HaveFun.NOW

DURTBAGS ~ Durty Harry's Stage at Rick's Entertainment Complex
2026-01-31 21:00 - 2026-02-01 03:00 (America/New_York)
Experience the electrifying energy of The Durtbags, Key West’s premier party rock band, at Durty Harry’s Stage in Rick’s Entertainment Complex. Performing Thursday through Sunday, this dynamic group delivers the ultimate soundtrack for unforgettable nights. Dance and sing along to their high-energy sets in the heart of Old Town’s vibrant nightlife.

DJ Duke ~ Rick's Bar Upstairs at Rick's Entertainment Complex
2026-01-31 21:00 - 2026-02-01 04:00
Experience an electrifying night with DJ Duke at Rick’s Bar, nestled in the vibrant Rick’s Entertainment Complex. As Key West’s premier DJ, Duke crafts unforgettable sets that keep the energy high and the dance floor alive. Join the pulsating nightlife scene for an exhilarating musical journey.

Karaoke w/ Jason ~ Rick's Bar Downstairs at Rick's Entertainment Complex
2026-01-31 23:59 - 2026-02-01 04:00
Join the lively atmosphere of Rick’s Bar at Rick’s Entertainment Complex for an unforgettable night of karaoke with Jason. Known for his engaging stage presence, Jason brings a unique flair to each performance, encouraging everyone to sing along and enjoy the vibrant nightlife of Old Town Key West.

Yoga on the Beach - Ft Zachary Taylor
2026-02-01 08:15 - 09:45, 2026-02-02 08:15 - 09:45, 2026-02-03 08:15 - 09:45, 2026-02-04 08:15 - 09:45
Join a unique yoga experience with renowned instructors at Yoga on the Beach at Fort Zachary Taylor. Set against the backdrop of Key West’s historic Civil War fort, participants can immerse themselves in a session that balances mind and body while enjoying stunning ocean views and the serenity of nature.

Tea Dance at La Te Da
2026-02-01 16:00 - 18:00
Experience a vibrant evening at Tea Dance at La Te Da, featuring the incredible Randy Roberts. Delight in raunchy drag performances and masterful impersonations of icons like Bette Midler and Cher. Enjoy unforgettable entertainment in Key West’s top-notch nightlife venue, with live shows and more at this iconic cabaret destination.

801 Karaoke - Hosted by Jeff
2026-02-01 16:00 - 21:00
Join the unforgettable Sunday karaoke at 801 Bourbon Bar, hosted by the charismatic Jeff. Known for his engaging personality, Jeff takes center stage, making each performance a memorable experience. Nestled in Old Town Key West, this lively gay bar offers vibrant drag shows and a friendly, inclusive atmosphere. Don’t miss out!

Sunset Celebration at Mallory Square
2026-02-01 17:00 - 21:00, 2026-02-02 17:00 - 21:00, 2026-02-03 17:00 - 21:00
The Sunset Celebration at Mallory Square in Key West is a must-see event. Renowned street performers captivate audiences with their vibrant talents, creating an unforgettable atmosphere. This historic waterfront location transforms with lively acts, local artisans, and delicious food vendors, all set against stunning sunset views, providing an enchanting experience for all ages.

Nick Norman With Shane Williams & Warren Bazemore at Key West Theater
2026-02-01 19:00 - 21:00
Experience the soulful sounds of Nick Norman at Key West Theater, joined by talented musicians Shane Williams and Warren Bazemore. Set in the historic and intimate Back Stage Listening Room, this performance promises an unforgettable evening of live music. Immerse yourself in Nick Norman’s captivating artistry at this iconic Key West venue.

80s & 90s Trivia Night
2026-02-01 19:00 - 22:00
Join 80s & 90s Trivia Night at The Retro Room in Old Town, Key West, where an engaging entertainer takes you on a nostalgic journey. Enjoy diverse drinks, arcade and board games, and relive iconic decades in a lively atmosphere. Perfect for trivia enthusiasts and beer lovers, all for just $10-$20!

daytime event to test 18
2026-02-02 05:00 - 17:59 | test venue 7, 416 Applerouth Ln, Key West, FL, 33040, United States
Do not fear mistakes. There are none.

