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Have Fun In Key West

adventure 0 beach 0 Comedy 76 dancing 13 drag show 5 festival 5 fishing 1 food 6 Games 1 Happy Hour 2 karaoke 12 Key Lime Pie 2 late night 17 lifestyle 0 live music 90 Magic 5 New Years Eve 2 null 1125 on the water 0 outdoors 8 Parade 1 party 8 sunset 23

Key West

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TV Tim's Picks

30 September 2025

Brian Roberts at Sloppy Joe’s Bar

September 30 (Tuesday) 12:00 pm - September 30 (Tuesday) 4:45 pm
Sloppy Joe’s Bar, 201 Duval St
Key West, FL 33040 United States
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Brian Roberts at Sloppy Joe’s Bar
30 September 2025

Tony Baltimore at Hank’s Hair of the Dog Saloon

September 30 (Tuesday) 2:30 pm - September 30 (Tuesday) 4:30 pm
Hank’s Hair of the Dog Saloon, 409 Caroline Street
Key West, FL 33040 United States
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Free
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Tony Baltimore at Hank’s Hair of the Dog Saloon
30 September 2025

Jay at Hank’s Hair of the Dog Saloon

September 30 (Tuesday) 5:30 pm - September 30 (Tuesday) 8:30 pm
Hank’s Hair of the Dog Saloon, 409 Caroline Street
Key West, FL 33040 United States
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Maecenas massa nisl, placerat

Free
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Jay at Hank’s Hair of the Dog Saloon
30 September 2025

Burning Bridges at Sloppy Joe’s Bar

September 30 (Tuesday) 5:30 pm - September 30 (Tuesday) 9:30 pm
Sloppy Joe’s Bar, 201 Duval St
Key West, FL 33040 United States
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Maecenas massa nisl, placerat

Free
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Burning Bridges at Sloppy Joe’s Bar
30 September 2025

Caribe of Key West at El Meson de Pepes on Mallory Square

September 30 (Tuesday) 6:00 pm - September 30 (Tuesday) 9:00 pm

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Caribe of Key West at El Meson de Pepes on Mallory Square
30 September 2025

Sunset Celebration at Mallory Square

September 30 (Tuesday) 6:00 pm - September 30 (Tuesday) 9:00 pm
Mallory Square, 1 Whitehead Street
Key West, FL 33040 United States
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Sunset Celebration at Mallory Square
30 September 2025

Happy Dog at The Alamo

September 30 (Tuesday) 6:00 pm - September 30 (Tuesday) 9:00 pm
The Alamo Key West, 4 Charles Street
Key West, FL 33040 United States
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Free
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Happy Dog at The Alamo
30 September 2025

Barret Thomas at Hank’s Hair of the Dog Saloon

September 30 (Tuesday) 8:30 pm - September 30 (Tuesday) 11:55 pm
Hank’s Hair of the Dog Saloon, 409 Caroline Street
Key West, FL 33040 United States
+ Google Map

Maecenas massa nisl, placerat

Free
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Barret Thomas at Hank’s Hair of the Dog Saloon
30 September 2025

Karaoke at RockHouse Live

September 30 (Tuesday) 9:00 pm - October 1 (Wednesday) 2:00 am
RockHouse Live Key West, 135 Duval Street
Key West, FL 33040 United States
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Karaoke at RockHouse Live
30 September 2025

World Famous 801 Girls

September 30 (Tuesday) 9:00 pm - September 30 (Tuesday) 10:30 pm
801 Bourbon Bar, 801 Duval Street
Key West, FL 33040 United States
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World Famous 801 Girls
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1600 x 900
September 30 @ 12:00 pm - 4:45 pm
Tuesday, 30-Sep-2025
12:00 pm-04:45 pm

Brian Roberts at Sloppy Joe’s Bar
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Sloppy Joe’s Bar, 201 Duval St
1600 x 900
September 30 @ 2:30 pm - 4:30 pm
Tuesday, 30-Sep-2025
02:30 pm-04:30 pm

Tony Baltimore at Hank’s Hair of the Dog Saloon
Lorem ipsum dolor sit amet, consectetur adipiscing elit. Fusce sit amet nisi dignissim, facilisis neque at, molestie mauris. Suspendisse consectetur quam elit, vitae finibus nunc imperdiet...
Hank’s Hair of the Dog Saloon, 409 Caroline Street
1600 x 900
September 30 @ 5:30 pm - 8:30 pm
Tuesday, 30-Sep-2025
05:30 pm-08:30 pm

