December Calendar of Events
- Krystal Thomas
- Nov 28, 2025
- 2 min read
Holiday Magic in Paradise: Your 2025 Guide to Key West’s Festive Events
December 1 World Aids Day Memorial
December 3
December 4 Mac Mcanally @Key West Theater
December 5 Mac Mcanally @Key West Theater
Montessori United 5K Run/Walk
December 6 Key West Hometown Holiday Parade
December 7 Key West Woman’s Club Community Open House
December 9 Scrooge Macbeth @ Red Barn Theater
December 10 Femmes of Rock @ Key West Theater
Holiday Tours On The Trolley
Fury's Annual Sunset Sail With Santa Benefiting Wesley House
December 12 Holiday Lights Conch Tour Train
Holiday Concert & Bazaar
December 13 Irreverent Warriors Key West Silkies Hike
A Positive Step of Monroe County 5K Run/Walk
December 14 Stock Island Lighted Boat Parade
Monthly Artisan Market
December 15 Holiday Tours On The Trolley
December 17 Holiday Tours On The Trolley
December 18 Holiday Tours On The Trolley
December 19 Holiday Tours On The Trolley
December 20 5k & Jingle Bell Mile
December 21 Monthly Artisan Market
December 22 Holiday Tours On The Trolley
December 23 Holiday Tours On The Trolley
December 24
December 25 Christmas Ultimate Adventure H2.0
December 27
December 28 Monthly Artisan Market
December 29
December 30
December 31 New Year's Eve Shoe Drop
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