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Ambitious Morning Runners at White Street Pier in Key West is a vibrant event that captures the essence of oceanfront beauty. While the scenic locale offers serene sunrise views and…

Join the Fishmonster Max for a memorable daily party boat fishing adventure departing from A & B Marina in Key West's historic seaport. Experience lively entertainment on board, creating the…

Experience serenity with Yoga on the Beach at Fort Zachary Taylor State Park in Key West. Immerse yourself in nature's tranquility as an expert instructor guides your practice amidst historic…

Experience the vibrant energy of Victoria Leigh at Sloppy Joe's Bar, where her captivating performances light up the stage. Known for feel-good covers, creative mashups, and engaging original songs, Victoria…

Join Monica Haskell for Prime of Life Yoga, a rejuvenating experience set amidst the lush surroundings of the Key West Tropical Forest & Botanical Garden. Monica, a seasoned yoga instructor,…

Experience the vibrant nightlife atmosphere at Key West First Legal Rum Distillery in the Historic Seaport. Enjoy daily free tours, rum samples, and mojito-making classes. Discover Key West's rich history…

Join the Mojito Class at Key West Legal Rum Distillery, where a charismatic entertainer guides you through the art of crafting the perfect mojito. Set in the lively atmosphere of…

Explore the vibrant marine life of the Florida Keys on the Glass Bottom Boat Cruise, departing from Fury Key West. This captivating experience promises unforgettable views of underwater wonders. However,…

Oren Polak captivates audiences at Schooner Wharf Bar in Key West with his versatile musical talent and engaging performances. As a dynamic band leader, he brings a unique sound that…

Brian Roberts, a captivating singer/songwriter based in the Florida Keys, enchants audiences at Sloppy Joe's Bar with his live performances. Known for his engaging style and musical talent, Brian invites…

Brian Roberts, a talented singer/songwriter based in the Florida Keys, captivates audiences at Sloppy Joe's Bar with his engaging live performances. Known for his evocative music, he performs every Tuesday…

The Cardboard Kings — indie rock — live at Scraddle's Place.Jangly, earnest, and suspiciously good at harmonies for a band this loud.Tuesday, September 8. Doors at 12:00, two-hour set. Matinee.…

Join a delightful Key Lime Pie Tour led by a charismatic local entertainer in Key West's historic seaport. Over 1.5 hours, enjoy their engaging storytelling while savoring three delectable Key…

Experience the mesmerizing Glass Bottom Boat Cruise in Key West, featuring a captivating entertainer who brings the marine wonders to life. Depart from Fury Key West for an unforgettable journey,…

Join us for Industry Night at The Retro Room in Old Town Key West. Although the event description is missing specifics about the entertainer, the venue promises an exciting atmosphere…

Neon Possum — synthwave — live at Scraddle's Place.Analog synths, one fog machine, zero apologies.Tuesday, September 8. Doors at 14:30, two-hour set. Happy Hour. $5 at the door.

Experience the captivating performance of Tera Lynne Fister at Tiki House Key West. Known for her dynamic stage presence and soulful music, Tera Lynne brings a unique blend of charisma…

Experience the soulful melodies of Josh Kiser at the Old Sailor Bar. Originally from Cleveland, Tennessee, Kiser captivates audiences with his distinct blend of '90s sounds and soul. Now based…

Experience the ultimate aquatic adventure with Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise at Sunset Watersports, Key West. Guided by skilled entertainers, explore vibrant coral reefs, encounter playful…

Experience the vibrant sounds of emerging musician Jesse Lee Jr. at Rick's Bar Downstairs Stage in Key West. Originally from New Jersey, Jesse moved to Florida in 2024 to pursue…

Tony Baltimore is a dynamic singer/songwriter known for his genre-bending alternative roots-rock sound. With a strong work ethic born from his Italian immigrant upbringing, he captivates audiences in Key West.…

Embark on the Glass Bottom Boat Cruise from Key West with a stellar entertainer elevating the journey. Enjoy captivating commentary and lively performances as you explore the vibrant marine life…

Third Shift Choir — gospel-soul — live at Scraddle's Place.Twelve voices, no microphones needed. The room will feel it.Tuesday, September 8. Doors at 17:00, two-hour set. Early Set. $10 at…

