Experience the Vintage Charm of Anna Maria Island

| August 15, 2023

There is something timeless about Anna Maria Island. Standing on the pristine white sand beaches and staring out into the vast, endless ocean, it is easy to forget that time exists at all. There is a vintage charm about Anna Maria Island. Recently featured in Southern Living Magazine, it is no surprise that Anna Maria Island is growing in popularity and topping so many ‘must visit’ lists. The streets of Anna Maria Island are lined with boutique shops, locally owned restaurants, and unique galleries to explore.

One Island. Three Cities.

Anna Maria Island is divided into three municipalities: Anna Maria, Bradenton Beach, and Holmes Beach. Each of the three cities brings its own sense of style and charm to the island.

Anna Maria (The City)

Anna Maria is the northernmost city on the island and home to favorites for locals and tourists alike. The city is home to attactions such as the Anna Maria Pier, the Anna Maria Historical Society, and a handful of parks. 

Bradenton Beach

Bradenton Beach is located on the south side of the island. The beach was initially known as Cortez Beach due to the close proximity to the Cortez community on the mainland of Florida. The name was changed in the 1920s to help convince prospective buyers during the Florida land boom of the time that it was closer to Bradenton on the mainland. Bradenton Beach is where a bridge connects the mainland to Anna Maria Island. While the bridge was originally constructed out of wood, it was replaced in the 1950s with a concrete bridge.

Fun fact: Elephants were paraded across the new concrete bridge that connected the mainland of Florida to the city of Bradenton Beach to convince tourists and locals of the bridge’s strength. 

Check out even more Anna Maria Island History Here! 

Holmes Beach

Holmes Beach, the central city of Anna Maria Island, is the largest residential community on the island. The newest incorporated city on the island, it was voted into existence in 1950.

Fun Fact: The City of Holmes Beach also includes the area of Key Royale. Holmes Beach is a must-visit full of boutiques, galleries, watersports, and restaurants.

What is it that makes Anna Maria Island So Charming?

That Vintage Florida Feel…

The architecture of Anna Maria Island harkens back to a simpler time. Many buildings are original and hold an old Florida charm of days past. There are no high rises on the island; the tallest building on the island is a three-story condo building that is grandfathered into current construction clauses. The thriving art community helps keep the small town, big charm vibe that has made Anna Maria Island a sought-after destination.

Boutiques Galore!

You will find few chain stores or outlets on Anna Maria Island. Instead, you will discover one-of-a-kind, locally-owned boutiques, and shops that perfectly capture how delightful Anna Maria Island is.
For some truly unique shopping spots, check out our list below!

Sun & Surf

5418 Marina Dr, Holmes Beach, FL. 34217

Known as “The Shop With the Birds,” Sun & Surf has you covered for all of your beachy and souvenir needs. Famous for the dozen or so parrots that sit outside the store and act as greeters for guests. 

Shiny Fish Emporium

306 Pine Ave, Anna Maria, FL, United States, Florida

The Shiny Fish Emporium is most loved for the unique paint-you-own-sanddollar they offer visitors. Sweet treats, beach fashion, souvenirs, and home decor are also available at the Sony Fish Emporium.

The Red Barn Flea Market 

1707 First Street East Bradenton, FL 34208

The Red Barn Flea Market is a local market that boasts 600+ Vendors on over 20 acres. You are sure to find a treasure in at least one booth. No worries about the heat, much of the market is indoors and air-conditioned. Plan for a full day. This isn’t your typical market. The Red Barn Flea Market is open year-round and has many local events and delicious food. This is a must-visit for tourists and locals looking for a hidden gem. 

The Green Turtle Gift Shop

701 Gulf Drive N Bradenton Beach, FL 34217

The Green Turtle Gift Shop in Bradenton Beach on Anna Maria Island is a must-visit. Get a gift for everyone on your list and then for you. This charming shop is sure you have you visiting again and again. 

Deliciously Independent and Locally Owned restaurants 

Anna Maria is home to first-class shopping as well as genuinely outstanding dining. 

Some restaurants that you might check out during your time on Anna Maria Island.  

Ugly Grouper

The Ugly Grouper is a 100% outdoor dining experience highlighted by the giant statue of the restaurant’s namesake, an ugly grouper fish. It stands 14ft tall and 20ft long. The sculpture was made by Tampa artists with Rustic Steel Creations from components of used cars, Harley Davidson motorcycles, and various found objects.

Grouper Statue | The Ugly Grouper | Anna Maria Island, FL.

The menu focuses on locally caught seafood and has options for people of all dietary restrictions and preferences. The Ugly Grouper boasts live music every day of the week, weather permitting. 

City Pier Grill 

The City Pier Grill has a menu that will bring back memories of a simpler time. Breakfast is served from 7 am-11 am and lunch/dinner continues until closing time at 11 pm. 

Hometown Desserts

Treat yourself after a day exploring the vintage charm of Anna Maria Island with a custom sweet from Hometown Desserts. Stop in for a build-your-own cupcake, or order a cake or pie for a delightful highlight for your gathering or event. This bakery has two convenient locations on the island and has options for all dietary restrictions. 

Anna Maria Island Must Visit!
Bridge Street Pier, Bradenton Beach
The Bridge Street Pier is a local hot spot that is sure to have something to charm everyone. Bridge Street is a part of the Old Town Historic District and a perfect stop for travelers and locals alike. Initially built in the 1920s, the pier has been revitalized after storm damage in recent years. 
Fishing from the picturesque pier is a favorite pastime. Bridge Street Pier is perfect for an energetic and exciting trip to experience the vintage charm of Anna Maria Island.

Beautiful and Peacful Beaches 

Bean Point

Looking for picture-perfect white sand beaches? Bean Point Beach is one of the island’s most secluded beaches. Perfect for a bit of peace and relaxation.

Anna Maria Beach

Anna Maria Beach is at the tip of the island. They share the same namesake and the same beauty. This quiet beach is wonderful place to reflect and take in the wind and the waves. 

Holmes Beach

Fun for the whole family! Lifeguards staff the beach, volleyball nets invite players of all ages and skill, and a litany of shops and restaurants line the nearby streets. There are even beach chairs and umbrellas to rent to make your beach day more comfortable.

Charming Homes for Your Anna Maria Island Stay

The charm extends far beyond the beach, boutiques, or brunch– many homes reflect ‘Old Florida’ perfection and comfort to make your stay relaxing, productive and memorable. Serendipity has a number of such homes.

Serendipity Gulf

This home’s peaceful approach to decor strips away all the unnecessary to leave you with a serene oasis out to the beach that lies just beyond the back door. The clean, white decor within the home leaves plenty of opportunity for your eyes to travel out the back sliding glass doors to the ocean just beyond. As the sun melts over the island, your worries will melt away, too. As night falls, your group will retreat into their own space.


Welcome to beachfront paradise! LimeFish’s luxurious, bohemian aura makes it the perfect vacation spot. The open floor plan features 3 remodeled bedrooms, and 3 full bathrooms, and is the perfect accommodation for your group. With a sleeper sofa in the living room and bunks in one of the bedrooms, you can fill the house with your family and friends for the beach trip of a lifetime.


This house is nestled on the sought-after North End of Anna Maria Island. Playful dolphins dance in the waves and year-round award-winning sunsets paint the sky. Soak up the captivating beauty that surrounds you. Sink your toes into the sugar sand beach, explore charming local shops, and savor the flavors of exceptional restaurants.

Check out all of the available homes for you rental needs here!

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