Anna Maria Island | Legendary Florida Charm Awaits Your Visit

You have all heard of these Florida cities ~ Orlando, Miami, Daytona Beach, and have maybe even visited one of these amazing cities. We have been lucky enough to have enjoyed visiting them, but there are so many other fabulous places in Florida to discover. Anna Maria Island is one of them. It is a hidden gem on the Gulf Coast of Florida that has become the place that continues to draw us back time and time again.

Anna Maria Island is a barrier island on the gulf coast of Florida, just south of Tampa. This 7-mile long island has the laid-back feel and charm of island life at its best. The highest posted speed limit is 35 mph. A free trolley runs from one end of the island to the other, stopping every 2-4 blocks, taking beach lovers to their desired destinations. Bicycles and walking seem to be the favored modes of transportation when exploring the island.

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What is Anna Maria Island known for?

Anna Maria Island is known for its white sandy beaches, crystal blue water, sunsets that take your breath away, friendly locals, mouthwatering seafood, and peaceful waterfront dining. It’s my tropical vacation without even leaving the States. Signs on store doors let you know you have arrived and life is relaxing on Anna Maria Island – Bare feet and Swimsuits are welcome!

Crossing the draw bridge signals the entrance to the island, and life is about to change. You are greeted by beautiful water on both sides of you, with just a glimpse of old Florida’s charming buildings ahead. Just driving across the bridge, your breathing slows, and you can almost feel your blood pressure drop. Even the welcome to Anna Maria Island is darn right irresistible.

With a welcome like this, wait till you see what this rare, unspoiled island with vintage charm known as Anna Maria Island has to offer.

The History of Anna Maria Island

Anna Maria Island was first settled at the beginning of the twentieth century by Tampa Mayor Madison Post, who named the island after his sister-in-law Anna and his wife, Maria. Before 1921, the only main inhabitants of the island were temporary fishermen and nautical types.

The first permanent resident of Anna Maria Island was George Emerson Bean. Until 1921 the island was only accessible by boat. At that time, the first bridge connecting the fishing village of Cortez with Bradenton Beach was built.

Soon after the bridge was built, actor Paul Gilmore purchased 40 island acres with the intent of building a film colony. Only one movie was filmed there, “The Isle of Destiny.” The movie itself was unsuccessful.

Today three small cities, Anna Maria, Holmes Beach, and Bradenton Beach make up Anna Maria Island.

Anna Maria Island Beaches

The beaches of Anna Maria Island are breathtaking. The island is home to several beaches with one thing in common, white sand and emerald blue water. Yet each of the beaches has its own characteristics and are very different depending on where they are located on this small island.

The following beaches are some of our current favorites and ones that we love visiting.

• Cortez Beach has a southern beach feel. You cross small wooden footbridges to get from the parking to the beach. The breathtaking Cortez Beach is safely hidden by tall grass. Keep your eyes open. This is a great beach for finding sand dollars.
• Coquina Beach is for strolling. You’ll enjoy discovering local shells, including the tiger’s paw and, of course, tiny coquinas, which look like little butterflies on the beach. Keep your eyes peeled. You may even find a shark’s tooth, sand-dollar, or a starfish.
• Bradenton Beach is the center of all the action. After crossing the bridge, you enter Bradenton Beach. It is also within this general area that you will find plenty of unique shopping opportunities, bars, and restaurants.
• Holmes Beach has clean sand, tons of shells, and the water is always gorgeous. A highly accessible beach that is quiet, low-key, and peaceful. This beach has an outside shower to get the sand off your feet before you get back on the trolley.
• Anna Maria Beach is great. The water is calm and clear. This beach is great for watching the sunset. Not many shells, but the sand is beautiful, and there is plenty of potential for a sandcastle.
• Bean Point is named after the original settler, George Bean. This is where Tampa Bay meets the Gulf of Mexico. It’s one of the most beautiful beaches you will ever step foot on. The sand is super soft white, and the emerald blue water is filled with schools of fish and manatees almost within touching distance. It is advised that you NOT SWIM here because of the riptide.

No matter the time of year, don’t hesitate to dip your feet in the Gulf of Mexico. Warm or cool the water is always welcoming!

Kick-off your shoes and stay awhile, its time to feel the sand between your toes.

Walking the beach, playing in the sand, and looking for shells, seems to be daily activities of both young and old.

