Fall often represents fallen leaves, cool weather and a touch of mystery in the air. Trade in the dead leaves for powdery sand between your toes and a refreshing Gulf breeze in an Anna Maria Island fall getaway.

The perfect Fall getaway can mean something a little different to everyone. Attractions across the island will appeal to the traditional Halloween lover, the outdoor adventurer, even the most keen foodie.

30th Annual Pumpkin Festival

A local favorite is the upcoming 30th Annual Pumpkin Festival hosted by Hunsander Farms. This family friendly Fall celebration has live music, live shows, hayrides, pony rides, even a corn maze and more. Food vendors offer an array of cuisine and don’t forget to try some local pumpkin pie.

Fright Night on St. Armands

In the mood for some trick-or-treating and an evening of entertainment? Fright Night on St. Armands will satisfy your Halloween craving. Downtown St. Armands Circle gets into the spirit with spooky decorations, costumes to match, and some trick-or-treating with local retailers and restaurants. 

Before you dig into all that delicious candy, enjoy a great meal at one of the many nearby restaurants. Halloween spirited promotions are around every corner with great deals and fun entertainment.

Horseback Riding & Fishing Charters

Fall weather in Southwest Florida is know for it’s fantastic balance between cool air and hot sunshine. A perfect way to enjoy the day is a soothing horseback ride on a clear Gulf beach. Wade though the crystal clear water on one of the beautiful rescue horses at C Ponies.

Want to catch your dinner for the evening? Take a family friendly fishing charter to toss a line in the water and relax. Captain Kim’s Charters offers a number of tours from snorkeling, sandbar hopping, dolphin watching, and intimate special events.

Bridge Street Shopping

Stroll through the historic old town vibe of Bridge Street on Anna Maria Island. Here you’ll experience a variety of shops, restaurants, art and more. Before dinner test your mini-golf skills at Fish Hole Adventure Golf. After dinner at one of the many seafood themed restaurants, slow down the evening with a breathtaking sunset on the beach.

Island Dining

Foodies looking for unique hidden treasures need to search no more. Across the island are options that you won’t see anywhere else. The Rod & Reel Pier features a relaxed atmosphere overlooking the water with fresh seafood eats. 

Don’t miss the giant ugly grouper statue at The Ugly Grouper. Beyond the beach themed decor, you can expect live music, fresh local seafood or games for the whole family.

Soak in the cool island breeze as you sip a hot coffee in the morning or a cold beverage in the afternoon at the French themed My Ami. Brought to you straight from France, the owners have whipped up a mouth watering menu.

Regardless of the kind of adventure you or your family wants, Anna Maria Island has what you need to make it a Fall favorite. Let Serendipity help you discover the perfect vacation destination to compliment your experience.