24 Hours in Anna Maria Island

by Michael C.Upton  |  Published May 19, 2023

The pastel-colored homes of Anna Maria Island (AMI) sit on sandy loam dotted with palm trees. Overlooking Anna Maria Sound, which separates it from mainland Florida, many describe AMI as one of the best beach destinations in the United States.

Anna Maria Island beaches offer the perfect sunset views over the Gulf of Mexico (Photo: Michael C. Upton for TravelMag)

Sunset views over the Gulf of Mexico (Photo: Michael C. Upton for TravelMag)

Anna Maria Island is a low-key resort town with pretty architecture, and an array of shops and dining options. The calm beauty of the Gulf shore, with crystal blue water and pure, pale sand attracts beachgoers of all ages and demographics from all over the world. Many return visitors come from western Pennsylvania as nearby Bradenton is home to the MLB’s Pittsburgh Pirates spring training facility and home of the single-A Bradenton Marauders.

The beauty of the island’s architecture is protected by Anna Maria Island Preservation Trust, and many of the homes have been turned into guest houses. Although only 7 miles long and 1.5 miles wide, AMI is made up of three municipalities: from north to south they are Anna Maria, Holmes Beach, and Bradenton Beach. All have agreed to limit new construction to a certain height. As such, only two buildings reach three stories high.

Greetings from Anna Maria Island’s Pine Ave (Photo: Michael C. Upton for TravelMag)

Getting around the island is easy using the MCAT bus system, which is free. Real time bus information is available by scanning a QR code at marked bus stops, by using the myStop app, or by calling an information line. Golf carts, a popular mode of transport, are as much a frequent sight as cars.

What to Do

The most prevalent past time on AMI is relaxing on the beach or by a pool. But Pine Avenue, which touts itself as the “greenest Main St. in America,” beckons shoppers with boutiques, island décor, and a few kitschy antiques. Fun eateries along Pine Avenue offer ice cream, deluxe waffles, and cold coffee drinks.

Colorful and fun Pine Ave (Photo: Michael C. Upton for TravelMag)

A gem in the fishing world, Anna Maria Island is growing in stature as visitors to the island increase. By boat, the smaller bays and lagoons are prime fishing areas for redfish and spotted seatrout. In June, many anglers come to the area to catch red snapper. Surf fishing is popular on both the gulf side and the shallows and most fisherman prefer to cast their lines in the morning. The gulf is full of fish.

The City Pier provides amazing panoramic views (Photo: Michael C. Upton for TravelMag)

The Anna Maria City Pier (100 N Bay Blvd., Anna Maria), a 700 ft. boardwalk into the Gulf, is good for fishing and sightseeing. The smaller Rod and Reel Pier (875 N Shore Dr, Anna Maria) caters to anglers. And the Bridge Street Pier (1 Laverne Dr., Bradenton Beach) is home of the Anna Maria Oyster Bar and a good place to pick up boat charters; Bridge St. is another shopping destination on the island.

Where to Stay

In 2022, the Seaside at Anna Maria Island Inn (2200 Gulf Drive North, Bradenton Beach) underwent a massive renovation making it one of the hippest places to stay on the island. As one of the hotels closest to the water, Seaside comes complete with all the bar tools—including blender—needed for cocktails on the semi-private veranda leading into the white sand. Comfort is key as each room is stocked with extra pillows, sheets, and blankets as well as pool/beach towels. Each room comes with unobstructed views of the sunset.

Anna Maria Island Inn offers direct access to white sand (Photo: Michael C. Upton for TravelMag)

Situated on a stretch of private beach, luxury abounds at Mainsail Beach Inn (101 66th St., Holmes Beach). A heated pool and hot tub are perfect for visits when the Gulf waters are a bit cooler. Large accommodations, with space for up to 10 in unit 12, make this a perfect choice for families.

For those seeking a cheeseburger in paradise, Compass Hotel (12324 Manatee Ave. West, Bradenton) is a Margaritaville property serving plenty of Margaritas at their Compass Bar & Chill. The off-island hotel sits just across Anna Maria Island Bridge and is as accessible by boat as it is by car. Amenities include complimentary breakfast, bike rentals, and a happening pool.

Where to Eat

From fine dining to fish shacks, fresh seafood is a true highlight in this foodie destination. With few exceptions, seafood is the star of every menu at AMI’s restaurants. The most sought-after local specialty is stone crab claws. Most seafood at these restaurants comes straight from the Gulf or nearby coastal bays.

