October in the Florida Keys: Find Your Fantasy
FLORIDA KEYS (September 24, 2025) From flamboyant costumed parades to oceanfront races, foodie feasts, and even a Jimmy Buffett–inspired tour, October in the Florida Keys & Key West is packed with creativity, culture, and fun. Dive into the over-the-top revelry of Fantasy Fest, savor the flavors of Taste The Keys, or join in a roster of music, running, fishing, and family-friendly events that make this destination the place to celebrate all month long.
FANTASY FEST
Taking place October 17-26, 2025, Fantasy Fest is a one-of-a-kind celebration where wild creativity, costuming, and Key West’s famously quirky spirit collide in a 10-day extravaganza of freedom and self-expression. Unlike any other festival — though it can rival Mardi Gras in bacchanalian energy — Fantasy Fest has a distinctly tropical, free-spirited twist that makes it uniquely Key West. First celebrated in 1979, it attracts over 75,000 revelers each year.
From the family-friendly Goombay Festival (October 18) kicking things off in Bahama Village with Caribbean music and food, to the glitzy Headdress Ball (October 23), and the famously flamboyant Fantasy Fest Parade (October 24), the festival embraces both outrageous adult revelry and all-ages fun.
Where else can you find a Pet Masquerade, a Zombie Bike Ride, body painting contests, and a Masquerade March of costumed characters banging on drums through the streets? Whether you're covered in feathers, body paint, or a tutu, Fantasy Fest invites everyone to shed their inhibitions and celebrate life island-style. This year’s theme is “Bedtime Stories & Magical Monsters” — so dress accordingly!
Good to know: If you’re staying in Fort Lauderdale, Miami, Marathon, Duck Key, or somewhere in between, you can get to Fantasy Fest easily via an air-conditioned Up The Keys van. Learn more.
For a complete schedule of events and more information, visit fantasyfest.com.
TASTE THE KEYS
This October, food lovers and adventure seekers alike are invited to savor the Florida Keys like never before during Taste The Keys, a month-long culinary celebration spotlighting the unique flavors, vibrant culture, and community spirit of Key Largo and the Upper Keys.
More than a mere food festival, Taste The Keys is a flavor-packed journey through the region’s top restaurants and culinary gems. From October 1-31, 2025, indulge in specially curated prix-fixe three-course menus for brunch, lunch, or dinner at participating restaurants, each one offering a deliciously local twist that highlights the distinct personality of the Florida Keys.
- Signature Experiences: Select restaurants and hotels will take dining to the next level with Signature Dining Experiences that go beyond traditional offerings, including beachside tastings, interactive chef-led dinners, and themed nights.
- Foodie Trolley Tours: On select Thursday evenings in October, board the Taste The Keys Foodie Trolley Tour, where for one flat fee, guests enjoy small plates from appetizers to desserts, plus a cocktail at each stop.
- Signature Dish Showdown: One of the event’s most exciting elements is the Signature Dish Showdown, a month-long culinary competition where participating restaurants nominate one standout item from their prix-fixe menu. Diners can sample as many as they like and then cast their votes online at TasteTheKeys.com.
For a complete schedule of events and more info at TasteTheKeys.com.
MORE OCTOBER EVENTS
STACK’D WEEKEND Music Festival
October 10–12, Key West
Curated by local artist Mike Stack, this music-meets-island-vibes fest features hip hop, reggae, country, and DJ sets across iconic venues like Sunset Pier. Eight events in three days make this an October must-do. Learn more.
Southernmost Half Marathon & 10K
October 12, Key West
Runners and walkers are invited to experience the Conch Republic with a scenic race route along the waterfront. Whether you're chasing a personal best or a Key lime pie after the finish line, this tropical race is a bucket list event. Learn more.
REEF Fest 2025
October 16–19, Key Largo
Celebrating its 10th year, REEF Fest is a must-attend for divers, snorkelers, and marine life lovers. The festival blends educational ocean seminars with conservation-minded fun, outdoor activities, and social gatherings. Learn more.
Treasure Treat Night
October 23, Islamorada
Get in the spirit of the spooky season! During this fun event, kids and families explore haunted exhibits at the History of Diving Museum, complete with a costume contest. Learn more.
Order of the Sleepless Knights Tour
October 31 – November 1, Key West
Parrotheads, this one is for you. The Order of the Sleepless Knights tour is a Jimmy Buffett-themed journey through 35 sites in Old Town related to the late/great singer-songwriter. Learn more.
