Anna Maria Island is renowned for its serene beaches, stunning sunsets, and charming small-town feel. But beyond the island’s natural beauty and tranquil ambiance lies a vibrant community that comes together year-round to celebrate with an array of exciting and unique events. From festive parades and local markets to food and music festivals, there’s always something happening on the island.
At Once Upon A Beach, we believe that timing your stay with one of these signature island events can elevate your vacation experience. Whether you’re joining us for the lively celebrations of Bayfest, the charm of the Holiday Walk on Pine, or the flavor-packed Cortez Seafood and Music Festival, here’s our guide to the best annual events on Anna Maria Island.
1. Bayfest
- When: Mid-October
- Where: Pine Avenue, Anna Maria
Kicking off the fall season, Bayfest is one of Anna Maria Island’s most beloved annual events. Hosted on Pine Avenue, this family-friendly street festival is a lively celebration filled with live music, delicious food, arts and crafts vendors, and plenty of entertainment for all ages.
Bayfest is known for its Classic Car Show, where vintage and collectible cars are showcased along Pine Avenue, drawing car enthusiasts from all over the region. The festival also features local food vendors serving everything from seafood and BBQ to classic festival fare. For those with little ones, the festival includes a kids' zone packed with fun activities like face painting and games.
Live music is a highlight of the event, with local bands performing throughout the day, creating an energetic and festive atmosphere.
Why We Love It: Bayfest brings the entire community together and embodies the friendly, laid-back spirit of Anna Maria Island. It’s the perfect way to experience local culture, food, and entertainment in a relaxed beachside setting.
2. Holiday Walk on Pine
- When: Early December
- Where: Pine Avenue, Anna Maria
As the holiday season approaches, Pine Avenue transforms into a winter wonderland for the annual Holiday Walk on Pine. This magical event invites locals and visitors to stroll along the beautifully decorated street, where businesses and galleries stay open late to offer holiday treats, warm drinks, and seasonal shopping specials.
The festive atmosphere is enhanced by Christmas lights adorning the trees and storefronts, carolers singing holiday tunes, and a special appearance by Santa Claus. The holiday walk offers a perfect opportunity to pick up unique gifts and support local artisans while soaking in the seasonal charm of the island.
Why We Love It: The Holiday Walk on Pine captures the warmth and community spirit of Anna Maria Island during the most magical time of the year. The twinkling lights, festive music, and holiday treats create a cozy, charming experience that makes the island feel even more special during the holidays.
3. St. Patrick’s Day Parade
- When: Mid-March
- Where: Holmes Beach
Anna Maria Island’s St. Patrick’s Day Parade is a lively and festive celebration that brings out the island’s Irish spirit. Organized by the Beach Bistro, the parade kicks off in Holmes Beach and is filled with colorful floats, marching bands, and participants decked out in their best green attire.
The parade route travels down Marina Drive, with locals and visitors lining the streets to catch candy and cheer on the parade’s participants. After the parade, many head to local pubs and restaurants for Irish-themed food, drinks, and live music, keeping the celebration going throughout the day.
Why We Love It: The St. Patrick’s Day Parade on Anna Maria Island is a family-friendly event that’s full of fun and festive energy. It’s a great way to celebrate the holiday while enjoying the island’s sense of community and tradition.
4. 4th of July Parade
- When: July 4th
- Where: Gulf Drive, Anna Maria Island
There’s no better place to celebrate Independence Day than on the shores of Anna Maria Island. The island’s 4th of July Parade is a patriotic display of floats, classic cars, and local pride, traveling the length of Gulf Drive from the City of Anna Maria to Coquina Beach.
After the parade, families and friends gather on the beaches to enjoy a day of fun in the sun, complete with picnics, games, and beach activities. As the sun sets, the sky lights up with locals setting off fireworks, which can be viewed from various spots along the beach.Why We Love It: The 4th of July on Anna Maria Island is a classic summer celebration with a beachy twist. The combination of a festive parade makes for an unforgettable day of family fun and community spirit.
5. Symphonies in the Sand
- When: November
- Where: Coquina Beach, Bradenton Beach
Symphonies in the Sand is one of the island’s most elegant and unique events, combining live orchestral music with the natural beauty of the beach. Held on Coquina Beach, this annual event is organized by the Anna Maria Island Concert Chorus & Orchestra and features a full symphony performance right on the sand.
