October is Family Fun for Everyone

| September 7, 2021

Why does Christmas and Thanksgiving seem to steal all the fun? Raise your hand if you love Halloween. Same here!

In the month of October, Anna Maria Island hosts fun Halloween spirited activities that’ll appeal to the whole family. Whether you’re into a spooky Halloween ensemble, a festival person or simply enjoy ocean life, Anna Maria Island has you covered.


A cold beverage in hand with an island breeze in your face doesn’t get much better. We have just that and more at the local Bayfeston Pine Street. The entire strip shuts down for over 100 vendors and a ton of fun. Enjoy a day of arts & crafts, food, live music, and finish it off with a car show.

Keep the party going at Motorworks Brewing. Sip on any one of the 20+ local craft beers from the tap room. In the beer garden, you can take a load off from walking the festival all day and bask in a starry night. For those with a competitive streak check out the weekly events from trivia, darts, ski ball and more.


Bring your best Halloween getup and participate in a costume show at theBoofest of Lakewood Ranch Community. On the Premier Sports Campus Performing Arts Stage the whole family can enjoy a spheres bubble show, a ventriloquist show, pumpkin decorating and more. Come with an appetite because local food trucks are waiting to serve you.

After the festivities head to the docs of Sarasota and take a sunset cruise at Marina Jack ’s. There’s no better way to experience the Gulf of Mexico than on the water. Take in a breathtaking view on the open air outside deck and let the experience carry you to your happy place.

The Nautical Flea Market

The Florida Maritime Museum, adjacent to the Cortez Cultural Center, offers the Nautical Flea Market. For the boat and fishing enthusiast, this is the event for you. Here you’ll find local fisherman and vendors selling nautical goods, fishing equipment, and art. 

Imagine being caught in a hurricane with equipment from a century ago. Take a deep dive into maritime history inside the museum located on site. Explore over 100 years of hurricane history and the impact it’s had on Florida’s maritime industry.

Nature’s Beauty

Aside from all the remarkable local events the beach is an open treasure for everyone. October is the perfect month to take a walk on the beach and soak up a golden sunset. Equally as soothing is a bike ride by the Gulf. 

At Anna Maria Island Bike Rentalsyou’ll have your choice of cruisers, low riders, kids’ bikes, tandem bikes and more. They even have free delivery for your convenience. When the cool evening air rolls in as the sun goes down it makes for the perfect cap to any evening.

Being on an island is already magical, but when you have the rightluxury vacation rental it becomes perfection. When you’re ready to plan your trip to Anna Maria Island contact us to find the perfect fit for your Halloween getaway.

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