HaveFun.NOW

Cachete at Tiki House Key West
2026-02-14 23:00 - 2026-02-15 02:00 (America/New_York)
Experience the vibrant rhythms of Cachete at Tiki House Key West. This talented entertainer brings an infectious energy and captivating performance style that will leave you mesmerized. Join us for an unforgettable night filled with dynamic music and tropical vibes in the heart of Key West’s lively atmosphere. Don’t miss this exceptional performance!

Karaoke w/ Jason ~ Rick's Bar Downstairs Stage
2026-02-14 23:59 - 2026-02-15 04:00
Join Jason for an unforgettable karaoke night at Rick’s Bar on the Downstairs Stage. As a charismatic entertainer, Jason brings energy and excitement, transforming the night into a lively, interactive experience. Located in Key West’s largest club, enjoy a vibrant atmosphere filled with music, dancing, and an array of refreshing drinks.

Fishmonster Max- Daily Party Boat Fishing
2026-02-15 08:00 - 13:00
Join Fishmonster Max for an unforgettable daily party boat fishing adventure in Key West, where entertainment meets the thrill of fishing. Whether it’s a family outing or a corporate event, our skilled crew ensures a lively experience, offering fishing tips, tales, and laughter amidst stunning ocean views. Enjoy quality fishing with comfort and fun!

Yoga on the Beach - Ft Zachary Taylor
2026-02-15 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.

Chris Thomas at Sloppy Joe's Bar
2026-02-15 10:00 - 11:45
Renowned musician Chris Thomas electrifies audiences at Sloppy Joe’s Bar, a historic Key West landmark. Known for his captivating performances, Thomas brings a dynamic blend of energy and musical talent to the stage, creating an unforgettable experience. Enjoy his live show amidst the vibrant atmosphere of this iconic venue on Duval Street.

Bradd Shadduck at Irish Kevin’s Bar
2026-02-15 11:00 - 14:30
Experience the dynamic energy of musician Bradd Shadduck at Irish Kevin’s Bar in the heart of Key West’s Old Town. Known for his engaging performances and lively audience interaction, Bradd captivates with his vibrant musical talent. Enjoy his tunes alongside Irish Kevin’s extensive drink selection and delicious pub grub for an unforgettable night.

Mojito Class by Key West Legal Rum Distillery - Min 4 people
2026-02-15 11:00 - 17:00
There is a minimum of 4 people. Please contact mojitoclass@gmail.com to schedule. Please put how many people and date in the subject line. Join Key West Legal Rum Distillery’s Mojito Class led by Crystal Menta. Having sailed to Cuba and back, Crystal shares the secrets of crafting the perfect mojito. Enjoy mixing and muddling in this interactive session, complete with a mojito tumbler, muddler, and bar spoon. A must-do Key West experience!

Distillery Tour - Key West Legal Rum Distillery
2026-02-15 11:00 - 17:00
Experience an engaging distillery tour at Key West Legal Rum Distillery, featuring a skillful entertainer who brings the history and craft of rum making to life. Enjoy free tastings of unique, vegan-friendly spirits made on this historic site, as well as lessons in mojito making, all amidst the charming Key West seaport. Free tours every 30 minutes and tours last about 15 minutes.

Glass Bottom Boat - Key West's Window to the sea
2026-02-15 11:30 - 14:00, 2026-02-15 13:30 - 16:00, 2026-02-15 16:00 - 19:30

Glass Bottom Boat - Key West's Window to the sea
2026-02-15 11:30 - 14:00
Embark on the Glass Bottom Boat – Key West’s Window to the Sea tour for an unforgettable experience with Captain and crew as your guides. They offer captivating eco-tours, sharing insights into the vibrant underwater world teeming with over 300 fish species and North America’s only living coral reef.

Harley Ray ~ Rick's Downstairs Stage
2026-02-15 12:00 - 16:00
Experience the electrifying performance of musician Harley Ray at Rick’s Downstairs Stage in Old Town Key West. Known for his dynamic sound and captivating presence, Harley Ray brings life to the vibrant nightlife of Rick’s Entertainment Complex, where live music and a lively atmosphere create an unforgettable evening.

John LaMere at Sloppy Joe's Bar
2026-02-15 12:00 - 16:45
John LaMere has captivated audiences at Sloppy Joe’s Bar since 2011, with his dynamic performances and extensive song list. A weekly fixture on the iconic Key West stage, he masterfully engages the crowd, ensuring an unforgettable experience. His musical versatility makes him a standout entertainer at this historic venue.

Mylo O'maolain at Schooner Wharf Bar
2026-02-15 12:00 - 17:00
Experience the captivating sounds of Mylo O’Maolain at Schooner Wharf Bar, a lively open-air venue in Key West. Known for his dynamic performances, Mylo enchants audiences with his unique musical style in this vibrant waterfront setting. Enjoy his unforgettable melodies alongside fresh seafood and stunning dockside views.

