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Dmtb at Key West Theater
2026-02-25 20:00 - 22:00 (America/New_York)
Experience the dynamic performance of Dmtb at the Key West Theater, a beautifully restored historic venue. Known for their captivating acoustic sets and engaging stage presence, Dmtb delivers an unforgettable concert experience. Don’t miss this chance to see a top-tier performer in an intimate setting that highlights the transformative power of music.

Kristen McNamara at The Bull & Whistle Bar
2026-02-25 20:00 - 23:59
Experience the enchanting performance of Kristen McNamara at The Bull & Whistle Bar. Known for her captivating voice and dynamic stage presence, Kristen enthralls audiences with a mix of popular hits and original songs. Enjoy her unforgettable live music while basking in the vibrant atmosphere of Key West’s iconic nightlife spot.

DJ Duke ~ Rick's Bar Upstairs Stage
2026-02-25 20:00 - 2026-02-26 04:00
Experience an unforgettable night with DJ Duke at Rick’s Bar Upstairs Stage. Nestled in the vibrant atmosphere of Key West’s largest club, DJ Duke electrifies the crowd with his dynamic beats and energetic mixes. Dive into the lively scene of Rick’s Entertainment Complex for an exhilarating evening of music and dance.

Marshall Morlock Band at General Horseplay
2026-02-25 20:00 - 2026-02-26 23:00
Experience an unforgettable night with the Marshall Morlock Band at General Horseplay. Known for their dynamic performances, this talented band brings a unique energy to Old Town Key West. Enjoy rhythmic tunes and eclectic vibes while savoring craft cocktails in a lively, laid-back atmosphere, perfect for music and entertainment lovers.

Bone Island Haunted Pub Crawl & Ghost Tour
2026-02-25 20:30 - 22:30
Join the Bone Island Haunted Pub Crawl & Ghost Tour for an enthralling evening led by a charismatic entertainer. With captivating narration, journey through America’s most haunted destinations, experiencing spine-tingling tales and local ghost lore. Enjoy a lively, suspenseful atmosphere, complete with a keepsake tour T-shirt, perfect for thrill-seeking adults.

CRANK SINATRA~ Durty Harry's Stage
2026-02-25 20:30 - 2026-02-26 02:00
Experience the electrifying performance of Krank Sinatra at Durty Harry’s Stage in Rick’s Entertainment Complex. This high-energy band delivers an unforgettable show, blending captivating rock tunes with charismatic stage presence. Immerse yourself in Key West’s vibrant nightlife, enjoying Krank Sinatra’s dynamic sound among talented bartenders and spirited crowds for an unmatched entertainment experience.

Pierce August at Hank's Hair of the Dog Saloon
2026-02-25 21:00 - 23:45
Experience the captivating performances of Pierce August at Hank’s Hair of the Dog Saloon in vibrant Key West. With electrifying live music, Pierce August transforms the night, offering unforgettable entertainment. Enjoy mojitos and savory fish tacos under the open sky, making it an ideal setting for music lovers and nightlife seekers alike.

Mike Stone Band at Hog's Breath Saloon
2026-02-25 21:00 - 2026-02-26 01:00
The Mike Stone Band brings electrifying live music to the vibrant Hog’s Breath Saloon in Key West. Known for their dynamic performances, the band creates an energetic atmosphere perfect for dancing. Enjoy the show on the saloon’s outdoor patio while indulging in local favorites like smoked fish dip and conch fritters.

Karaoke at Bobby's Monkey Bar
2026-02-25 21:30 - 2026-02-26 03:00
Join the vibrant scene at Bobby’s Monkey Bar in Old Town Key West for an unforgettable karaoke night. The spirited entertainer keeps the energy high, ensuring everyone has a blast. Dive into the lively atmosphere as you sing your heart out amidst a fun-loving crowd. Don’t miss the daily happy hour!

New Normal at Sloppy Joe's Bar
2026-02-25 22:00
Experience the electrifying sounds of New Normal at Sloppy Joe’s Bar, a historic Key West landmark on Duval Street. From 10:00 pm to 2:00 am, this dynamic band from Bethlehem, PA, delivers unforgettable live performances. Enjoy lively music, delicious American fare, and a vibrant atmosphere at this must-visit destination.

Karaoke w/ Davis ~ Rick's Bar Downstairs Stage
2026-02-25 23:00 - 2026-02-26 04:00
Join Davis for an unforgettable evening of karaoke at Rick’s Bar Downstairs Stage, located in the heart of Old Town Key West. Known for his engaging personality and dynamic performances, Davis will have you singing along and enjoying every moment. Experience the vibrant nightlife at Key West’s largest club with endless fun and entertainment.

