Yes, we know, we’ve run this schedule of holiday events before, but there’s a lot going on this month.
Whether you delight in the fun and funky, the enchantingly elegant, or all the above, revelers of all ages can immerse in a solid month of tropical warmth infused holiday magic and merry-making.
Through New Year’s Eve, Key West Harbor Walk of Lights at the Historic Seaport: Lighted palm trees, Christmas trees, ships, shops, restaurants and watering holes.
Through Christmas Eve, the MARC annual Christmas tree lot: Christmas trees, wreaths, garlands, accessories, ornaments and gifts. More than 1,500 trees are available until they run out or Christmas Eve, whichever comes first. 1401 Seminary St.
Through Dec. 11, Nutcracker Key West: Sixty local children and adults and 15 professional dancers present this recreation of Key West’s version of “The Nutcracker” ballet at the Tennessee Williams Theater.
Dec. 8, 11-13, 16-23, Conch Tour Train Holiday Sights and Festive Nights Tours depart from Key West High School and convey caroling passengers through streets and neighborhoods to revel in the illuminated city of Key West.
Dec 8-23, Old Town Trolley Holiday Lights & Sights Tours begin at Mallory Square and convey caroling passengers through magically decorated streets and neighborhoods.
Friday, Dec. 9, Holiday Historic Inn Tours – Night 1, 6 to 8 p.m.: Tour four decorated island locales: Key West Butterfly Conservatory, The Mermaid & the Alligator, Winslow’s Bungalows, and Weatherstation Inn.
Friday, Dec. 9, 5 to 9 p.m. 5th annual Holiday Concert & Bazaar at Custom House Museum features local artisans, musicians and choirs, along with a holiday light show.
Friday, Dec. 9, 5:30 p.m. Stock Island Lighted Boat Parade presented by the Rotary Club of Key West at The Perry Hotel.
Friday, Dec. 9 & Saturday, Dec. 10, 7 p.m. Key West High School Band’s Holiday Concert in the school auditorium. Both nights feature the Jazz Band, Percussion Ensemble, Combined Concert Band, Wind Ensemble, Colorguard, Steel Pan Band, Chorus Ensembles and all 150-plus musicians in a special combined piece.
Saturday, Dec. 10, 10 a.m. to 2 p.m. (9 a.m. check-in), 9th annual Parade of Paws & Holiday Bazaar at Higgs Beach / Higgs Dog Park: Benefits the Florida Keys SPCA. Costumes encouraged.
Saturday, Dec. 10, 8 p.m. Schooner Wharf annual Key West Lighted Boat Parade. Arrive at the Key West Bight Marina at the Historic Seaport early in order to stroll through the Key West Harbor Walk of Lights.
Saturday, Dec. 10 and Dec. 17, Visit Santa at the North Pole, 2 to 4 p.m.
at the Southernmost “North Pole,” upstairs at the Shops at Mallory Square, 291 Front St. Letter-writing stations and a mailbox will be available for the younger set.
Friday, Dec. 16, Holiday Historic Inn Tours – Night 2, 6 to 8 p.m. Tour four decorated island locales: Hemingway’s Library @ Papa’s Pilar Distillery, The Marquesa Hotel, The Gardens Hotel and Island City House.
Saturday, Dec. 17, 7 a.m. check-in, 8 a.m. start, A Positive Step 5K Rudolph Red Nose Run starting and ending at the Southernmost Beach Café, 1405 Duval St. Don your festival holiday jammies. Runners and walkers of all ages and abilities are welcome; first 100 registrants receive a free T-shirt.
Sunday, Dec. 18, 11 a.m. to 3 p.m., Holiday Classic Car Show at 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.
Sunday, Dec. 18, 5 p.m. City of Key West Menorah Lighting Ceremony at Bayview Park.
Dec. 25, Holiday Jazz in the Gardens, 5 to 7 p.m. The Gardens Hotel, 526 Angela St. hosts outdoor jazz in its garden, with a full cash bar on site and a 20% Christmas discount on bottled wine and bubbly.
Saturday, Dec. 31 – For your midnight toast, chose from an abundance of Key West New Year’s Eve Celebrations: The Conch Shell Drop at Sloppy Joe’s Bar on Duval Street; the Red High Heel Drop with Sushi the Drag Queen at Bourbon St. Pub; the Pirate Wench Drop at the Historic Seaport; and the Key Lime Wedge in a Margarita Glass drop at Ocean Key Resort.
