Longboat Key to Anna Maria Island: A Drive Worth Taking

Longboat Key and Anna Maria Island are neighboring barrier islands, and the drive between them is one of the easiest half-day plans in the area. It is a relaxed route, which makes it a good fit for a convertible or a grand tourer.

The route

Start on Gulf of Mexico Drive on Longboat Key and head north. The road runs along the island, past resorts and residential streets, and then crosses the bridge over Longboat Pass onto Anna Maria Island. The whole drive is short, so you can treat it as a leisurely loop and still have time for a stop.

What the drive feels like

Traffic on both islands is slow by design, with lower speed limits, pedestrians and bicycles. This is a drive for presence and scenery, not performance. The Rolls-Royce Dawn, Bentley Bentayga or the Corvette C8 Convertible all work well here.

Parking on the island

Anna Maria Island is popular, and parking can be tight on weekends and in high season. Arrive earlier in the day, read signs carefully and avoid narrow spaces for a wide car. A lunch stop is easier if you pick a place with its own lot or a spot you can pull straight into.

Best time to go

Morning gives you light traffic and cooler air. Late afternoon into sunset is good for photos, but plan for more people. In summer, check the sky before you set out, since afternoon storms can interrupt an open-top plan.

We deliver to Longboat Key, Anna Maria Island and the surrounding area, so you can start wherever you are staying.