For the 50+ Traveler

With stunning white-sand beaches, Old Florida buildings, and a fast-growing culinary scene, Anna Maria Island is a true tropical paradise. The island is only 7 miles long and comprises three cities: Anna Maria, Holmes Beach, and Bradenton Beach, the last of which connects to Bradenton on mainland Florida. In recent years, the island has become a popular snowbird destination for retirees wanting an extended stay.

Wherever you visit, you’ll find something to do, and even if you spend most of your time lounging on the beaches, you’ll leave with some incredible memories. With that said, if you’re not content to lie on a beach -- or if you want to add a few excursions to your itinerary in between your regular swimming and sunbathing sessions -- you’ll have plenty of options.

Here are a few wonderful ways to spend your time on Anna Maria Island.

Take A Relaxing Walk Along Pine Avenue

Any trip to Anna Maria Island should include a stop by Pine Avenue, a shopping area that offers a glimpse of Old Florida. Here, you’ll find the Historic Green Village, which is entirely powered by renewable energy sources, and the Anna Maria Historical Society Museum, which is located in the former home of the Anna Maria Jail. Even if you’re not much of a history buff, the museum is worth a quick visit, since the remnants of the city jail make for a great photo op.

One of the main attractions of Pine Avenue was the City Pier, which was severely damaged by Hurricane Irma in 2017. The city has dedicated nearly $3.7 million to the restoration of the pier, and restoration efforts are moving along quickly, so check to see whether the City Pier is accessible prior to your visit.

Bradenton Beach on Anna Maria Island.

Get Away From (Most Of) The Tourists At Bean Point

Named for Anna Maria Island’s founder, George Emerson Bean, Bean Point is one of the best places to take in unobstructed views of the ocean. It generally has smaller crowds than other beaches on the island, although its popularity as a tourist destination has risen significantly in recent years. Manatees sometimes swim in the shallow waters, getting up close and personal with swimmers (don’t worry -- the sea cows aren’t a threat).

There are a few important caveats: You’ll need to walk for a bit to get to Bean Point, since you won’t find any parking lots nearby, and there are no facilities on the beach. To get there, head to the intersection of Gladiolus Street and North Shore Drive or Fern Street and North Shore Drive and follow the signs. A free trolley also runs to Bean Point, but expect to walk for about a mile regardless of your route.

Go Parasailing On Bradenton Beach

On my first parasailing trip, I worried that I’d lose my mind once I got up into the air (I’m not great with heights). Fortunately, those fears were unfounded; properly captained boats will gently lift parasailers into the air, and once you’re up, your only job is to enjoy the breathtaking views of the ocean.

Parasailing vessels generally spend some time on the water, so budget at least an hour for this activity, and dress accordingly: If you’re visiting Anna Maria Island in the winter, you may want to bring a sweatshirt, since the weather can get chilly when you’re floating 800 feet in the air.

You’ll need to make a reservation before you head out. Parasailing services on Anna Maria Island include Bradenton Beach Parasailing and YOLO Adventures.

A dolphin tour on Anna Maria Island.

Take A Dolphin Tour

There’s a good chance that you’ll see dolphins while frequenting Anna Maria Island’s beaches, but if you want a closer look, you’ll need to take a dolphin tour. You can book a canoe, paddleboat, or sea boat, and then head out with a guide to some of the animals' favorite spots.

Tours are available through Happy Paddler Kayak Tours, M/V Minnow Boat Tours, and YOLO Adventures. The kayak tours might be the best option, since kayaks can access coastal mangroves that larger vessels can’t.

Go Surfing… On A Horse

Take a 20-minute trip from Anna Maria Island to Bradenton, and you can ride a horse into the ocean. Yes, we’re serious.

Palma Sola Bay is one of the only places in Florida where you can legally ride a horse on the beach, and Great World Adventures offers travelers convenient access to this unique experience. Take their Thrill Ride tour, and you can actually ride a horse as it swims into the ocean.

The service can accommodate young children, seniors, riders with disabilities, and very heavy riders, so as long as you enjoy the water, you’ll have a great time. The horses are highly trained, as are the instructors -- and if you’ve ever wanted to make a truly fantastic water polo joke, this is just about the best scenario imaginable.

Still, if you don’t want to ride into the water, a variety of other beachfront horseback rides are available, including private rides.

Charter A Boat To Egmont Key

Egmont Key State Park is a secluded island with incredible scenery and wildlife. The key is only accessible via boat, and because it’s a wildlife refuge, tourist access is limited.

Still, you can enjoy some quiet time on the beach, snorkel off the coast, and stop by the ruins of Fort Dade, an abandoned military outpost that the Union used to blockade the Confederacy during the Civil War.

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Eating On Anna Maria Island

Anna Maria Island has a remarkable culinary culture, and whether you’re looking for tacos, German comfort food, or a gourmet dining experience, you’ll find it here. We’ve got a full piece on the island’s best restaurants, but if you’re looking for a few must-try foods, here are the essentials.

Key Lime Pie

Key lime pie is a Florida classic, and many restaurants on Anna Maria offer wonderful versions of this dessert. Hometown Desserts might be the best place to pick up a full pie, and The Waterfront Restaurant near Pine Avenue serves a great slice.

Fresh Seafood

Hey, you can’t visit an island in the Gulf Coast without trying the fish (provided that you like seafood, of course). The aforementioned The Waterfront Restaurant is one of the many places to find fresh, locally sourced seafood, including shrimp, mollusks, and more. The Sandbar, located on Spring Avenue, is another excellent option, with a full menu of specialty dishes including seared scallops, grilled salmon, and a half Maine lobster.

The Donut Experiment

Granted, The Donut Experiment is quickly becoming a national chain, but the company started out on Anna Maria Island in 2012. Visitors build their own freshly made cake donuts, choosing from an array of traditional and not-so-traditional toppings.

The Key lime donut and sriracha donut are two of the more exotic options, but even if you opt for the simple glazed donut, you’ll satisfy your sweet tooth.

Shopping On Anna Maria Island

The most famous shopping area on Anna Maria Island is unquestionably Bridge Street. Located in Bradenton Beach, this historic area has plenty of souvenir shops, including Back Alley Treasures and The Lot. On Sundays from November through April, Bridge Street hosts the Bridge Street Market, a worthwhile stop for grabbing local produce, artwork, antiques, and much more.

Nearby, you’ll find beautiful Coquina Beach, which is also the site of the Beach Market. Open on Sundays from November through July, this marketplace is a great place to pick up jewelry and other crafts.

If you’re looking for a special piece of artwork to commemorate your trip, you’ll probably want to head to Pine Avenue, which has several galleries including Bob Brown Art, Joyce Lazzara Gallery, and Emerson’s Studio Store.

Alternatively, you could simply stroll the beaches and collect some shells -- sometimes, the simplest souvenirs are the most memorable.