Things to do in Key West in October 2025
Looking for the best things to do in Key West in October 2025? This tropical island in the Florida Keys is a vibrant destination known for its lively festivals, world-class boating, and endless sunshine. While much of the U.S. is cooling down with pumpkin spice lattes, Key West stays warm and festive with Fantasy Fest, the Goombay Festival, and the start of stone crab season. From sandbar charters to sunset cruises, this guide highlights the top October events and activities to help you plan the ultimate Key West getaway.
TL;DR – Things to Do in Key West in October 2025
- Fantasy Fest (Oct 17–26): Key West’s biggest costume party and parade
- Goombay Festival: Family-friendly street party in Bahama Village
- Stone Crab Season: Fresh claws available starting mid-October
- Sandbar Trips & Boat Rentals: Perfect weather for days on the water
- Heroes & Villains 5K + Mrs. Roper Romp: Fun themed October events
Stone Crab Season in Key West (October Kickoff Guide)
October arrives in the Florida Keys, bringing with it a month of extraordinary culinary delight. This is the season when the stone crab season opens, and the waters teem with the delectable bounty of these crustaceans. The Florida Keys are a treasure trove of seafood, with approximately 40 percent of Florida’s stone crab harvest originating from these waters. Seafood enthusiasts can savor the renowned stone crab claws for the next seven months, indulging in the rich flavors that make the Keys a seafood lover’s paradise.
Key West Sandbar Trips & Boat Rentals in October
Spend your vacation like a local, at the sandbar!
Explore the turquoise blue waters of Key West on your own boat rental. Stop at remote sandbars or just tour the island. There’s no better way to see Key West.
Be your own captain with a boat rental or let us do the driving and take one of our sandbar charters.
Goombay Festival in Key West: Bahama Village October Celebration
Goombay Festival, a week-long celebration for adults, is actually a family-friendly event. Head over to Bahama Village for a vibrant street party that showcases island arts, crafts, music, and delicious food. From noon to midnight, live entertainment will grace the stage at the corner of Petronia Street and Emma Street. Don’t miss out on this free event, and join us for a night of fun and festivities!
Fantasy Fest 2025: Key West’s Biggest October Event
Fantasy Fest 2025 in Key West – running October 17-26, 2025 – is a ten-day celebration of costumes, parades, and island adventure in the heart of the Florida Keys. You’ll find marquee events like the Fantasy Fest Parade on Duval Street, elaborate masquerade balls, themed street fairs, and family-friendly gatherings such as the Bahama Village Goombay Festival. Many events are free, though some of the more exclusive parties and VIP experiences require advance tickets, which tend to sell out well before festival week. Lodging in Old Town or along Duval Street fills up fast, so booking early is essential—and staying a short walk from the main events is worth it for experiencing the full Key West vibe.
Heroes and Villains 5K Race at Fantasy Fest
This exhilarating race to a Glowing NEW LEVEL begins at the Tiki House on 203 Duval Street at 6:00 PM. Embark on a neon-themed journey down Duval Street, stopping by Mary Ellen’s Bar for a refreshing Neon Jelly Shot. Cross the finish line and bask in the glow of your GLOW IN THE DARK Neon Race Medal. Continue the celebration at the Post-Race Party at the Tiki House, where music and delicious Twinkies await. Don’t forget to grab your Rad Neon 90’s Gear and join the fun!
Mrs. Roper Romp Key West: Costume Party & Sunset Fun
Get your Caftans ready and that signature curly red wig for a groovy party filled with stunning sunsets, music, photo opportunities, dancing, trivia, games, prizes and funtastic specialty drinks! Come and Knock On Our Door for all the Three’s Company Fun you can stand! Donations accepted
Scooter, Golf Cart & Electric Cart Rentals in Key West
Cruise around Key West, island-style, with eco-friendly electric golf carts, Scooter Rentals, or gas-powered Golf Cart rentals. Discover the thrill of our roadworthy rentals, as they get you from one bucket-list spot to the next with a smooth and safe ride, perfect transportation experience for your vacation.
