Anna Maria Island Labor Day Weekend Events

While there is simply no bad holiday to plan a vacation to Anna Maria Island, Labor Day is a particularly special time. Spending your Labor Day weekend on Anna Maria Island gives you the opportunity to escape the hustle and bustle of everyday life without missing out on any of your favorite Labor Day celebrations. You can take advantage of the beaches, shops, and restaurants that are available year-round, as well as special activities and events unique to this weekend. Here’s everything you’ll need to know about staying in one of our rental homes on Anna Maria for this year’s Labor Day weekend.

What to Do

Activities

Anna Maria Island is full of family-friendly activities for you to enjoy whether you’re coming for the Fourth of July, Labor Day weekend, or any other time. Bring the whole group to Coquina Beach or Manatee Public Beach to let the kids run around in the sand while you work on your tan. For something a bit more private, Bean Point Beach is great for a sunset picnic with your loved one. Get your shopping done on Bridge Street or Pine Avenue, then bring your history buff to Desoto National Memorial Park or the Anna Maria Island Historical Society. Let out your competitive side at The Fish Hole Miniature Golf, or explore the incredible nature at Leffis Key Preserve. The possibilities are endless!

One of the best things about Anna Maria Island is the close proximity to several awesome day trips. There is a free island trolley that will take you all around AMI, and for a small fee, you can even ride the trolley onto the mainland. If you’re willing to drive a little, visit Lido Key, about half an hour away. This is the ultimate destination for wildlife lovers. Shopaholics want to visit St. Armands Circle, while Siesta Key is certainly worth it if you’re willing to drive about an hour away. Sarasota and Tampa are two more nearby destinations for you to enjoy.

Events

Runner on the beach in Anna Maria Island

In addition to the usual summer activities, there are tons of Anna Maria Island Labor Day events you won’t want to miss out on. Kicking off the start of Labor Day weekend is the Ringling Underground, a live music festival held just on the mainland in nearby Sarasota. The event tends to run from around 8 p.m. until 11 p.m., and admission is cheap at around $5 to $10 per person. Head to the Ringling Museum of Art to enjoy live music from some of the area’s best up-and-coming artists.

If you’re looking to get some exercise on your Labor Day weekend vacation, register for the annual Venice Triathlon! This USAT-sanctioned event is open to both individuals and teams and is typically held on the Saturday of Labor Day weekend. In the past, the event has been held at Sharky’s on the Pier and takes participants through the city, ending in downtown Venice.

What’s Labor Day weekend without a parade? The annual Pioneer Days Parade is held in nearby Englewood and wraps up the two-week Pioneer Days celebration. The parade typically starts at 9 a.m. and goes from Olde Englewood Road to North McCall Road. Your kids will love getting to watch the fun and unique floats ride by and collect as much candy as they can!

If there’s an art lover in your group, be sure to take them to the annual Downtown Venice Craft Festival! There’s always a wide selection of local, affordable, and unique crafts, and you can get to know the local artisans while you’re browsing the selections. You can also pick up some food from local vendors as well as other kitchen necessities like gourmet sauces and spices.

Wrap up the weekend with the Annual Country Fest, bringing you all the best country music and delicious food to finish out your Labor Day celebrations. This is another family-friendly way to spend your vacation and provides the ultimate finish to your festivities. The event runs all afternoon and costs $10 per person. The festivities take place in downtown Venice.

Where to Eat

Between all of the fun Labor Day celebrations, you’re sure to work up an appetite! Luckily, there’s an Anna Maria Island restaurant for every occasion. If you’re looking for a casual seafood restaurant that the whole family can enjoy, look no further than Rod and Reel Pier. You can grab dinner with a view and head right out to the water when you’re done! The Waterfront has long been a staple of the Anna Maria Island community, and Beach House Restaurant is perfect for island-inspired fare that comes with the perfect view. Other great options include the Anna Maria Oyster Bar on the Pier or the Anna Maria Island Beach Cafe.

If you’re looking for something a bit more upscale, check out Beach Bistro, where you can sample the freshest local seafood inside the stunning dining room or on the breathtaking patio. Similarly, Blue Marlin Seafood Restaurant offers Gulf Coast seafood in a nautical setting with live music for you to enjoy. Wanting to try some global cuisine? Visit Isola Bella Italian Eatery for classic Italian dishes, Island Ocean Star for traditional Japanese cuisine, or Island Creperie for a French bistro experience.

After dinner, you can’t forget dessert! If you want some ice cream or yogurt to cool you off in the hot day, visit Dips Ice Cream, Two Scoops, or Holy Cow. The Donut Experiment is a popular spot to take pictures and make your own donut, or you can head to Cupcake Delights to sample one of their unique varieties. Anna Maria Island Creamery and Bakery has a wide selection of fresh-baked pastries, and locals and visitors alike have been loving Hometown Desserts for years. You just can’t go wrong!

If you’re not in the mood for something sweet, maybe you want to finish the evening with a drink with your friends. Slim’s Place is the perfect spot to grab a cold beer and watch the game. You might also enjoy the drinks and seafood fare at Island Time Bar and Grill. The Doctor’s Office provides a wide array of specialty cocktails in a unique atmosphere, while Hurricane Hank’s is perfect if you’re looking for a welcoming pub environment. Other local favorites include Skinny’s Place, Duffy’s Tavern, and The Kokonut Hut.

Beach View Retreat Holmes Beach

Where to Stay

After all of this fun in the sun, you’ll need a place to rest your head. We are proud to be the top resource for Anna Maria Island rental homes, offering something to suit every size group and every budget. It doesn’t matter whether you’re taking a family vacation, a weekend getaway with your sweetheart, a holiday trip, or a family reunion. We’ve got room for everyone!

Our staff is friendly and knowledgeable, always available to assist you with any concerns. We can help you resolve an issue with your rental or give you a recommendation for the best souvenir shop. Our goal is to make you feel right at home, and by the end of your stay, you may find you don’t want to leave! If you’re planning a Labor Day vacation to Anna Maria Island, consider staying in one of our Anna Maria Island rentals. Contact us today to learn more!

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