November in the Florida Keys & Key West

FLORIDA KEYS (October 21, 2025) – November in the Florida Keys is a time for community, celebration, and all-around good vibes. While much of the country is seeking refuge from sweater weather, The Florida Keys & Key West are bringing the heat with a lineup of events and experiences that combine culture, adventure, and authentic island character. From world-class film festivals to scenic bike rides that give back, here is a curated look at what visitors can enjoy in the month ahead. 

KEY WEST FILM FESTIVAL 

Named one of MovieMaker Magazine’s “Top 25 Coolest Film Fests in the World,” the Key West Film Festival is a paradise for cinephiles.  From November 12-16, 2025, Florida’s best filmmakers, industry panelists, student award winners, and major names from Hollywood, will gather in the Southernmost city to celebrate the art of film.  

• Get your All-Access pass to the festival for $399, granting admission to all films, parties and events during the five-day festival.
• The recipient of the Key West Film Festival’s Golden Key Award for Artistic Excellence is legendary comedian and performer Billy Connolly. Connolly will be in attendance at the festival to coincide with a screening to celebrate the 20^th Anniversary of The Aristocrats, the groundbreaking film about the dirtiest joke ever told, in which Connolly is featured.
• The festival will also celebrate its 10^th annual Golden Key Award for Excellence in Costume Design, honoring Academy Award-winning costume designer Deborah L. Scott. Scott will participate in a discussion of her work moderated by Addie Morfoot of Variety. 

TOUR DE KEYS CHARITY RIDE White sand beaches. Iconic bridges. Ocean breezes. And conch-shell celebrations. On November 22, 2025, Tour de Keys offers these, plus a “pedal with purpose” experience unlike any other. Participants have two options, each one including the famous Seven Mile Bridge and panoramic ocean views and island charm at every turn.  

• 100-Mile Century Ride: Start in Key Largo and ride the entire length of the iconic Overseas Highway, ending in vibrant Key West.
• 50-Mile Ride: Start in Marathon and join midway for a rewarding and scenic journey to the finish line. 

This year’s event marks 10 years of Tour de Keys, which supports two vital nonprofits serving the Florida Keys — MARC Inc. and AH Monroe. Together, they empower adults with developmental disabilities and provide life-changing health and housing support throughout the community. 

MORE NOVEMBER EVENTS 

Race World Offshore 

November 2-9 The ocean becomes a makeshift battleground as Race World Offshore returns to Key West. Get ready for eight thrilling days of high-speed competition featuring cutting-edge boats and world-class teams during a celebration of nautical power and the relentless pursuit of victory. Learn more.  

Rams Head Presents at the Key West Theater 

This November, Rams Head brings a stellar lineup of live music tributes to the Key West Theater, celebrating some of the greatest legends in music history. 

• Elton Dan & The Rocket Band (November 12): A dazzling Elton John experience complete with costume changes, multimedia magic, and unforgettable performances.
• The Garcia Project (November 15): A soul-stirring tribute to the music and legacy of the Jerry Garcia Band.
• The Broken Hearts: A Tribute to Tom Petty & The Heartbreakers (November 29): A powerful homage by former bandmates and top musicians honoring one of Florida’s greatest musical exports.  

Fishing in the Florida Keys is a year-round affair, and anglers of all skill levels can join in the fun during these November events:  

• Cheeca Lodge & Spa All-American Backcountry Tournament (November 13-15): In Islamorada, honor war heroes during Veterans Day weekend with this all-release tournament targeting snook, redfish, bonefish, tarpon, and permit. The event benefits the Bonefish & Tarpon Trust. Learn more.
• Sugarloaf Showdown (November 13-15): Fish for bonefish, permit, and barracuda in this catch-and-release challenge hosted by the Lower Keys Guides Association. Proceeds support the Florida Keys Guides Trust Foundation. Learn more.  

As Thanksgiving approaches, the destination celebrates with performing arts and Turkey-themed activities:  

Florida Man – The Musical 

November 21-30 Back by popular demand at the Tennessee Williams Theatre! The Key West International Dance Company presents this hilarious, irreverent musical where famed naturalist David Attenborough narrates the wild escapades of the infamous “Florida Man.” Learn more.  

Southernmost Turkey Trot 5K & 1-Mile Rooster Romp 

November 27 Lace up and race your way through Thanksgiving morning at the 3^rd Annual Turkey Trot. Registration includes a festive medal, a mimosa bar (21+), and a post-race party at the Southernmost Point Bar. Learn more.  

High-resolution images, photo credits, and captions are available at this link.  

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Film critics discuss the year’s top movies and industry trends during the 2024 Key West Film Festival Critics Panel, held at Hank’s Hair of the Dog Saloon in Key West, Fla. From left are moderator Shirrel Rhoades of The Key West Citizen, David Rooney of The Hollywood Reporter, David Fear of Rolling Stone, Stephanie Zacharek of Time, and Lovia Gyarkye of The Hollywood Reporter. The annual panel, free and open to the public, will return for the 2025 festival Nov. 12-16. (Larry Blackburn/KWFF)