HaveFun.NOW

Barrett Thomas at Hog's Breath Saloon
2026-02-19 12:00 - 2026-02-20 16:00 (America/New_York)
Experience the dynamic performance of musician Barrett Thomas at Hog’s Breath Saloon, where his captivating tunes energize the venue’s lively atmosphere. Nestled in Key West’s Mallory Square, the dive bar offers a backdrop of delicious pub fare and outdoor seating. Join the vibrant crowd for an unforgettable evening of rhythm and revelry.

Marjory Lee at Sunset Pier
2026-02-19 13:00 - 16:00
Experience the captivating sounds of musician Marjory Lee at Sunset Pier, where her enchanting performances complement the vibrant ambiance of Key West’s waterfront. Nestled where Duval Street meets the Gulf of Mexico, the venue offers unforgettable views and an island vibe. Enjoy tropical seafood, refreshing mojitos, and breathtaking sunsets in an unforgettable setting.

Tony Baltimore at Hank's Hair of the Dog Saloon
2026-02-19 13:00 - 16:00
Tony Baltimore brings his captivating musical talent to Hank’s Hair of the Dog Saloon in Key West. Known for his dynamic performances, Tony enchants audiences with his engaging style and infectious energy. Enjoy his live music while savoring savory fish tacos and mojitos, all in a vibrant, dog-friendly atmosphere on Duval Street.

Truman Waterfront Farmers Market
2026-02-19 13:00 - 18:00
Enjoy the vibrant atmosphere at Truman Waterfront Farmers Market, where local entertainers set the mood with captivating performances. Every Thursday from 2 to 7 pm, immerse yourself in fresh produce, exquisite crafts, and fine cuisine. The waterfront location, stunning sunsets, and engaging entertainment make it a must-visit community gathering.

Jon Hollywood at Tiki House Key West
2026-02-19 14:00 - 17:00
Join the charismatic Jon Hollywood at Tiki House Key West for an unforgettable evening of entertainment. Known for his captivating performances and energetic stage presence, Jon Hollywood brings a unique blend of music and showmanship that promises to engage and delight audiences. Don’t miss this electrifying event!

David Warren at The Bull & Whistle Bar
2026-02-19 14:00 - 18:00
Experience the captivating performance of David Warren at The Bull & Whistle Bar in Key West. Known for his dynamic stage presence and soulful tunes, Warren brings the vibrant spirit of Duval Street alive. Enjoy his live music in this iconic bar’s lively atmosphere, complete with balcony seating and potent cocktails.

Irish Kevin at Irish Kevin’s Bar
2026-02-19 14:30 - 18:30
Experience the charismatic performances of Irish Kevin at Irish Kevin’s Bar in Key West’s Old Town. Known for his engaging live music and dynamic crowd interaction, Kevin brings the heart of Ireland to this lively pub. Enjoy his spirited tunes while savoring craft beers and hearty pub grub in a vibrant atmosphere.

Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise
2026-02-19 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.

Jeff Harris ~ Rick's Bar Downstairs Stage
2026-02-19 15:00 - 19:00
Experience the captivating talent of musician Jeff Harris at Rick’s Bar Downstairs Stage. Located in vibrant Old Town Key West, this venue is part of the largest club south of Miami. As Harris takes the stage, enjoy an eclectic mix of live music that sets the perfect tone for an unforgettable night.

Glass Bottom Boat Cruise - Key West's Window to the Sea
2026-02-19 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.

Dan Harvey Duo at Hog's Breath Saloon
2026-02-19 16:30 - 2026-02-20 20:30
Experience the vibrant sounds of the Dan Harvey Duo at Hog’s Breath Saloon. Known for their captivating performances, this talented musical duo creates an unforgettable atmosphere in Key West’s Mallory Square District. Enjoy their live music on Hog’s Breath’s lively outdoor patio, perfect for dance and relaxation amidst delicious pub fare.

World Famous 801 Girls- 5pm Show
2026-02-19 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.

Elle Haley at Hank's Hair of the Dog Saloon
2026-02-19 17:00 - 20:00
Elle Haley captivates audiences at Hank’s Hair of the Dog Saloon with her mesmerizing musical performances. Known for her dynamic vocals and engaging stage presence, Elle transforms this vibrant Key West hotspot into an unforgettable live music experience. Revel in the lively atmosphere with mojitos, delicious fish tacos, and feel-good vibes at this dog-friendly venue.

Sunset Celebration at Mallory Square
2026-02-19 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
2026-02-19 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.

Reggae Lou and The Kind Buda at Sunset Pier
2026-02-19 17:30 - 20:30
Experience the captivating rhythms of Reggae Lou and The Kind Budz at Sunset Pier, Key West. This dynamic band infuses the air with reggae vibes, setting the perfect tropical ambiance against breathtaking ocean views. Enjoy their vibrant performance as you sip mojitos and savor seafood, creating an unforgettable evening by the water.

Pete & Larry Sloppy 2nds at Sloppy Joe's Bar
2026-02-19 17:30 - 21:30
Catch the dynamic duo Pete & Larry, better known as Sloppy 2nds, at the iconic Sloppy Joe’s Bar. With their infectious humor and lively performances, they guarantee an evening filled with laughter and musical joy. Their engaging presence ensures an unforgettable night at this historic Key West venue.

