Curator’s statement
Anna Maria Island feels like stepping into an older version of Florida, before the high-rises and rush. I grew up coming here for summers and holidays, with my grandparents spending their winters on the island, so it’s woven into my sense of what Florida should feel like. It’s bike paths, pastel beach cottages, Gulf sunsets, and mornings that start barefoot. The water is calmer and clearer on this side of the state, and the pace is noticeably slower. This guide reflects the way I’ve always experienced it: simple days, good seafood, and ending every evening facing west.
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Things to do on Anna Maria Island
Sunset at Bean Point
Sunset at Bean Point: At the northern tip of the island, Bean Point offers wide-open Gulf views and fewer crowds. It’s the quietest place to watch the sun drop into the water.
Bike the entire island: Rent cruiser bikes from Beach Bums and ride from the north end down through Holmes Beach and Bradenton Beach. The island is flat, easy, and best explored at a slow pace.
Browse Pine Avenue: Small boutiques, local art, and beachy home stores line Pine Avenue. It’s easy to wander without an agenda.
Fresh grouper or stone crab (seasonal): If visiting during stone crab season (October–May), order them wherever you see them on the menu. Gulf seafood is the highlight here.
Eat at Cortez Fishing Village: Just off the island, this historic fishing village gives you a glimpse of Florida’s working waterfront culture. Eat at Cortez Kitchen right on the water!
Low-tide walks: When the tide pulls back, the shoreline stretches wide and is perfect for long walks. You’ll often spot shells and sand dollars.
Places to eat & drink on Anna Maria Island
The Doctor's Office happy hour
The Sandbar Restaurant: A true Anna Maria classic right on the beach. Go for sunset and order fresh Gulf seafood, it’s toes-in-the-sand dining at its best.
The Waterfront Restaurant: Slightly more elevated but still relaxed, with a strong wine list and seasonal menu. Great for date night or a nicer dinner without leaving the island.
Pizza Social on Pine: One of my personal favorites. Casual, easy, and perfect after a long beach day, the kind of place you return to more than once during a trip.
The Ugly Grouper: Laid-back, open-air, and fun. Great for live music, casual bites, and a no-frills island dinner.
Ginny & Jane E’s Café: Part café, part bakery, part local hangout. Perfect for breakfast or coffee before a beach morning.
Anna Maria Island Beach Café: Classic beachfront breakfast and lunch spot. Unlimited pancakes for $7, omelets, and Gulf views.
The Doctor’s Office: A speakeasy-style cocktail bar tucked above the island’s main strip. Intimate, thoughtfully crafted drinks, and a completely different vibe from the typical beach bar scene, ideal for a date night or late-evening cocktail.
Need to know
Anna Maria Island is busiest from January through April, when winter visitors and spring breakers overlap. March and early April bring beautiful weather but higher demand for rentals and restaurants, so plan accommodations and dinner reservations well in advance. Summer offers warmer water and a more local feel, though afternoon storms are common.
Hurricane season runs from June through November, with peak activity typically late August through October. It’s also worth checking for red tide conditions before travel, as water clarity can vary seasonally.
The island is extremely walkable and bike-friendly, and many visitors rent bikes or golf carts instead of relying on cars. Parking can be limited near popular beach access points, especially at Bean Point, so plan to arrive early. Many businesses operate on relaxed island hours, and some smaller shops close midday.
Anna Maria’s charm comes from its simplicity, no high-rises, no chain restaurants, and no rush. Plan less than you think you need to, and leave room for long beach days and sunset every evening.
Travel Advisor
Alyssa Juris
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For more inspiration and insider recommendations, visit our Anna Maria Island page.