Name: Sid Ordoyne at Hank’s Hair of the Dog Saloon
Start: 2026-02-15T13:00:00-05:00
End: 2026-02-15T16:00:00-05:00

February 2026
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Chris Thomas at Sloppy Joe’s Bar

February 15 @ 10:00 am - 11:45 am

Renowned musician Chris Thomas electrifies audiences at Sloppy Joe's Bar, a historic Key West landmark. Known for his captivating performances, Thomas brings a dynamic blend…

Free

Categories:
Bar Crawl Concert Entertainment Live Music Music Nightlife
Tags:
American Cuisine Attractions Bar Cocktails entertainment Historic Landmark Live Music Musician People Watching
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Bradd Shadduck at Irish Kevin’s Bar

February 15 @ 11:00 am - 2:30 pm

Experience the dynamic energy of musician Bradd Shadduck at Irish Kevin’s Bar in the heart of Key West's Old Town. Known for his engaging performances…

Free

Categories:
Concert Entertainment Live Music Music Nightlife
Tags:
Audience participation Craft beers entertainment Live Music Lively Atmosphere Musician Pub grub
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Mojito Class by Key West Legal Rum Distillery – Min 4 people

February 15 @ 11:00 am - 5:00 pm

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…

$75.00

Categories:
Class Cocktail Event Food & Drink Tours & Experiences Workshop
Tags:
Alcohol Tasting Bartending Skills beverage Experience Cocktail Making Fun Activity Handmade Cocktails Mojito Class Mojito Crafting
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Distillery Tour – Key West Legal Rum Distillery

February 15 @ 11:00 am - 5:00 pm

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…

Free

Categories:
Food & Drink Historic Tour Rum Tasting Tours & Experiences Walking & Guided Tours
Tags:
Craft Distillery Free Tours Gluten Free Rum Historic Site Homemade Cocktails Mojito Making Rum Distillery Rum Tasting Seaport History Spirit Sampling Sugar Cane Rum Tourist Attraction Vegan Friendly
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Glass Bottom Boat – Key West’s Window to the sea

February 15 @ 11:30 am - 2:00 pm

$69.95
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Glass Bottom Boat – Key West’s Window to the sea

February 15 @ 11:30 am - 2:00 pm

Embark on the Glass Bottom Boat - Key West's Window to the Sea tour for an unforgettable experience with Captain and crew as your guides.…

$69.95

Categories:
Boat Tour Eco Tour Scenic & Nature Tours & Experiences Water-Based Tours Wildlife Tour
Tags:
aquatic adventure coral reef eco-tour jet skiing marine life parasailing scuba diving Snorkeling tropical paradise underwater vistas
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Harley Ray ~ Rick’s Downstairs Stage

February 15 @ 12:00 pm - 4:00 pm

Experience the electrifying performance of musician Harley Ray at Rick's Downstairs Stage in Old Town Key West. Known for his dynamic sound and captivating presence,…

Free

Categories:
Club Night Live Music Music Nightlife Party
Tags:
Bars Dance Club entertainment Fun Karaoke Live Music Musician Nightclubs nightlife
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John LaMere at Sloppy Joe’s Bar

February 15 @ 12:00 pm - 4:45 pm

John LaMere has captivated audiences at Sloppy Joe's Bar since 2011, with his dynamic performances and extensive song list. A weekly fixture on the iconic…

Free

Categories:
Concert Entertainment Live Music Music Nightlife
Tags:
American Cuisine Bar Cocktails entertainment Historic Landmark Live Music Musician People Watching Restaurant
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Mylo O’maolain at Schooner Wharf Bar

February 15 @ 12:00 pm - 5:00 pm

Experience the captivating sounds of Mylo O'Maolain at Schooner Wharf Bar, a lively open-air venue in Key West. Known for his dynamic performances, Mylo enchants…

Free

Categories:
Concert Food & Drink Live Music Music Nightlife
Tags:
entertainment happy hour island cuisine laid back Live Music Local atmosphere Musician seafood Waterfront
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Aaron Blumer at Hog’s Breath Saloon

February 15 @ 12:00 pm - February 16 @ 4:00 pm

Experience an unforgettable evening with musician Aaron Blumer at Hog's Breath Saloon, located in Key West's bustling Mallory Square District. Known for his captivating performances,…

Free

Categories:
Concert Live Music Music Nightlife
Tags:
Dive Bar entertainment Live Music live performance Musician Outdoor Entertainment Pub Food
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Sheldon Benton at Sunset Pier

February 15 @ 1:00 pm - 4:00 pm

Sheldon Benton captivates audiences at Sunset Pier, Key West, with his dynamic live performances. Known for his engaging stage presence and versatile repertoire, Benton adds…

Free

Categories:
Concert Food & Drink Live Music Music Nightlife Waterfront Dining
Tags:
Caribbean cuisine entertainment Live Music Seafood Delights Sunset Views tropical vibes vibrant atmosphere Waterfront Experience
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Sid Ordoyne at Hank’s Hair of the Dog Saloon

February 15 @ 1:00 pm - 4:00 pm

Sid Ordoyne brings his captivating musical talent to Hank's Hair of the Dog Saloon, enchanting guests with his soulful performances. Set in the vibrant ambiance…

Free

Categories:
Concert Food & Drink Happy Hour Live Music Music Nightlife
Tags:
Dog Friendly Food Truck happy hour Live Music nightlife Outdoor Venue

February 2026