Labor Day, falling on the first Monday of September each year, is a time to honor American workers while enjoying a well-deserved break. And what better place to spend this long weekend than on Anna Maria Island? Known for its laid-back “Old-Florida” charm, pristine beaches, and a plethora of activities, AMI offers the perfect setting to unwind and create lasting memories.
Events to Look Forward To
Labor Day weekend on AMI is packed with events that cater to every interest:
- 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.
- 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: Live music at Harrys Grill. Address: 9903 Gulf Drive Bradenton, Florida 34216 Phone: (941) 567-5999 Time: 6pm-8:30pm
- 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
Activities
Here are some timeless activities enjoyed year round by locals and visitors alike:
- Sightseeing on AMI: Explore the island by the free island trolley, stopping every four blocks, or take a boat tour to spot manatees, dolphins, and other marine life.
- Fishing Charters: Experience the thrill of fishing in the waters surrounding Anna Maria Island with expert fishing charters. Whether you’re a novice or seasoned angler, these charters offer guided trips to catch a variety of fish species while enjoying the beautiful Gulf Coast scenery.
- Beaches: Bring the family to Manatee Public Beach or Coquina Beach for sun and fun. If you’re seeking a quieter spot, explore Bean Point, located at the northernmost tip of the island for a more secluded experience.
- Hiking Trails: Leffis Key Preserve on the southern end of Anna Maria Island features a scenic boardwalk and trails through mangrove forests and tidal marshes, perfect for birdwatching and observing native wildlife. Adjacent to Leffis Key Preserve, Coquina Bay Walk offers a peaceful stroll along the bay with stunning views of Sarasota Bay
Dining
No need to worry about finding a place to eat on Labor Day. Anna Maria Island boasts an array of dining options to suit every palate:
- Ginny’s & Jane’s Café: Indulge in their famous ginormous cinnamon rolls or opt for a hearty lunch surrounded by quirky island charm. 9807 Gulf Dr, Anna Maria, FL 34216 Open daily: 7am-3pm Contact: (941) 778-3170
- The Donut Experience: Create your own gourmet donuts with a variety of toppings and icings, perfect for a sweet start to your day. 210 Pine Ave, Anna Maria, FL 34216 Open daily: 7am-1pm Contact: (941) 896-3172
- Rod n Reel Pier: Enjoy casual dining with stunning Gulf views and try your hand at fishing right off the dock. 875 N Shore Dr, Anna Maria, FL, 34216 Contact: (941) 778-1885
- Anna Maria Island Beach Café: Relax on a beachfront patio overlooking Manatee Beach indulging in American cuisine, ice cream, and cocktails. 4000 Gulf Dr, Holmes Beach, FL 34217 Contact: (941)778-0784
- Beach Bistro: For a more upscale dining experience, savor a four-course meal as you watch the sunset over the Gulf. 6600 Gulf Dr, Holmes Beach, FL 34217 Contact: (941) 778-6444
There are tons of options to choose from, but here are a few favorites to get your imagination flowing!
Shopping
Pine Avenue and Bridge Street are definitely the hotspots for shopping and strolling in town, but don’t miss out on the cool shops scattered all over. You’ll stumble upon plenty of charming gift shops, boutiques, and sweet spots around every corner. The best part is most of these shops are locally owned and operated, there are practically no big-name stores, adding to the famous Old Florida feel.
- Back Alley Treasure, on Historic Bridge Street, is a funky spirited shop that has local art, jewelry, clothing, and more to discover while sipping on smoothies or enjoying a refreshing beer. Address: 108 Historic, Bridge St, Bradenton Beach, FL 34217 Contact: (224) 209-1480
- West Coast Surf Shop– Florida’s oldest surf shop that carries all the major surf brands and even trendy boutique items. Address: 3902 Gulf Dr, Holmes Beach, FL 34217 Contact: (941) 778-1001
- The Island Cabana, on Pine Ave, is a trendy women’s brand resort wear, jewelry, home décor, and souvenirs. Address: 403C Pine Ave, Anna Maria, FL 34216 Contact: (941) 896-4946
- The Sand Dollar Boutique is a coastal beach gift shop filled with everything from unique souvenirs to stunning home décor. Address: 5302 Marina Dr, Holmes Beach, FL 34217 Contact: (941) 251-6464
Vacation Rentals
Looking to make the most of your Labor Day getaway? Consider booking a vacation rental on Anna Maria Island with Island Real Estate! Whether you fancy a beachfront villa, a cozy cottage, or a charming condo, we’ve got accommodations to fit every taste, group size, and budget. Our team is here to assist you with any questions or recommendations you may need. We strive to make your stay feel like AMI is your home away from home!
Why wait? Book your stay today and start planning your Labor Day escape to Anna Maria Island!
