As the calendar pages flip from summer to fall, you may already be feeling a bit nostalgic over the fun you had this past summer while also looking forward to the flavors of fall, eagerly awaiting pumpkin everything while also mourning sunny days and carefree nights. What if we told you that you can have the best of both worlds, and all it requires is a journey to Anna Maria Island in Florida and a stay in our Anna Maria Life vacation rentals? Summer lingers in our island town, cooling down just enough to stay comfortable but not so much that you have to pack away your swimsuits. Even better, this fall Anna Maria Island food guide to our island will help you enjoy the flavor packed taste of fall you crave!
Anna Maria Island Coffee Shack, 5500 Marina Drive
For most people, the season starts with the first sightings of pumpkin spice lattes, and so our story begins with a cuppa from Anna Maria Island Coffee Shack. Also offering breakfast sandwiches, baked goods, and pastries, this also might be a great place to get a pumpkin muffin, or maybe another fall type muffin.
The Donut Experiment, 210C Pine Avenue
For as far back as we can remember, cider donuts were our first taste of fall, and although we can’t promise that the Donut Experiment will offer cider donuts, this create your own donut spot is certain to provide the flavors of the season. Offering a variety of icings (maple seems quite fall-like), cinnamon and powder sugar coatings (both of which make us think of the season), a ton of different toppings, and a smattering of drizzles, you can create the donut that most makes you feel all autumnal and happy!

Ginny & Jane E’s Café & Gift Shop, 9807 Gulf Drive
If you’re looking for a breakfast food that is a little more substantial, Ginny & Jane E’s may be where you want to head next, offering the best breakfast in town and a cute little shop that will offer a seasonal ambience that may just make you feel as if you are on a mountain getaway—until you step outside that is! Their bakery is one of our favorite parts of AMI, offering scones, muffins, and yes, once September arrives, you will find pumpkin pies for dessert.
Skinny’s Place, 3901 Gulf Drive
Is there anything better than a delicious bowl of chili on a cool fall day? Well, even though it more than likely won’t get cool during your fall visit to Anna Maria Island, your taste buds are used to craving the spicy dish, and Skinny’s Place won’t you let you down. Selling chili dogs or simply a side of chili, we know it is good stuff, because if anything sells out at Skinny’s, it is generally going to be the chili! Don’t worry, though, they won’t sell out of beer, and it is highly probable that they will offer a pumpkin porter for your seasonal beverage cravings.
Mademoiselle Paris, 9906 Gulf Drive
Although we still have a ways to go before Tom Turkey flies into town, for those planning ahead, it is nice to know that there will be some restaurants on the island that will be open for dinner, including Mademoiselle Paris. Offering a taste of France that is hearty and soul satisfying, they do offer a special four-course menu with pumpkin soup and turkey for the holiday. You can’t get more fall like than that!
The Doctor’s Office, 5312 Holmes Boulevard #B
No, we’re not suggesting you search for fall Anna Maria Island food at an actual clinic, we are directing you to The Doctor’s Office, a speakeasy-like cocktail bar housed in what was formerly a doctor’s office. We can’t explain it, but there is something about a speakeasy that just seems to complement the crisp beauty of a fall day, and this wonderful spot will offer specialty cocktails that will enhance your seasonal adventures.
Feasting at Home with Anna Maria Life Vacation Rentals
The fully equipped kitchens of our Anna Maria Life Vacation Rentals seasonal sanctuaries are designed to make cooking fun again, and the farmers markets in the area can help you create a fall menu that will be devoured in much less time than it took to make it. The Anna Maria Famer’s Market is now open and runs every Tuesday from 8:30am – 2:00pm. Also check out the Coquina Beach Market every Wednesday from 10am – 2pm. The Sarasota Farmer’s Market, located at Lemon Avenue in the downtown area, is open for business every Saturday from 7 AM until 1 PM and will be a great source from which to harvest fresh produce, sauces, and homemade baked goods. Every forkful of fall flavor will have you feeling like you are starring in your own personal seasonal romance movie, only without the cold and bad weather! Reserve your favorite fall retreat today.