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.

Goombay Festival Key West

Celebrate the Culture of Bahama Village


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®


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).

Conch Tour Train Promotion

Double the Fun for Half the Price

Now – November 10th, 2020

Grab a sightseeing, history-loving partner for Historic Tours of America’s Key West offer. This special 50% off on an adult admission for a vacation package, which includes a ride aboard the Conch Tour Train plus admission to Truman Little White House, Key West Aquarium and Key West Shipwreck Treasure Museum. Experience the best of Key West with The Nation’s Storyteller.

Couple jet skiing in Key West

A Special Treat For Our Sunshine State Friends

Now – December 20, 2020

It’s a beautiful thing in Key West right now; the weather is gorgeous & the frenzy of tourists is nowhere to be found. If you’re a Florida resident, you can have paradise all to yourself with these special deals on all our most popular trips. It’s great to be a Floridian!

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.

Last Updated 09/14/2020