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.

Conch Tour Train Promotion

Double the Fun for Half the Price

Offer valid through November 18, 2018

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.

Key West Stone Crab Season

Get the Mustard Sauce Ready, Stone Crab Season Begins!

October 15, 2017

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.

SUP, Competitor?

Oct 12-14, 2018

Whether you’re a paddling pro or you just enjoy a sunny day on the water, make your way to the Stand Up Paddle Invitational. The 2-mile paddle board and beach obstacle course is open for all skill levels and supports the Special Olympics Florida – Monroe County organization. Race entry includes a t-shirt plus it sponsors one Special Olympics Florida SUP athlete during race weekend. All events are located on Smathers Beach. Don’t have a paddle board but still want to participate? Lazy Dog will be renting boards at $10 each.

See Key West from Every Angle

Offer valid through February 28, 2019

It may be approaching the holiday season, but that doesn’t mean it’s time to pack away your beach gear. Join us for an epic adventure on the waters of Key West as we rev our engines for a Jet Ski Tour around the island. And for a limited time, purchase the Fury 360 package and experience Key West like never before. Included are a double rider guided Jet Ski Tour plus your choice of one or two additional trips for two people. Trip selections include Glass Bottom Boat Reef Eco Tour or Glass Bottom Boat Sunset Combo, Parasail, Morning Snorkel, Rum & Reggae snorkel and sunset combo and Reefs & Ritas afternoon snorkel. Pack the fun into one day or separate days to better fit your schedule. Either way, this is sure to be a check off the bucket list!

Goombay Festival Key West

Celebrate the Culture of Bahama Village

October 19-20, 2018

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®

October 19-28, 2018

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 07/15/2019