Filming Sit with Kit Podcast Episodes
2026-02-19 18:00 - 21:00
Join charismatic host Kit in filming Sit with Kit podcast episodes at Angelina’s Pizzeria in Key West. Known for its vibrant energy and engaging conversations, the podcast captures Kit’s unique style and wit. Enjoy a behind-the-scenes experience while savoring delicious NY-style pizza in the heart of Old Town.

Bria Ansara at Berlin's Cocktail Bar
2026-02-19 18:00 - 21:00
Immerse yourself in an unforgettable evening with Bria Ansara at Berlin’s Cocktail Bar. Nestled in Key West’s A&B Lobster House, this hidden gem offers a captivating blend of live jazz by the talented Bria Ansara and vintage ambiance. Indulge in classic cocktails and savor exquisite dishes while soaking in views of the Gulf of Mexico.

Nick Brownell at Schooner Wharf Bar
2026-02-19 18:30 - 22:30
Nick Brownell brings his musical talents to the iconic Schooner Wharf Bar, a beloved Key West venue known for its relaxed atmosphere and stunning dockside views. Revel in Brownell’s captivating performances against a backdrop of live music, fresh seafood, and island cuisine. Experience unforgettable moments with this talented musician in a truly authentic setting.

Catch The Mania Trivia at Brady's Pub
2026-02-19 19:00 - 21:00
Join us at Brady’s Pub for Catch The Mania Trivia, hosted by an enigmatic entertainer who promises a night of fun and excitement. Dive into a lively atmosphere filled with challenging questions, laughter, and camaraderie. Enjoy traditional Irish fare and happy hour specials while testing your knowledge in a captivating setting.

Andy's Cabana Open Mic No Mic Night
2026-02-19 19:00 - 22:00
At Andy’s Cabana Open Mic No Mic Night, the real star is the performer who captivates the audience with raw, acoustic talent. In the heart of Key West’s Bahama Village, entertainers deliver authentic, unamplified performances that resonate through the cozy venue, creating an intimate and unforgettable musical experience.

Joe the Show ~ Rick's Bar Downstairs Stage
2026-02-19 19:00 - 23:00
Experience the electrifying performance of Joe the Show at Rick’s Bar Downstairs Stage in the heart of Key West. This dynamic musician captivates audiences with unforgettable live music, transforming the vibrant nightlife at Rick’s Entertainment Complex into a must-see extravaganza. Don’t miss Joe’s spellbinding set amidst eight renowned bars and endless entertainment.

Magic Of Frank Everhart at Schooner Wharf Bar
2026-02-19 19:00 - 23:59
Experience the enchanting Magic of Frank Everhart at Schooner Wharf Bar in Key West’s Seaport. A master magician, Everhart captivates audiences with mesmerizing illusions and spellbinding performances. Amidst the bar’s laid-back, open-air setting, enjoy his unforgettable act alongside live music, seafood delights, and unforgettable island vibes. Don’t miss this magical evening!

DJ Marty ~ Red Garter Saloon Stage
2026-02-19 19:00 - 2026-02-20 04:00
Experience the electrifying beats of DJ Marty on the Red Garter Saloon Stage at Rick’s Entertainment Complex in Key West. Known for his high-energy sets, DJ Marty masterfully blends genres to keep the crowd dancing all night long. His dynamic performances make for an unforgettable night in this vibrant nightlife hotspot.

Hot Girl Bummer at General Horseplay
2026-02-19 19:00 - 2026-02-20 22:00
Join the excitement at General Horseplay with Hot Girl Bummer, an electrifying entertainer known for her dynamic performances and infectious energy. Located in vibrant Old Town Key West, this lively cocktail bar is the perfect backdrop for an unforgettable night of craft cocktails, live music, and endless fun on Duval Street.

Marty Stuart And His Fabulous Superlatives at Key West Theater
2026-02-19 20:00 - 22:00
Experience the legendary Marty Stuart and His Fabulous Superlatives as they bring their electrifying performance to the historic Key West Theater. Known for his mastery of country music, Marty Stuart captivates audiences with his charismatic stage presence and exceptional musicianship. Don’t miss this intimate concert in a venue that celebrates the transformative power of live entertainment.

Sandra Lee at The Bull & Whistle Bar
2026-02-19 20:00 - 23:59
Sandra Lee captivates audiences at The Bull & Whistle Bar in Key West with her electrifying performances. Known for her dynamic musical talent, Sandra brings energy and charisma to the stage. Her lively sets, perfectly complement the bar’s vibrant atmosphere, making every visit a memorable experience for music lovers and nightlife enthusiasts alike.

DJ Chaka ~ Rick's Bar Upstairs Stage
2026-02-19 20:00 - 2026-02-20 04:00
Experience an electrifying night with DJ Chaka on the Rick’s Bar Upstairs Stage. Known for spinning an eclectic mix of tunes that keep the crowd dancing, DJ Chaka transforms the heart of Old Town Key West into a pulsating haven for music lovers. Don’t miss this dynamic DJ in the largest club south of Miami.

The Tiki Bombs at Tiki House Key West
2026-02-19 20:30 - 23:30
Experience an unforgettable night with The Tiki Bombs at the Tiki House Key West. This electrifying band brings a vibrant, energetic performance, delivering explosive sounds and captivating melodies. Join the fun and immerse yourself in a lively atmosphere, where the rhythm of The Tiki Bombs creates the ultimate party vibe.