Jay at Hank’s Hair of the Dog Saloon
Lorem ipsum dolor sit amet, consectetur adipiscing elit. Fusce sit amet nisi dignissim, facilisis neque at, molestie mauris. Suspendisse consectetur quam elit, vitae finibus nunc imperdiet...
Hank’s Hair of the Dog Saloon, 409 Caroline Street
1600 x 900
September 30 @ 5:30 pm - 9:30 pm
Tuesday, 30-Sep-2025
05:30 pm-09:30 pm

Burning Bridges at Sloppy Joe’s Bar
Lorem ipsum dolor sit amet, consectetur adipiscing elit. Fusce sit amet nisi dignissim, facilisis neque at, molestie mauris. Suspendisse consectetur quam elit, vitae finibus nunc imperdiet...
Sloppy Joe’s Bar, 201 Duval St
1600 x 900
September 30 @ 6:00 pm - 9:00 pm
Tuesday, 30-Sep-2025
06:00 pm-09:00 pm

Caribe of Key West at El Meson de Pepes on Mallory Square
Lorem ipsum dolor sit amet, consectetur adipiscing elit. Fusce sit amet nisi dignissim, facilisis neque at, molestie mauris. Suspendisse consectetur quam elit, vitae finibus nunc imperdiet...
No Venue Found
1600 x 900
September 30 @ 6:00 pm - 9:00 pm
Tuesday, 30-Sep-2025
06:00 pm-09:00 pm

Sunset Celebration at Mallory Square
Lorem ipsum dolor sit amet, consectetur adipiscing elit. Fusce sit amet nisi dignissim, facilisis neque at, molestie mauris. Suspendisse consectetur quam elit, vitae finibus nunc imperdiet...
Mallory Square, 1 Whitehead Street
1600 x 900
September 30 @ 6:00 pm - 9:00 pm
Tuesday, 30-Sep-2025
06:00 pm-09:00 pm

Happy Dog at The Alamo
Lorem ipsum dolor sit amet, consectetur adipiscing elit. Fusce sit amet nisi dignissim, facilisis neque at, molestie mauris. Suspendisse consectetur quam elit, vitae finibus nunc imperdiet...
The Alamo Key West, 4 Charles Street
1600 x 900
September 30 @ 8:30 pm - 11:55 pm
Tuesday, 30-Sep-2025
08:30 pm-11:55 pm

Barret Thomas at Hank’s Hair of the Dog Saloon
Lorem ipsum dolor sit amet, consectetur adipiscing elit. Fusce sit amet nisi dignissim, facilisis neque at, molestie mauris. Suspendisse consectetur quam elit, vitae finibus nunc imperdiet...
Hank’s Hair of the Dog Saloon, 409 Caroline Street
1600 x 900
September 30 @ 9:00 pm - October 1 @ 2:00 am
Tuesday, 30-Sep-2025
9:00 pm - 2:00 am

Karaoke at RockHouse Live
Lorem ipsum dolor sit amet, consectetur adipiscing elit. Fusce sit amet nisi dignissim, facilisis neque at, molestie mauris. Suspendisse consectetur quam elit, vitae finibus nunc imperdiet...
RockHouse Live Key West, 135 Duval Street
1600 x 900
September 30 @ 9:00 pm - 10:30 pm
Tuesday, 30-Sep-2025
09:00 pm-10:30 pm

World Famous 801 Girls
Lorem ipsum dolor sit amet, consectetur adipiscing elit. Fusce sit amet nisi dignissim, facilisis neque at, molestie mauris. Suspendisse consectetur quam elit, vitae finibus nunc imperdiet...
801 Bourbon Bar, 801 Duval Street
1600 x 900
September 30 @ 11:00 pm - October 1 @ 3:00 am
Tuesday, 30-Sep-2025
11:00 pm - 3:00 am

Karaoke at Ricks
Lorem ipsum dolor sit amet, consectetur adipiscing elit. Fusce sit amet nisi dignissim, facilisis neque at, molestie mauris. Suspendisse consectetur quam elit, vitae finibus nunc imperdiet...
Rick’s Bar Key West, 202 Duval Street
1600 x 900
October 1 @ 9:00 am - 12:00 pm
Wednesday, 01-Oct-2025
09:00 am-12:00 pm

Garden Guardians at the KW Tropical Forest & Botanical Gardens
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No Venue Found

