HaveFun.NOW

Fishmonster Max- Daily Party Boat Fishing
2026-02-25 08:00 - 13:00 (America/New_York)
Fishmonster Max offers a thrilling daily party boat fishing experience in Key West, perfect for families and groups. With its stable twin hulls, the boat ensures a smooth, comfortable ride. Dive into the fun-filled fishing adventure where every trip feels like a celebration at sea, creating unforgettable memories.

Yoga on the Beach - Ft Zachary Taylor
2026-02-25 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
2026-02-25 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.

Izzy Zaidman at Sloppy Joe's Bar
2026-02-25 10:00 - 11:45
Izzy Zaidman, a talented musician who relocated to Key West in 2021, captivates audiences at Sloppy Joe’s Bar with his Steel Resonator guitar. Bringing the rich sound of American Roots music to life, Izzy weaves soulful melodies into the vibrant atmosphere of this historic venue on Duval Street, creating unforgettable experiences.

Distillery Tour - Key West Legal Rum Distillery
2026-02-25 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
2026-02-25 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
2026-02-25 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.

Wednesday Filet Day at Mary Ellen's
2026-02-25 11:30 - 2026-02-26 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.

Michael Corleto ~ Rick's Bar Downstairs Stage
2026-02-25 12:00 - 15:00
Experience the dynamic performance of Michael Corleto at Rick’s Bar Downstairs Stage, located in Key West’s premier entertainment hub. Renowned for his captivating stage presence and versatile musical repertoire, Michael delivers an electrifying evening of live music. Dive into the vibrant energy and nightlife at Rick’s Entertainment Complex.

Brian Roberts at Sloppy Joe's Bar
2026-02-25 12:00 - 16:45
Experience the captivating performances of Brian Roberts at Sloppy Joe’s Bar, a renowned Key West landmark. Known for his dynamic presence and musical prowess, Roberts energizes the crowd with every note. Enjoy the infectious rhythms and lively atmosphere as you savor classic American fare and cocktails in this historic venue, steeped in entertainment tradition.

Tony Baltimore at Schooner Wharf Bar
2026-02-25 12:00 - 17:00
Tony Baltimore captivates audiences at Schooner Wharf Bar with his dynamic musical performances. Nestled in Key West’s historic seaport, this open-air gem provides picturesque dockside views and a relaxed atmosphere. Tony’s engaging energy and musical talent make every visit memorable, blending seamlessly with the bar’s vibrant spirit and island charm.

Andy Mauerman at Hog's Breath Saloon
2026-02-25 12:00 - 2026-02-26 16:00
Experience the vibrant sounds of musician Andy Mauerman at Hog’s Breath Saloon. Mauerman captivates audiences with his energetic performances, making each visit unforgettable. Enjoy his live music on the saloon’s outdoor patio in Key West’s Mallory Square District, where lively melodies complement the bar’s delicious food and lively atmosphere. Don’t miss this musical treat!

Claire Finley at Sunset Pier
2026-02-25 13:00 - 16:00
Claire Finley enchants Sunset Pier with her captivating live music, creating a vibrant atmosphere against the stunning backdrop of Key West’s famous sunsets. Her soulful melodies and charismatic performance complement the pier’s tropical ambiance, offering guests an unforgettable evening of entertainment, delicious seafood, and refreshing mojitos, all with breathtaking views of Mallory Square.

Shastina Chiles at Hank's Hair of the Dog Saloon
2026-02-25 13:00 - 16:00
Shastina Chiles, a talented musician, brings her vibrant energy and soulful tunes to Hank’s Hair of the Dog Saloon in Key West. Known for captivating performances, Shastina enchants audiences in this lively, dog-friendly venue. Enjoy her live music alongside mojitos and fish tacos, making for an unforgettable night on Duval Street.

Glass Bottom Boat Cruise - Key West's Window to the Sea
2026-02-25 13:30 - 16:00
Experience the magic of Key West’s marine life aboard the Glass Bottom Boat. While our knowledgeable captain and crew guide you on an informative eco-tour, the true star is the vibrant underwater world. Discover the majestic elkhorn coral and over 300 fish species through special windows to the reef, a breathtaking journey usually reserved for divers.

