Upcoming Fall Events in Anna Maria Island

Are you thinking of Anna Maria Island with its powdery-white beaches, aquamarine water, and Old Florida feel? The island has all the makings of a tropical paradise while retaining the “Old Florida” feel that so many other beach destinations have lost to development and high-rise condos. But are you also hoping to avoid crowds and extreme summer heat? Consider booking an Anna Maria Island vacation in the fall.

September through November are the perfect months to enjoy a mild temperature while avoiding summer and winter-break crowds. And if you’re the kind of person who can’t spend an entire vacation relaxing in the sand, during fall months, there are plenty of local activities to keep you entertained.

Cocktails at Set The Bar Competition in Sarasota

Set the Bar Cocktail Competition

On October 4, Sarasota’s annual cocktail competition brings together the region’s best bartenders, distillers, and other professionals to demonstrate the creative beverage talents behind locally-owned restaurants. Guests will enjoy live entertainment, prizes, and delicious dishes presented by participating restaurants. Anyone 21 and up may purchase general admission tickets for $45. A portion of proceeds goes to The Child Protection Center. Buy your tickets now as availability is limited!

Sarasota Pirates and Rum Festival

At the Van Wezel Performing Arts Hall on Saturday, October 5, you are welcome to join Sarasota’s biggest event in October for cancer awareness. There will be live music, exotic cuisines, pirates, soul food, and rum brands from around the world. General admission is $20 and includes rum samples and access to all stages.

Anna Maria Island Bayfest

Come on down to Pine Avenue on Saturday, October 19, for Anna Maria Island’s 19th annual Bayfest! There will be plenty of food vendors, refreshments, and snacks, but the main attraction will be the block after block of artisans, crafters, and vendors with one-of-a-kind items for sale. A kids’ area will also provide a funhouse and inflatables, enough to entertain the kids for hours while mom and dad shop! The Bayfest runs from 10 am to 9 pm, so be sure to drop by.


Similar to Bayfest, ArtsHOP is an event offering a wide variety of crafts, music, and food. In addition, guests can enjoy public art exhibits, dramatic performances, and symphonic performances by the local chorus and orchestra. ArtsHOP takes place in early November each year, so be sure to plan a trip then if you want to get a taste of local arts and culture.

Cortez Flea Market in Florida

Cortez Nautical Flea Market

The 22nd Annual Cortez Nautical Flea Market will be taking place on Saturday, October 26 from 8 am to 1 pm. If you have a taste for all things nautical, then this is the market for you! A wide variety of vendors will be selling and trading items like fishing supplies, powerboat equipment, diving gear, and sailing gear. Between 10 a.m. and 1 p.m., the market will feature live music.

Trail of Treats

The last weekend of October offers kids the chance to show off their Halloween best. Games, parades, and even a costume contest are part of the celebrations. The Trail of Treats offers kids a safe way to Trick or Treat throughout the island. It includes lots of candy and many different local cafes and art galleries participate.

Vacation Rentals

Visiting Anna Maria Island, you certainly won’t be bored! There’s something for everyone in the family, and additionally, it’s easy to find a great place to stay with Anna Maria vacation rentals. We have luxury, condo, waterfront, and pet-friendly rentals. Don’t miss out on our assortment of Anna Maria Island rentals today. Secure your vacation escape and make sure everyone can have a blast for the upcoming fall season.