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Bar Music 642 Cabaret & Shows 163 Christmas & Holidays 4 Fishing 1 Food & Drink 16 Fundraiser 6 History 10 Island Festivals 5 Members Only 0 Music Concerts 119 null 81 Other Fun 166 Parades 2 Parties 7 Seminars 0 Shopping 2 Speaker Series / Classes 6 Special Tours 2 Sports & Outdoors 30 Sunset 59 The Arts 37 Theatre 1
Show Filters
1600 x 900
30
Sep
Tue
12:00 pm-04:45 pm
Brian Roberts at Sloppy Joe’s Bar
Sloppy Joe’s Bar, 201 Duval St
Free
1600 x 900
30
Sep
Tue
02:30 pm-04:30 pm
Tony Baltimore at Hank’s Hair of the Dog Saloon
Hank’s Hair of the Dog Saloon, 409 Caroline Street
Free
1600 x 900
30
Sep
Tue
05:30 pm-08:30 pm
Jay at Hank’s Hair of the Dog Saloon
Hank’s Hair of the Dog Saloon, 409 Caroline Street
Free
1600 x 900
30
Sep
Tue
05:30 pm-09:30 pm
Burning Bridges at Sloppy Joe’s Bar
Sloppy Joe’s Bar, 201 Duval St
Free
1600 x 900
30
Sep
Tue
06:00 pm-09:00 pm
Caribe of Key West at El Meson de Pepes on Mallory Square
No Venue Found
null
1600 x 900
30
Sep
Tue
06:00 pm-09:00 pm
Sunset Celebration at Mallory Square
Mallory Square, 1 Whitehead Street
null
1600 x 900
30
Sep
Tue
06:00 pm-09:00 pm
Happy Dog at The Alamo
The Alamo Key West, 4 Charles Street
Free
1600 x 900
30
Sep
Tue
08:30 pm-11:55 pm
Barret Thomas at Hank’s Hair of the Dog Saloon
Hank’s Hair of the Dog Saloon, 409 Caroline Street
Free
1600 x 900
30
Sep
Tue
9:00 pm - 2:00 am
Karaoke at RockHouse Live
RockHouse Live Key West, 135 Duval Street
null
1600 x 900
30
Sep
Tue
09:00 pm-10:30 pm
World Famous 801 Girls
801 Bourbon Bar, 801 Duval Street
null
1600 x 900
30
Sep
Tue
11:00 pm - 3:00 am
Karaoke at Ricks
Rick’s Bar Key West, 202 Duval Street
null
1600 x 900
01
Oct
Wed
09:00 am-12:00 pm
Garden Guardians at the KW Tropical Forest & Botanical Gardens
No Venue Found
null

Event / Venue

Bar Music 642 Cabaret & Shows 163 Christmas & Holidays 4 Fishing 1 Food & Drink 16 Fundraiser 6 History 10 Island Festivals 5 Members Only 0 Music Concerts 119 null 81 Other Fun 166 Parades 2 Parties 7 Seminars 0 Shopping 2 Speaker Series / Classes 6 Special Tours 2 Sports & Outdoors 30 Sunset 59 The Arts 37 Theatre 1
Show Filters
1600 x 900
30
Sep
Tue
12:00 pm-04:45 pm
Brian Roberts at Sloppy Joe’s Bar
Sloppy Joe’s Bar, 201 Duval St
Free
1600 x 900
30
Sep
Tue
02:30 pm-04:30 pm
Tony Baltimore at Hank’s Hair of the Dog Saloon
Hank’s Hair of the Dog Saloon, 409 Caroline Street
Free
1600 x 900
30
Sep
Tue
05:30 pm-08:30 pm
Jay at Hank’s Hair of the Dog Saloon
Hank’s Hair of the Dog Saloon, 409 Caroline Street
Free
1600 x 900
30
Sep
Tue
05:30 pm-09:30 pm
Burning Bridges at Sloppy Joe’s Bar
Sloppy Joe’s Bar, 201 Duval St
Free
1600 x 900
30
Sep
Tue
06:00 pm-09:00 pm
Caribe of Key West at El Meson de Pepes on Mallory Square
No Venue Found
null
1600 x 900
30
Sep
Tue
06:00 pm-09:00 pm
Sunset Celebration at Mallory Square
Mallory Square, 1 Whitehead Street
null
1600 x 900
30
Sep
Tue
06:00 pm-09:00 pm
Happy Dog at The Alamo
The Alamo Key West, 4 Charles Street
Free
1600 x 900
30
Sep
Tue
08:30 pm-11:55 pm
Barret Thomas at Hank’s Hair of the Dog Saloon
Hank’s Hair of the Dog Saloon, 409 Caroline Street
Free
1600 x 900
30
Sep
Tue
9:00 pm - 2:00 am
Karaoke at RockHouse Live
RockHouse Live Key West, 135 Duval Street
null
1600 x 900
30
Sep
Tue
09:00 pm-10:30 pm
World Famous 801 Girls
801 Bourbon Bar, 801 Duval Street
null
1600 x 900
30
Sep
Tue
11:00 pm - 3:00 am
Karaoke at Ricks
Rick’s Bar Key West, 202 Duval Street
null
1600 x 900
01
Oct
Wed
09:00 am-12:00 pm
Garden Guardians at the KW Tropical Forest & Botanical Gardens
No Venue Found
null