Aqua Yoga at Southernmost Beach Resort
2026-02-02 09:00 - 10:00, 2026-02-04 09:00 - 10:00
Join an invigorating Aqua Yoga session at Southernmost Beach Resort, led by our expert instructor, who brings energy and tranquility to this unique waterside experience. Immerse yourself in a session that blends mindful movement with the soothing ocean backdrop, offering a refreshing escape in the heart of Key West’s historic charm.

World Famous 801 Girls- 5pm Show
2026-02-02 17:00 - 18:30, 2026-02-03 17:00 - 18:30
The World Famous 801 Girls captivate audiences with their dazzling performances at the lively 801 Bourbon Bar in Old Town Key West. Known for their charisma and talent, these entertainers deliver unforgettable drag shows filled with energy and creativity. Join the 5pm show to witness the magic and embrace the vibrant nightlife atmosphere.

Caribe of Key West at El Meson de Pepes on Mallory Square
2026-02-02 17:00 - 21:00, 2026-02-03 17:00 - 21:00
Caribe of Key West delivers an electrifying performance at El Meson de Pepe on Mallory Square, infusing the vibrant atmosphere with lively music. As you enjoy authentic Cuban cuisine, the band’s captivating rhythms set the stage for an unforgettable evening. Experience a fusion of culture and entertainment in this historic Key West locale.

Martini Monday at Virgilios
2026-02-02 18:00 - 2026-02-03 01:00
Experience the soulful tunes of a talented live entertainer at Martini Monday, held at Virgilio’s in Key West. Enjoy the chic ambiance of this premier martini bar while savoring classic cocktails and exquisite Italian cuisine. Revel in a night of music and relaxation, with late-night menu options extending the evening’s enjoyment.

Karaoke at Bobby's Monkey Bar
2026-02-02 21:30 - 2026-02-03 03:00, 2026-02-03 21:30 - 2026-02-04 03:00
Join the vibrant scene at Bobby’s Monkey Bar in Old Town Key West for an unforgettable karaoke night. The spirited entertainer keeps the energy high, ensuring everyone has a blast. Dive into the lively atmosphere as you sing your heart out amidst a fun-loving crowd. Don’t miss the daily happy hour!

daytime event to test 19
2026-02-03 05:00 - 17:59 | test venue 7, 416 Applerouth Ln, Key West, FL, 33040, United States

Ambitious Morning Runners
2026-02-03 06:00 - 07:30
Join the Ambitious Morning Runners at White Street Pier in Key West for an invigorating start to your day. While there isn’t a specific entertainer, the true star is the breathtaking sunrise over the ocean. Enjoy peaceful surroundings and the serene beauty of this scenic spot as you energize your morning routine.

Prime of Life Yoga with Monica Haskell
2026-02-03 10:00 - 11:15
Join Monica Haskell for Prime of Life Yoga, a rejuvenating experience amidst the serene beauty of the Key West Tropical Forest & Botanical Garden. Known for her inspirational teaching style, Monica guides participants through tailored yoga sessions focused on enhancing vitality and well-being, offering a refreshing escape in a tranquil natural setting.

Glow Hours on Hugh's View
2026-02-03 17:00 - 19:00
Experience captivating performances at Glow Hours on Hugh’s View, perched atop the vibrant Studios of Key West. Set against the stunning backdrop of Key West’s skyline, this event showcases exceptional entertainers who light up the stage with their talent, creating an unforgettable evening of artistic brilliance and community celebration.

daytime event to test 20
2026-02-04 05:00 - 17:59 | test venue 7, 416 Applerouth Ln, Key West, FL, 33040, United States

Wednesday Filet Day at Mary Ellen's
2026-02-04 11:30 - 2026-02-05 02:00
Every Wednesday at Mary Ellen’s Bar in Old Town Key West, enjoy Filet Day alongside live entertainment that electrifies the neighborhood atmosphere. While savoring comfort food like gourmet grilled cheese, immerse yourself in the vibrant sounds of local artists, ensuring an energetic and memorable night enhanced by frozen Irish coffee delights.
