Bradenton decorated for the holidays

Situated along the stunning Florida Gulf Coast, Anna Maria Island and its neighboring areas offer more than just pristine beaches and turquoise waters. Throughout the year, the island comes alive with a variety of annual events that capture the essence of the local culture and community spirit. We’ve compiled some of the top annual events that locals and visitors to Anna Maria Island and Bradenton enjoy each year. We hope you’ll consider planning your next trip to Anna Maria Island around an event or a holiday, and we look forward to hosting you!

Cortez Commercial Fishing Festival

The annual Cortez Commercial Fishing Festival in February celebrates the area’s rich seafood heritage with delicious seafood, environmental exhibits, live music, kid’s activities and a craft fair. Located just over the bridge from Anna Maria Island, this family-friendly event is a fundraiser for the Florida Institute for Saltwater Heritage and all proceeds go to support their mission. 

Bradenton River Regatta

Boats racing in the Bradenton River Regatta

Head to the Bradenton Riverwalk in February to watch supercharged powerboat racing at the Bradenton River Regatta. This family-friendly event features thrilling super league powerboat races, live entertainment and a stunning drone light show along the scenic Manatee River.

Anna Maria Island Heritage Day

The Anna Maria Island Historical Society hosts its annual Heritage Day in March to celebrate the history of the island. The family-friendly event includes tours of the museum, living history exhibits, food and live entertainment. This is a fundraising event and all proceeds benefit the AMI Historical Society.

Sarasota Film Festival

Film aficionados won’t want to miss the Sarasota Film Festival, a premier cinematic event held annually in April. Just a short drive from Anna Maria Island, this festival showcases a diverse selection of films, bringing together filmmakers and enthusiasts for a weeklong celebration of cinematic arts

Sarasota Powerboat Grand Prix

Feel the adrenaline at the Sarasota Powerboat Grand Prix Festival in July. This high-performance racing event showcases powerboats competing along a technical course through the Gulf of Mexico, creating an exciting spectator experience for seasoned powerboat enthusiasts and newcomers alike.

Independence Day

fireworks 4th of july on the beach on Anna Maria island florida

Independence Day is celebrated in style on Anna Maria Island. The Anna Maria Island Privateers 4th of July Parade is very popular, with pirates throwing beads and candy, and sometimes dousing the crowd with water. On nearby Longboat Key, the “Shortest Parade in America” sets out along a quarter-mile parade route that ends at Bicentennial Park with a festival including food and kid’s activities. Set up your chair on the beach at sunset to catch an unobstructed view of the fireworks display. Learn more about July 4th on Anna Maria Island in our blog post.


BayFest is an annual celebration of island life on Anna Maria Island. Every October, festival attendees are treated to a street festival with live music, local food vendors, artisans and a classic car show. This popular one-day event is a chance for visitors to come together with the local community to enjoy what the island has to offer.

Symphony on the Sand

Anna Maria Island Symphony on the Sand

Symphony on the Sand is a musical event in November featuring the Anna Maria Island Concert Chorus and Orchestra. The elegant event is held on beautiful Coquina Beach, where the 45-member ensemble performs classical favorites, Broadway hits and film scores while attendees dine on gourmet food from local restaurants.


Anna Maria Island has many holiday events during the month of December, including tree lighting ceremonies and holiday markets, a popular holiday boat parade and a Christmas parade featuring Santa and the Anna Maria Island Privateers

No matter the season, Anna Maria Island and surrounding areas beckon visitors with a calendar full of exciting events. Consider planning your getaway around one of these captivating events to truly experience the magic of this charming island. Book your Anna Maria Island vacation rental.

Dolphins jumping off coast of Anna Maria Island

Anna Maria Island is a charming Gulf Coast barrier island that offers a perfect blend of natural beauty and diverse activities for visitors of all ages. From pristine beaches to unique wildlife encounters and delicious dining options, Anna Maria Island offers a little slice of paradise. Let’s dive into the Top 10 Anna Maria attractions and activities that make this island so appealing.

