Fun Labor Day Events on Anna Maria Island 2024



Labor Day, marking the first Monday of September, is not just a tribute to American workers but also an ideal time for a well-deserved getaway. Anna Maria Island (AMI), known for its turquoise beaches, relaxed atmosphere, and rich community culture, provides the perfect backdrop for a memorable holiday weekend.

AMI offers a range of activities and events to suit every interest. From beautiful shorelines to vibrant local eateries and unique shops, this island paradise promises an unforgettable experience.

Exciting Events and Activities on Labor Day weekend:

  • August 31, – September 2, 2024: The 76th Annual Labor Day Regatta at the Sarasota Sailing Squadron is the southeast’s oldest running regatta since 1946. With five racecourses, a Friday welcome party, Saturday dinner, and Sunday awards ceremony, it draws sailors from across the U.S. and Canada. Free for spectators. Address: 1717 Ken Thompson Parkway, Sarasota, FL 34236.
  • September 2, 2024: Enjoy free admission to the Ringling Museum of Art on Mondays. Wander through the Bayfront Gardens, visit the Museum of Art, and explore the Glass Pavilion. Note that there are additional fees for entry to the Circus Museum and Ca’d’Zan Mansion. Immerse yourself in a rich cultural experience that combines art, history, and entertainment, all within the waterfront setting of Sarasota, just an hour’s drive from Anna Maria Island. 5401 Bay Shore Rd, Sarasota, FL34243. Phone: (941) 359-5700. Hours: Open 10am-5pm.
  • September 2, 2024 Karaoke at the Freckled Fin Irish Pub.  Address: 5337 Gulf Drive Holmes Beach, FL 34217 Phone: (941) 251-3930. Hours: 7:30pm-11:30pm
  • September 2, 2024: Live music at Harrys Grill. Address: 9903 Gulf Drive Bradenton, Florida 34216 Phone: (941) 567-5999 Time: 6pm-8:30pm

Dine at these Local Favorites:

Address: 100 Spring Ave, Anna Maria, FL 34216

Phone: (941) 778-0444

Hours: Open daily: 11am-10pm

  • Harry’s Grill – A laid-back eatery known for its burgers, tacos, and seafood dishes, complemented by a selection of craft beers and cocktails.

Address: 9903 Gulf Dr. Anna Maria, FL 34216

Phone: (941) 567-5999

Hours: Monday-Thursday 11:30am- 9:30pm, Friday and Saturday 11:30am-10pm, Sunday 1pm-10pm

  • Anna Maria Oyster Bar: A local favorite for casual dining with a focus on seafood, offering a lively atmosphere and daily specials in a family-friendly setting.

Address: 200 Bridge St, Bradenton Beach, FL 34217

Phone: (941) 778-2662

Hours: Open daily 11am-10pm

  • Smoqehouse: Serves up delicious, no-frills barbecue favorites like smoked meats and classic Southern sides in a laid-back atmosphere.

Address: 1701 Gulf Dr N, Bradenton Beach, FL 34217

Phone: (941) 242-5340

Hours: Monday-Saturday 11am -8pm , closed on Sundays

Find Unique Souvenirs and Gifts at these Local Shops:

Shiny Fish Emporium: A boutique featuring handmade jewelry, art, and home décor by local artisans.

Address: 306 Pine Ave, Anna Maria, FL 34216

Phone: (941) 896-9742

Monday-Friday 10am-5:30pm, Saturday 10am-5pm, Sunday 11am-4pm

Island Cabana: Browse stylish resort wear, beach accessories, and unique gifts for every occasion.

Address: 403C Pine Ave, Anna Maria, FL 34216

Phone: (941) 896-4946

Hours: Open daily 10am-5pm

Bridge Street Bazaar: Explore this eclectic shop for clothing, gifts, and souvenirs with a bohemian flair.

Address: 107 Bridge St, Bradenton Beach, FL 34217

Phone: (941) 778-3400

Hours: Open daily 9am-10pm

Plan Your Stay

Make the most of your Labor Day weekend with a stay in a cozy beachfront cottage or a luxurious vacation rental on Anna Maria Island. Whether you prefer a relaxing getaway or an adventure-filled escape, AMI has something for everyone.

Ready to experience Labor Day on Anna Maria Island like a local? Consider booking your stay with Island Real Estate Vacations and discover why this charming island is a favorite destination. We offer accommodation to suit every style, group size, and budget, making sure all our guests feel at home when they visit Anna Maria Island. For a stress-free experience, book with Island Real Estate and let us handle all the details.

Leave a Reply

Your email address will not be published. Required fields are marked *