Insider Tips for Visiting Key West in October
- Book Early for Fantasy Fest: Hotels in Old Town and near Duval Street fill up months in advance. Staying within walking distance saves on parking hassles during parades. See the official Fantasy Fest page.
- Pack Light Costumes: Fantasy Fest is creative but hot. Go for breathable fabrics, body paint, and accessories instead of heavy outfits.
- Try Stone Crab Locally: Skip the tourist traps and head to smaller seafood shacks or local markets for the freshest claws at better prices. We like Dante’s at Happy Hour for Crab Claws.
- Sandbar Sundays: October Sundays are perfect for locals-only sandbar gatherings – rent a boat or book a sandbar charter to join the fun.
- Rain Plan Ready: Keep one indoor attraction in mind (like Hemingway House or a rum distillery) in case of an afternoon storm. See our Rainy Day Guide for Key West.
- Best Sunset Spots: Mallory Square is famous, but locals love sunset views from Fort Zachary Taylor beach or aboard a sunset boat cruise. See our Sunset Watching Guide.
Need Help Choosing the Right Boat Rental or Sandbar Tour in Key West?
Since 2007, Key West Boat Rentals has helped visitors explore Key West by boat – from sandbar trips and reef snorkeling to fishing adventures and family cruises. Whether you’re booking a pontoon rental for a group, a deck boat for sightseeing, or want a center console for sport fishing, we’ll help you find the perfect fit. Call or text today to reserve your boat rental in Key West.
Prefer to relax while someone else takes the helm? Ask us about our private sandbar charters with a licensed captain. It’s the easiest way to kick back, sip a drink, and enjoy the beauty of Key West without lifting a finger.
Contact us and we’ll point you in the right direction
Frequently Asked Questions About Key West in October
What is the weather like in Key West in October?
October in Key West averages around 82°F with warm ocean temperatures. It’s a great month for boating, snorkeling, and outdoor festivals. Afternoon showers are common, but storms usually pass quickly.
Is October a good time to visit Key West?
Yes! October is one of the best months to visit Key West. Crowds are smaller than in winter, hotel rates are lower, and major events like Fantasy Fest and the Goombay Festival take place. Plus, a great time to get on a boat to a sandbar.
When does Fantasy Fest 2025 happen in Key West?
Fantasy Fest 2025 runs from October 17–26, with parades, themed parties, costume contests, and family-friendly events in Bahama Village.
What seafood is in season in Key West in October?
October marks the start of stone crab season in the Florida Keys. Visitors can enjoy fresh stone crab claws at local restaurants through mid-May. Plus, it’s still Lobster Season.
What are the best things to do in Key West in October if it rains?
On rainy days, visit the Key West Aquarium, Hemingway House, local museums, or indoor attractions like distillery and brewery tours. Many tours also continue rain or shine.
Can you rent a boat or do a sandbar trip in October?
Absolutely! October is a fantastic month for boat rentals and sandbar charters. The water is warm, visibility for snorkeling is excellent, and fewer crowds mean a more relaxed experience.
Is Key West family-friendly in October?
Yes, while some October events like Fantasy Fest are geared toward adults, there are plenty of family-friendly activities in Key West. Families can enjoy the Goombay Festival, sandbar trips, snorkeling tours, and visits to the Aquarium or the Butterfly Conservatory.
What is the best family-friendly festival in October?
The Goombay Festival is the top family-friendly event in October. It’s a lively street party in Bahama Village with music, food, and activities that kids and adults can both enjoy.
What outdoor activities can families enjoy in October?
Families can rent boats or book sandbar charters, go snorkeling in calm waters, or take eco-tours to explore mangroves and wildlife. October weather is ideal for spending time on the water together.
Is October in Key West just about Fantasy Fest?
Not at all. While Fantasy Fest is the most famous October event, Key West offers much more this month. Visitors can enjoy the start of stone crab season, the Bahama Village Goombay Festival, family-friendly races like the Heroes & Villains 5K, and unforgettable sandbar boat trips. October is also one of the best months for snorkeling, fishing, and cruising thanks to warm waters and smaller crowds.
