Your Summer Doesn’t Have to End

[Sponsored] In Florida’s Bradenton Gulf Islands, you can hold onto the lightness of summer straight through the end of the year.

By Kim Knox Beckius

Aug 23 2023

Bicycle on Coquina

The bicycle-riding season never ends in Florida’s Bradenton Gulf Islands.

Photo Credit : Bradenton Area Convention and Visitors Bureau

Sponsored by the Bradenton Area Convention and Visitors Bureau.

If you’re one of those ritualists who packs away shorts and sandals the moment mornings turn chilly and there’s a hint of auburn to the leaves, make this the year you toss summerwear into a carry-on bag instead. It’s never been easier to hop a direct, low-priced getaway flight to Sarasota-Bradenton International Airport: gateway to islands where pastel beach cottages, coastal-chic shops, and on-the-water seafood restaurants make a fall stay feel like an epilogue to summer in New England. October days are beach days in the Bradenton Gulf Islands; farmers’ markets are just getting underway in November; and a moonlit paddle in December feels like an act of defiance for anyone who’s accustomed to the shifting seasons up north.

The sun still cranks out daytime temperatures in the 80s through much of the fall on Anna Maria Island and Longboat Key, narrow barrier beaches in the Gulf of Mexico connected to the mainland and each other by bridges. You’ll love how it warms your shoulders, yet not the pearly quartz sand that remains cool as it cushions sunset walks. Mornings are the best time to spy dolphins and manatees feeding in the turquoise-to-cobalt ombré waters that whoosh gently toward shore, leaving swirly lace patterns and seashells at your feet. 

Coquina Beach on Anna Maria Island, Florida
Anna Maria Island’s beaches remain welcoming and warm during the fall and early winter months. Visit October through December, and you’ll beat the snowbird rush.
Photo Credit : Bradenton Area Convention and Visitors Bureau

Remarkably, the travel time here from Northeast airports like Westchester, Tweed, Bradley, T.F. Green, and Logan—about three hours in the air and less than 30 minutes’ drive or ride to the beach—is less than it would take to get yourself from Boston to Acadia National Park, from Greenwich to Lake Champlain. And, a recent proliferation of inexpensive, flexible flights (such as Breeze Airways’s introductory $39 one-ways and $0 change/cancellation fees) has placed the Bradenton Area within many more travelers’ reach.

This is vintage Florida, with the Caribbean’s carefree spirit and “Floribbean” cuisine, heavy on the local harvest of oysters, grouper, and conch. A place where you can hop on the free Anna Maria Island Trolley from 6 a.m. until 10:30 p.m. and explore this 7-mile, three-tiny-city isle end-to-end, beach-to-beach. It’ll take you to Publix for groceries. To Ginny’s and Jane E’s for a mango-pineapple smoothie and enormous cinnamon roll. To Shiny Fish Emporium to paint a sand dollar. To Anna Maria City Pier for fishing, heron and pelican watching, and glorious views across Tampa Bay from the end of the planked walk.

Partying means raising a beer with other refugees from the North at a tiki bar, while a guitarist strums a forgotten ’90s tune. Or sharing a bottle of wine on your vacation home’s lanai. Most visitors choose rentals, although inns and resorts, most with pools, welcome many guests, too.

Stone Crab in Cortez, Florida
Celebrating 100 years in business, Star Fish Company is the perfect waterside destination for seafood lovers who want to try stone crab.
Photo Credit : Kim Knox Beckius

Before your reprieve from the march of the seasons comes to an end, indulge in the ideal farewell tour: A seafood-loaded omelet or Coconut-battered French toast at the Rod and Reel Pier; a stroll through a tunnel of tropical vegetation and across soft sand dunes to secluded Bean Point Beach at Anna Maria Island’s northern tip; and a stop at Star Fish Co. in Cortez on the way to the airport. Celebrating a century in business, it’s your dockside destination to try luscious stone crab while this delicacy is in season. Served cold with mustard sauce or warm with butter for dunking, it is, dare we say, sweeter than lobster.

Begin planning your Gulf Islands getaway at

A Mother-Daughter Getaway That Will Renew Your Sense of Awe
A Destination for Seafood Lovers