Key West's Unforgettable Fall Festivities: Fantasy Fest and Offshore World Championship

The excitement is brewing as fall has arrived, and now it’s time to get ready for two of our favorite fall festivals and events. First up, in October, immerse yourself in the 10-day colorful costuming extravaganza and celebration of Fantasy Fest, themed “Uniforms & Unicorns—200 Years of Sailing into Fantasy.” Then, in November, brace yourself for the adrenaline-fueled Key West Offshore World Championship. Together, they craft an extraordinary fall escape that captures the very essence of Key West’s character. Both Fantasy Fest and the Key West Offshore World Championship Races are a fusion of creativity and adrenaline, an adventure that promises to redefine your fall experience in Key West.

October – Fantasy Fest Key West

Uniforms & Unicorns—200 Years of Sailing into Fantasy

October 20-29

Every October, Key West bursts into vibrant colors, costumes, and parties that span a full 10 days. Whether you plan to dress up or dress down, every day offers an excuse to delve into a celebratory spirit. The only way you’ll stand out from the crowd is if you forgo a costume altogether!

Fantasy Fest is renowned for its creativity, boasting themed parties and events across the island. This year’s theme, ‘Uniforms & Unicorns—200 Years of Sailing into Fantasy,’ salutes both the Keys’ bicentennial and that of the U.S. Navy in Key West. It also pays homage to the islands’ unique individuality and mystical appeal. Revelers are encouraged to let their imaginations run wild and embrace the theme wholeheartedly.

Throughout the festival, you can expect a plethora of Street Parties, Pool Parties, Parades, Body Painting, and Masquerade Fun. Participants often go the extra mile, artistically representing the theme in their body painting and masquerade designs. With glitter, paint, and colorful expressions in abundance, we’re eager to see this year’s floats, costumes, and artistic displays.  

Fantasy Fest is a 10-day artistic extravaganza filled with costume competitions, parties, and parades, and Southernmost Beach Resort and our Sister Property, The Marker Key West Harbor Resort, are proud sponsors of Fantasy Fest and the Boat Races.  


Here’s what’s happening at our resorts during Fantasy Fest: 


Friday, Oct 20th

Barbie’s Pink Pool Party for Breast Cancer Awareness
(Official Fantasy Fest Event) 

Join The Marker Key West Harbor Resort for a splashy pool party. Deck out in your best Barbie or Ken pink costumes, sway to the beats of DJ Tommy Tangie, and contribute to a noble cause – Making Strides Against Breast Cancer in the Florida Keys. 4-7 PM. FREE! Reserve your space HERE.


Tuesday, Oct 24th

Rob Benton, Sunset Beach Bash Live at Southernmost Beach Resort
(Official Fantasy Fest Event)

Experience a mesmerizing beach sunset while grooving to the eclectic beats of Rob Benton, known for his unique fusion of acoustic rhythms with beatboxing, looping, and electrified rock elements. 6:30-9:30 PM. FREE! Reserve your space HERE.


Thursday, Oct 26th

Red Elvises Pool Party at The Marker Resort
(Official Fantasy Fest Event) 

Time to don your swimsuits and revel with the ever-energetic Red Elvises band. 4-6 PM. Free!! Reserve your space HERE.

Fantasy Fest Trivia, Southernmost Beach Resort

Bring your entourage for a Halloween-themed trivia night. Players in costume receive bonus points! Starts at 6 PM sharp. FREE! Reserve your space HERE.


Sunday, Oct 29th

Reggae Rehab Pool Party at The Marker with Reggae by Channel 3
(Official Fantasy Fest Event)

Recuperate with soothing reggae rhythms by Channel 3. 2-5 PM at The Marker Key West Harbor Resort. Free! Reserve your space HERE.


Photo courtesy of IG: marinabraska at Southernmost Beach Resort.


Hangover Pool Party at SoMo’s Pineapple Pool
(Official Fantasy Fest Event)

Unwind and rejuvenate with DJ beats and drink specials. 1-4 PM at Southernmost Beach Resort’s Pineapple Pool. FREE! Reserve your space HERE.

For costume inspiration, schedule of events and all things Fantasy Fest, please visit the festival website.  (Photos courtesy of Fantasy Fest.)


November – Key West Offshore World Championship Races

Offshore World Championships: November 5th – 12th

This November, the waters of Key West will come alive with roaring engines and incredible speed during the Key West Offshore World Championship. These adrenaline-charged events draw speed enthusiasts from around the world, as sleek powerboats cut through the crystal-clear waters, vying for the title of World Champion.

Race World Offshore (RWO) is thrilled to usher in teams and fans to Key West for an unparalleled Offshore World Championship experience. Recognized as the leading Offshore Racing Sanctioning body in the United States, RWO is dedicated to curating an unforgettable week of speed, thrill, and maritime mastery.

Schedule of Event Highlights:

  • Race Village, located at Truman Waterfront Park, is open from 9 AM to 5 PM.
  • Three Days of Intense Racing is slated for Wednesday, Friday, and Sunday.
  • Kick off the festivities with the World’s Fastest Boat Parade on Duval Street on the Sunday before the races, starting at 4:00 PM.
  • Conclude your week with a blast at the Duval & Greene Street Block Party on Friday, showcasing some of your favorite Race Boats.
  • For a comprehensive rundown of all the activities during this eventful week, check out the 2023 Daily Event Schedule. Photo credit Race World Offshore.

Rob Benton LIVE in Concert – Fall Cocktail Classic Bartender Battle

Friday, November 10th | 4 pm – 7 pm at The Marker Key West Harbor Resort

Also happening during Race Week is a poolside concert with Rob Benton and a Fall Cocktail Classic Bartender Battle. So many things to do but this one you don’t want to miss. Join us for an unforgettable evening of live music and mixology at the Fall Cocktail Classic Bartender Battle featuring the incredible talent of Rob Benton. Get ready to be blown away by his soulful voice and electrifying performance. Learn more.

The Harmonious Intersection of Fantasy and Speed

While Fantasy Fest and the Key West Powerboat Races might seem like two completely different worlds, they share an undeniable spirit of celebration and exhilaration. The fall season in Key West combines the imaginative freedom of Fantasy Fest with the heart-pounding energy of the boat races, creating a dynamic and unforgettable experience.  Enjoy the festivities and don’t forget to share your favorite moments with us! #somolife