Name: Glass Bottom Boat Cruise – Key West’s Window to the Sea
Start: 2026-02-22T13:30:00-05:00
End: 2026-02-22T16:00:00-05:00

February 2026
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Distillery Tour – Key West Legal Rum Distillery

February 22 @ 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 Tourist Attraction Tours & Experiences Walking & Guided Tours
Tags:
Craft Distillery Free Samples Gluten Free Rum Mojito Making Rum Tasting Vegan Friendly Rum
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Glass Bottom Boat Cruise – Key West’s Window to the Sea

February 22 @ 11:30 am - 2:00 pm

Experience the captivating Glass Bottom Boat tour in Key West, where our knowledgeable captain and crew offer an engaging eco-tour. Enjoy unparalleled views of North…

$69.95

Categories:
Boat Tour Eco Tour Scenic & Nature Tours & Experiences Water-Based Tours Wildlife Tour
Tags:
Captain and Crew coral reef eco-tour Fish Species glass bottom boat Marine Ecosystem marine life Scuba Divers underwater vistas
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Harley Ray ~ Rick’s Downstairs Stage

February 22 @ 12:00 pm - 4:00 pm

Experience an electrifying night with musician Harley Ray at Rick's Downstairs Stage in Key West. Renowned for his captivating performances, Harley Ray brings a dynamic…

Free

Categories:
Club Night Concert Live Music Music Nightlife
Tags:
Dance Club entertainment Fun Karaoke Live Music Musician nightlife nightlife venues Rock
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Behind Bootleg at Sloppy Joe’s Bar

February 22 @ 12:00 pm - 4:45 pm

Experience the captivating sounds of Behind Bootleg at the iconic Sloppy Joe's Bar, a vibrant venue on Duval Street in Key West. Known for its…

Free

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

February 22 @ 12:00 pm - 5:00 pm

Mylo O'Maolain captivates audiences at the Schooner Wharf Bar with his soulful melodies and vibrant energy. This talented musician transforms the historic Key West venue…

Free

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

February 22 @ 12:00 pm - February 23 @ 4:00 pm

Experience an unforgettable evening with the talented musician Aaron Blumer at Hog's Breath Saloon in Key West's vibrant Mallory Square District. Known for his captivating…

Free

Categories:
Concert Live Music Music Nightlife
Tags:
Dive Bar Food and Drink Gift Shop Live Music Musician Outdoor Patio Pub Restaurant
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Big Bad Voodoo Daddy at Key West Theater

February 22 @ 1:00 pm - 3:00 pm

Join Big Bad Voodoo Daddy at the Key West Theater for an unforgettable night of swing and jazz. Known for their high-energy performances and exceptional…

$

Categories:
Concert Live Music Music Nightlife
Tags:
big band concert entertainment Jazz Music live performance swing revival
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Farm Open House

February 22 @ 1:00 pm - 3:00 pm

Experience captivating entertainment at the Farm Open House in Key West. Held at the Monroe County Sheriff's Office Animal Farm, this community-focused event features live…

Categories:
Community Event Educational Kids Event Family & Kids Family Event Nonprofit Event Wildlife Tour
Tags:
Animal sanctuary Community centers Community focused Donations welcome Educational Tours Exotic animals Family friendly Free admission Non-profit sanctuary Parks Rescued animals
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Jon Hollywood at Tiki House Key West

February 22 @ 1:00 pm - 4:00 pm

Experience an unforgettable evening with Jon Hollywood at Tiki House Key West. Renowned for his captivating performances and magnetic stage presence, Jon delivers a vibrant…

Free

Categories:
Club Night Concert Live Music Music Nightlife Party
Tags:
concert entertainment fun night out Live Music live performance Music Event nightlife Party Performance tropical vibes
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Belle and McKenna at Sunset Pier

February 22 @ 1:00 pm - 4:00 pm

Belle and McKenna, a dynamic musical duo, captivate audiences at Sunset Pier with their vibrant performances and eclectic repertoire. Their live music creates an unforgettable…

Free

Categories:
Concert Food & Drink Live Music Music Nightlife Waterfront Dining
Tags:
Bars Caribbean cuisine entertainment Live Music live music venues seafood restaurant Sunset Views tropical drinks waterfront dining
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Victoria Leigh at Hank’s Hair of the Dog Saloon

February 22 @ 1:00 pm - 4:00 pm

Victoria Leigh captivates audiences at Hank's Hair of the Dog Saloon with her dynamic performances. As a talented musician, she brings vibrant energy to Key…

Free

Categories:
Concert Happy Hour Live Music Music Nightlife Outdoor Venue
Tags:
Dog Friendly Food Truck happy hour Live Music Musician nightlife Outdoor Venue
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Glass Bottom Boat Cruise – Key West’s Window to the Sea

February 22 @ 1:30 pm - 4:00 pm

Experience the magic of Key West's marine life aboard the Glass Bottom Boat. While our knowledgeable captain and crew guide you on an informative eco-tour,…

$69.95

Categories:
Boat Tour Eco Tour Scenic & Nature Tours & Experiences Walking & Guided Tours Water-Based Tours Wildlife Tour
Tags:
Brain Coral coral reef eco-tour glass bottom boat Majestic Elkhorn Marine Eco-systems marine life Ocean Views tropical paradise underwater vistas window to the sea

February 2026