Top Annual Events Anna Maria Island

Catch the top annual events Anna Maria Island style! No matter what time of year you vacation on Anna Maria Island there is always an event to discover. The Island is home to over a dozen annual events happening throughout the year. From food to the arts, and even classic car shows; Anna Maria Island loves a celebration. Anna Maria Island events often put an emphasis on a family friendly atmosphere. They cater to all ages groups with activities for both young and old within the same event.

Annual Events Anna Maria Island

Below we have compiled a list of the top annually running events on Anna Maria Island. Don’t miss these during your stay! They have been conveniently organized by the season in which they occur. Starting with Winter and ending with Fall.


Anna Maria Island winter events
Winter Events on Anna Maria Island offer family fun!

This is a fun time of year as cool weather drives locals and visitors off the beaches into warmer activities. Unless you have a wet suit to keep you warm, or are staying in a rental with a heated pool, many folks don’t care for swimming. Even in the mild Florida winter weather. Winter events on Anna Maria Island provide a great opportunity for unique holiday shopping. Also enjoy entertainment across the island’s three cities.

There are five holiday related events found on the island in the month of December. These include the Privateers Christmas Parade, Winter Fest, The lighting of Bridge Street and the Lighted Boat Parade. Click on the link here to read about these holiday happenings. Pine Avenue in the city of Anna Maria also offers a holiday walk. Typically happening in mid December the Pine Avenue Holiday walk offers carolers and shopping along with refreshments provided by Pine Avenue businesses.

One of the areas most popular events happening in the middle of winter is the Cortez Commercial Fishing Festival.  This event actually takes place off island in the old Cortez Fishing Village located just over the Cortez Bridge. This event has been running for over 30 years drawing a crowd of 10,000. The Cortez Fishing Festival happens in February, usually the second weekend of the month. A celebration of the commercial fishing industry in Cortez, this event raises funds to preserve local mangrove wetlands to ensure and protect a healthy fish and wildlife population.



Spring on Anna Maria Island brings us gorgeous weather. There are many days of clear skies, perfectly crisp breezes and warm sunshine. There are four annual Spring events you can’t miss if you are visiting at this wonderful time of year.

A fun annual event for 18 years and counting, the Beach Bistro St. Patricks Day Parade usually features dancers, cyclists, bag pipers, live animals and a rowdy bunch of green clad island folks ready for a party. Hosted by the Beach Bistro, this event always offers fun and laughs for all ages.

A celebration of local arts and artists, Spring Fest has been hosted by the Anna Maria Island Art League for 28 years. In addition to arts and crafts, Spring Fest offers live music and fabulous food vendors. This event takes place in the Holmes Beach city field located at 5901 Marina Drive. This event usually takes place the first weekend in March or April.

The Annual Sandbar Easter Egg Hunt is always a crowd pleaser for the entire family. Kids search for Eggs on the beach, then everyone joins in on the Easter parade down Pine Avenue for kid games, face painting and refreshments provided by the Sandbar.

Food and Wine on Pine is a fabulous foodie event offering selections from the area’s best restaurants along with great wine selections. Enjoy live music while you taste your way through this fun event.


Summer fun on Anna Maria Island
Hot Summer days end with gorgeous sunsets on Anna Maria Island.

Summer is a favorite time of year on Anna Maria Island. The summer island life consists of hot days, rainy afternoons and relaxing beach goers. Find crowded beaches lined with turtle nests, baby shorebirds begging for fish, and happily sunbathing patrons. Temperatures of the Gulf of Mexico are warm. Perfect for relaxing on a floaty with a cold drink in hand. While the beach is really the main attraction during summer months, the island also offers a few fun events.

While technically falling in the Spring, Memorial Day Weekend is the start of summer fun and warm Florida weather. A bustling weekend full of people swimming, tanning and spending a long weekend with family, Memorial Day is a great time to simply enjoy being a beach bum. There are no big events, However, Memorial Day does serve as a great time to trolley hop around Anna Maria Island. You’ll enjoy exploring different beaches, fabulous shopping, and amazing restaurants.

There’s nothing more fun than a small town patriotic parade, and Anna Maria Island’s 4th of July Parade is the perfect example. Starting on the southern end of the Island at Coquina Beach the parade makes it’s way up the island throwing candy, beads and trinkets for the kids spreading 4th of July cheer along the way.

Every year there are two public fireworks displays put on by Chiles Restaurant Group at the Beach House and Sandbar restaurants. Most years the Beach House fireworks show happens July 3rd with the Sandbars display following on the 4th. Occasionally the fireworks display has been canceled at the Beach House out of respect to the island’s precious nesting shorebirds that enjoy the strip of coast in very close proximity to the restaurant.



Fall on Anna Maria Island brings us a slight respite from hot days transitioning into warm days allowing the swimming season to continue up until December in most years. This time of year brings the island several great family fun events!

Fall is packed with Annual events!

Bay Fest is the largest running event on Anna Maria Island. This event takes place on Pine Avenue. At Bay Fest you’ll enjoy food, music, vendors and a car show.

The Anna Maria Island Fall Festival happens in the Holmes Beach city field at 5901 Marina Drive in Holmes Beach. Taking place just before Halloween, this event kicks off with a Halloween Parade starting at Anna Maria Island elementary and ending at the city field.

Trick or Treating house to house is not a popular tradition among island neighborhoods. Therefore, the Anna Maria Island Chamber of Commerce hosts a three city wide Trail of Treats sponsored by local businesses. The Trail of Treats starts with a kids costume contest at the Chamber of Commerce located at 5313 Gulf Drive. After the contest kids and parents are welcome to stroll around the Holmes Beach town center collecting candy from businesses from 4-6pm. After cruising through Holmes Beach, head up to Pine Avenue or down to Bridge Street for additional trick or treating from 5-8pm. Typically this event happens on or just before Halloween depending if the Holiday falls on a weekend.

Anna Maria Islanders greatly anticipate Stone Crab Season. Starting in mid October, Floridians and Island locals begin harvesting Stone Crabs by the bucket load. The Cortez Stone Crab Festival, happening in early November, is a fabulous way to enjoy this locally sourced seafood.

Wrapping up autumn events the annual Arts Hop is a great way to experience local arts, crafts, music and food. This island wide celebration of arts and culture is organized by the Cultural Connections of Anna Maria Island. This three day event includes art walks, theater performances and a beach front chorus and orchestra performance called “Symphony on the Sand”.

Enjoy Annual Events Anna Maria Island Style!

Vacation Rentals and Accommodations on Anna Maria Island

When looking for the perfect accommodation on Anna Maria Island, Island Real Estate is the best choice with the island’s largest selection of vacation rental homes to choose from.

North Beach Village Anna Maria Island vacation rental
North Beach Village unit 63 is tucked into a quiet neighborhood just a short walk to gulf beaches. This Holmes Beach Vacation rental sleeps up to 6 guests, and is centrally located putting you near all the island’s best events! Click on the image above to reserve your stay at North Beach Village 63 today.


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