The relaxed atmosphere at Tide Tables (Photo: Michael C. Upton for TravelMag)

Tide Tables (12507 Cortez Rd. West, Bradenton) owner Bobby Woodson spent years in the Bradenton area restaurant world and built Tide Tables by hand in 2014. Grouper is his favorite dish, and his restaurants serves 12,000 lbs. of the Gulf-caught fish monthly in bites, sandwiches, and baskets. This casual eatery, just across the Cortez Bridge, is perfect for diners who enjoy watching boats on the water, relaxing with a cold beer, and feeling like a local.

Fully embracing local sustainability, Beach House Waterfront Restaurant (200 Gulf Dr. North, Bradenton Beach) is farm-to-table, water-to-table, and even operates its own bakery. The chic setting provides beachfront dining with an upscale menu created by Chef Thomas Villetto.

Travelers and locals looking for a romantic, beachfront dining experience frequent Beach Bistro (6600 Gulf Drive, Holmes Beach). The intimate, fine dining restaurant maintains a superb cocktail program and offers two prix fixe menus, one vegetarian. Pro tip: leave room for dessert or an “encore cocktail.”

Sunset fine dining on the sand at Beach Bistro (Photo: Michael C. Upton for TravelMag)

Simple breakfast options are plentiful on the island. Fresh and creative doughnuts can be found at Island Donut Company (110 Bridge St, Bradenton Beach), which offers pre-order services for treats, bagels, and breakfast sandwiches perfect for the busy beach season. The Cheesecake Cutie & Café (3324 E Bay Dr, Holmes Beach) offers ‘to go’ bites and sit-down service for specialties like the Danish pastry-style flatbreads, parfaits, and oatmeal. Anna Maria Bake House sells croissants, muffins, and more at Gamble Creek Farms (14950 Golf Course Rd., Parrish). Gamble Creek provides sustainable and eco-friendly produce for area restaurants like Beach House.


There would be little to see on Anna Maria Island if it were not for Native Americans and settlers who took up residence in what would become Cortez, one of the oldest, continually active fishing villages in the United States. Located across the Anna Maria Sound from Bradenton Beach, Cortez is inhabited by the people who fish these waters and most of those people are related to the founding families of the late 1800s.

Many guests come by boat to Star Fish Company (Photo: Michael C. Upton for TravelMag)

Restaurants like the Swordfish Grill and Star Fish Company rub shoulders with working fish houses. Traps and netting take up parking spaces. And some of the people working the boats to bring in fresh seafood in the morning are the same people serving it to hungry patrons at local eateries in the evening.

The Florida Maritime Museum (4415 119th St West, Cortez) makes its home here, housing historical exhibits, model boats and tools, and interactive events. Experiences like fish painting with local artist Kelly Hunt, oyster shell decoupage, and navigation classes are part of the Museum’s Folk School, which makes its home in the restored Burton Store, the first commercial building in Cortez.

Experience the waterman’s heritage at Florida Maritime Museum (Photo: Michael C. Upton for TravelMag)

The Cortez Historic District was designated in 1995 and contains 97 buildings. Preservation of “old Florida” is key in Cortez, from preserving The Kitchen off the coast to celebrating during the Cortez Commercial Fishing Festival in February. The town’s history is preserved at the Cortez Cultural Center (11655 Cortez Rd. West, Cortez).

Beaches and Nature

Listed here from north to south, Anna Maria Island has five “top billing” beaches with other secluded points and private beaches along the shore. Bean Point Beach and Anna Maria Island Beach are both located on the northernmost point of the island. Holmes Beach is reached directly from Anna Maria Island Bridge. Bradenton Beach is across the Cortez Bridge. Coquina Beach is the largest beach located on the extreme southern tip of the island and has plenty of picnic tables, changing stations, and lifeguards on duty during the day year-round.

Nature lovers flock to a pair of preserves across the Anna Maria Bridge. The Neal Preserve is for hikers, walkers, and bird watchers—no pets or bikes allowed. The 600-acre Robinson Preserve is perfect for kayak and paddleboat enthusiasts; rentals can be made through Surferbus.com (9800 Manatee Ave West, Bradenton).

This Anna Maria Island resident casts his lines (Photo: Michael C. Upton for TravelMag)