around it. The bayfront parks beside them are open and lovely in the meantime.

Common questions

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