Name: Marjory & Sid at Sloppy Joe’s Bar
Start: 2026-02-24T17:30:00-05:00
End: 2026-02-24T21:30:00-05:00

February 2026
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Jessie Cotton Stone at The Bull & Whistle Bar

February 24 @ 2:00 pm - 6:00 pm

Jessie Cotton Stone electrifies the atmosphere at The Bull & Whistle Bar in Key West’s Old Town. Known for his captivating performances, Jessie brings a…

Free

Categories:
Concert Happy Hour Live Music Music Nightlife Party
Tags:
balcony seating Bars and Clubs Cocktails entertainment happy hour Live Music live music venues Nightclubs nightlife
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Reef Snorkeling, Dolphin Watch Eco Tour & Sunset Cruise

February 24 @ 3:00 pm - 6:30 pm

Join us for a vibrant aquatic adventure in Key West with our Reef Snorkeling, Dolphin Watch Eco Tour, and Sunset Cruise. Our passionate and friendly…

$79.95

Categories:
Dolphin Tour Eco Tour Outdoor Adventure Snorkeling Tour Sunset Cruise Tours & Experiences Water-Based Tours
Tags:
aquatic adventure coral reef dolphin tour marine life ocean breeze snorkeling experience sunset cruise tourism travel vacation
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Jesse Lee ~Rick’s Bar Downstairs Stage

February 24 @ 3:00 pm - 7:00 pm

Experience the captivating musical talent of Jesse Lee Jr at Rick's Bar Downstairs Stage in Key West. Known for his engaging performances and exceptional musicianship,…

Free

Categories:
Club Night Concert Live Music Music Nightlife Party
Tags:
Dance Club entertainment Karaoke Live Music Musician nightlife People Watching rock bands
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Glass Bottom Boat Cruise – Key West’s Window to the Sea

February 24 @ 4:00 pm - 7:30 pm

Experience an unforgettable journey with Glass Bottom Boat - Key West's Window to the Sea. With an engaging and knowledgeable captain and crew, embark on…

$69.95

Categories:
Boat Tour Eco Tour Scenic & Nature Tours & Experiences Water-Based Tours Wildlife Tour
Tags:
aquatic adventure coral reef eco-tour glass bottom jet skiing marine eco-system marine life parasailing Snorkeling tropical paradise underwater vistas window to the sea
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Mark Teague & Rick Fusco at Hog’s Breath Saloon

February 24 @ 4:30 pm - February 25 @ 8:30 pm

Experience the captivating sounds of Mark Teague and Rick Fusco at Hog's Breath Saloon, Key West. With their engaging performances, these talented musicians bring vibrant…

Free

Categories:
bar Concert Live Music Music Nightlife Pub
Tags:
Bars Dive Bar Food Drink Gift Shop key lime pie Live Music live music venues Musician Outdoor Patio Pub Restaurant
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World Famous 801 Girls- 5pm Show

February 24 @ 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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Glow Hours on Hugh’s View

February 24 @ 5:00 pm - 7:00 pm

Experience captivating performances at Glow Hours on Hugh's View, perched atop the vibrant Studios of Key West. Set against the stunning backdrop of Key West's…

Categories:
Art Festival Arts & Performance Community Event Exhibit Gallery Show Live Performances
Tags:
art events art exhibits artist residencies arts culture community events contemporary art creative community cultural events Live Performances performing arts theater productions
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Jay Klein at Hank’s Hair of the Dog Saloon

February 24 @ 5:00 pm - 8:00 pm

Jay Klein will captivate audiences at Hank's Hair of the Dog Saloon in Key West with his mesmerizing musical performances. Known for his dynamic presence,…

Free

Categories:
Concert Food & Drink Happy Hour Live Music Music Nightlife
Tags:
Dog Friendly Food Truck happy hour Live Music Musician nightlife Outdoor Venue
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Sunset Celebration at Mallory Square

February 24 @ 5:00 pm - 9:00 pm

The Sunset Celebration at Mallory Square in Key West is a must-see event. Renowned street performers captivate audiences with their vibrant talents, creating an unforgettable…

Free

Categories:
Arts & Performance Live Music Outdoor Adventure Street Fair
Tags:
Attractions entertainment food vendors historic waterfront Live Music local artists public spaces street performers sunset celebration Waterfront
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Caribe of Key West at El Meson de Pepes on Mallory Square

February 24 @ 5:00 pm - 9:00 pm

Caribe of Key West delivers an electrifying performance at El Meson de Pepe on Mallory Square, infusing the vibrant atmosphere with lively music. As you…

Categories:
Concert Cultural Festival Food & Drink Live Music Music Outdoor Seating
Tags:
Attractions authentic dishes Cuban Influence family-owned Food and Drink historical building Live Music mojito outdoor seating sunset celebration
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CC and The Sunsetters at Sunset Pier

February 24 @ 5:30 pm - 8:30 pm

Experience the captivating rhythms of CC and The Sunsetters at Sunset Pier. This dynamic band brings vibrant live music to Key West's stunning waterfront setting.…

Free

Categories:
Concert Food & Drink Live Music Music Nightlife
Tags:
Band Performance Caribbean cuisine entertainment Live Music Sunset Views Tropical seafood waterfront dining
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Marjory & Sid at Sloppy Joe’s Bar

February 24 @ 5:30 pm - 9:30 pm

Join Marjory Leigh and Sid the Bayou Kid at the iconic Sloppy Joe's Bar in Key West for an unforgettable live music experience. Known for…

Free

Categories:
Concert Live Music Music Nightlife Party
Tags:
American Cuisine Attraction Drinks entertainment Historic Landmark Live Music nightlife People Watching

February 2026