Key West is a unique place with a lively culture and vibe that marches to the beat of its own drum. This rings especially true during the fall. While visitors to other vacation destinations around the United States begin wearing scarves and drinking pumpkin spice lattes, visitors to Key West can enjoy watersports, outdoor festivals and other island pursuits that are typically associated with summer. Read our guide of things to do in Key West during October to experience this one-of-a-kind tropical paradise.

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Image of Couple on Fury bike rentals outdoors in key west

Enjoy the Weather & Bike Around The Island

Kick your vacation into two-wheel drive as you pedal your way through paradise on a rental bike from Fury. Explore Key West’s historic landmarks, unique architecture and picturesque ocean vistas while cruising through town using the locals’ preferred mode of transportation.

Get the Mustard Sauce Ready, Stone Crab Season Begins!

October 15th, 2023

October marks a very special, and delicious, month in the Florida Keys. It’s the opening of stone crab season and all of the crustacean’s tasty goodness. The Florida Keys are a gold mine as about 40 percent of Florida’s stone crab harvest will come from these waters. Seafood lovers can enjoy the famed stone crab claws for the next seven months.

Listen to Ghost Stories On The Ghosts & Gravestones Tour

The Ghosts & Gravestones tour takes you through the streets of Key West aboard the trolley of the doomed for a narrated tour of the creepy history of the island’s old wooden homes. You’ll also visit the haunted East Martello Tower, a Civil War fort and barracks that once served as quarantine for soldiers suffering from yellow fever. Here, you’ll meet Robert the Doll, considered the world’s most haunted toy.

Celebrate the Culture of Bahama Village

October 20 & 21, 2023

While the week-long party is for adults, Goombay Festival is for the families. Head over to Bahama Village for a street party celebrating island arts, crafts, music and food. Live entertainment will take place on stage at the corner of Petronia Street and Fort Street from Noon to Midnight. Join either night for free.

Carved Jack-O-Lantern smiling with candle inside sitting on the sidewalk in front of a white fence.

Trick or Treat Key West Style During Fantasy Fest®

October 20-29, 2023

Who said you’re too old to dress up for Halloween? Certainly not a resident of Key West. The island’s premier, and perhaps most famous, annual event returns with even more festive flair. Get ready for 10 days of events, adult beverages and shenanigans. Put on your best Halloween attire and leave the little ones at home for an adults’ night out (or week).

Image of Key West Fury catamaran

Customize A Private Charter For An Epic Experience On The Water

Discover the pristine blue waters of Key West aboard your very own private charter. We offer a fleet of high-performance catamarans that can transport your party on a private boat excursion of your choice for a truly unforgettable experience. Private Charters are completely customizable for your group and can include snorkeling, dolphin watching, kayaking, sandbar trips and more. Whether you’re looking for a relaxing full-day on the water sipping your favorite cold beverage, or an adventurous half-day excursion, our team is prepared to help you plan the perfect day in paradise!

parasailing in key west with fury

Parasail Above Paradise

Enjoy panoramic views of Key West with our exciting Parasail tour. Experience this tandem or triple adventure with friends and family, as the tropical breeze lifts you safely into the air. Soar above the emerald blue waters and get a bird’s eye view of paradise. Ocean dips are also available for our thrill-seekers.

Last Updated 09/19/2023