Looking for more…Check out a few of our other posts…
*Unique Finds For the Serious Traveler
*How to Stay Healthy and Safe While Traveling
*Romantic Things to do on Tybee Island, Georgia

Anna Maria Island Accommodations

Anna Maria Island is home to various vacation accommodations ranging from well-known hotels, landmark resorts, beachfront cottages, resorts, villas, and private homes. There are accommodations to fit just about anyone’s needs.

The Bridgewalk in Bradenton Beach’s historic district is a landmark resort, centrally located at the bridge’s edge. These apartment-style accommodations have an old Florida vibe.

Tortuga Inn is the kind of place that sweeps you off your feet. It comes with its own private white sand beach across the street. Beach chairs and umbrellas await you. There are three heated pools and a boat dock for guests to enjoy.

We have stayed at both of these places and have been wowed by everything about each of them.

Anna Maria Island Restaurants

I could write an entire guide on just the amazing restaurants available on Anna Maria Island. Maybe someday I’ll spend a month on Anna Maria Island and do just that! These are the ones we have visited, enjoyed, and would recommend.

One of the first places we set out to enjoy was a restaurant on the island’s north point. My daughter Cassie and I had visited this pier restaurant on a previous girls’ trip.

I wanted so much to share The City Pier with Gary, but when we got there, it was gone. I was so disappointed to discover that a recent hurricane had destroyed The Anna Maria City Pier.

On the previous visit with my daughter, we had enjoyed great food, locals relaxing while fishing, and friendly conversation all on The City Pier.

We have heard that The City Pier has now been rebuilt and has reopened, complete with restaurant. I can’t wait to go back and enjoy The New City Pier Restaurant with Gary.

At the recommendations of locals, we headed over to The Sandbar. We were delighted we did! We sat outside overlooking the ocean at sunset. 

The food was good, but not exceptional, the view was spectacular, the mood very romantic and the conversation was perfect! 

We visited the Tide Tables twice during our visit. This place is definitely a favorite among the locals. The perfect place for fried shrimp and ice cold beer while enjoying the view.

We loved Anna Maria Island Beach Cafe. It is beachfront casual dining at its best. Besides good food, they offer live weekly music, a tiki bar, cold beer, and island ice cream.

Burgers, Fish Tacos, and even ice cream taste better-served beachfront.

The Waterfront Restaurant has some of the best food we’ve eaten on the island. I had never had pineapple coleslaw until I ate it at the Waterfront Restaurant. It is the perfect pairing with their grouper tacos. This is one place on the island you might want to see if they take reservations.

Food on the island does not stop at seafood. It’s just the best place to get the freshest seafood. If you are looking for something different, a little exploring, and you will find other exceptional options.

For sweets you need, I repeat, NEED to stop and try out The Donut Experiment. The fresh donuts at The Donut Experiment are creative, and they know what tastes great on a donut.

Located near The City Pier is Two Scoops, it is unquestionably the spot to stop for the best ice cream, sundaes, shake, floats, or even fresh brewed coffee.

Anna Maria Island Trolley

The Anna Maria Island Trolley offers a free service that takes locals and vacationers up and down the island between Anna Maria Island and Coquina Beach. It runs seven days a week from 6 am to 10 pm. There are trolley stops every 2 – 4 blocks making it easy to enjoy the services offered. After a long day at the beach, catching the trolley back to your condo is the perfect transportation.

The trolley adds to the calm laid back vibe of Anna Maria Island, allowing vacationers to park their car and vacation without the hustle and bustle of being car to car.

If you love Anna Maria Island you would enjoy some of our other Couples’ vacations in Florida.

Things to do on Anna Maria Island

As if the beach and seafood are not enough to draw you to Anna Maria Island, there is so much more enjoyment the island has to offer. The island is truly an outdoor lovers paradise.

While on Anna Maria Island, you can enjoy combing the beach for shells, stand-up paddle-boarding, swimming (watch for waves and undertows), kayaking, diving, and snorkeling. Keep your eyes open for a chance to see sharks, rays, and manatees.

If going under the water is not your thing, try your hand at parasailing. or deep-sea fishing for ~ grouper, mackerel, or snapper.

For an extremely relaxing time on the water, let Paradise Boat Tours take you on a leisurely cruise in hopes of spotting dolphins.

