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DTSTART;VALUE=DATE:20261016
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SUMMARY:FANTASY FEST 2026
DESCRIPTION:Get ready for one of the Florida Keys’ most legendary celebrations! Fantasy Fest returns to Key West in October 2026 with this year’s theme\, “Musical Icons & Iconic Musicals.” \nThis world-famous celebration transforms Key West into a colorful spectacle of elaborate costumes\, creativity\, music\, parties\, parades\, entertainment\, and unforgettable island fun. Throughout the festival\, visitors can enjoy a packed schedule of themed events and festivities leading up to the signature Fantasy Fest celebrations. \nWhether you come for the incredible costumes\, lively atmosphere\, famous Key West nightlife\, or simply to experience one of the island’s most iconic traditions\, Fantasy Fest is an experience unlike anywhere else. \nTheme: Musical Icons & Iconic MusicalsLocation: Key West\, FloridaDates: October 16–25\, 2026 \n   \nAbove Images by Carol Tedesco\, Below Images by Eva Polizze\n  \n          \nThe Captain Morgan Masquerade March\, aka “Local’s Parade” and its companion Paparazzi Row party will take place in Old Town Key West on Friday\, Oct 23. (Photo: Carol Tedesco/Fantasy Fest)\nHeld at Rick’s Upstairs\, the 2026 Fantasy Fest LUV2GLOW party theme is LIQUID FREQUENCY – where light\, sound\, and energy unite. (Photo: Nick Doll/Fantasy Fest)\nThe Bahama Village Goombay Festival\, a two-day celebration of island arts and crafts\, culture\, music and food will welcome revelers of all ages throughout the historic Bahama Village neighborhood on Oct. 16 and 17. (Photo: Carol Tedesco/Fantasy Fest)\nPets and their people will costume up and strut their stuff at the annual Fantasy Fest Pet Masquerade\, set for Wednesday\, Oct. 21\, at the Coffee Butler Amphitheater. (Photo: Carol Tedesco/Fantasy Fest)\nThis year’s Deep Eddy Vodka Fantasy Fest Parade with its magical floats\, marvelous marching groups and crazy kinetic creations will kick off in Old town Key West at 7:00pm on Saturday\, Oct. 24. (Photo: Carol Tedesco/Fantasy Fest)\n  \nIndividual event dates\, times\, locations\, and admission requirements vary. Schedule is subject to change. Visit the official Fantasy Fest website for the latest schedule and event information.
URL:https://thefloridakeysmagazine.com/event/fantasy-fest-2026/
LOCATION:FL
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DTSTART;VALUE=DATE:20261101
DTEND;VALUE=DATE:20261109
DTSTAMP:20260912T032021Z
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UID:4789-1793491200-1794182399@thefloridakeysmagazine.com
SUMMARY:Race World Offshore Key West World Championship
DESCRIPTION:Get ready for high-speed action in Key West as the Race World Offshore Key West World Championship returns November 1–8\, 2026\, bringing an exciting week of offshore powerboat racing to the Florida Keys. \nBased around Truman Waterfront Park\, championship week brings together world-class racing teams\, powerful offshore boats\, racing fans\, and visitors for one of Key West’s most thrilling annual sporting events. \nOne of Key West’s most exciting annual sporting traditions\, championship week combines world-class offshore racing with the unmistakable atmosphere of the island. Powerful race boats compete on the waters surrounding Key West\, giving spectators the opportunity to experience the speed\, sound\, and excitement of offshore racing from numerous locations around the island. \nThe Key West races serve as a major championship event for offshore powerboat racing\, attracting professional teams\, crews\, racing enthusiasts\, and visitors from around the country and beyond. Competitors navigate a challenging course through the waters surrounding Key West\, where changing conditions add another element to the competition. \nWhere to Watch\nSpectators can experience the races from several locations around Key West. Popular viewing areas traditionally include Truman Waterfront Park\, Fort Zachary Taylor Historic State Park\, Mallory Square\, Sunset Pier\, Simonton Street Beach\, and waterfront locations overlooking the racecourse. \nRace Village at Truman Waterfront Park is also a center of activity during championship week\, giving racing fans an opportunity to get closer to the boats\, teams\, and excitement surrounding the event. \nBeyond race day\, visitors can enjoy the festive atmosphere throughout Key West as racing teams and fans fill the island for several days of competition and events. \nExperience Key West During Race Week\nThe championship is more than a powerboat race—it is an opportunity to experience Key West during one of its most energetic weeks of the year. Between races\, visitors can explore historic Old Town\, enjoy waterfront restaurants and bars\, watch a famous Key West sunset\, visit local attractions\, and experience the island lifestyle. \nWhether you are a longtime offshore racing fan or simply looking for an exciting reason to visit the Florida Keys\, the Key West World Championship offers an unforgettable combination of speed\, competition\, waterfront views\, and island fun. \nLocation: Key West\, FloridaEvent: Race World Offshore Key West World ChampionshipDates: November 2026 \nRace schedules\, viewing locations\, admission requirements\, and individual event times may change. Visitors should confirm the official event schedule and ticket information before attending.
