Anna Maria Island…

Offers a taste of Old Florida

Three communities, each with its own distinct personality, make up this popular vacation destination.

From Sarasota Magazine

By Ilene Denton January 4, 2021

An aerial view of Anna Maria Island

Welcome to Anna Maria Island, a picturesque oasis boasting a seven-mile stretch of pristine white-sand beaches, where the rhythm of the waves beckons travelers to indulge in the laid-back charm of Old Florida. Here, the swaying palms and azure waters, you'll discover a vibrant tapestry of lively seafood restaurants, tiki bars perched right on the sand, and inviting fishing piers that extend into the horizon.

As you wander through the island's quaint streets, lined with charming souvenir shops and mom-and-pop boutiques, you'll feel transported to a bygone era where simplicity and authenticity reign supreme. Anna Maria Island is a sanctuary for those seeking refuge from the hustle and bustle of modern life, where every moment is imbued with the timeless allure of coastal living.

Voted the 26th best island in the entire world in the Conde Nast Traveler Reader Choice Awards, Anna Maria Island captivates the hearts of travelers from near and far, drawing them into its embrace with promises of sun-soaked adventures and unforgettable experiences. Yet, beyond its appeal as a vacationer's paradise, many are drawn to make Anna Maria Island their permanent home, enchanted by the allure of the sand-in-your-shoes lifestyle and the sense of community that thrives within its shores.

From sunrise strolls along the beach to evenings spent sipping cocktails under the stars, Anna Maria Island offers a slice of paradise unlike any other. Whether you're a seasoned traveler or a lifelong adventurer, come discover the magic that awaits on the shores of this beloved island paradise. Welcome home to Anna Maria Island, where every day feels like a vacation and memories are made to last a lifetime.

Beach Bums on Anna Maria Island

Embark on a delightful journey across Anna Maria Island aboard the popular free municipal trolley, a charming mode of transport that effortlessly zips up and down the island, ferrying vacationers and residents alike to beloved hotspots nestled within the three small cities that collectively form the heart of AMI: Bradenton Beach, Holmes Beach, and the City of Anna Maria.

Zoning restrictions serve as guardians of its unique character, limiting building heights and preserving its timeless allure. As a result, instead of towering high-rise condo buildings or sprawling hotels dominating the skyline, you'll discover a delightful array of architectural treasures that reflect the island's rich history and coastal charm.

Meander along quaint streets adorned with timeworn wooden beach cottages, each exuding its own distinct personality and charm. Amidst the palm-fringed avenues, modest concrete-block ranch-style residences from the 1960s stand as testaments to a bygone era, while low-rise '70s-era condos offer cozy retreats nestled among lush landscapes.

Venture further, and you'll encounter multimillion-dollar bayfront and Gulf-front estates, where luxury meets tranquility in an exquisite fusion of elegance and natural beauty. From sweeping vistas of azure waters to lush tropical gardens, these magnificent properties embody the epitome of island living, promising unparalleled comfort and serenity.

As you explore the diverse tapestry of architectural styles that grace Anna Maria Island, you'll uncover a sense of nostalgia intertwined with modern comforts, where each structure tells a story of enduring charm and timeless elegance. Whether you're drawn to the quaint simplicity of a beach cottage or the opulent grandeur of a waterfront estate, Anna Maria Island welcomes you to experience the magic of coastal living at its finest.

City of Anna Maria

Nestled at the northern tip of Anna Maria Island, this charming little town, with its full-time population of 1,800, embodies the quintessential beachy ambiance while embracing modernity with open arms. Over the past decade, investors have transformed many of the humble 1960s-era concrete-block residences into multi-story mega vacation rental homes, ushering in a new era of coastal living. Today, nearly 70 percent of homeowners double as rental owners, fostering a dynamic atmosphere characterized by a constant turnover of weeklong visitors.

Venture along scenic Pine Avenue, where bicycles and golf carts whisk guests away to a vibrant array of shops, dining spots, and leisurely strolls along the Anna Maria City Pier and the Rod ’N Reel Pier, offering breathtaking views of the Sunshine Skyway bridge. These picturesque landmarks serve as beacons of tranquility and wonder, inviting visitors to immerse themselves in the island's natural beauty.

Amidst this bustling landscape, venerable institutions such as the Island Players community theater, a weekly farmers market, and the Studio at Gulf and Pine art gallery stand as pillars of community engagement. From captivating performances to hands-on art classes, these cultural gems foster a sense of unity and belonging, enriching the fabric of our town with creativity and camaraderie.