FISHING EVENTS
- “Ladies, Let’s Go Fishing!” Saltwater Seminar & Tournament (October 17–19): This award-winning weekend is designed for women looking to learn or sharpen their angling skills. The event includes hands-on seminars and optional fishing charters, culminating in the fun and friendly Fishing Fever Tournament. Learn more.
- Casting for Cats Backcountry Tournament (October 17–18): Now with both women’s and co-ed divisions, this charitable tournament in Islamorada supports feral cat control efforts in the Upper Keys. Anglers compete for points by catching a range of backcountry species including bonefish, redfish, and tarpon. Learn more.
- Fall Backcountry Fly Championship (October 31 – November 2): Fly-fishing enthusiasts will compete to land the longest snook and redfish in this high-stakes, skill-focused tournament. Prizes include the prestigious “King of the Backcountry” title. Learn more.
High-resolution images, photo credits, and captions are available at this link.
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A group depicting an offbeat “Conch-tucky Derby” for unicorns performs on Duval Street during the Fantasy Fest Parade in Key West, Fla. The elaborate procession of floats and costumed marchers will return Saturday, Oct. 25, 2025, as the highlight of the 10-day Fantasy Fest celebration, themed “Bedtime Stories and Magical Monsters,” running Oct. 17-26. FOR EDITORIAL USE ONLY (Andy Newman/Florida Keys News Bureau)
Participants in elaborate neon-accented costumes light up Duval Street in Key West, Fla., during the Fantasy Fest Parade. The flamboyant procession of floats, marching groups, and costumed characters is set to return Saturday, Oct. 25, 2025, as the centerpiece of the 10-day Fantasy Fest celebration, themed “Bedtime Stories and Magical Monsters,” running Oct. 17-26. FOR EDITORIAL USE ONLY (Carol Tedesco/Florida Keys News Bureau)
Donna Jocelyn of Miami, FL (left) earned Top Offshore at a previous Ladies, Let’s Go Fishing event with a 35.5 lb. cobia landed aboard Sea Horse with Capt. Rick Rodriguez. Don’t miss your chance to join the excitement at the next LLGF Keys University and Fishing Fever Tournament, October 17–19, 2025 in Tavernier and Islamorada. Learn more at ladiesletsgofishing.com. (Photo courtesy of Ladies Let’s Go Fishing)
Janet Steiner of St. Augustine, FL celebrated her first-ever inshore fishing experience with a 33.5-inch snook release, earning Top Inshore honors with Capt. Chris Hanson of Scales2Tales during a previous Ladies, Let’s Go Fishing event. Anglers can share in the excitement at the upcoming LLGF Keys University and Fishing Fever Tournament, October 17–19, 2025 in Tavernier and Islamorada. Learn more at ladiesletsgofishing.com. (Photo courtesy of Ladies Let’s Go Fishing)
Fishing with Capt. Rick Rodriguez aboard Sea Horse, Kim Royal of Orlando, FL released a sailfish to clinch First Place Offshore Release at a previous Ladies, Let’s Go Fishing event. Anglers can experience the thrill at the upcoming LLGF Keys University and Fishing Fever Tournament, October 17–19, 2025 in Tavernier and Islamorada. Learn more at ladiesletsgofishing.com. (Photo courtesy of Ladies Let’s Go Fishing)
Daniel Bitnar, center, leads a blue-winged group depicting the U.S. Navy’s elite Blue Angels Flight Demonstration Squadron Friday, Oct. 24, 2025, in the Captain Morgan Masquerade March in Key West, Fla. Thousands of Florida Keys residents and visitors are expected to participate in the procession, a highlight of the 10-day Fantasy Fest costuming and masking extravaganza that runs through Sunday, Oct. 26. The festival’s 2025 theme is “Bedtime Stories and Magical Monsters.” FOR EDITORIAL USE ONLY (Andy Newman/Florida Keys News Bureau)
A costumed duo channels celebrity pals Martha Stewart and Snoop Dogg during the Fantasy Fest Pet Masquerade in Key West, Fla. The over-the-top competition featuring pets and their people in matching or themed costumes returns Wednesday, Oct. 22, 2025, at the Coffee Butler Amphitheater as part of the 10-day Fantasy Fest celebration, themed “Bedtime Stories and Magical Monsters,” running Oct. 17-26. FOR EDITORIAL USE ONLY (Carol Tedesco/Florida Keys News Bureau)
