HaveFun.NOW

Naked Karate Girls at Sloppy Joe's Bar
2026-02-22 22:00 (America/New_York)
Experience the electrifying energy of the Naked Karate Girls, the ultimate party band hailing from Cincinnati. Known as The Best Band in the Galaxy, their dynamic performances turn every night into an unforgettable celebration. Don’t miss their show at Sloppy Joe’s Bar for an epic night of live music and entertainment.

Karaoke w/ Jason ~ Rick's Bar Downstairs Stage
2026-02-22 23:59 - 2026-02-23 04:00
Join Jason for an unforgettable night of karaoke at Rick’s Bar Downstairs Stage. Known for his infectious energy and dynamic hosting skills, Jason creates a lively atmosphere that makes everyone feel like a star. Sing your heart out and enjoy a vibrant evening in Key West’s largest entertainment complex.

Fishmonster Max- Daily Party Boat Fishing
2026-02-23 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
2026-02-23 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.

Aqua Yoga at Southernmost Beach Resort
2026-02-23 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.

Joe The Show at Sloppy Joe's Bar
2026-02-23 10:00 - 11:45
Experience the captivating performance of Joe The Show at Sloppy Joe’s Bar, Key West’s iconic venue. Renowned for his vibrant stage presence and musical talent, Joe energizes the historic landmark with electrifying live music. Enjoy a memorable evening of entertainment and atmosphere in this beloved Duval Street destination.

Distillery Tour - Key West Legal Rum Distillery
2026-02-23 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.

Mojito Class by Key West Legal Rum Distillery - Min 4 people
2026-02-23 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!

Glass Bottom Boat Cruise - Key West's Window to the Sea
2026-02-23 11:30 - 14:00
Experience the captivating Glass Bottom Boat tour in Key West, where our knowledgeable captain and crew offer an engaging eco-tour. Enjoy unparalleled views of North America’s only living coral reef and vibrant marine life through special glass windows to the reef. An unforgettable journey exploring Key West’s underwater wonders awaits.

Webb Dillard ~ Rick's Bar Downstairs Stage
2026-02-23 12:00 - 15:00
Experience the electrifying performance of Webb Dillard on Rick’s Bar Downstairs Stage at Rick’s Entertainment Complex in Old Town Key West. As a talented musician, Webb Dillard delivers dynamic live music in a vibrant setting, making it an unforgettable night. Enjoy his captivating tunes while exploring the largest club south of Miami.

Tim Hollohan at Sloppy Joe's Bar
2026-02-23 12:00 - 16:45
Tim Hollohan captivates audiences at Sloppy Joe’s Bar, an iconic venue in Key West. Originally from Columbia, South Carolina, Tim graces the stage almost daily, delivering energetic performances that engage and delight. His dynamic presence and musical talent make him a beloved fixture, enhancing the lively atmosphere of this historic landmark.

Jay Klein at Schooner Wharf Bar
2026-02-23 12:00 - 17:00
Experience a captivating evening with musician Jay Klein at the Schooner Wharf Bar. Nestled in Key West’s Seaport, this popular venue combines dockside views with a relaxed atmosphere. Enjoy Klein’s engaging live performance, featuring a blend of local and national musical influences, while savoring fresh seafood and island-inspired cuisine.

Zack Seemiller at Hog's Breath Saloon
2026-02-23 12:00 - 2026-02-24 16:00
Zack Seemiller brings his captivating musical talent to Hog’s Breath Saloon in Key West. Known for his dynamic performances, Seemiller’s eclectic setlist transforms the lively dive bar into a vibrant hub of sound and energy. As he engages the audience under the outdoor patio’s twinkling lights, patrons enjoy an unforgettable musical experience.

Rolando Rojas at Sunset Pier
2026-02-23 13:00 - 16:00
Experience the captivating performances of Rolando Rojas at Sunset Pier. Renowned for his dynamic musical talent, Rojas enchants audiences with his vibrant melodies and charismatic presence. Set against the breathtaking backdrop of Key West sunsets, his live shows promise an unforgettable evening of music and entertainment at this stunning waterfront location.

