Matthew Curry Band at Hog’s Breath Saloon
The Matthew Curry Band, led by the outstanding guitarist and vocalist Matthew Curry, electrifies audiences with its dynamic blend of blues, rock, and soul. Known…
Free
31 events found.
Events for June 14, 2026
Ongoing
Karaoke at Bobby’s Monkey Bar
Experience a night of vibrant entertainment at Bobby's Monkey Bar in Key West's Old Town, where the star of the show is the charismatic karaoke…
Gemini at Irish Kevin’s Bar
Experience the dynamic performance of Gemini at Irish Kevin's Bar, where this captivating entertainer brings energy and enthusiasm to the lively venue. Nestled in Old…
Free
Fishmonster Max- Daily Party Boat Fishing
Join the Fishmonster Max daily party boat fishing excursion at A & B Marina in Key West's historic seaport. While the details of the entertainer…
$85.00
Yoga on the Beach – Ft Zachary Taylor
Yoga on the Beach at Fort Zachary Taylor in Key West provides a serene setting with historic charm and stunning ocean views. The real highlight…
$20
Tim Bradach at Irish Kevin’s Bar
Tim Bradach energizes Irish Kevin's Bar with his captivating performances, drawing audiences into the vibrant heart of Old Town Key West. Known for his dynamic…
Free
Distillery Tour – Key West Legal Rum Distillery
Explore the Key West First Legal Rum Distillery, nestled in the Historic Seaport. Delight in daily tours and rum samples while embracing vibrant nightlife vibes.…
Free
Mojito Class by Key West Legal Rum Distillery – Min 4 people
Join the Mojito Class at Key West First Legal Rum Distillery, where a charismatic entertainer will guide you through a lively mojito-making experience. Delight in…
$75.00
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Join the Glass Bottom Boat Cruise in Key West for an unforgettable journey beneath the sea. While soaking in vibrant marine life through crystal-clear waters,…
$69.95
Aaron Blumer at Hog’s Breath Saloon
Aaron Blumer, a free-spirited musician, brings his wandering soul to Hog's Breath Saloon in Key West. Known for his spontaneity and exploration, Blumer captivates audiences…
Free
Mylo O’Maolain at Schooner Wharf Bar
Mylo O'Maolain, an Irish-born musician, electrifies audiences at Schooner Wharf Bar in Key West with his vibrant performances. Fusing Irish traditions with modern flair, Mylo…
Free
Farm Open House
Visit the Monroe County Sheriff's Office Animal Farm in Key West for a delightful Farm Open House. Enjoy an engaging day with diverse rescued animals,…
Glass Bottom Boat Cruise – Key West’s Window to the Sea
The Glass Bottom Boat Cruise in Key West offers a unique marine adventure, enhanced by a captivating entertainer who brings the vibrant sea life into…
$69.95
Jeff Harris at Irish Kevin’s Bar
Jeff Harris, a versatile American artist, performs at Irish Kevin's Bar in Key West, captivating audiences with his unique blend of music and comedy. Known…
Free
Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise
Experience an unforgettable adventure with Sunset Watersports' Reef Snorkeling, Dolphin Watch Eco Tour, and Sunset Cruise in Key West. Guided by knowledgeable and engaging staff,…
$79.95
Tea Dance at La Te Da
Experience an unforgettable evening at the Tea Dance at La Te Da in Key West. Enjoy the captivating performances of talented drag queen Randy Roberts,…
Free
Glass Bottom Boat Cruise – Key West’s Window to the Sea
Embark on the Glass Bottom Boat Cruise in Key West for an unforgettable maritime adventure. While the vibrant marine life and crystal-clear waters captivate, it's…
$69.95
Royal South at Hog’s Breath Saloon
Experience an unforgettable night with Royal South at Hog's Breath Saloon in Key West. This dynamic band captivates audiences with their lively music, blending country…
Free
801 Karaoke – Hosted by Jeff
Join the lively atmosphere at 801 Bourbon Bar's Karaoke night hosted by the charismatic Jeff. Nestled in Old Town Key West, Jeff's dynamic energy makes…
Free
World Famous 801 Girls- 5pm Show
The World Famous 801 Girls deliver an electrifying 5pm drag show at the iconic 801 Bourbon Bar in Key West. Known for their charismatic performances…
QMitch Drag Queen Bingo at 22&Co
Experience the vibrant world of QMitch Drag Queen Bingo at 22&Co in Old Town Key West. Known for unforgettable performances, QMitch dazzles with charisma and…
Free
Sunday Jazz at the Gardens
Experience the enchanting Sunday Jazz at the Gardens, where the spotlight shines on renowned jazz performers amidst the lush, tropical backdrop of The Gardens Hotel.…
Free
Caribe of Key West at El Meson de Pepes on Mallory Square
Caribe of Key West enchants audiences at El Meson de Pepe's on Mallory Square. Known for their captivating live performances, Caribe infuses the vibrant Cuban…
Sunset Celebration at Mallory Square
Experience the vibrant Sunset Celebration at Mallory Square in Key West, where the famous cat man and other street performers captivate audiences against a stunning…
Free
Oren Polak at Irish Kevin’s Bar
At Irish Kevin’s Bar, Oren Polak delivers a captivating performance as a versatile musician and band leader. Known for his unique sound and charismatic stage…
Free
80s & 90s Trivia Night
Join us for an unforgettable 80s & 90s Trivia Night at The Retro Room, featuring an engaging entertainer who will take you on a nostalgic…
Free
Tony Baltimore Band at Schooner Wharf Bar
Experience the dynamic energy of Tony Baltimore and The Wilde Awake Band at Schooner Wharf Bar. Known for their captivating performances, Tony Baltimore brings an…
Free
Magic Of Frank Everhart at Schooner Wharf Bar
Experience the enchanting performances of Frank Everhart at Schooner Wharf Bar, where his legendary magic captivates audiences with innovative tricks and compelling storytelling. Renowned for…
Free
Matthew Curry Band at Hog’s Breath Saloon
Experience the electrifying energy of the Matthew Curry Band at Hog's Breath Saloon. Fronted by virtuoso guitarist and singer Matthew Curry, the band delivers captivating…
Free
Karaoke at Bobby’s Monkey Bar
Experience an unforgettable evening at Bobby's Monkey Bar with dynamic karaoke sessions led by an engaging and talented entertainer. Nestled in Key West's Old Town,…
Mylo O’Maolain at Irish Kevin’s Bar
At Irish Kevin's Bar in Key West, Mylo O'Maolain enchants audiences with his vibrant and soulful performances. Irish-born and ******** with charisma, Mylo effortlessly fuses…
Free