Name: Pierce August at Hank’s Hair of the Dog Saloon
Start: 2026-02-15T17:00:00-05:00
End: 2026-02-15T20:00:00-05:00

February 2026
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Jeff Harris at Irish Kevin’s Bar

February 15 @ 2:30 pm - 6:00 pm

Experience the dynamic performance of Jeff Harris at Irish Kevin’s Bar in Key West. Known for his engaging live music, Jeff captivates audiences with his…

Free

Categories:
Concert Live Music Music Nightlife
Tags:
Audience participation Craft beers entertainment Live Music Lively Atmosphere Musician Pub grub
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Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise

February 15 @ 3:00 pm - 6:30 pm

Join an exhilarating aquatic adventure with the Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise. Led by our passionate and expert staff, enjoy thrilling…

$79.95

Categories:
Boat Tour Dolphin Tour Eco Tour Snorkeling Tour Sunset Cruise Tours & Experiences
Tags:
aquatic adventure coral reef dolphin watch eco-tour marine life Snorkeling sunset cruise Sunset Views watersports
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Tea Dance at La Te Da

February 15 @ 4:00 pm - 6:00 pm

Experience a vibrant evening at Tea Dance at La Te Da, featuring the incredible Randy Roberts. Delight in raunchy drag performances and masterful impersonations of…

Free

Categories:
Arts & Performance Club Night Dance Performance Drag Show Live Entertainment Nightlife Party
Tags:
Attractions Bars cabaret shows drag performances hotels impersonations landmarks Live Entertainment live music venues nightlife over-21s only Restaurants tea dance theaters
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Glass Bottom Boat – Key West’s Window to the sea

February 15 @ 4:00 pm - 7:30 pm

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

February 15 @ 4:00 pm - 7:30 pm

Join us on the Glass Bottom Boat tour in Key West, where our charismatic captain and crew bring the underwater world to life. As you…

$69.95

Categories:
Boat Tour Eco Tour Scenic & Nature Tours & Experiences Water-Based Tours Wildlife Tour
Tags:
coral reef eco-tour glass bottom boat jet skiing marine ecosystems marine life parasailing Snorkeling tourism tropical paradise underwater vistas vacation
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Trenton Chandler ~ Rick’s Bar Downstairs Stage

February 15 @ 4:00 pm - 8:00 pm

Catch Trenton Chandler, a talented country musician and songwriter from Shallowater, Texas, live on the Rick's Bar Downstairs Stage. Influenced by legends like Elvis and…

Free

Categories:
Club Night Concert Live Music Music Nightlife
Tags:
Bars Country Music Dance Club entertainment Karaoke Live Music Musician Nashville nightlife rock bands Songwriter Texas
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801 Karaoke – Hosted by Jeff

February 15 @ 4:00 pm - 9:00 pm

Join the unforgettable Sunday karaoke at 801 Bourbon Bar, hosted by the charismatic Jeff. Known for his engaging personality, Jeff takes center stage, making each…

Free

Categories:
Karaoke LGBT Friendly Nightlife Nightlife & Social Party
Tags:
Cabaret Drag Shows entertainment Gay Bar Karaoke LGBT Friendly nightlife
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Sheldon Benton at Hog’s Breath Saloon

February 15 @ 4:30 pm - February 16 @ 8:30 pm

Sheldon Benton captivates audiences at Hog's Breath Saloon with his electrifying live performances. Known for his dynamic sound, Sheldon infuses the lively Key West atmosphere…

Free

Categories:
Concert Live Music Nightlife Nightlife & Social
Tags:
Bar Dance Dive Bar Food and Drink Live Music nightlife Outdoor Entertainment Pub Atmosphere Restaurant
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World Famous 801 Girls- 5pm Show

February 15 @ 5:00 pm - 6:30 pm

The World Famous 801 Girls captivate audiences with their dazzling performances at the lively 801 Bourbon Bar in Old Town Key West. Known for their…

Categories:
Arts & Performance Cabaret Dance Performance Drag Show Entertainment LGBT Friendly Nightlife
Tags:
Bachelorette Party Cabaret Drag Show entertainment LGBT Friendly nightlife
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QMitch Drag Queen Bingo at 22&Co

February 15 @ 5:00 pm - 7:00 pm

Experience an unforgettable night with QMitch Drag Queen Bingo at 22&Co in Old Town Key West. Renowned for dazzling performances and unmatched charisma, QMitch transforms…

Free

Categories:
Bingo Drag Queen Bingo Games & Interactive Happy Hour Nightlife Theme Night
Tags:
Bingo Cocktails Drag Queen entertainment Fun Bar Glitter Drinks happy hour nightlife
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Sunday Jazz at the Gardens

February 15 @ 5:00 pm - 7:30 pm

Experience the soulful melodies of Sunday Jazz at the Gardens, where talented musicians serenade guests in the enchanting ambiance of The Gardens Hotel. Amidst lush…

Free

Categories:
Jazz Night Live Music Music Nightlife
Tags:
Boutique Hotel entertainment Jazz Night Live Music Luxury Accommodation Tropical Gardens
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Pierce August at Hank’s Hair of the Dog Saloon

February 15 @ 5:00 pm - 8:00 pm

Experience the captivating performance of Pierce August at Hank's Hair of the Dog Saloon, Key West's vibrant nightlife gem. Known for delivering unforgettable live music,…

Free

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

February 2026