Name: Ambitious Morning Runners
Start: 2026-02-19T06:00:00-05:00
End: 2026-02-19T07:30:00-05:00

February 2026
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Kristen McNamara at The Bull & Whistle Bar

February 18 @ 8:00 pm - 11:59 pm

Experience the mesmerizing talent of Kristen McNamara at The Bull & Whistle Bar. Known for her captivating performances, Kristen brings a unique blend of soulful…

Free

Categories:
Bars and Clubs Concert Entertainment Live Music Music Nightlife
Tags:
balcony seating Bars Cigar Friendly entertainment happy hour Live Music Musician Nightclubs nightlife potent cocktails
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DJ Duke ~ Rick’s Bar Upstairs Stage

February 18 @ 8:00 pm - February 19 @ 4:00 am

Experience the electrifying sounds of DJ Duke at Rick's Bar Upstairs Stage, where his vibrant beats set the perfect mood for an unforgettable night. Known…

Free

Categories:
Club Night DJ Electronic Nightlife Nightlife & Social Party
Tags:
Dance Club DJ entertainment Fun Live Music nightlife
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Marshall Morlock Band at General Horseplay

February 18 @ 8:00 pm - February 19 @ 11:00 pm

Experience the electrifying performances of the Marshall Morlock Band at General Horseplay, an iconic venue on Duval Street in Old Town Key West. Known for…

Free

Categories:
Concert Live Music Music Nightlife Party
Tags:
Band Cocktail Bar Craft Cocktails entertainment Good Times Late Night Music Live Music nightlife vibrant atmosphere
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Bone Island Haunted Pub Crawl & Ghost Tour

February 18 @ 8:30 pm - 10:30 pm

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…

$29.95

Categories:
Ghost Hunt Immersive Experience Nightlife Paranormal & Mystery Storytelling Tours & Experiences Walking Tour
Tags:
Atmospheric Walk Ghost Tour Haunted Immersive Narration Spine Tingling Tales storytelling Thrilling Experience
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CRANK SINATRA~ Durty Harry’s Stage

February 18 @ 8:30 pm - February 19 @ 2:00 am

Join Krank Sinatra on Durty Harry's Stage at Rick's Entertainment Complex in Key West's vibrant Old Town. Known for their electrifying performances, Krank Sinatra delivers…

Free

Categories:
Club Night Concert Live Music Music Nightlife
Tags:
Bars Dance Club entertainment Fun Karaoke Live Music nightlife People Watching Rock Band
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Andy Sands at Hank’s Hair of the Dog Saloon

February 18 @ 9:00 pm - 11:45 pm

Experience the captivating performance of musician Andy Sands at Hank's Hair of the Dog Saloon in Key West. Known for his engaging stage presence and…

Free

Categories:
Concert Food & Drink Live Music Music Nightlife Outdoor Venue
Tags:
Bars Dog Friendly Event Rentals Food Truck happy hour Live Music Musician nightlife Outdoor Venue Restaurants VIP Seating
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Alex Anthony Band at Hog’s Breath Saloon

February 18 @ 9:00 pm - February 19 @ 1:00 am

Experience the electrifying Alex Anthony Band live at Hog's Breath Saloon, where Alex's dynamic performance lights up Key West's favorite dive bar. Known for their…

Free

Categories:
Concert Live Music Music Nightlife Party
Tags:
Conch Fritters Dancing Dive Bar entertainment Event key lime pie Live Music Musician nightlife outdoor seating Performance Pub Food Smoked Fish Dip
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Karaoke at Bobby’s Monkey Bar

February 18 @ 9:30 pm - February 19 @ 3:00 am

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,…

Categories:
Karaoke Nightlife Nightlife & Social Party
Tags:
entertainment Evening entertainment.fun evening happy hour Karaoke Lively Atmosphere nightlife Pool Table tourists
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Naked Karate Girls at Sloppy Joe’s Bar

February 18 @ 10:00 pm

Experience the electrifying energy of the Naked Karate Girls, the ultimate party band hailing from Cincinnati. Known as The Best Band in the Galaxy, their…

Free

Categories:
Concert Entertainment Live Music Music Nightlife Party
Tags:
American Cuisine Band Performance Cocktails entertainment Epic Experience Historic Landmark Live Music Lively Atmosphere nightlife People Watching Professional Musicians
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Kari Wolf at Irish Kevin’s Bar

February 18 @ 10:00 pm - February 19 @ 2:00 am

Experience the electrifying performance of Kari Wolf at Irish Kevin’s Bar in Key West. Known for her dynamic stage presence and musical talent, Kari captivates…

Free

Categories:
Concert Live Music Music Nightlife
Tags:
Audience participation Craft beers entertainment Live Music Lively Atmosphere Musician Pub grub
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Karaoke w/ Davis ~ Rick’s Bar Downstairs Stage

February 18 @ 11:00 pm - February 19 @ 4:00 am

Join Davis for an unforgettable night of karaoke at Rick's Bar Downstairs Stage in Old Town Key West. Known for his dynamic energy and engaging…

Free

Categories:
Club Night Karaoke Live Music Nightlife Nightlife & Social
Tags:
Bars Bartenders Dance Club entertainment Fun Karaoke Live Music nightlife People Watching
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Ambitious Morning Runners

February 19 @ 6:00 am - 7:30 am

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,…

Free

Categories:
Community Event Outdoor Adventure Run Walk Scenic & Nature Sports & Fitness
Tags:
Attractions Biking Fishing Memorials Ocean Views Peaceful Atmosphere Scenic Spot Sunrise Sunset Tourist Attraction Walking Waterfronts

February 2026