Take A Trip To Anna Maria Island This Fall

Every season on Anna Maria Island has its perks, but fall offers the best of it all. It’s sunny and warm, but there’s typically some relief in the early mornings and evenings. The island is also relatively quiet, as kids have returned to school and the winter break vacationers haven’t yet arrived. Book a stay at our Anna Maria Island Beach Resort in September, October, and November for some of the best weather in Anna Maria Island. 

Just seven miles long, the island offers unending stretches of pristine beach, plenty of wildlife, and tons of delicious restaurants and coffee shops to enjoy — all steps from the warm Gulf of Mexico waters. Plus, there are plenty of island activities for kids and adults alike. 

There is an endless list of fun things to do on Anna Maria Island that everyone in your vacation group will love, and we’ve built this guide to help you plan the perfect autumn adventure!

Anna Maria Island Fall Weather 

AMI is known for its year-round sun and warm temperatures. But some say fall might have the best Anna Maria Island weather!

The hot season, which peaks during summer with average highs nearing 90, ends in October, which is also the start of the dry season. The chance of showers drops to about 20 percent by October, so you can expect sunshine and less humidity during your trip!

September is a little wetter, with a 40 to 50 percent chance of rain on average, but it’s also a little warmer, so if you’re looking to escape the cold, September might be the best fall month to visit Anna Maria Island. Like October, November is dry, and the air temperature is cooler, making it an excellent time for both beach and island exploration. 

If you like a little adventure with your beach vacation, fall is the perfect time to stay at our beach resort. With near-perfect weather and milder temperatures, you can experience everything the island has to offer during your stay. Spend the day exploring and spotting some of the region’s wildlife in their natural habitats as you hike nearby trails, such as Leffis Key Preserve, located right on AMI, and Perico and Neal Preserves near Bradenton. 

Swim trunks, T-shirts, and tank tops are the outfit of choice during September, October, and November on Anna Maria Island, but be sure to bring a sweater or jacket for breezy fall evenings. It’s a sunny season, so don’t forget sun protection for long days on the beach, patio lunches, and exploring the island’s quaint towns.

boy running to the ocean

Local Events


Each year, on the third Saturday in October, the community comes together for an annual festival celebrating island life. One of the top things to do in Anna Maria Island, BayFest features live music, vendors selling locally made arts and crafts, delicious food and drink from some of Anna Maria Island’s local restaurants, and, in true Florida style, a classic car show from mid-morning to mid-afternoon. Typically, there’s a kick-off event the Friday night before to warm up for the big day.

The festival takes place from morning to night along Pine Avenue, one of the island’s bustling commercial streets. Here, you’ll find plenty of restaurants and cafes for food and drink and tons of shopping. If you need it while on vacation, it’s on Pine Avenue!

We recommend booking your vacation around this long-running community street event that is a guaranteed good time for all. Drop in for a few tunes and a pint on your way to the beach, or stay the whole day!

Plan Your Anna Maria Vacation

If you’re looking for a week of fun in the sun, our Anna Maria Island resort is a top choice for convenience and comfort. Skip traditional Florida crowds and book an unforgettable fall vacation on pristine, laid-back Anna Maria Island with us today!

Trail of Treats

Coming to our Anna Maria Island beach resort in late October? Be sure to pack costumes for all the kids and kids-at-heart in your group! Since the spooky season falls in October, you’ll want to make sure the kids get a chance to trick-or-treat near their home away from home.

Celebrate Halloween island-style with Trail of Treats, an annual Halloween event hosted by the Anna Maria Island Chamber of Commerce involving a costume contest for kids ages 0 to 12 and trick-or-treating at local businesses around the island. Get dressed up and show up mid-afternoon to show off your costume!

Trail of Treats is also a great way to meet other families living or vacationing on the island and connect with the larger AMI community. After you meet the island’s friendly faces, you’ll want to come back year after year.

Seasonal Farmer’s Market

Closed during the summer months, the much-anticipated Bridge Street Farmer’s Market reopens in November, just in time for fall vacationers to enjoy.

Located in the community of Bradenton Beach, this farmer’s market is the perfect place to pick up a souvenir or Christmas gift for someone special in your life. The market runs from 10 a.m. to 3 p.m. every Sunday, drawing local creators, such as artists, jewelers, musicians, woodworkers, and more, to this historic part of the island.

Enjoy delicious food while listening to tunes performed by Florida musicians from the island and beyond. While you’re perusing the tents, pick up some locally grown fruits and veggies to snack on during your stay. In addition to the market, Bridge Street is home to plenty of permanent shops, restaurants, ice cream, and more, as well as the famous Bridge Street Pier. Make a day of it and explore the area, including white-sand Cortez Beach, a short walk away!

Where To Stay on Anna Maria Island

Now that you know your fall vacation plan, you’ll need the perfect place to stay, and there’s no better spot than Anna Maria Beach Resort! Our Anna Maria Island resort rooms offer a mix of modern luxury and Old Florida charm that can’t be beaten.

We have 31 tastefully decorated rooms with a variety of sizes and amenities. Whether you’re a honeymooning couple, a family with kids, or a group of friends on a beach getaway, we have accommodations to suit your needs. Rooms are on the ground and second floors, so you’ll never be far from the resort’s lagoon-style pool, tiki hut, and grassy lawn with a plethora of games. 

Lounge in a poolside cabana with a book and cold glass of Chardonnay, or take a dip in the sparkling pool. The resort boasts stunning views of the Gulf’s aquamarine waters and is just steps away from the beach. Complimentary beach umbrellas, chairs, private balconies, patios, and bright, breezy suites are just part of the Anna Maria Beach Resort experience. Book your fall getaway and come experience a fall getaway like no other today!