Anna Maria Island is a charming slice of Florida living, thanks to the quaint restaurants and boutiques that line Pine Avenue.


Located 30-minutes north of The Resort at Longboat Key Club, sits Anna Maria Island, recently voted the #2 “most charming small town in Florida,” according to Travel + Leisure. According to the experts, it isn’t just the beaches that make the little town so great (though they are definitely a plus), it’s the combination of the beaches and the shops, galleries, and restaurants visitors can check out on their stroll down Pine Avenue.

Get the Anna Maria Island Look at Pink and Navy

This Pine Ave boutique offers a romantic take on traditional beachwear. Imagine flowing floral dresses and effortlessly cool linen two-piece sets. While the shop focuses on women’s clothing, there are sections for both men and children. After one visit, the whole family will be stepping out in true Florida fashion.

Anna Maria Island City Pier

For a taste of old-school Florida, visit the pier, which was once the landing site for ferries full of day-trippers. Now, it tends to be quieter. Rather than crowds of visitors, there are always a handful of fishermen casting their lines over the side and families walking to the souvenir shop at the end of the pier for an ice cream cone and to look out at the view of the Sunshine Skyway Bridge in the distance.

Add a Piece to Your Art Collection at The Studio at Gulf and Pine

Tired of the same cheap touristy souvenirs? Check out the artworks hanging at The Studio at Gulf and Pine. The walls are covered in an eclectic array of styles with one commonality: All of the artwork has been created by artists who call AMI home. Find a quality keepsake in a photo print by Rusty Chinnis or a moody, atmospheric landscape by Charles Townsend.

Historical Society

Over the years, the Historical Society building has been an icehouse, automotive garage, and sea turtle hatchery. Now, the exhibits in the museum cover everything from the first settlers of the island to the area’s long history as a haven for MLB players like Yankee’s first baseman Earl Torgeson, who bought a home on the island after visiting during spring training. The museum also offers biking and walking tours around AMI as well as tours of the historic Belle Haven cottage. 

The Donut Experiment

Everyone is familiar with the concept of a coffee and a donut. But, what if your morning sweet treat was made right before your eyes and to your specifications? That was the idea behind the Donut Experiment. The steps are simple: Pick from one of six frosting flavors; pick a topping, like Fruity Pebbles, bacon, or cinnamon sugar; pick your drizzle, and let the maestros behind the counter work their magic. The restaurant has become so popular, they are popping up across the US, but the company will always think of Anna Maria Island as home. 

Where to Stay Lido Beach Resort | The Resort at Longboat Key Club | Zota Beach Resort