There is never a shortage of activity on Key West. A new year is here and the events keep on coming. Culinary delights start off the year here in the Keys; with events like the Seafood Festival and the Food and Wine Festival foodies are in heaven! There are also many marathons and other physical events like flag football and SUP for those athletic types. And let’s not forget about the art scene; concerts, art openings, seminars and plays are abundant throughout the year, starting off with the Annual Literary Seminar in January. So no matter when you visit our island Paradise, you will find as much action and entertainment or relaxation as you are looking for.
2024
December 2024
December 1-31, 2024
- Key West Holiday Festival – A merry range of celebrations during Key West’s busy holiday season traditionally includes the Harbor Walk of Lights, Holiday Historic Inn Tours and a lighted boat parade with festively lit vessels and good cheer. Other events include the annual hometown holiday parade, festive island lights tours via the Conch Tour Train and Old Town Trolley, seasonal artisan markets and bazaars, and New Year’s Eve “drops” that spoof New York City’s annual Times Square “ball drop.”
December 4-15, 2024
- Nutcracker Key West – Performed every other year, Nutcracker Key West is a sumptuous, artful theatrical experience wrapped as a perfect holiday gift for the Southernmost City, returning December 2024. The Key West production comes complete with chickens, roosters, sea fans, anemones, and yes, even a conch shell. Exact dates are to be determined.
December 5, 2024
- Pet Pictures with Santa, hosted by All Animal Clinic, 6-8 p.m. at the nautical tree at the foot of William Street at the Key West Harbor. $25 cash donation.
- The 11th Annual POSH (Paws Often Steal Hearts) Florida Keys SPCA Fundraiser, 6 p.m. A catered gala at the Audubon House featuring live dance music raffles, and a silent auction.
December 6, 2024
- Holiday Historic Inn Tours – Night 1, 6-8 p.m.: Explore four decorated locations and their unique architecture and history while enjoying light sweet and savory holiday treats and libation samplings. Tickets at keystix.com/allevents/#holidayhistoricinntour or call 305-296-4959.
- Wesley House Family Services Holiday Village and BeLighted Bike Ride at Coffee Butler Amphitheater, 5-9 p.m.: A family-friendly party with Santa Claus, music, crafts, food trucks and rides for the kids, followed by a lighted bike ride through Key West. Ride leaves the amphitheater at 8 p.m. Admission fee includes Holiday Village and Bike Ride, and benefits Wesley House Family Services.
December 7, 2024
- Key West Hometown Holiday Parade, 6:30-9 p.m.: The homegrown parade kicks off at Bayview Park and travels along Truman Avenue and Duval Street with floats and marching groups.
December 8, 2024
- Photos with Fido holiday pet photos by Nick Doll, benefit the Florida Keys SPCA from 11 a.m. to 4 p.m. $100 donation. Only a few slots remain, so contact jennifer@fkspca.org or call 305-294-4857.
- Monroe County Sheriff’s Office Christmas on the Animal Farm, 1-3 p.m.:Come meet the animals during its annual Christmas on the Farm event. 5501 College Road, Stock Island. Donations welcome.
- Eaton Street Christmas Stroll, 3:30-7:30 p.m.: Stroll Eaton Street between Whitehead and Simonton, and enjoy stops at venues like Williams Hall, Tropic Cinema and The Studios, ending at St. Paul’s for a Christmas concert. Admission is free; tickets required and available at tropiccinema.com/.
December 9-10 and 13-23, 2024
- Conch Tour Train Holiday Sights and Festive Nights Tours: Multiple nightly tours depart from Key West High School and convey caroling passengers through streets and neighborhoods to revel in the magically illuminated city of Key West.
- Old Town Trolley Holiday Lights & Sights Tours: Multiple nightly tours begin at Mallory Square and convey caroling passengers through magically decorated streets and neighborhoods.
December 13-23 and 26-28, 2024
- Key West Waterfront Winter Wonderland: The Coffee Butler Amphitheater at Truman Waterfront Park becomes a holiday wonderland with lighting displays, an ice skating rink, rides, attractions, music and more.
December 13, 2024
- Holiday Historic Inn Tours – Night 2, 6-8 p.m.: Explore four decorated locations while enjoying holiday treats and libation samplings. Tickets can be purchased at https://keystix.com/allevents/#holidayhistoricinntour or call 305-296-4959.
- Holiday Concert & Bazaar at the Key West Museum of Art & History at the Custom House, 5-9p.m.: This free party features Key West artisans, musicians and choirs, along with a holiday light show. 281 Front St.
December 14, 2024
- A Positive Step 5K Rudolph Red Nose Run, 7 a.m. check-in, 8 a.m. start: Don your holiday jammies and join run, starting and ending at the Southernmost Beach Café, 1405 Duval St. Runners and walkers of all ages and abilities are welcome.
- Schooner Wharf Annual Key West Lighted Boat Parade, 8 p.m.: A glittering parade of illuminated boats. Arrive at the Key West Bight Marina at the Historic Seaport early to stroll the magical Key West Harbor Walk of Lights.
December 15, 2024
- Holiday Classic Car Show, 11 a.m.-3 p.m.: See classic cars from a variety of eras in the Conch Republic Seafood Co. parking lot at the corner of Greene and Elizabeth streets. Bring an unwrapped toy for the Monroe County Domestic Abuse Shelter.
December 15 & 22, 2024
- Christmas Cantata concerts at Fifth Street Baptist Church, 1311 Fifth St., 11 a.m.: The church choir performs contemporary music and Christmas carols.
December 18-24, 2024
- Cocoa and Carols: Live Holiday Music Cruise Aboard Schooner America 2.0, 7-8:30 p.m.: A cruise featuring holiday live music, hot cocoa, cookies and cheer aboard the 105-foot Schooner America 2.0.
December 22, 2024
- Key West Artisan Market Shop featuring Santa Claus at Indigenous Park at Higgs Beach, 10 a.m.-2 p.m.: Shop for the holidays at an outdoor market offering crafts and art, food and drinks, local musicians and authors and ocean views.
- Holiday Jazz in the Gardens, 5-7 p.m.: The Gardens Hotel, 526 Angela St., offers outdoor jazz in its famous garden, with a full cash bar on site and a 20% Christmas discount on bottled wine and bubbly.
December 25, 2024
- Christmas Day Brunch aboard Schooner America 2.0, 10 a.m.-12:30 p.m.: A 2.5 hour Christmas Day Brunch with complimentary mimosas, Bloody Marys, wine, beer and soft drinks. Brunch includes spiraled ham, bagels and pastries, meats and cheeses, smoked salmon, crudités and other holiday treats.
December 29, 2024
- City of Key West Menorah Lighting, 5 p.m. at Bayview Park.
December 31, 2024
- New Year’s Eve Celebrations! – Pirate Wench Drop at the Schooner Wharf, Shoe Drop Celebration, Conch Shell Drop at Sloppy Joe’s.
2025
January 2025
More About Key West
For more information about the fun side of Key West, things to do and see in our island city, go to our Key West Web Site. And, remember to check out our restaurant reviews as you surely must eat while down here!
Island Genn – Key West Concierge