Colorful extraterrestrial characters and other out-of-this-world costumes parade through Key West, Fla., during Fantasy Fest. The city’s signature celebration of costuming and creativity returns Oct. 17-26, 2025, with the theme “Bedtime Stories and Magical Monsters.” The 10-day festival culminates Saturday, Oct. 25, with the spectacular Deep Eddy Vodka Fantasy Fest Parade. FOR EDITORIAL USE ONLY (Carol Tedesco/Florida Keys News Bureau)
Hop aboard the Conch Tour Train and join fellow Parrotheads for the Order of the Sleepless Knights Tour, Oct. 31–Nov. 1. This Jimmy Buffett–themed journey winds through 35 iconic Old Town stops connected to the late, great singer-songwriter. From palm-shaded streets to legendary haunts, celebrate Buffett’s island spirit and discover the Key West that inspired his music. (Image courtesy of Historic Tours of America)
Get ready to Taste the Keys! From October 1 to 31, 2025, Key Largo comes alive with a month-long celebration of food, culture, and community. Indulge in specially priced menus, unique dining experiences, and the thrill of the Signature Dish Showdown. Learn more at TasteTheKeys.com. (Image courtesy of Key Largo Chamber)
This October, Key Largo invites you on a flavor-packed culinary journey during Taste the Keys. Explore prix-fixe menus, hop aboard foodie trolley tours, and cast your vote in the Signature Dish Showdown. The celebration takes place from October 1 to 31, 2025. Visit TasteTheKeys.com for details. (Image courtesy of Key Largo Chamber)
Taste the Keys is back. For the entire month of October 2025, discover why the Florida Keys are a top destination for food lovers. From fresh local seafood to Caribbean-inspired creations, the celebration brings together flavors as vibrant as the islands themselves. Find out more at TasteTheKeys.com. (Image courtesy of Italian Food Company)
Celebrate the tastes of the Florida Keys this fall. Taste the Keys runs from October 1 to 31, 2025, with chef-led dinners, trolley tours, and the Signature Dish Showdown. Do not miss your chance to savor the best of Key Largo. Full details are available at TasteTheKeys.com. (Image courtesy of Playa Largo Resort)
Thousands of costumed participants take over the streets of Key West, Fla., for the annual Fantasy Fest Zombie Bike Ride. The family-friendly event returns Sunday, Oct. 19, 2025, inviting “zombies” of all ages to pedal from Fort East Martello into Old Town as part of the island city’s 10-day Fantasy Fest celebration, themed “Bedtime Stories and Magical Monsters,” running Oct. 17-26. FOR EDITORIAL USE ONLY (Carol Tedesco/Florida Keys News Bureau)
Ryan Stachurski, left, and Tony Lopez, right, pedal their Tour de France-inspired “Tour de Mort” creation during the Fantasy Fest Zombie Bike Ride in Key West, Fla. The quirky, family-friendly event returns Sunday, Oct. 19, 2025, inviting several thousand “zombies” to cycle from Fort East Martello into Old Town as part of the 10-day Fantasy Fest celebration, themed “Bedtime Stories and Magical Monsters,” running Oct. 17-26. FOR EDITORIAL USE ONLY (Carol Tedesco/Florida Keys News Bureau)
ABOUT THE FLORIDA KEYS & KEY WEST
The Florida Keys & Key West is a premier getaway destination located at the southernmost tip of Florida and the continental United States. The Keys stretch over 125 miles connected by 42 bridges and bordered by the Atlantic Ocean and the Gulf. Discover the spectacular array of diverse activities offered in the Florida Keys like fishing, diving, natural wonders, fine dining and cultural heritage. From large resorts, secluded waterfront hideaways and courtyard guest houses, visitors can uncover the perfect place for their vacation. Restoration, renovation and preservation have become a way of life in the Florida Keys. Whether you’re driving or flying into the Keys, one thing is for sure: there’s simply no place quite like it. Want more reasons to visit The Florida Keys & Key West? Get inspired at visitfloridakeys.com and follow us @thefloridakeys on social media.
MEDIA CONTACTS
Mary B. Haban
Senior Director of Public Relations
Visit Florida Keys & Key West
(305) 394-3142
Visit Florida Keys & Key West PR Agency Team (TURNER)