URL:https://thefloridakeysmagazine.com/event/race-world-offshore-key-west-world-championship/
LOCATION:FL
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DTSTART;VALUE=DATE:20261118
DTEND;VALUE=DATE:20261123
DTSTAMP:20260912T041925Z
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SUMMARY:Key West Film Festival 2026
DESCRIPTION:KEY WEST FILM FESTIVAL 2026\nNovember 18–22\, 2026 | Key West\, Florida \nFilm\, creativity\, and island culture come together during the Key West Film Festival\, returning November 18–22\, 2026\, for five days of cinema in one of Florida’s most distinctive destinations. \nThe annual festival brings filmmakers\, actors\, industry professionals\, movie lovers\, and visitors together in Key West for a celebration of independent film and storytelling. Screenings and special programs take place at venues throughout the island\, creating an experience that combines the excitement of a film festival with the relaxed atmosphere and historic charm of Key West. \nFestival programming traditionally includes a diverse selection of feature films\, documentaries\, short films\, independent productions\, and special presentations\, giving audiences an opportunity to discover new work as well as films generating attention during the upcoming awards season. \nBeyond the screenings\, the Key West Film Festival offers opportunities for audiences to connect with the creative community through filmmaker discussions\, panels\, special guests\, receptions\, and festival events. The intimate nature of Key West creates a film-festival experience where conversations can continue beyond the theater and into the restaurants\, streets\, and gathering places of Old Town. \nFilm Meets Island Life\nPart of what makes this festival unique is its setting. Between screenings\, visitors can explore historic Key West\, stroll Duval Street\, visit galleries and museums\, enjoy waterfront dining\, or watch the sunset over the Gulf of Mexico. \nRather than separating the festival from the destination\, the experience becomes part of Key West itself—combining cinema\, culture\, history\, creativity\, and island life over five memorable days. \nWhether you are passionate about independent filmmaking\, looking for the next standout movie\, or simply searching for a different way to experience Key West\, the Key West Film Festival offers an engaging celebration of storytelling at the southernmost end of the Florida Keys. \nDates: November 18–22\, 2026Location: Key West\, Florida \nIndividual screening times\, venues\, ticket requirements\, special guests\, and festival programming vary. Check the official Key West Film Festival schedule for current information before attending.
URL:https://thefloridakeysmagazine.com/event/key-west-film-festival-2026/
LOCATION:Key West\, Key West\, Florida\, United States
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DTSTART;TZID=America/New_York:20261205T180000
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SUMMARY:KEY WEST HOLIDAY PARADE 2026
DESCRIPTION:KEY WEST HOLIDAY PARADE 2026\nSaturday\, December 5\, 2026 | Key West\, Florida \nCelebrate the holidays with a tropical twist at the Key West Holiday Parade\, taking place Saturday\, December 5\, 2026. This beloved annual tradition fills the streets of Key West with festive floats\, music\, lights\, community groups\, and plenty of holiday cheer. \nAs evening arrives\, spectators gather along the parade route to watch a colorful procession make its way through Key West. Expect creatively decorated floats and vehicles\, marching bands\, local schools and organizations\, performers\, and holiday characters joining together for one of the island’s favorite family-friendly celebrations. \nAnd\, of course\, no holiday parade would be complete without Santa Claus\, bringing a little North Pole magic to the southernmost city. \nChristmas\, Key West Style\nThe Key West Holiday Parade captures everything that makes celebrating the season in the Florida Keys so much fun. Traditional Christmas decorations meet palm trees\, warm December weather\, historic island architecture\, and the wonderfully creative personality for which Key West is known. \nFamilies line the streets as music fills the air\, illuminated entries pass by\, and parade participants spread holiday cheer throughout the crowd. Children can look forward to the excitement of seeing Santa\, festive characters\, and plenty of colorful displays along the route. \nThe parade is also a celebration of the local community\, with schools\, businesses\, organizations\, and residents coming together to create an evening enjoyed by locals and visitors alike. \nMake a Night of It\nArrive early and enjoy Key West before the parade begins. Explore Old Town\, grab dinner at a local restaurant\, admire the holiday decorations\, and find a good viewing spot along the parade route. \nWith festive lights\, island weather\, and the unmistakable spirit of Key West\, the Holiday Parade is a wonderful way to begin the Christmas season in the Florida Keys. \nDate: Saturday\, December 5\, 2026Location: Key West\, FloridaAdmission: Free \nParade start time\, route\, and event details may be subject to change. Check official event information before attending.