A Day at the Beach

The beaches of Anna Maria Island are unparalleled, with soft, powdery white sand and warm, clear water. There are a number of beaches along the island’s coast, with each offering something special. From building sand castles and playing in the waves at lively Manatee and Coquina Beach, to a relaxing sunset at serene Bean Point Beach, there is a beach for everyone to enjoy.

Kayaking and Paddle Boarding

Kayaking on Anna Maria Island

Rent a kayak or paddleboard to explore the mangrove tunnels and serene bays along Anna Maria Island. This is an activity perfect for nature lovers, providing a chance to observe local wildlife up close, including manatees, dolphins and shore birds. Several companies offer daily and weekly water sports rentals, as well as guided tours.

Dolphin-Watching Tours

Experience a thrilling up-close encounter with dolphins in their natural habitat by going on a dolphin watching tour off Anna Maria Island. Dolphin-watching tours provide the opportunity to spot dolphins frolicking in the wild, which truly is one of the most wonderful sights to see! Several charter companies offer comfortable boats and take you to local places of interest for both wildlife viewing and collecting seashells.

World-Class Fishing

Whether you’re an experienced angler or a beginner, fishing excursions are a great way to spend your time on Anna Maria Island. Charter a fishing boat for deep-sea adventures, or cast a line from Anna Maria Island Pier or Longboat Pass for a relaxed and rewarding activity. 

Horseback Riding

There are a few unique horseback experiences you can find in and around Anna Maria Island. Ride on trails and into the bay for a magical horseback swimming experience. Or book a Sand & Surf Sunset Ride to take in the natural beauty of the area while you interact with these calm creatures.

Miniature Golf

This classic family favorite is a fun activity for all ages on Anna Maria Island. The compact course at The Fish Hole is located a block away from the historic Bridge Street shopping district and provides a challenge for all ages. This course is especially fun after dark, as string lights lend a cozy and festive atmosphere.

Explore the Island by Bike

Palmetto Riverwalk walking path on Anna Maria IslandAnna Maria Island is a bicycle-friendly town, with flat terrain and dedicated bike lanes making it an easy way to get around and a fun way to sight see. Seeing the island on two wheels is a great way to stay active, avoid sitting in traffic and soak in the island’s beauty at your own pace. There are a variety of bikes and trailers available to rent across the island, as well as e-bikes and scooters at some locations.

Art Galleries and Workshops

Anna Maria Island has a thriving arts scene. Visit a local art gallery and sign up for an art workshop if you’re feeling creative. Painting, pottery, and other artistic experiences are a great activity for visitors looking to express themselves or try something new. Most galleries and studios can be found along Pine Avenue on the north side of the island.

Restaurants and Shopping

Anna Maria Island has two main entertainment districts, which both provide unique local art, souvenirs and dining experiences. Historic Bridge Street in Bradenton Beach offers a compact walkable area, with several restaurants like the family-friendly Daiquiri Deck, and small boutiques focused on unique gifts. Pine Avenue on the north end of the island is a bit more spread out, with local galleries and quirky souvenir shops stretching the width of the island down to Anna Maria Island Pier on the east end. The local favorite Sandbar Seafood and Spirits is a beachfront gem with classic dishes and fresh-caught seafood.

Cruise Out on the Water

Boat cruises are a great way to explore the waterways of Anna Maria Island. Adventurous visitors may enjoy a snorkeling tour to Egmont Key, a wildlife refuge that is only accessible by boat, with incredible underwater views and pristine beaches. Or a more laid-back sunset cruise may be the key to soak in the stunning scenery and spectacular Florida sunset.

Anna Maria Island offers a variety of activities and attractions that are sure to appeal to individual travelers and families alike. From amazing beaches and spectacular natural surroundings to enjoying all of the coastal Florida charm, Anna Maria Island is a must-visit destination for an unforgettable vacation adventure. Our vacation rental accommodations offer all of the comfort, space and convenience you need for a seamless stay. Book your Anna Maria Island vacation rental and get started planning your Gulf Coast getaway today!