Calendar of Events

Current Key West Events

• Nov 27, 2019 - Dec 31, 2019 Location: Key West Category: Arts & Culture
• Key West Holiday Fest
• Website
• A merry range of celebrations during Key West's busy holiday season includes lighting of 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, pet photos with Santa, a “Violins in Motion” concert and multiple New Year’s Eve “drops” that spoof New York City’s annual Times Square “ball drop.”

• Dec 12, 2019 Location: Key West
• Full 'Cold' Moon Kayak Tour and Adventure
• SIGN UP 305-209-8303 Email Website
• Paddle under the glowing sunset and the rising moon. Perfect for all ages and skill level. This trip will have you howlin’ at the moon with the cool breeze and sounds of water splashing against your kayak as you paddle. During the paddle, we break for our popular S’Mores, an American tradition consisting of graham cracker, marshmallow and Hershey chocolate sandwiched together. A delight with everyone. Guests are welcome to bring small coolers filled with favorite beverages and snacks. From 6-8 p.m., depart from Sunset Marina, 5555 College Rd. Book online or call to reserve.

• Dec 12, 2019 - Dec 28, 2019 Location: Key West Category: Arts & Culture
• Waterfront Playhouse presents: Around the World in 80 Days
• Website
• Stampeding elephants! Raging typhoons! Runaway trains! Unabashedly slapstick! Hold onto your seats for the original amazing race! Characters such as Phileas Fogg, Detective Fix, Passepartout, Sir Francis, Aouda and the British Council make for an evening of live entertainment. Showtimes 8 p.m.

• Dec 14, 2019 Location: Key West
• Sixth Annual Parade of Paws and Shopping Bazaar
• 305-294-4857 Website
• Bring your dogs, wear a t-shirt with a picture of your kitty with pride, or walk with a paddle displaying your pet's photo! Shopping Bazaar inside the dog park features entertainment, food vendors, a Kissing Booth, holiday gifts for that special snuggle bug and more! A unique opportunity to support the lifesaving mission caring for the Keys' community's homeless animals, the event supports the Florida Keys SPCA. Check in is 9 a.m. Event is from 10 a.m. to 2 p.m., Higgs Beach, at the Higgs Dog Park. Bring four-legged friends to meet the reigning King and Queen.

• Dec 14, 2019 Location: Key West
• 29th Annual Schooner Wharf Bar Annual Lighted Boat Parade
• 305-292-3302 Website
• Lighted and decorated vessels from rowboats to tall ships proceed around Key West's Historic Seaport and harbor areas. Festivities are to begin at 6 p.m. with the children of Gerald Adams Elementary Steel Your Heart Band! Parade is scheduled to begin at 8 p.m. Holiday revelers can watch and applaud from bars, restaurants and resorts in and around the Historic Seaport as vessels of all shapes and sizes dazzle the crowd.

• Dec 14, 2019 Location: Key West
• 12th Annual Rudolph Red Nosed 5k Run
• Website
• Don your festive holiday running attire, affix your ruby-red nose, and join in the fun, starting and ending at the Southernmost Beach Café,1405 Duval St. Race day check-in starts at 7 a.m. with 8 a.m. start time. After the race, enjoy refreshments, fun, prizes and a huge silent auction.

• Dec 15, 2019 Location: Key West
• Key West Artisan Market: Holiday Shop Local edition
• Website
• Enjoy a full bar, coffee, smoothies, natural juices and cut fruit, multiple food trucks and stalls, from 10AM to 2PM. Shop a curated outdoor market offering fine crafts, art and jewelry from talented Florida Keys makers. Stock your pantry and fridge with fresh produce, artisan cheeses, local seafood, honey, pickles and so much more. Free entry & parking. From 10 a.m. to 2 p.m., at Clarence H. Higgs Memorial Beach. Bring your own bags. A fantastic, family-friendly, free event. The show will be stocked with keys-made items perfect for gift giving this holiday season.