While rooted in tradition, our town is a testament to adaptability and growth, seamlessly blending cherished nostalgia with contemporary allure. Join us as we celebrate the timeless charm and modern vibrancy of our beloved Anna Maria Island, where every visit promises unforgettable experiences and cherished memories.

Anna Maria’s Pine Avenue

The allure and enchantment of our beloved town lies a realization: the prestige of Anna Maria Island comes with a price tag. In 2018, our city earned a coveted spot on Zillow's list of 24 U.S. cities with a median price soaring to $1 million, a testament to the undeniable allure and desirability of our coastal haven.

Recent real estate transactions have captured headlines and imagination alike, illustrating the unparalleled value of our island paradise. In 2019, a remarkable 14-bedroom compound resting on nearly two acres of Anna Maria Island Gulf-front shattered records, fetching an astonishing $8,825,000. Local media buzzed with excitement as reports revealed that the property found a new owner in a business management firm representing none other than country music icon, Garth Brooks. Formerly the domain of the Norfolk Southern Railway Company, this private retreat had once catered to the leisure and pleasure of company employees, now poised to embark on a new chapter of luxury and opulence.

Simultaneously, the echoes of history intertwined with modern aspirations as a new-build custom residence in the Wells Harbor neighborhood claimed the spotlight with a remarkable sale of $4,075,000. This transaction, breaking the previous bayfront record set earlier that year in nearby Key Royale, underscores the enduring allure and investment potential of our coastal enclave.

As our town continues to evolve and captivate, these notable sales serve as a testament to the timeless appeal and enduring value of Anna Maria Island. Amidst the whispers of sea breeze and the glistening shores, each transaction tells a story of prestige, aspiration, and the boundless promise of coastal living. Welcome to a world where dreams take flight and luxury knows no bounds, where Anna Maria Island stands as a beacon of elegance and sophistication surrounded by the azure waters of the Gulf.

A colorful home on Holmes Beach

Holmes Beach

Just a stone's throw to the south lies Holmes Beach, a quaint town spanning just under two square miles and boasting a year-round population of 3,913 residents. Here, a distinct residential charm infuses the air with a laid-back vibe that captures the essence of coastal living.

Vacation rentals dot the landscape, featuring a mix of unpretentious older concrete-block homes spanning around 1,400 square feet, alongside newer, more spacious pastel-colored Key West-style residences. Among the tranquil streets, Key Royale stands out—a canal-front community adorned with executive homes and its very own nine-hole golf course, where a flurry of updates and renovations add to its allure. Boaters revel in Key Royale's convenient access to Tampa Bay and the Gulf, setting the stage for endless nautical adventures.

Manatee Public Beach emerges as the town's crown jewel, drawing visitors with its pristine shores and captivating vistas. For those seeking leisure and recreation, Holmes Beach offers a new municipal skate park and a public library, inviting moments of relaxation and discovery. Meanwhile, fishing enthusiasts can embark on thrilling excursions from Keyes Marina, charting a course for unforgettable angling experiences amidst the azure waters.

Holmes Beach beckons with its timeless appeal and array of attractions, promising moments of serenity and adventure amidst its charming coastal landscape. Discover the allure of this coastal gem, where every corner reveals a new story waiting to unfold.

Golden light at Bradenton Beach

Bradenton Beach

Nestled on the southern tip of Anna Maria Island, Bradenton Beach stands out as the epitome of eclectic beachfront living. Set apart from Longboat Key by the picturesque Longboat Pass, this vibrant town exudes a distinctively laid-back, yet undeniably lively atmosphere.

Tourism takes center stage here, with a charming array of old wooden cottages and low-rise vacation condos lining the streets just steps away from the sandy shores. Bustling Bridge Street serves as the heartbeat of the community, offering an eclectic mix of shell shops, a delightful mini-golf course, and an array of dining options that cater to every palate. Choose between the vibrant ambiance of the big new Daiquiri Deck bar and restaurant or the timeless allure of the atmospheric old Drift In cocktail lounge, both offering a taste of island hospitality.

