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…

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.…

Experience the dynamic talent of Joe The Show at Sloppy Joe's Bar, where his electrifying performances captivate audiences nightly. Known for his engaging stage presence…

Tim Hollohan, a musician from Columbia, South Carolina, captivates audiences almost daily at the iconic Sloppy Joe's Bar in Key West. Known for his energetic…

Experience the captivating sounds of musician Jay Klein at Schooner Wharf Bar. Nestled in Key West's seaport, this open-air venue offers stunning waterfront views, fresh…

Experience the dynamic performances of musician Webb Dillard at Rick's Bar, nestled in Key West's vibrant entertainment scene. Renowned for captivating live music, Webb brings…

Experience an unforgettable evening with Just George at Rick's Bar, located in the vibrant Rick's Entertainment Complex. As a talented musician, Just George captivates audiences…

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…

Join the legendary Preacher Pete at Sloppy Joe's Bar for an unforgettable musical experience. Known for his captivating performances, Pete is a Key West icon…

Experience the captivating performance of Joe The Show at Schooner Wharf Bar in Key West. Known for his dynamic musical talent, Joe brings energy and…

Experience the electrifying performance of musician Aaron Hudgins at Rick's Bar, nestled within Key West’s vibrant Rick's Entertainment Complex. Renowned for his dynamic presence and…

Experience the captivating sounds of The Phil Collins Experience at Key West Theater, where this talented band pays tribute to the legendary musician with unmatched…

Saltwater Saints bring their electrifying performance to the iconic Sloppy Joe's Bar in Key West. Known for their energetic and captivating live shows, this talented…

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,…

Do not fear mistakes. There are none.

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…

Collette Campbell, a talented musician, takes the stage at Sloppy Joe's Bar, captivating audiences with her dynamic performance from 10:00 am to 11:45 am. Renowned…

Brian Roberts captivates audiences at Sloppy Joe's Bar with his dynamic musical performances. Surrounded by the vibrant atmosphere of this historic Key West landmark, Roberts…

Oren Polak enchants audiences at the iconic Schooner Wharf Bar with his captivating music. Set in Key West's historic seaport, this open-air venue features Polak's…

Enjoy an unforgettable evening with the Shanty Hounds at Rick's Bar, nestled in the heart of Old Town Key West. This talented band delivers an…

Experience the electrifying performance of musician Jesse Lee at Rick's Bar, nestled within Key West's largest entertainment hub. Known for his captivating live music, Jesse…

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…

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…

Experience the dynamic tunes of Two in the Pink at Sloppy Joe's Bar. This talented duo features Sid The Bayou Kid on guitar and vocals,…

Gary Hempsey delivers captivating live performances at Schooner Wharf Bar in Key West. Known for his engaging stage presence and diverse musical repertoire, Hempsey enchants…

Experience the vibrant energy of Saltwater Saints at the iconic Sloppy Joe's Bar in Key West. Known for their captivating performances, Saltwater Saints bring a…

Do not fear mistakes. There are none.

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…

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.…

Izzy Zaidman, a passionate musician with his Steel Resonator guitar, fills Sloppy Joe's Bar with the rich sounds of American Roots music. Since moving to…

Experience the captivating melodies of Brian Roberts at Sloppy Joe's Bar, a historic Key West landmark. Renowned for its vibrant atmosphere, the bar comes alive…

Experience the captivating talent of musician Tony Baltimore at the iconic Schooner Wharf Bar. Nestled in Key West's vibrant seaport, Tony's live performances resonate through…

Experience the soulful tunes of Trenton Chandler at Rick's Bar in Key West's vibrant entertainment complex. A gifted country musician and songwriter from Shallowater, Texas,…

Experience the electrifying performance of musician Harley Ray at Rick's Bar, located in the heart of Old Town Key West's vibrant nightlife scene. Known for…

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…

Victoria Leigh captivates audiences at Sloppy Joe's Bar with her dynamic performances and inventive mashups. A Florida Keys–based singer, guitarist, and loop artist, she infuses…

Jeff Clark sets the scene at Schooner Wharf Bar with his captivating musical performances. As a talented musician, he enchants audiences with his rhythmic melodies…

Experience the mesmerizing Magic of Frank Everhart at Schooner Wharf Bar, where this talented magician captivates audiences with his enchanting performances. Set in Key West's…

Experience the electrifying performance of Joe the Show at Rick's Bar, nestled in the heart of Old Town Key West. Known for his captivating stage…

Experience the captivating sounds of Alice Howe & Freebo at the historic Key West Theater. Known for her soulful voice and evocative songwriting, Alice Howe,…

At Comedy Key West Open Mic, entertainers take the spotlight in a lively night of comedy, music, and variety acts. Hosted in the cozy Comedy…

The Juliano Brothers, a dynamic trio from West Deptford, NJ, are set to electrify Sloppy Joe's Bar with their vibrant live performance. Known for their…

Do not fear mistakes. There are none.