Guests are treated to a gourmet meal, fine wine, and beautiful table settings as they enjoy the live music with the backdrop of the Gulf of Mexico. The orchestra performs a mix of classical and contemporary pieces, making for a memorable and enchanting evening under the stars.
Why We Love It: Symphonies in the Sand is a one-of-a-kind cultural experience that blends fine dining and music with the relaxed, natural setting of the beach. It’s a magical evening that showcases the island’s artistic side while taking advantage of its stunning surroundings.
6. Cortez Beach Market
- When: November through April (Every Sunday)
- Where: Cortez Fishing Village
The Cortez Beach Market is a must-visit for anyone who enjoys shopping for fresh, local products and handmade goods. Located just off Anna Maria Island in the historic Cortez Fishing Village, this weekly market offers everything from fresh produce and seafood to handcrafted jewelry, artwork, and unique gifts.
As one of the oldest fishing villages in Florida, Cortez is steeped in history and tradition, and the market is a great way to experience local culture while supporting local vendors. The market also features live music and food vendors, making it a fun and lively destination for a Sunday morning stroll.
Why We Love It: The Cortez Beach Market is the perfect way to spend a Sunday morning. With its mix of local products, handmade crafts, and a historic backdrop, it offers a charming and authentic experience just a short drive from Anna Maria Island.
7. Cortez Seafood and Music Festival
- When: February
- Where: Cortez Fishing Village
A celebration of fresh seafood and local culture, the Cortez Seafood and Music Festival is one of the region’s most popular events. Held in the historic Cortez Fishing Village, this festival draws visitors from across the state to enjoy a weekend of incredible seafood dishes, live music, and family-friendly activities.
At the festival, you can sample fresh fish, shrimp, crab, and other seafood delights, all prepared by local vendors who know how to cook it just right. In addition to the food, the festival features live performances by local bands, arts and crafts booths, and educational exhibits about the area’s rich fishing heritage.
Why We Love It: The Cortez Seafood and Music Festival is a celebration of everything that makes the Gulf Coast special—delicious seafood, live music, and a deep connection to the area’s fishing traditions. It’s a fantastic way to experience the local flavor while enjoying a fun and lively atmosphere.
- When: Late October - Early November
- Where: Cortez Fishing Village
The Cortez Stone Crab & Music Festival is a lively, family-friendly celebration that highlights the region’s rich seafood heritage, focusing on the prized Florida stone crab. Held annually in the historic Cortez Fishing Village, one of the oldest working fishing communities in Florida, the festival brings together locals and visitors for a weekend filled with delicious seafood, live music, and coastal charm.
At the heart of the festival are the freshly harvested stone crabs, a local delicacy known for their sweet, tender meat. Vendors serve them up in a variety of ways, from classic stone crab claws to creative seafood dishes featuring crab as the star ingredient. In addition to stone crabs, you’ll also find a range of other seafood delights like shrimp, oysters, and grouper, all prepared by local vendors and restaurants.
The festival is not just about food—it’s also a vibrant music festival, with live performances from local and regional bands playing everything from rock and blues to country and reggae. The sounds of live music create a festive backdrop as attendees enjoy the beautiful setting of the fishing village, which is situated right along the water.
Why We Love It: The Cortez Stone Crab & Music Festival offers plenty of entertainment and activities for all ages. There are arts and crafts vendors, family-friendly games, and educational exhibits that highlight the area’s maritime history and the importance of sustainable fishing. Offering a perfect blend of culinary indulgence, lively music, and community spirit in the charming, old-Florida atmosphere of Cortez Village. It’s a must-visit event for seafood lovers and anyone looking to experience the authentic, laid-back culture of Florida’s Gulf Coast.
Experience the Best of Anna Maria Island with Once Upon A Beach
Whether you’re visiting during the colorful parades of St. Patrick’s Day or the elegant sounds of Symphonies in the Sand, there’s always something exciting happening on Anna Maria Island. These annual events offer a unique way to experience the island’s charm, culture, and sense of community.
At Once Upon A Beach, we’re here to help you plan the perfect luxury vacation. Let us find you the ideal vacation rental that puts you close to the island’s best events, parades, and festivals. Whether you’re attending a lively celebration or simply relaxing on the beach, your time on Anna Maria Island will be filled with unforgettable memories and special moments