• Dec 15, 2019 Location: Key West Category: Arts & Culture
• Rams Head Production presents: Bret Michaels at Key West Theater
• Website
• As front man for the legendary rock band Poison, Bret Michaels has sold 25 million records and scored an amazing 15 chartbusting Top 40 singles including "Talk Dirty To Me," "Something To Believe In," "Nothing But A Good Time" and the timeless #1 smash "Every Rose Has Its Thorn." After more than 25 years in the business this award winning, multi platinum superstar's career continues to move at warp speed. Doors open 7 p.m., show starts 8 p.m.

• Dec 15, 2019 Location: Key West
• Christmas on the Sheriff's Animal Farm
• 305-293-7300 Website
• From 1-3 p.m., kids and adults can visit the furry, fluffy and feathered residents of the Animal Farm and petting zoo and get a photo taken with Santa. The Monroe County Sheriff's Office Animal Farm is situated at the county's detention center just outside Key West at 5501 College Road. This event is free and open to the public. The Sheriff's Animal Farm is open the second and fourth Sundays of the month.

• Dec 17, 2019 Location: Key West
• South Florida National Parks Trust presents 'Tortugas Tales'
• Website
• Staged at the Florida Keys Eco Discovery Center, 35 E. Quay Rd., the event is to feature stories from the Dry Tortugas as presented by award-winning authors James Kushlan and Kirsten Hines and updates on Dry Tortugas National Park and its education programs by park manager Glenn Simpson and lead ranger Curtis Hall. 'Tortugas Tales' coincides with the release of a new history book on the Dry Tortugas as an opportunity to feature Dry Tortugas National Park, its human and natural history, current stewardship, visitor opportunities, and to highlight Dry Tortugas National Park educational programs supported by the South Florida National Parks Trust. Event is free and open to the public. Doors open 6 p.m., presentations begin 6:30 p.m. RSVP online.

• Dec 18, 2019 Location: Key West Category: Arts & Culture
• Key West Art & Historical Society Hosts Holiday Concert & Bazaar at Custom House Museum
• Website
• From 5-9 p.m., located on the sweeping historic porch and walkway of the Custom House Museum. The immensely popular celebration will feature some of Key West’s finest artisans, musicians and choirs, food and libations, free entrance to the museum and its two stories of exhibits, and a dazzling holiday light show of magical vector projections on the face of the Custom House. Browse hundreds of unique gift options while enjoying the music, food and libations on and around the island’s architectural crown jewel, with eggnog to lift the frazzled ‘final shopping days’ spirits and Santa on hand for last minute requests and ‘selfie’ photos.

• Dec 19, 2019 - Dec 20, 2019 Location: Key West Category: Arts & Culture
• Tennessee Williams Theater presents: The Play That Goes Wrong
• Website
• This Olivier Award-winning comedy is a hilarious hybrid of Monty Python and Sherlock Holmes. Welcome to opening night of The Murder at Haversham Manor where things are quickly going from bad to utterly disastrous. With an unconscious leading lady, a corpse that can’t play dead, and actors who trip over everything (including their lines). Showtimes 8 p.m., Tennessee Williams Theater, 5901 College Rd.

• Dec 21, 2019 Location: Key West
• Discovery Saturday Educational Series: Coral Crafts
• Website
• Kids in kindergarten through fifth grade are invited to join the free, fun-filled Discovery Saturday at the Florida Keys Eco-Discovery Center (35 East Quay Road, Key West) from 10-11 a.m. Hosted by Reef Relief, children will make candy coral crafts and learn. Free admission, free parking. Discovery Saturday is held the third Saturday of every month. Pre-registration is recommended. The Florida Keys Eco-Discovery Center is located at 35 East Quay Road on the Truman Annex waterfront in Key West.

• Dec 22, 2019 Location: Key West
• Candy Canes and Kayaks
• Website
• From 5:30 - 7:30 p.m., Blue Moon Kayak Key West will take you on the Gulf and around Stock Island to view the twinkling holiday lights across the water. Join a family-friendly event with candy canes for everyone! $50 per person. Departs from Sunset Marina, 5555 College Rd.

