Anna Maria Island—just up the road from Cannons Marina, Boat Sales & Rentals’ location on Longboat Key—has been named one of the 50 best places to travel in 2024 by Travel + Leisure magazine. The magazine calls Anna Maria Island—or AMI, as it’s known locally—an “under-the-radar destination” known for its “no-high-rises shoreline, incredible sunsets, and small-town feel.”
We love Anna Maria’s Old Florida feel, and whether you’re visiting for the first time or the fiftieth, there’s always something wonderful to experience there. Here’s our local advice.
Things to Do on Anna Maria Island
Rent a Boat at Cannons Marina, Boat Sales & Rentals
One of the best ways to experience Anna Maria Island is by water, and Cannons Marina, Boat Sales & Rentals offers a fleet of dual- and center-console rentals that cater to any on-the-water activity you can imagine. Spend the day fishing or drop anchor at a sandbar. Just don’t forget the SPF!
Eat a Hamburger
Skinny’s Place and Duffy’s Tavern are known on Anna Maria Island and beyond for their hamburgers—and their rivalry. No matter which you pick, you’re guaranteed a great burger and an authentic beachy vibe.
Learn About the Island’s History
The Anna Maria Island Historical Society‘s museum building was constructed in 1920 as an icehouse, then went on to serve as an automotive garage, a sea turtle hatchery and a public administration building. In 1992, the City of Anna Maria began leasing the building to the Historical Society for use as a museum. The museum’s exhibits tell the story of the first settlers on the island and the legacy they left behind, as well as the island’s fishing and baseball history. It includes archives of records and newspapers for research into families and businesses. Don’t forget to stop at the Old City Jail, which was built in 1927 to “quarter the rowdies” who had had a bit too much to drink at the local tavern and dance hall. According to the Historical Society, the jail was used until the 1940s, when it caught fire. The wooden roof burned away, but the original tabby structure remained. The city decided to use the old jail as a photo op for visitors.
Stay at a Funky Inn or Vacational Rental
Travel + Leisure highlights two new-ish arrivals to the island as fun places to stay, and we agree—Joie Inn and Mello on the Beach offer all the comfort and amenities you expect in stylish, funky settings. They’re great places to call your home base on your visit.
Toast the Sunset
There’s nothing like watching a technicolor sunset dip below the horizon on the Gulf Coast. Plan to have dinner at a waterfront restaurant, like much-lauded Beach Bistro or The Waterfront, and raise your glass as you try to spot the green flash. (Prefer to clink glasses in the air conditioning? We love the Doctor’s Office for its hip craft cocktails, too.)
Visit a Pier
The Anna Maria City Pier is a picturesque historic site where visitors have been sightseeing for decades. A visit to the City Pier is a must while on island time. Originally built in the early 1900s, it was damaged during Hurricane Irma in 2017 and repaired and reopened in 2020. The pier is a great spot to fish—or simply take a walk and enjoy the area’s abundant sunshine and turquoise water. Meanwhile, at the end of the Rod & Reel Pier, you’ll find a restaurant serving Florida favorites like peel and eat shrimp, grouper sandwiches and Key lime pie, as well as gorgeous views of the water.
Get an Ice Cream Cone
After a day in the sun, cool off with an ice cream cone from one of the mom-and-pop shops that dot the island. Try Anna Maria Island Creamery and Bakery, or head to Dips or Two Scoops and enjoy your cone on the Anna Maria City Pier.
Take Home a Coastal Treasure
The White Egret family of stores is spread out over Anna Maria Island, and you can find a gift for yourself or someone you love at any of them. The Egret’s Landing offers home furnishings and interior design, The White Egret is a purveyor of home accents and gifts, and The Egret’s Nest is a clothing boutique. Ginny and Jane E’s sells postcards, jewelry and other odds and ends, as well as coffee and a legendary cinnamon roll. Meanwhile, shopping on the island’s Pine Avenue includes the well-stocked Anna Maria General Store and Olive Oil Outpost; Pink & Navy, a trendy clothing boutique; and AMI Beach & Dog Supply, where you can pick up treats for you and your furry friend.
Spend Time at the Beach (Of Course!)
Our beaches are world-renowned for good reason—and there’s nothing like starting your morning with a walk along the shore, spending a sunny day splashing in the turquoise Gulf water, or settling in to watch the sunset in the evening.