Experience the vibrant melodies of Caribe of Key West at El Meson de Pepes on Mallory Square. This family-owned Cuban restaurant offers not only authentic cuisine but also lively performances…

Experience the unparalleled talent of the World Famous 801 Girls at their 5pm show. Known for their dynamic performances and captivating presence, these drag queens take center stage at 801…

Experience a captivating evening with Ericson Holt at Two Friends Patio Restaurant in Key West. Known for his soulful performances, Ericson brings a unique blend of blues and Americana to…

The Happy Dog Band, an improvisational jam band, electrifies the Green Parrot Bar in Key West with their psychedelic rock sound. Known for dynamic live performances, they capture the spirit…

Experience the electrifying energy of Burning Bridges at Sloppy Joe's Bar, a historic Key West venue. Known for their dynamic performances, this Upstate SC band offers an eclectic mix of…

The Sunset Celebration at Mallory Square in Key West is an unforgettable experience, showcasing breathtaking sunsets and vibrant street performances. The highlight is the entertainment, featuring an array of talented…

Experience live local music from talented entertainers during Glow Hours on Hugh's View at The Studios of Key West. This weekly event features captivating performances against a stunning sunset backdrop.…

Join Trivia Tuesday at Mary Ellens, a vibrant event in Old Town Key West. From 6:30pm to 8:30pm, challenge your knowledge and win exciting prizes. Immerse yourself in this lively…

Experience the electrifying energy of DJ Todd at the Red Garter Saloon Stage. Renowned for his eclectic mixes and dynamic performances, DJ Todd captivates audiences with his unique soundscapes, blending…

At Schooner Wharf Bar, Gary Hempsey delivers an unforgettable performance with his soulful voice and impressive instrumental skills. As an acclaimed musician, his blend of rock, folk, and blues captivates…

Experience the extraordinary talent of Joe The Show on the Downstairs Stage at Rick's Bar. Known for his tireless work ethic and captivating performances, Joe enchants audiences with his dynamic…

Experience the captivating performance of Will Parker at the Old Sailor Bar, a lively venue echoing Key West’s maritime legacy. Known for his engaging and charismatic style, Will Parker breathes…

Hush Puppy Revival — country — live at Scraddle's Place.Songs about trucks that don't run and people who should have left sooner.Tuesday, September 8. Doors at 19:30, two-hour set. Main…

Experience the vibrant tunes of Happy Dog Band at the iconic Green Parrot Bar in Key West. Known for their improvisational jam sessions and psychedelic rock spirit, the band turns…

Experience an unforgettable night at Kaya Island Eats with their dynamic karaoke events. The spotlight shines on a talented entertainer who brings energy and flair to the stage, creating a…

DJ Kori brings unparalleled energy to Rick's Bar Upstairs Stage, transforming any night into an unforgettable memory. With a vast music library and captivating light displays, DJ Kori tailors every…

Join The Original Key West Pub Crawl and experience entertainment like never before. While exploring historic sites and vibrant local culture, be captivated by local performers who add charm and…

Kari Wolf, a dynamic musician from Key West, Florida, brings her captivating performances and soulful melodies to Hank's Hair of the Dog Saloon. With her unique style, Kari enchants the…

Experience the electrifying performances of LUVBOM at Durty Harry's Stage. This dynamic entertainer, renowned for his skills as a vocalist, guitarist, songwriter, and producer, captivates audiences in Key West. Feel…

Join the Bone Island Haunted Pub Crawl & Ghost Tour for an enthralling evening led by a charismatic entertainer. With captivating narration, journey through America's most haunted destinations, experiencing spine-tingling…

Enjoy a vibrant evening of karaoke at Bobby's Monkey Bar in Key West's Old Town. This lively venue features talented local entertainers who bring excitement to the stage, encouraging everyone…

The Ambulance Chasers — punk — live at Scraddle's Place.Fourteen songs, twenty-two minutes, one broken cymbal stand.Tuesday, September 8. Doors at 21:45, two-hour set. Late Set. $15 at the door.

Experience the electrifying sounds of Audio Graffiti at Sloppy Joe's Bar, where this dynamic entertainer ignites the stage with a fusion of vibrant beats and infectious energy. Join the lively…

Join DJ Jorge for an electrifying karaoke night at Rick's Bar Downstairs Stage in Key West. Known for his dynamic beats and vibrant performances, DJ Jorge keeps the energy high…