The journey along Bridge Street culminates at the iconic Bridge Street Pier, where adventure awaits with boat tours of Sarasota Bay, promising glimpses of coastal beauty and marine wonders. Coquina Beach emerges as a local favorite, drawing visitors with its pristine sands and crystalline waters. Across the road lies Leffis Key Preserve, a natural sanctuary where trails wind through lush landscapes to reveal a remarkable 26-foot hill at its center. From this vantage point, panoramic 360-degree views of Sarasota Bay and the Gulf of Mexico unfold, offering a breathtaking glimpse into the natural splendor of the region.

Bradenton Beach invites exploration and discovery, where each corner holds the promise of new adventures and cherished memories. Immerse yourself in the vibrant tapestry of this beachfront oasis, where the essence of Anna Maria Island comes alive in every wave and whisper of the sea.

A picturesque Cortez cottage


As you venture beyond the shores of Anna Maria Island via the iconic Cortez Bridge, immerse yourself in the timeless charm of the historic fishing village of Cortez. Nestled along the shores of Sarasota Bay, Cortez beckons with its rich maritime heritage and picturesque landscapes.

Step back in time as you meander through the narrow streets lined with quaint old wood cottages and weathered fish houses, each bearing the indelible mark of the village's pioneering families. A testament to Cortez's storied past, an impressive 97 structures grace the National Register of Historic Places, preserving the essence of a bygone era.

Wander through the village and discover hidden treasures at every turn, from bustling seafood markets offering the day's fresh catch to cozy cafes serving up delectable dishes infused with coastal flavors. Engage with local artisans and fishermen, who proudly carry on the traditions of their forebears, sharing stories of resilience and community spirit.

Cortez is more than just a village—it's a living, breathing testament to the enduring connection between man and sea. Take a moment to pause at the waterfront, where the rhythmic ebb and flow of the tides echo the heartbeat of this vibrant community. From breathtaking sunsets to the gentle lapping of the waves, Cortez offers a glimpse into a simpler way of life, where time slows down and moments of serenity abound.

As you explore the nooks and crannies of Cortez, you'll find yourself transported to a world where history and hospitality intertwine, inviting you to become part of the fabric of this cherished coastal enclave. So, whether you're a seasoned traveler or a curious explorer, Cortez welcomes you with open arms, inviting you to uncover the magic that lies within its storied streets and shores.

Fishing boats in Cortez

This is where you’ll find popular seafood restaurants, too. The annual Cortez Commercial Fishing Festival, held the third weekend in February, draws more than 20,000 visitors to hear live music, admire nautical arts and crafts and enjoy fresh-off-the-boat seafood.

“In other words, you’ve stepped into the Florida of decades ago, with one major difference: New amenities enhance the old charm for a winning combination.” – Southern Living


Discover paradise on our award-winning beaches, where soft white quartz sand meets Caribbean-like turquoise blue waters, creating a breathtaking backdrop for your getaway.

Immerse yourself in a water lover's paradise, perfect for surfing, bodyboarding, and kayaking, as you ride the waves and explore the endless adventures awaiting you.

Indulge in the culinary delights of our island, boasting award-winning and unique dining options infused with local flair, ensuring every meal is a memorable experience.

Leave your worries behind as you explore the island without the need for a car, opting instead to cruise via trolley, bike, or golf cart, soaking in the charm and beauty at your own pace.

Experience the vibrant tapestry of our community through its locally-owned businesses and boutique shopping, where each storefront tells a story and every purchase supports the spirit of our island.

From sunrise to sunset, discover an array of events and activities tailored to vacationers of all ages, ensuring every moment is filled with excitement and wonder.

Cast your line and reel in the adventure with plenty of fishing opportunities available, whether from the beach, boat, or pier, where the thrill of the catch awaits.

Welcome to a place where every moment is a celebration, and the wonders of our island await your exploration.

Check out Bradenton Gulf Islands Visitor Information Page

Award Winning Island

  • #3 of America’s Prettiest Towns” by Forbes in 2013 
  • Top 30 Islands in the World” by Condé Nast Traveler in 2014
  • Top 10 Island Beaches for Perfect Sand” by Condé Nast Traveler in 2015
  • TripAdvisor Traveler's Choice Destination Winner 2013 and 2014
  • 14 Best Small Beach Towns in America" by Thrillist in 2015
  • Top 10 Happiest Seaside Towns” by Coastal Living in 2018
  • 26th best island in the entire world in the Conde Nast Traveler Reader Choice Awards

Spend 7 Perfect Days with CN Traveler Recommendations

“In other words, you’ve stepped into the Florida of decades ago, with one major difference: New amenities enhance the old charm for a winning combination.” – Southern Living