• Dec 26, 2019 - Dec 31, 2019 Location: Key West Category: Arts & Culture
• Fringe Theater presents: An Evening Lost with Lillian Baxter
• 305-731-0581 Email Website
• 1970s TV icon Lillian Baxter just had her show cancelled. What’s a "everything's coming up roses" girl to do? Industrial musicals, game shows, sitcoms, and Broadway for a start! Lillian reminds us that what is lost can always be found. Performance 7 p.m. at Little Room Jazz Club, 821 Duval St. Fringe Theater is Key West's community-focused theater providing unique opportunities for people to see and do theater. 

• Dec 27, 2019 - Dec 28, 2019 Location: Key West
• 60th Annual Key West Home Tours
• 305-294-9501 Website
• Presented by the Old Island Restoration Foundation, the annual self-guided tours from 3-6 p.m. each day showcase festively dressed Key West homes and gardens. Tickets are $35 in advance, $40 day-of-tour. You will be enchanted by exquisite restorations, creative renovations and delightful interiors featuring art collections, antiques, and much more. All proceeds from the tours stay in the Key West local community fulfilling OIRF’s mission of “Celebrating and sustaining Key West’s unique architecture, culture and history.” 

• Dec 28, 2019 Location: Key West Category: Arts & Culture
• Rams Head Productions presents: Blackberry Smoke
• Website
• Scorched-blues and Southern rock fans are going to love this show! Performances also from Georgia Satellites and Bishop Gun, of Natchez, Mississippi, rooted in the history and sounds of their home and the surrounding Delta, featuring a blend of rock and roll, soul and blues. Starts at 4 p.m. Key West Amphitheater, Truman Waterfront at 21 Quay Rd. Tickets available online.

• Dec 31, 2019 Location: Key West
• Old Island Restoration Foundation presents: 1860s or 1960s Costume Gala
• Website
• Travel back to the 1960’s for our 60th year anniversary themed NYE party. The fabulously dressed 21-plus crowd sets the scene. This is an exclusive event at the Garden at the Oldest House Museum, 322 Duval St. Limited Seating. The porch will also be open to watch the revelers promenade on Duval Street. Gate opens 6:00 pm; Dinner 8:15pm; Countdown at midnight. Tickets $225pp, available online.

• Dec 31, 2019 - Jan 1, 2020 Location: Key West
• New Year's Eve: Conch Shell Drop at Sloppy Joe's
• Website
• The arrival of 2020 is to be heralded on the island's Duval Street with the "drop" of a gigantic manmade conch shell, the symbol of the Florida Keys, to the flat roof of Sloppy Joe's Bar, 201 Duval. Thousands of spectators gather on Duval for the annual gala, emceed by a rooftop host starting at 10 p.m. and featuring dancing in the street and a countdown to midnight recorded on a huge clock.

• Dec 31, 2019 - Jan 1, 2020 Location: Key West
• New Year's Eve: Pirate Wench Drop at Schooner Wharf
• Website
• For piratical partiers, a New Year's Eve salute to Key West's rowdy seafaring roots is scheduled at the island's Historic Seaport. At midnight, a winsome pirate wench is to descend from the top of the mast of the tall ship America 2.0 as cannon blasts welcome 2020. Scallywags in attendance can expect live music all day, dancing and festivities at the Schooner Wharf Bar, 202 William St.

• Dec 31, 2019 Location: Key West
• Key West Dachshund Walk
• Website
• Frost-free Key West becomes a "wiener wonderland" when about 200 dachshunds and their owners take a noontime New Year's Eve stroll through the island's picturesque downtown. Spectators can watch the fun and meet the canine participants on Fleming Street between Whitehead and Duval streets.

• Dec 31, 2019 - Jan 1, 2020 Location: Key West
• New Year's Eve Shoe Drop Celebration
• Email Website
• The Southernmost City celebrates with a descending 6-foot red high heel shoe carrying drag queen Sushi at the Bourbon Street Pub/New Orleans House complex, 724 Duval St. Seconds before midnight, the high heel bearing a lavishly gowned and coiffed Sushi is to be lowered from the second-story balcony of the complex toward the cheering crowds below. As midnight strikes and the New Year officially begins, she will land and gleefully pop the cork on a ceremonial bottle of champagne.