Aaron Blumer at Hog's Breath Saloon
2026-02-15 12:00 - 2026-02-16 16:00
Experience an unforgettable evening with musician Aaron Blumer at Hog’s Breath Saloon, located in Key West’s bustling Mallory Square District. Known for his captivating performances, Aaron brings a vibrant energy to the dive bar’s lively atmosphere, making it the perfect spot for enjoying live music on the outdoor patio while savoring delicious pub favorites.

Sheldon Benton at Sunset Pier
2026-02-15 13:00 - 16:00
Sheldon Benton captivates audiences at Sunset Pier, Key West, with his dynamic live performances. Known for his engaging stage presence and versatile repertoire, Benton adds a vibrant energy to the stunning waterfront setting. Enjoy tropical seafood delights while experiencing unforgettable entertainment against the backdrop of breathtaking Gulf sunsets, making for an unforgettable evening.

Sid Ordoyne at Hank's Hair of the Dog Saloon
2026-02-15 13:00 - 16:00
Sid Ordoyne brings his captivating musical talent to Hank’s Hair of the Dog Saloon, enchanting guests with his soulful performances. Set in the vibrant ambiance of Key West’s favorite dog-friendly bar, visitors enjoy live music, refreshing mojitos, and savory fish tacos. Experience an unforgettable night where Sid’s melodies enhance the lively spirit of Duval Street.

Glass Bottom Boat - Key West's Window to the sea
2026-02-15 13:30 - 16:00
Discover the vibrant marine life of Key West aboard the Glass Bottom Boat, where an experienced captain and crew transform an eco-tour into an unforgettable adventure. Marvel at North America’s only living coral reef and over 300 species of fish, all from the comfort of your aquatic window to the sea.

The Reverend TJ at Tiki House Key West
2026-02-15 13:30 - 16:30
Join The Reverend TJ for an unforgettable evening at Tiki House Key West. Known for his dynamic performances and engaging stage presence, The Reverend TJ brings a unique blend of music that captivates audiences. Don’t miss the opportunity to experience his lively show in the vibrant atmosphere of Tiki House.

David Warren at The Bull & Whistle Bar
2026-02-15 14:00 - 18:00
David Warren brings his dynamic musical talents to The Bull & Whistle Bar, a vibrant nightlife spot in Key West’s Old Town. Known for his engaging performances, David captivates audiences with his unique sound. Enjoy his music amidst potent cocktails and vibrant crowds in this open-air venue, a key stop on Duval Street.

Jeff Harris at Irish Kevin’s Bar
2026-02-15 14:30 - 18:00
Experience the dynamic performance of Jeff Harris at Irish Kevin’s Bar in Key West. Known for his engaging live music, Jeff captivates audiences with his vibrant energy and crowd interaction. Immerse yourself in the lively atmosphere as Jeff’s electrifying presence enhances the enjoyment of delicious drinks and hearty pub grub at this iconic venue.

Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise
2026-02-15 15:00 - 18:30
Join an exhilarating aquatic adventure with the Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise. Led by our passionate and expert staff, enjoy thrilling encounters with dolphins, vibrant snorkeling excursions, and breathtaking views on a stunning sunset cruise. Immerse yourself in nature’s wonders while our friendly crew ensures an unforgettable experience.

Tea Dance at La Te Da
2026-02-15 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.

Glass Bottom Boat - Key West's Window to the sea
2026-02-15 16:00 - 19:30
Join us on the Glass Bottom Boat tour in Key West, where our charismatic captain and crew bring the underwater world to life. As you journey over North America’s only living coral reef, their engaging eco-tour and insightful commentary offer a captivating glimpse into the vibrant marine ecosystem beneath the waves.

Trenton Chandler ~ Rick's Bar Downstairs Stage
2026-02-15 16:00 - 20:00
Catch Trenton Chandler, a talented country musician and songwriter from Shallowater, Texas, live on the Rick’s Bar Downstairs Stage. Influenced by legends like Elvis and Waylon Jennings, Chandler delivers heartfelt performances with his band. Experience his captivating mix of classic and contemporary country sounds in the vibrant nightlife of Key West.

801 Karaoke - Hosted by Jeff
2026-02-15 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!

Sheldon Benton at Hog's Breath Saloon
2026-02-15 16:30 - 2026-02-16 20:30
Sheldon Benton captivates audiences at Hog’s Breath Saloon with his electrifying live performances. Known for his dynamic sound, Sheldon infuses the lively Key West atmosphere with energy and charisma. While guests enjoy signature pub delights, Sheldon’s music sets the perfect backdrop for an unforgettable night of dance and enjoyment at this iconic dive bar.

World Famous 801 Girls- 5pm Show
2026-02-15 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.

QMitch Drag Queen Bingo at 22&Co
2026-02-15 17:00 - 19:00
Experience an unforgettable night with QMitch Drag Queen Bingo at 22&Co in Old Town Key West. Renowned for dazzling performances and unmatched charisma, QMitch transforms bingo into a riotous extravaganza. Join in the fun at this lively bar, famous for its tutu-clad bartenders, creative cocktails, and vibrant atmosphere.
