Anna Maria Island


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With its unpretentious seafood shacks, funky beach bars, and historic fishing piers, seven-mile-long Anna Maria Island exudes a calm and laid-back Old Florida vibe.

It's easy to imagine this is the version of Florida that Ernest Hemingway must have fallen in love with decades ago. In fact, it's an island much more in line with the Key West he called home in the 1930s than most Florida resorts of today. Split among three towns (Bradenton Beach, Holmes Beach, and Anna Maria), the barrier island retains its small-town vibe very much by design. But, in the wrong hands, it might not have turned out so well. Enough people love the island's pristine white-sand beaches, that this place could easily have been overrun with spring breakers and high-rise condominiums.

Instead, local officials have kept out most fast-food restaurants, capped all island buildings at three stories tall, and restricted island-wide speed limits to 35 mph. In fact, you're probably better off exploring the island by bike or, better yet, from the sea by sailboat or kayak. Luckily for visitors, humans aren't the only ones to hear about the island's unspoiled reputation: Area waters attract manatees, dolphins, and schools of game fish, while the shores are a favorite for nesting sea turtles and shorebirds.

Saltwater Fishing

Whether it's from one of the island's two piers — the 350-foot Rod & Reel Pier or the 700-foot City Pier — or from a chartered boat, fishing is top-notch in the teeming waters of Tampa Bay and the Gulf of Mexico. Remember that you'll need to buy a saltwater fishing license when fishing anywhere off the coast of Florida, but the fee is more than worth it considering your chance of success here. This area has the luxury of great fish year-round, but as Gulf waters begin to heat up in the spring, it's the perfect time to catch migratory species like kingfish, cobia, and Spanish mackerel.

Sunset Time Guessing Contest at Sandbar Restaurant

Put a proper cap on those long summer days with a visit to the beachfront Sandbar Restaurant, known for its ultra-fresh seafood dishes, such as smoked fish dip, crab pasta salad, and signature grouper sandwiches. Sit on the tin-roofed, open-air deck for the best view of the setting sun, which actually plays a big role here: Each night, the diner who best guesses the exact minute when the sun passes below the horizon wins a free bottle of champagne!


Florida hurricane season runs from June 1 to Nov. 30, but the slight risk of storms comes with an unexpected bonus: High tides and thunderstorms churn up the sea, leaving behind a veritable trove for beachcombers. On Anna Maria Island, you're likely to encounter sand dollars, huge conches, dime-sized coquinas, and brightly colored calico scallops. Be sure to keep an eye out for the rare junonia shell, which is creamy white and covered with rows of brown spots.

Valentine's Day at Beach Bistro

Celebrate Valentine's Day at Beach Bistro, one of the most romantic restaurants on the Gulf Coast — though, really, any night will do! The food is French-inspired, but always done with a tropical Florida accent. You might start with an order of "lobstercargots", which swaps out snails for local Florida spiny lobster, cooked with herbed spinach and garlic butter, or Bistro "White Castle" sliders, foie gras and prime tenderloin topped with demi-glace and béarnaise sauce. For an entree, try the grouper cheeks and throats, considered the "Captain's cut" of the Gulf Coast's favorite fish. And it's not just locals who are taking notice of the food here: Chef Peter Arpke received a 2013 James Beard nomination for best chef in the South!