Mic Smith at Tiki House Key West
2026-02-25 13:30 - 16:30
Mic Smith brings his captivating musical performance to Tiki House Key West, enchanting audiences with his dynamic stage presence and exceptional talent. Known for his engaging and soulful artistry, Mic delivers an unforgettable experience in the vibrant ambiance of this iconic venue, making it a must-see event for music lovers.

Mac Calhoun at The Bull & Whistle Bar
2026-02-25 14:00 - 18:00
Mac Calhoun captivates audiences at The Bull & Whistle Bar with his dynamic musical performances. Nestled on Key West’s vibrant Duval Street, this lively venue offers open-air charm, perfect for enjoying Mac’s soulful tunes. As you sip potent cocktails and savor cigars, Mac’s talent ensures an unforgettable night of entertainment and atmosphere.

Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise
2026-02-25 15:00 - 18:30
Join us for a vibrant aquatic adventure in Key West with our Reef Snorkeling, Dolphin Watch Eco Tour, and Sunset Cruise. Our passionate and friendly staff are the heart of the experience, guiding you through mesmerizing dolphin encounters and breathtaking snorkeling. As the sun sets, unwind with a refreshing drink on our luxurious vessel.

Harley Ray ~ Rick's Bar Downstairs Stage
2026-02-25 15:00 - 19:00
Experience the electrifying performance of Harley Ray at Rick’s Bar Downstairs Stage. Known for captivating audiences with a unique musical style, Harley Ray delivers an unforgettable live music experience at Key West’s largest entertainment venue. Join us for an exciting night filled with vibrant tunes and lively energy that will keep you dancing.

Glass Bottom Boat Cruise - Key West's Window to the Sea
2026-02-25 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
2026-02-25 16:30 - 2026-02-26 20:30
Experience the vibrant sounds of Mark Teague and Rick Fusco at Hog’s Breath Saloon in Key West. Known for their captivating performances, these talented musicians bring energy and charisma to this lively dive bar, providing the perfect backdrop to enjoy delicious pub delights and refreshing drinks on the outdoor patio. Don’t miss an unforgettable evening of live music!

World Famous 801 Girls- 5pm Show
2026-02-25 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.

Jay Bangles at Tiki House Key West
2026-02-25 17:00 - 20:00
Experience the captivating sounds of musician Jay Bangles at Tiki House Key West. Known for his vibrant performances, Jay blends various musical styles to create an unforgettable night. Join him for an evening of lively entertainment and tropical vibes at this iconic Key West venue. Don’t miss this musical delight!

Kari Wolf and Gigi at Hank's Hair of the Dog Saloon
2026-02-25 17:00 - 20:00
Kari Wolf captivates audiences with soulful melodies and dynamic performances at Hank’s Hair of the Dog Saloon. Known for her engaging stage presence, Kari enchants with her musical talent, creating unforgettable nights in Key West’s vibrant nightlife scene. Enjoy her live music alongside drinks and delectable bites at this dog-friendly venue.

Sunset Celebration at Mallory Square
2026-02-25 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
2026-02-25 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.

Jerica Rockabilly Quartet at Sunset Pier
2026-02-25 17:30 - 20:30
Experience the electrifying sounds of the Jerica Rockabilly Quartet at Sunset Pier. This dynamic band brings a fresh twist to classic rockabilly tunes, captivating audiences with high-energy performances amidst the stunning backdrop of Key West’s waterfront. Enjoy an unforgettable evening of live music, vibrant atmosphere, and mesmerizing sunsets at this iconic venue.

Victoria Leigh at Sloppy Joe's Bar
2026-02-25 17:30 - 21:30
Victoria Leigh, a dynamic Florida Keys–based musician, captivates audiences at Sloppy Joe’s Bar with her energetic performances and inventive mashups. As a singer, guitarist, and loop artist, Leigh skillfully blends reggae, pop, and rock genres, performing over 350 shows annually. Her vibrant style makes every night unforgettable at this historic Key West venue.