In case you want to get away from the water, try golfing at Timber Creek, mini-golfing at The Fish Hole, visit an orange orchard or even the local bird sanctuary.

Let’s not forget the Coquina Baywalk, which winds through inviting wildlife areas, and Motes Marine Aquarium. Our girls loved Sea World, and they love Motes just as much. They enjoyed all of the hands-on activities at Motes.

Anna Maria Island Weather

We have visited Anna Maria Island at all times of the year. I realize that weather does play a role in vacation fun. But cool or warm there is not a bad time to visit Anna Maria Island.

The summers are long and warm, with unexpected brief rain showers. The winters are short, cool, and windy. Over the course of the year, the temperatures vary from 55 to 90 and are rarely below 45 or above 92.

Based on the tourist score, the best times of year to visit Anna Maria Island for warm-weather activities are from late February to early May and from late October to early December.

Looking for even more…Check out a few of our other posts…
*What to Pack for a Beach Vacation
*Tips for Traveling as a Couple

When you are packing for a trip to Anna Maria Island, make sure these 5 items are on your packing list for winter or summer travel.

• Sunscreen ~ Sunscreen is a must all year round, especially if you are visiting the beach. The glare of the sun off the ocean water is extra strong.
• Sunglasses ~ The southern glare of the sun makes sunglasses a desired commodity.
• Swimsuit ~ You don’t come to Florida and not enjoy the water at least daily.
• Hat ~ Having a nice wide-brimmed hat is encouraged. It will offer protection from the sun on your face and your hair from the occasional wind and a seagull overhead.
• Camera ~ This budget-friendly Canon camera is our favorite. We wouldn’t travel without it. You don’t want to be caught without a camera on Anna Maria Island.

Top 10 Things You Must Do on Anna Maria Island
* Visit the Beaches ~ Although all the beaches are beautiful, Bean Point is the beach you need to make every effort to visit. The secludedness and scenics of the beach make it perfect for a romantic walk.
* Make your own Donuts at The Donut Experience ~ get creative with your own unique combinations at Anna Maria Islands favorite donut stop.
* Dine at The Rod and Reel ~ Enjoy some of the best seafood around. Although open for breakfast, lunch, and dinner, don’t hesitate to sit and enjoy the beautiful sunsets on the Pier.
* Shop at Pine Avenue ~ These are not your typical shops. These trendy shops will transport you to a tropical island just by walking through the doors.
* Paddleboard and kayaking ~ The perfect way to see the scenery and soak up the Florida sunshine. You might spot a dolphin or manatee.
* Stroll Historic Bridge Street ~ Eat, shop, drink, and even enjoy a round of miniature golf.
* Charter Fishing ~ The gulf is the perfect place to try your hand at fishing and is home to
* Ride the Trolley ~ The Anna Maria Trolly is the best way to get around. After a morning coffee, the trolley will transport you to almost anywhere on the island. This is a great way to visit several beaches throughout your day without the hassle of fighting traffic.
* Enjoy the Nightlife ~ Be sure to enjoy some of Anna maria Islands’ favorite nightspots on the beach for a couple of your favorite drinks. Everything tastes better on the beach, even a nightcap.
* Enjoy the Sunset ~ Anna Maria is known for having some of the most beautiful sunsets around. Find that perfect spot on the beach and watch as the sun seems to disappear into the gulf and dolphins gracefully jump in the moonlight.

Best way to get to Anna Maria Island

The closest airport to Anna Maria Island is Sarasota-Bradenton International Airport. It is a short drive of fewer than 20 minutes from the airport to the island. If you plan on using the trolley and just staying on the island, I would use uber or Conscious Cab of Sarasota to take you to your condo.

If you are looking to fly into a larger airport, Tampa International Airport is the closest. From the airport, you can rent a car and drive one hour to Anna Maria Island. This is worth it just to experience the Sunshine Skyway Bridge between Tampa and Sarasota. Shop for fares and car rentals on Skyscanner.

We use Skyscanner for the majority of our searching for flights and either book with them or, in a few cases, directly through the airlines’ website. By filling out the form below, you can do some fun searching for possible vacations.

We have visited many beach towns and have loved all of them, but most of them had that tourist feel. Anna Maria Island does not have that feel. It’s Anna Maria Island’s slow pace and beauty that keeps calling us back. It’s that place where we can just breathe and relax. We are hoping to get married on Anna Marie Island in 2021.

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