Shastina Chiles at Hank's Hair of the Dog Saloon
2026-02-23 13:00 - 16:00
Enjoy an electrifying evening with musician Shastina Chiles at Hank’s Hair of the Dog Saloon in Key West. Known for her captivating performances, Shastina’s music sweeps you into the vibrant nightlife. With live tunes every night, this dog-friendly venue offers an unforgettable experience complete with mojitos and fish tacos from Garbo’s food truck.

Jay Nokes at Tiki House Key West
2026-02-23 13:30 - 16:30
Experience the captivating performance of Jay Nokes at Tiki House Key West. Renowned for his engaging stage presence and musical talent, Jay delivers an unforgettable evening filled with vibrant tunes and lively entertainment. Join us for a night where music meets tropical paradise, creating a perfect atmosphere for relaxation and enjoyment.

Derek Dunbar at The Bull & Whistle Bar
2026-02-23 14:00 - 18:00
Derek Dunbar brings his electrifying presence to The Bull & Whistle Bar, captivating audiences with dynamic performances and exceptional musical talent. His engaging style complements the vibrant atmosphere of this iconic Key West venue. As he strums and sings, the lively crowd, potent cocktails, and muralled open-air space create an unforgettable nightlife experience.

Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise
2026-02-23 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.

Just George ~ Rick's Bar Downstairs Stage
2026-02-23 15:00 - 19:00
Experience the phenomenal musical talent of Just George at Rick’s Bar Downstairs Stage in Key West. Renowned for his captivating performances and dynamic presence, Just George entertains with an unparalleled blend of charisma and masterful musicianship, creating a memorable night for all. Enjoy his live act amidst the vibrant ambiance of Rick’s Entertainment Complex.

Glass Bottom Boat Cruise - Key West's Window to the Sea
2026-02-23 16:00 - 19:30
Experience an unforgettable journey with Glass Bottom Boat – Key West’s Window to the Sea. With an engaging and knowledgeable captain and crew, embark on a captivating eco-tour showcasing Key West’s vibrant marine life through special glass windows. Witness North America’s only living coral reef with over 300 species of colorful fish.

Mark Teague & Rick Fusco at Hog's Breath Saloon
2026-02-23 16:30 - 2026-02-24 20:30
Experience the vibrant energy of Mark Teague and Rick Fusco at Hog’s Breath Saloon in Key West’s Mallory Square District. With their dynamic live music performances, these talented entertainers create a lively atmosphere, inviting patrons to dance and revel under the stars. Savor a memorable night of tunes, bites, and fun.

World Famous 801 Girls- 5pm Show
2026-02-23 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.

Glow Hours on Hugh's View
2026-02-23 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.

Jay Bangles at Tiki House Key West
2026-02-23 17:00 - 20:00
Experience the captivating sounds of musician Jay Bangles at Tiki House Key West. Known for his dynamic performances and infectious energy, Jay delivers an unforgettable musical journey that resonates with all. Join us for an evening of exceptional entertainment in the vibrant atmosphere of Tiki House, where Jay’s talent truly shines.

Scott Morlock at Hank's Hair of the Dog Saloon
2026-02-23 17:00 - 20:00
Scott Morlock electrifies Hank’s Hair of the Dog Saloon with his dynamic musical talent. A must-see performer, Scott keeps the vibrant Key West nightlife alive with engaging live music that enraptures both locals and visitors. Enjoy his enthralling performance while sipping mojitos and savoring Garbo’s delicious fish tacos in this lively, dog-friendly venue.

Sunset Celebration at Mallory Square
2026-02-23 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.

Caribe of Key West at El Meson de Pepes on Mallory Square
2026-02-23 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.

The 4 Amigos at Sunset Pier
2026-02-23 17:30 - 20:30
Experience an unforgettable evening with The 4 Amigos at Sunset Pier, where their lively tunes and infectious energy create a captivating atmosphere. Set against the breathtaking backdrop of Key West’s sunsets, enjoy their vibrant performance while savoring tropical seafood delights and refreshing mojitos. It’s a perfect blend of music, stunning views, and culinary delights.

Preacher Pete Presents at Sloppy Joe's Bar
2026-02-23 17:30 - 21:30
Join the legendary Preacher Pete at Sloppy Joe’s Bar, where his enchanting musical prowess creates an unforgettable experience. Known for his captivating performances, Pete, alongside a guest musician, crafts spontaneous and magical moments that resonate with all who attend. Immerse yourself in the vibrant atmosphere of this historic Key West landmark.
