Labor Day is coming soon, and so is fun in the sun! Whether you’re interested in a great escape or a laid-back vacation, look no further than the beautiful Anna Maria Island! 

We’ll give you insights on the top events and activities for the ultimate Anna Maria Island Labor Day for couples, families, groups, or singles. 

Since COVID-related closures and restrictions are still in place and changing often, and lodgings book fast, your best bet to ensure peace of mind is to secure one of our stunning beach house properties

Things to Do on Labor Day Weekend

Known as the “Island in the Sun,” Anna Maria Island is one of Florida’s treasures and best-kept secrets. Don’t fret about the massive crowds in Miami and Orlando or the hassle of international travel. A beach vacation on Anna Maria Island for Labor Day is accessible, affordable, and there’s plenty of enjoyment for everyone! 

Here are our top recommendations:

Hit the Beaches

Anna Maria Island is renowned for its sugar-white beaches and turquoise waters. Those seeking solitude will enjoy the namesake Anna Maria Beach or Bean Point

Folks who love a vibrant, busy beach with plenty of activities and amenities like restaurants and fishing opportunities should head to Manatee Public Beach, Coquina Beach. Bayfront Beach is the best of both.

With the rental of one of our beachfront properties, we bring the beach directly to you! We have multiple rentals in the cities of Bradenton Beach and Holmes Beach. These vacation homes are conveniently located near the best beaches of Anna Maria Island and surrounded by waterways.

Cultural Events 

Photo Credit:

Perfect weather all year long makes Anna Maria the ideal spot for live entertainment and exciting arts and culture events. Labor Day weekend is a perfect time for those of all ages to enjoy those activities! 

Some special annual events and concerts have been canceled or postponed for safety precautions and construction work (like the Englewood Pioneer Days Festival), but plenty of options are still available. Because things are subject to change, be sure to check in advance.

The Center of Anna Maria Island

A cultural hotspot that’s a hit with locals and visitors alike, the Center of Anna Maria Island features various events all year, including The Bradenton Concert Series, Murder Mystery plays, and holiday extravaganzas. 

Check the schedule and website for regular updates.

The Ringling Underground

Step right up for a night of culture! On September 2, 2021, the Ringling Underground features live music from local and regional performers in the museum courtyard, where artists will be showing their work.

Admission is only $15 and free with an Art After Five admission, so why not make a day of it and visit the Ringling’s Circus Museum or Museum of Art too?

Nathan Benderson Park Rec Days

For those who love water activities that can satisfy the whole family or a group with different skill levels and interests, look no further than NBP Rec Days as your one-stop spot for water fun! 

Located at Nathan Benderson Park at the base of the finish tower on Regatta Island in Sarasota County, the itinerary for NBP Rec Day on September 4, 2021, will feature opportunities to go kayaking, canoeing, or try stand-up paddleboarding. Fishing is another option with a license. 

The price is right at $10 per adult or $5 when accompanying a child. Kids 6 and under are free.

12th Annual Labor Day Weekend Downtown Venice Craft Festival

Local artisans show off their functional art, handcrafted jewelry, ceramics, glass, and metal works at the annual craft event in Downtown Venice, Florida. The festival runs September 4-5th, so there are two opportunities to add it to your Labor Day schedule. 

While you’re there, you’ll want to check out the historic Downtown Venice area, known for The Venice Art Center and the gallery of famed photographer Clyde Butcher

For music lovers, Venice Beach Pavilion has live bands almost every night with free concerts at the Gazebo Stage in Centennial Park twice monthly. 

Sightseeing on Land or By Sea

One of the best ways for land lovers to see the sites and take in the scenery of Anna Maria Island is to cruise around in the free trolley that loops around from Anna Maria City Pier to Coquina Beach, stopping every four blocks. 

Those looking to ride waves instead of pavement and hoping to spot dolphins, manatees, rays, and other sea creatures should hop aboard the Paradise Boat Tour

The 90-minute narrated adventure through the glittering waters of Sarasota Bay promises that 95% of guests see dolphins!