Discover Florida’s 12 Best Islands: Explore Anna Maria Island

This once quiet, somewhat secret island has evolved over the last decade into a vacation hub offering all the amenities of the beach lifestyle and more.
Bikes At Anna Maria City Pier

Bicycle rentals are plentiful and one of the best ways to get around the island. (VANESSA RODGERS/BRADENTON AREA CVB)

This once quiet, somewhat secret island has evolved over the last decade into a vacation hub offering all the amenities of the beach lifestyle and more. A 7-mile-long barrier island that runs between the Gulf of Mexico and Bradenton on the mainland, Anna Maria is tightly packed with eclectic homes, from colorful bungalows to chic cottages with picket fences and 1950s motels that retain mid-century modern charm. Nestled among these vacation rentals are newly built two-story structures with widow walks adding height for scenic views. You won’t see high-rises, but you will definitely find accommodations ideal for multi-generational family vacations.

Gulf Drive runs the length of the island, linking three cities: Anna Maria City (north), Holmes Beach (middle) and Bradenton Beach (south). An old-fashioned trolley offers free transportation to folks traveling to popular sites along the route; however, golf carts, bicycles, surrey bikes, scooters and scoot coupes—if you’re not going too far—are easy to rent and are fun ways to navigate the island.

Head to the northern tip and stroll Anna Maria Pier, jutting into Tampa Bay. The historic wooden structure, built in 1911, accommodated paddle wheelers of the era. Today its rebuilt version welcomes children who fish off the edge. A grill and bait shop sells ice-cold beer and fish sandwiches. You can rent rods and reels if you get the urge to cast a line. Across the street a crowd congregates at Two Scoops Ice Cream Parlor waiting for cones of kid-friendly flavors like Muddy Sneaker and Gator Tracks.

The Gulf side of the island is blessed with soft white beaches with sand that literally squeaks when you step on it. A popular stretch is Coquina Beach at the far south end. It’s home to a cafe where dining with your toes in the sand is totally possible—umbrellas and tables are set right on the beach. On Wednesday and Saturday, Coquina hosts the Beach Market; vendors sell artwork, jewelry, baked goods, sundresses and more.

Not far from Coquina Beach is Historic Bridge Street, the epicenter of nightlife. After watching the sunset on the beach, cross Gulf Drive and explore the bars, restaurants and music venues crammed into this tiny stretch. For a laidback, flip-flop kind of night, stop at Bridge Tender Inn’s open-air tiki bar on the intracoastal shore.

Don’t Miss…

Waterline Marina Resort

The newest property in Holmes Beach, Waterline Marina Resort is an upscale addition to the lodging options. Designed around the colors of sand and surf, the two-bedroom villas have a luxurious island vibe. Gourmet kitchens, huge showers and balconies add to the comfort. At its Chateau Anna Maria restaurant, Chef Tyrene Matthew Crane, an Orlando native, creates French cuisine with Latin and Caribbean influences. His crab cake with mango salsa and tilefish with Spanish chorizo score points for flavor.

Cruising the Bay

Capt. Mike navigates Paradise Boat Tours’ big blue-and-white pontoon through the Intracoastal Waterway in search of dolphins and sunsets. Passengers scan the water’s surface for sightings of Flipper, manatees and other wildlife. At dusk the captain sails to Longboat Pass, rounding the southern tip of Anna Maria, for breathtaking sunset views over the Gulf. The narrated tours depart from the Bradenton Beach Pier.

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