Ambitious Morning Runners
2026-02-26 06:00 - 07:30
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, the true star is the breathtaking sunrise over the ocean. Enjoy peaceful surroundings and the serene beauty of this scenic spot as you energize your morning routine.

Fishmonster Max- Daily Party Boat Fishing
2026-02-26 08:00 - 13:00
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
2026-02-26 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.

Prime of Life Yoga with Monica Haskell
2026-02-26 10:00 - 11:15
Join Monica Haskell for Prime of Life Yoga, a rejuvenating experience amidst the serene beauty of the Key West Tropical Forest & Botanical Garden. Known for her inspirational teaching style, Monica guides participants through tailored yoga sessions focused on enhancing vitality and well-being, offering a refreshing escape in a tranquil natural setting.

Izzy Zaidman at Sloppy Joe's Bar
2026-02-26 10:00 - 11:45
Izzy Zaidman, a talented musician, electrifies the historic Sloppy Joe’s Bar in Key West with his Steel Resonator guitar. Since moving in 2021, he’s captivated audiences with his American Roots sound, creating an unforgettable experience amid the lively atmosphere of this iconic Duval Street venue. A must-see entertainer for music lovers.

Trenton Chandler ~ Rick's DownStairs Stage
2026-02-26 11:00 - 15:00
Experience the heartfelt tunes of Trenton Chandler at Rick’s DownStairs Stage in Key West. A Shallowater, Texas native, Trenton channels the spirit of legends like Elvis and Waylon Jennings in his authentic country performances. Known for his soulful songwriting and energetic presence, he transforms nights into memorable musical journeys.

Distillery Tour - Key West Legal Rum Distillery
2026-02-26 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
2026-02-26 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
2026-02-26 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.

Sid The Bayou Kid at Sloppy Joe's Bar
2026-02-26 12:00 - 16:45
Sid The Bayou Kid, a charismatic musician from Thibodaux, LA, captivates audiences with his swamp-infused sound. With over 30 years of experience, Sid brings his electrifying performances to Sloppy Joe’s Bar in Key West, turning the historic venue into a lively celebration of music, appealing to both locals and tourists alike.

Ross Brown at Schooner Wharf Bar
2026-02-26 12:00 - 17:00
Ross Brown brings his musical talents to the Schooner Wharf Bar, a beloved Key West venue renowned for its vibrant live music scene. In this open-air, waterfront setting, Ross captivates audiences with his engaging performances, adding a unique flair to the bar’s laid-back atmosphere. Experience unforgettable tunes alongside breathtaking dockside views.

Dan Harvey at Hog's Breath Saloon
2026-02-26 12:00 - 2026-02-27 16:00
Dan Harvey, a talented musician, captivates audiences at the vibrant Hog’s Breath Saloon in Key West’s Mallory Square District. Known for his engaging performances, Dan brings live music to the lively dive bar setting. Enjoy the energetic outdoor patio ambiance while savoring pub favorites and experiencing Dan’s unforgettable tunes.

Marjory Lee at Sunset Pier
2026-02-26 13:00 - 16:00
Experience the enchanting sounds of Marjory Lee at Sunset Pier, where her captivating performances enhance Key West’s vibrant atmosphere. Nestled at the Ocean Key Resort, Sunset Pier offers stunning sunsets and delightful waterfront dining. Enjoy tropical seafood, refreshing mojitos, and Marjory’s live music, creating unforgettable evenings at this iconic location.

Tony Baltimore at Hank's Hair of the Dog Saloon
2026-02-26 13:00 - 16:00
Tony Baltimore, a captivating musician, brings his vibrant performances to Hank’s Hair of the Dog Saloon in Key West. Known for his engaging live sets, Tony transforms the saloon into a lively music haven. Enjoy his dynamic sound while savoring mojitos and fish tacos, making for an unforgettable night on Duval Street.

Truman Waterfront Farmers Market
2026-02-26 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.

Glass Bottom Boat Cruise - Key West's Window to the Sea
2026-02-26 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.

Jefff Clark at Tiki House Key West
2026-02-26 14:00 - 17:00
Join us at the Tiki House Key West for an unforgettable musical experience with Jefff Clark. A talented musician known for his captivating performances, Jefff brings an vibrant energy to the stage, combining diverse melodies and engaging rhythms. Don’t miss the chance to enjoy his extraordinary artistry in a lively atmosphere.

David Warren at The Bull & Whistle Bar
2026-02-26 14:00 - 18:00
Experience an unforgettable night at The Bull & Whistle Bar with David Warren, a captivating entertainer known for his dynamic performances. His music creates an electric atmosphere in this lively Key West venue, nestled on Duval Street. Enjoy potent cocktails and vibrant energy as Warren’s tunes elevate the iconic nightlife experience.