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,…

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…

Izzy Zaidman, a dynamic musician, captivates audiences at Sloppy Joe's Bar with his soulful American Roots sound. Since relocating to Key West in 2021, his…

Ross Brown, a talented musician, captivates audiences with his lively performances at Schooner Wharf Bar in Key West. With the picturesque backdrop of the seaport,…

Experience the captivating sounds of Sid The Bayou Kid as he brings his swampy, soulful tunes to Sloppy Joe's Bar in Key West. With over…

Experience the musical magic of Jimmy Buffett at Comedy Key West with Caleb Hogan's one-of-a-kind tribute show, Burgers & Buffett Tunes. Hogan captivates audiences by…

Join talented musician Jeff Harris at Rick's Bar, nestled within Rick's Entertainment Complex in Key West. Experience his captivating live performances in Florida's largest club…

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…

Join Pete & Larry, the dynamic duo known as Sloppy 2nds, at the iconic Sloppy Joe’s Bar for an unforgettable night. With infectious humor and…

Nick Brownwell lights up Schooner Wharf Bar with his captivating performances, blending vibrant rhythms and soulful melodies in Key West's iconic open-air venue. As a…

Join musician Andrew B. at Rick's Bar Downstairs in Rick's Entertainment Complex for a captivating night of live music. Known for his dynamic performances, Andrew…

Experience the mesmerizing Magic of Frank Everhart at the Schooner Wharf Bar in Key West. Known for his captivating performances, Frank Everhart brings enchantment to…

Experience the captivating performance of Scott Kirby, a talented and renowned musician, at the iconic Key West Theater. Known for his engaging stage presence and…

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…

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…

Join us at Comedy Key West for a night of laughter with the legendary Jim Florentine. With a career spanning nearly 25 years, Florentine is…

The Juliano Brothers, a dynamic trio, light up Sloppy Joe's Bar with their exuberant performances, promising to elevate your mood with lively music. From 10:00pm…

Do not fear mistakes. There are none.

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…

Experience the electrifying Rolando Rojas at Sloppy Joe's Bar, where his unparalleled guitar skills and captivating stage presence redefine charisma and talent. As a top…

At Sloppy Joe's Bar, Tim Hollohan captivates audiences with his vibrant stage presence and interactive performances. Originally from Columbia, South Carolina, Tim's dynamic musical talents…

Experience the captivating performance of musician Wynn Taylor at Rick's Bar Downstairs Stage in Rick's Entertainment Complex. Known for his electrifying presence and musical prowess,…

At the historic Schooner Wharf Bar in Key West, experience the captivating sounds of musician Tony Baltimore. Known for his engaging performances, Tony brings a…

Experience the electrifying performance of Joe the Show at Rick's Bar Downstairs Stage in Key West's premier entertainment complex. Known for his dynamic musical talent,…

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…

Experience the uproarious antics of Pete & Larry Sloppy 2nds at Sloppy Joe's Bar, where this dynamic duo delivers nights filled with laughter and music.…

Join comedian James Scott Patterson at Comedy Key West for Hemingway in a Funny Way, where he hilariously explores the zanier side of Ernest Hemingway's…

Experience Dallas Remington live at Durty Harry's Stage in Rick's Entertainment Complex, Key West's iconic nightlife venue. Known for her captivating performances, Dallas brings a…

Experience the electrifying sounds of the Jeff Clark Band at the Schooner Wharf Bar, Key West's beloved open-air venue. Known for his captivating performances, Jeff…

Experience the mesmerizing Magic of Frank Everhart at Schooner Wharf Bar. Renowned for his captivating illusions and charismatic performance, Frank Everhart enchants audiences in this…

Enjoy an unforgettable night with Joe the Show at Rick's Bar, part of Key West's largest entertainment complex. Known for electrifying performances, Joe The Show…

Experience the captivating sounds of The Janzen Boys at the Key West Theater's Back Stage Listening Room. Renowned for their acoustic brilliance, The Janzen Boys…

Join us at Comedy Key West for a night of laughter with Jim Florentine, a comedic powerhouse renowned for his 25-year career across multiple media…

Join the Juliano Brothers, a vibrant trio from West Deptford, NJ, at Sloppy Joe's Bar, Key West. Known for infectious energy and uplifting tunes, they…

Do not fear mistakes. There are none.

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…

Justin Angelo captivates audiences at Sloppy Joe's Bar in Key West with his unique blend of folk and blues guitar. Known in Lancaster, PA, and…

Jeff Clark, an engaging musician, brings his lively performances to the iconic Sloppy Joe's Bar in Key West. Known for its vibrant atmosphere and rich…

Nick Brownwell captivates audiences at Schooner Wharf Bar with his vibrant musical performances. His energetic presence and diverse repertoire transform the historic waterfront venue into…

Zack Seemiller, a charismatic musician known for his engaging performances, takes the stage at Rick's Bar Downstairs in Rick's Entertainment Complex. Located in Key West's…

Experience the vibrant spirit of Key West with acclaimed musician and Buffett historian Caleb Hogan at Comedy Key West's Burgers & Buffett Tunes. Hogan dons…

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…

Experience the vibrant sounds of the Jerico Rockabilly Duo at Sloppy Joe's Bar, a legendary Key West venue since 1937. Known for their energetic performances,…

Experience the vibrant sounds of the Jeff Clark Band at Schooner Wharf Bar, a renowned Key West venue. Known for their lively performances and dynamic…

Experience the enchanting Magic of Frank Everhart at Schooner Wharf Bar in Key West. This master magician captivates audiences with spellbinding performances set against the…

Join us at Comedy Key West for a night of laughter with Jim Florentine, a seasoned comedian with nearly 25 years in the industry. Known…

Experience an unforgettable night with the talented musician Elle Haley at Rick's Bar Downstairs Stage, part of Key West's iconic Rick's Entertainment Complex. As she…

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…

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…

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…

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…

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…

Join 80s & 90s Trivia Night at The Retro Room in Old Town, Key West, where an engaging entertainer takes you on a nostalgic journey.…