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.

Dry Tortugas Hotel Promo

Check-in into Paradise
Your dream vacation starts at check-in with this exciting new offer

Sept 8 – Dec 16, 2020

We’ve got you covered from day to night with this exciting offer for your dream vacation! Start your day surrounded by the rich history and beauty of Fort Jefferson, as you explore the Dry Tortugas National Park. Book your voyage aboard the Yankee Freedom III and enjoy savings of $25*. Then, get the perfect night’s rest in your dream resort in paradise. Save up to 30% on nightly rates with this special offer from two of the premier hotels in Key West, The Gates and 24 North Hotels.

Key West Stone Crab Season

Get the Mustard Sauce Ready, Stone Crab Season Begins!

October 15th, 2020

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.

PARROTHEADS LIVE MUSIC SUNSET SAIL

ENJOY A SPECIAL PARROTHEADS LIVE MUSIC SUNSET SAIL

October 30th, 2020

Sail away on the pristine blue waters of Key West as the majestic sunset and musical stylings of John Frinzi, relax your mind aboard our Parrotheads Live Music Sunset Sail! Experience a breathtaking evening in paradise, as you dance the night away to a live performance from the prolific songwriter himself. Enjoy the warm ocean breeze and world-famous Key West sunset with free beer, margaritas, wine, sodas, and appetizers.

Couple jet skiing in Key West

Special Offer For Florida Residents

Now – December 20, 2020

There’s never been a better time for Sunshine State locals to discover an adventure in their own backyard! Florida Residents Save Big on some of our most exciting tours we offer here in paradise (aka Key West, Florida). Who doesn’t want to get some fresh air, sunshine and Ultimate Savings?! Use the code FLORIDA when booking your next trip before December 20, 2020, and explore the fun of the Key West waters above and below sea-level.

Couple jet skiing in Key West

What’s Open In Key West

Discover an island paradise filled with adventures worth exploring! Take a look at this collection of attractions, restaurants and local hot spots that will surely enhance your vacation itinerary. Add some island-style fun to your Key West experience.

Listen to Ghost Stories On The Ghosts & Gravestones Tour

Year-round

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.

Goombay Festival Key West

Celebrate the Culture of Bahama Village

CANCELLED IN 2020

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.

Trick or Treat Key West Style During Fantasy Fest®

CANCELLED IN 2020

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 parades, adult beverages and shenanigans. Put on your best Halloween attire and leave the little ones at home for an adults’ night out (or week).

Last Updated 11/23/2020