The Key West Lighted Boat Parade is an annual affair that combines with the Harbor Walk of Lights to celebrate the Christmas Holiday! Each year a variety of boats decorate their sails, masts, and hulls with Christmas Lights and festive cheer. There is an... Read More
Join the Key West Art & Historical Society for the eighth annual Holiday Concert and & Bazaar on Friday, December 12, 2025, from 5 pm to 8 pm, located on the sweeping historic porch and street in front of the Key West Museum of Art & History.... Read More
Open to all MWR authorized patrons with military issued ID. Holiday Lights Conch Tour Train Join us for MWR's annual HOLIDAY LIGHTS TOUR! Get in the Christmas spirit with a 1-hour joyous ride around Key West on the famous Conch Tour Train! * 1st Tr... Read More
Don your festive holiday jammies and join in the 17th Annual A Positive Step 5K, taking place Saturday morning, December 13th, 2025 starting and ending at the Southernmost Beach Café,1405 Duval Street, Key West. Race day check-in starts at 7:00am with 8:0... Read More
This is your chance to capture the magic of the season with Pet Photos with our special guest star Santa Qlaus and photos by Nick Doll. Join us! ~Saturday, December 13, 2025 ~Hank’s Hair of the Dog, 409 Caroline Street ~12 PM – 4 PM. ~$30 per photo (No... Read More
Tim returns to Key West with his Funky Friends! 3 sets Fri/Sat: 5:30pm, 9pm, 11pm 1 set Sunday: 5:30pm Rob Somerville on Sax/Vocals Beau Sasser on Bass/Keys Michelangelo Carubba on Drums Lets Party!... Read More
Buy your Holiday Lights Trolley ride today! Friday, December 12 @ 6:30pm https://givebutter.com/WobKNRer... Read More
Join us at Williams Hall for a festive Holiday Bake Sale & Bazaar! Indulge in a delightful bake sale featuring culinary creations by Chef Martha Hubbard and the Basilica Student Culinary Program, along with a variety of arts, local crafts, and season... Read More
Follow The Rabbit Bar Presents FOLLOW THE RABBIT... (9PM) Back Stage Listening Room SAT, 13 DEC 2025 at 09:00PM EST Ages: 21 & Over Doors Open: 08:45PM OnSale: Wed, 17 Sep 2025 at 12:00PM EDT Announcement: Tue, 16 Sep 2025 at 12:00PM EDT Our i... Read More
Irie Monte will be joined by Crispin Campbell on cello for an evening of beautiful string music on The Studios' Hugh's View Rooftop terrace. Let the music get you into the holiday spirit! Irie Monte has been playing violin for over 20 years. She was bles... Read More
A high-level conversation for individuals who want to protect, preserve, and multiply their wealth with greater sophistication.About this EventJoin us in Key West for an exclusive estate and wealth strategy meetup designe... Read More
Join us at the Shores Pool for our Community Swim on Saturday, December 13th at 6pm! These monthly events are open to the public and have live music, free swag, and Mermaid Dorian!... Read More
The 2nd Saturday of every month, the artists from Island Boy Arts, TooKeys Gallery, and Kemp Art Gallery gather together for a fun evening of creativity and charity upstairs in the Shops at Mallory Square! This partnership with Keys AHEC not only raises... Read More
Join us for a Holiday Fitness Event at Blue Flamingo! Santa Run + DJ led Pilates with Rikki Shea, wellness tents & holiday shopping!About this EventJoin us for an unforgettable Holiday Wellness Event! 🎅We’re t... Read More
Join us for a festive, hands-on gingerbread house building experience paired with complimentary hot cocoa. Crackers and a variety of candies, icings, and edible décor will be available to build the ultimate Key West gingerbread house. The event is free... Read More
| Date | Event | Venue |
|---|---|---|
| 13 Dec 2025 | 17th Annual Rudolph APSMC 5K | Southernmost Beach Resort, Key West |
| 13 Dec 2025 | Pet Photos with Santa Qlaus and Nick Doll | Hank's Hair Of The Dog Saloon, Key West |
| 13 Dec 2025 | Strategic Estate & Wealth Planning Meetup | Salute! On The Beach, Key West |
| 13 Dec 2025 | 2nd Saturday Celebration - Upstairs at Shops at Mallory Square | The Shops at Mallory Square, Key West |
| 13 Dec 2025 | Santa Run Pilates Wellness Event | Blue Flamingo Resort Key West |
| 13 Dec 2025 | Curry Ford Wests Sleigh The Ford | Curry Ford West, Key West |
| 13 Dec 2025 | Keys Choral Arts Holiday Concert | Tennessee Williams Theatre, Key West |
Customize your experience; only see the events that click with you!
Tune my vibeNever miss a single fun event; let us keep you updated!
