Name: Mylo O’maolain at Schooner Wharf Bar
Start: 2026-02-15T12:00:00-05:00
End: 2026-02-15T17:00:00-05:00

February 2026
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Karaoke w/ Jason ~ Rick’s Bar Downstairs Stage

February 14 @ 11:59 pm - February 15 @ 4:00 am

Join Jason for an unforgettable karaoke night at Rick's Bar on the Downstairs Stage. As a charismatic entertainer, Jason brings energy and excitement, transforming the…

Free

Categories:
Club Night Karaoke Live Music Nightlife Nightlife & Social
Tags:
Bars Dance Club entertainment Fun Karaoke Live Music lounges Nightclubs nightlife People Watching
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Fishmonster Max- Daily Party Boat Fishing

February 15 @ 8:00 am - 1:00 pm

Join Fishmonster Max for an unforgettable daily party boat fishing adventure in Key West, where entertainment meets the thrill of fishing. Whether it's a family…

$85.00

Categories:
Family Event Fishing Charter Group Trip Outdoor Adventure Tours & Experiences Water-Based Tours
Tags:
Boating Enthusiasts Comfortable Ride Corporate Charters Family Trip Fishing Experience Group Trips Outdoor & Recreation Party Boat
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Yoga on the Beach – Ft Zachary Taylor

February 15 @ 8:15 am - 9:45 am

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…

$20

Categories:
Fitness Class Nature Walk Outdoors Adventure Wellness Wellness & Mindfulness Yoga
Tags:
Beach Civil War History Nature Trails Outdoor Activities Snorkeling Sunset Views Tourist Attraction Yoga
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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

February 2026