URL:https://thefloridakeysmagazine.com/event/key-west-holiday-parade-2026/
LOCATION:Key West\, Key West\, Florida\, United States
ATTACH;FMTTYPE=image/jpeg:https://thefloridakeysmagazine.com/wp-content/uploads/2026/09/137.jpg
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DTSTART;TZID=America/New_York:20261231T180000
DTEND;TZID=America/New_York:20270101T030000
DTSTAMP:20260912T045858Z
CREATED:20260912T045721Z
LAST-MODIFIED:20260912T045858Z
UID:4803-1798740000-1798772400@thefloridakeysmagazine.com
SUMMARY:NEW YEAR’S EVE IN KEY WEST 2026
DESCRIPTION:NEW YEAR’S EVE IN KEY WEST 2026\nDecember 31\, 2026 | Key West\, Florida \nThere may be no place quite like Key West to ring in a new year. On December 31\, 2026\, the island says goodbye to 2026 with live entertainment\, packed streets\, celebrations throughout Old Town\, and two of Key West’s most famous midnight traditions—the Conch Shell Drop and the Red High Heel Shoe Drop. \nForget the traditional ball drop. This is New Year’s Eve\, Key West style. \nThe Conch Shell Drop at Sloppy Joe’s\nAt the corner of Duval and Greene Streets\, crowds gather outside Sloppy Joe’s Bar for the 33rd Annual Dropping of the Conch Shell. \nThe tradition dates back to 1993 and has become one of Key West’s signature New Year’s Eve celebrations. As midnight approaches\, a giant illuminated conch shell—the unmistakable symbol of the Florida Keys—descends above the crowd while revelers count down together to welcome 2027. \nFor 2026\, the celebration includes entertainment outside the bar beginning at 10 p.m.\, leading up to the Conch Shell Drop at midnight. Sloppy Joe’s says there is no door charge\, and tables are available on a first-come\, first-served basis. \nThe Red High Heel Shoe Drop\nFarther down Duval Street\, another uniquely Key West countdown takes center stage at Bourbon Street Pub. \nThe 29th Annual Key West New Year’s Eve High Heel Shoe Drop transforms the 700 block of Duval Street into a lively celebration as a giant red high heel is suspended above the crowd. At midnight\, the shoe descends with the newly crowned Queen of New Year’s Eve inside\, welcoming 2027 in unmistakable Key West fashion. \nThe 2026–2027 Red Shoe Drop celebration is scheduled from 8:00 p.m. on December 31 through 1:00 a.m. on January 1 at Bourbon Street Pub\, 724 Duval Street. \nOne Island\, Two Iconic Countdowns\nWhat makes New Year’s Eve in Key West special is that the celebration extends far beyond a single countdown. Duval Street and the surrounding Old Town fill with visitors and locals enjoying music\, entertainment\, restaurants\, bars\, and the wonderfully unconventional personality that makes the island famous. \nWhether you choose the giant Conch Shell\, the enormous Red High Heel\, or simply wander through Old Town soaking up the celebration\, New Year’s Eve in Key West offers a memorable way to welcome another year in paradise. \nCome for the countdown\, stay for the island atmosphere\, and start 2027 in the Florida Keys. \nDate: December 31\, 2026Location: Key West\, FloridaConch Shell Drop: Duval & Greene StreetsRed High Heel Shoe Drop: 724 Duval Street \nEvent schedules\, access\, entertainment\, and viewing arrangements may change. Check with individual venues for the latest information before attending.
URL:https://thefloridakeysmagazine.com/event/new-years-eve-in-key-west-2026/
LOCATION:Key West\, Key West\, Florida\, United States
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