Three Perfect Days on Anna Maria Island

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Three Perfect Days on Anna Maria Island

Calm turquoise water, white sandy beaches, homemade ice cream, and a quaint beach town are just a few of the things you’ll find on Anna Maria Island, a 7-mile island south of Tampa. If you’ve ever dreamed of finding a less-crowded and tourist-trap-free Clearwater beach, Anna Maria Island just might be your paradise.

After a 2.5 hour drive from Orlando, expect to be rewarded with beautiful sunsets, all the island cocktails you can dream of, and plenty of dining options to please foodies and beach bar lovers alike.

Post updated March 2021


You won’t find any high-rise hotels or condo complexes so typical of Florida’s more popular beaches, and that’s one thing to love about this little island.

If you want to go the hotel route, book a few nights at the Silver Surf Gulf Beach Resort. While the property isn't oceanfront, it's located right across the street from the beach and boasts a private strip of sand complete with beach loungers for guests. The central location makes it convenient to explore the island in either direction, and several notable eateries are within walking distance. This is my go-to for overnight stays.

While there are numerous small hotels to choose from, the best way to immerse yourself into island life is by staying at one of the many available beach rentals. Most rental properties are located in the wider north end, which is notably more residential, but is also home to some of the best shopping on the island. Bradenton Beach and Holmes Beach are other alternatives with shopping and dining districts of their own. Both and Island Real Estate have dozens of listings for you to peruse.

Pine Ave. vacation rental



The main draw of Anna Maria Island is of course the beach. It's the ideal place to soak up the sun, lounge in the clear, calm gulf waters, watch dolphins frolic and enjoy a beachfront bite. The biggest public beach areas are Manatee Beach and Coquina Beach, both of which have ample parking, food options, lifeguards on duty, picnic areas with grills, and restrooms. I'm more partial to Bean Point at the North End and the stretch of beach between Coquina Beach and Cortez Rd.

While it's perfectly acceptable to spend all of your days being a beach bum, there's plenty more to do if you're up for exploring.

Beach at Anna Maria Island
Anna Maria Island | Image credit: Stephanie Patterson


Hit the water in a tandem kayak to paddle through nearby preserves. Rent a kayak from Surfer Bus (temporarily on hiatus, check their Facebook page for the latest updates) for a 1-hour journey through Robinson Preserve to the park's observation tower. This local preserve is worth a return visit on foot, too! Or, head south and cross the bridge to Longboat Key to rent a kayak from Happy Paddler. From here, you can paddle to Jewfish Key near Longboat Pass, check out Beer Can Island and cruise out into the Gulf to take in views of Anna Maria Island from the water.

If you don't mind the 30-minute drive, follow Gulf Drive south to Lido Key for an afternoon spent kayaking in the mangroves. While you can certainly hire a guide, the mangroves are well marked and easy to navigate, and your rental company may also provide a map. Keep an eye out for manatees as they frequent the area at certain times of year.

Kayaking through magroves


Instead of driving, catch the trolley at one of the many stops along Gulf Drive. The trolley runs the entire length of the island and is completely free. Consider making a stop at Pine Avenue to visit the local shops and art galleries, the City Pier, and Bayfront Park. Stop by Shiny Fish Emporium to paint your own sand dollar for $15.


Fresh seafood is one of the many perks of a Gulf beach getaway, and there's no shortage of options on Anna Maria Island. For fish taco fans, The Waterfront Restaurant serves excellent grouper tacos with fresh salsa and jicama slaw. If you want to hang out where the locals go, cross the Cortez bridge and head to Tide Tables for super casual dining in a no-fuss setting. They put their own spin on fish tacos with a sesame ginger sauce, and a slice of key lime pie is perfect for dessert.


For beachfront dining at sunset, Sandbar Restaurantcan't be beat. Order a mojito and check out the daily specials while watching the sun dip below the horizon. There are tables right on the sand, so go ahead and slip off your shoes.

For an afternoon drink, pull up a seat at your own tiki hut table on the beach at The Kokonut Hut. Just across the street, you'll find my favorite lunch spot on the island: Wicked Cantina. This Tex-Mex joint owned by a husband and wife team serves up killer tacos (I love the shrimp tacos and carnitas street tacos), chips and salsa, and the best mango margaritas I've ever had. You'll frequently find a talented local musician on the patio out front. The patio has been expanded to allow for additional outdoor seating.

Wicked Cantina Bradenton Beach - Anna Maria Island
The infamous frozen mango margarita from Wicked Cantina

The Donut Experiment on Pine Ave. is the perfect spot to get your sugar fix. Fresh donuts are constantly being churned out and made fresh to order. Just pick up an order form and select your preferred glaze and toppings, then watch your donuts being made in real time.

For a slightly more upscale date night out, make your way to The Doctor's Office. This tiny cocktail bar has a killer craft cocktail menu and you'll be greeted with a “prescription” aka a taste test of a featured drink for the day upon being seated. While the food menu is small, it's sophisticated and includes items like cheese & charcuterie and duck tacos. There's typically a wait as only a certain number of people are permitted inside at a time, but the wait is worth it! Other personal favorites include Mar Vista in Longboat Key and the swanky Shore Longboat Key.


  • Beach House Restaurant for tropical cocktails and island cocktails (patio facing the beach)
  • Smoqehouse for creative BBQ
  • Skinny's Place for a classic burger
  • Ginny & Jane E's for smoothies and a hearty breakfast
  • The Waffle Press for indulgent waffles
  • Anna Maria Oyster Bar for casual seafood fare
The Kokonut Hut


While there’s certainly no wrong time to visit Anna Maria Island, April-early June is ideal. Late January through March should be avoided as this is the busy season and traffic can get pretty heavy. September/October are sleepy and quiet, which has its own benefits. There's also much to be said for an early December visit, when the island is practically deserted and weather can still be lovely.

If you plan on doing your own cooking, there is a Publix on the island along with various drugstores. If you'd like fresh seafood to prepare at home, Star Fish Company is a great seafood market located just off the island, across the Cortez bridge.

There are two main roads leading on and off the island. While both are sufficient, there are much fewer traffic lights on Manatee Ave. (FL-64).

The free trolley runs daily from 6:00am to 10:30pm every 20 minutes. To locate a trolley stop, look for a green sign with a trolley symbol on it. There are stops every few blocks along the route.

Stephanie Patterson, editor of Orlando Date Night GuideAbout the Author/Photographer:
Stephanie Patterson is the editor of Orlando Date Night Guide. She’s a talented professional food and travel photographer and writer with a passion for creativity, the beach and great eats. When she’s not taking photos or writing, you can find her exploring the state for her Florida travel blog, Travel Taste Click. Find her online at and


2 Responses to “Three Perfect Days on Anna Maria Island”

  1. Harold Pull

    Looking for prices for this.. looking to leave the 22nd to 23rd of September.

    • Stephanie Patterson

      Hey Harold! You’ll have to contact individual properties for pricing as this itinerary is just for reference. Anna Maria Island is one of my favorite places! I do have to mention though that the island is currently being affected by red tide. I suggest looking into this fully before booking something for September 2018. While I’ve seen some news about slight improvements, the wind seems to have shifted again so it’s back. This is just something to be aware of as you plan your visit as the beaches have sadly been very negatively affected this year. I’m really hoping it subsides soon as it’s really sad.


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