Skip navigation

Florida Keys Events Calendar

Key West /
November 28
December 18
Florida Residents Save at Ripley's Believe It or Not! Odditorium
Click to Enlarge
Florida residents can enjoy half-price tickets to Ripley's Believe It or Not! Key West Odditorium. Residents will need to show a local photo ID in order to receive the discount. All adults in the party will need to have proof of residency in order to receive the discount. the Odditorium is located at 108 Duval St.

Contact: 407-345-0501
Email: kasinski@ripleys.com
Key West /
December 1
31
A master of impersonations, both visually and vocally, with impeccable comic timing. The show is all LIVE, no lip-sync. Thrill to his parodies of Marilyn Monroe, Carol Channing, Madonna, Joan Rivers, Reba McEntire, Bette Midler, Tina Turner, Julie Andrews, Barbra Streisand, Liza Minnelli, Judy Garland, Eartha Kitt, Cher, Bette Davis, Lucille Ball, even Lady GaGa. Show dates are online. Show times 9 p.m., at La te da 1125 Duval St.

Contact: 305-296-6706
Key West /
December 2
17
Sponsored by the Key West Business Guild, these merry LGBT holiday weekends, sponsored by the Key West Business Guild, are full of festive activities as well as special retail opportunities on the island. Events include a Conch Train holiday lights tour and caroling. Holiday revelers also can celebrate with "Sandy Claws" at happy hours. Dates are Dec. 2-3, 9-10 & 16-17, 2016.

Key West /
December 3
31
Click to Enlarge
Each year a wide range of seasonal celebrations takes place throughout Key West during the month of December. Events include the lighting of the Harbor Walk of Lights, tours of historic decorated inns, a holiday parade and much more.

Key West /
December 4
May 13
Enjoy garden tours, as well as learn about the Florida Keys environment and how it affects gardening in a wide range of topics for discussion and education. Visit website for schedule of monthly lectures, typically scheduled to begin at 1:30 p.m., 5210 College Road.

Contact: 305-296-1504
Email: kwbgs@kwbgs.org
Key West /
December 5
Click to Enlarge
Along with 'New Song', a host of hits include 'Things Can Only Get Better', 'What is Love?', 'Pearl In The Shell', 'Like to Get To know You Well', 'Hide And Seek' (performed at Live Aid), 'Look Mama' and 'No One Is To Blame', which reached No.1 in the US. Highlights of his current high tech band features Jonathan Atkinson on electric drums and Robbie Bronnimann on sequencing and additional keyboards.

Contact: 305.985.0433
Email: boxoffice@thekeywesttheater.com
Key West /
December 7
Click to Enlarge
The Paws Often Steal Hearts, or POSH, party is to be held at the Audubon House & Tropical Gardens, 205 Whitehead St., to benefit the Florida Keys Society for the Prevention of Cruelty to Animals. Attendees are encouraged to wear island-style formal attire and "fascinator" hats. General admission tickets are $40 pre-purchased and $45 at the door, per person.

Contact: 305-304-1232
Key West /
December 7
The Lighted Bike Ride helps to gather the needed toys for the struggling, working families of Key West for the holidays. At the Holiday Helpers Store, eligible parents walk through the store, empowered by the ability to pick free, new toys their children will want instead of just allocating non-specific toys to parents. The ride is a family event beginning with a registration at 5:30 p.m. with the Lighted Bike Ride beginning at 7:00 p.m. Families and individuals with lighted and decorated bikes ride through the streets for the community to see. Registration for the ride is one unwrapped toy for the Key West Holiday Store. Register online.

Contact: Claire Hiller at 305-809-5000
Email: claire.hiller@wesleyhouse.org
Key West /
December 9
Pet Pictures with Santa
Hosted by All Animal Clinic of Key West. Santa is to pose for photos with pets from 6-8 p.m. at the nautical Christmas tree at the foot of William Street on the Harbor Walk of Lights. Sales of photos, priced from $20, are to benefit the Boys & Girls Clubs of the Keys Area Inc.

Contact: 305-294-5255
Email: allanimalclinic@gmail.com
Key West /
December 9
Click to Enlarge
Enjoy an enchanted evening of five decorated inns and a sampling of holiday treats and cheer at each property. From 6-8 p.m., tours are self guided. Free trolley transportation is provided between inns but participants are welcome to bike or use their own transportation. Call the Lodging Association for tickets.

Contact: 305-296-4959
Key West /
December 10
Click to Enlarge
The third annual pet parade at Higgs Beach Dog Park supports the Florida Keys SPCA's animal care fund. To participate, pets' humans gather funding pledges from family and friends. Top earners win bragging rights for titles of the 2016 Parade of Paws king, queen, prince, princess, duke or duchess for their treasured companions. Four-legged creatures and owners can take photos with Santa, enjoy entertainment, food and crafts, and mingle with animal and human friends from 10 a.m. to 2 p.m.

Contact: 305-294-4857
Islamorada /
December 10
11
Click to Enlarge
New this year, is the Friday "Beer Mile" event, that is quite simple: 1 Mile and 4 Beers. Do you have what it takes? There are to be cash prizes for the top 3 finishers for male/female in the half marathon and great awards for the top 3 finishers of the 10K.  In addition, prizes for those who place top 3 in their age groups for both races.  Register for all events online. Earlybird savings.

Contact: Robbie McClung 305-587-0901
Email: islamoradahalf@gmail.com
Key Largo /
December 10
The Lighted Bike Ride helps to gather the needed toys for the struggling, working families of Key Largo for the holidays. At the Holiday Helpers Store, eligible parents walk through the store, empowered by the ability to pick free, new toys their children will want instead of just allocating non-specific toys to parents. The ride is a family event beginning with a registration at 5:30 with the Lighted Bike Ride beginning at 6:30pm. Families and individuals with lighted and decorated bikes ride through the streets for the community to see. Registration for the ride is one unwrapped toy for the Key Largo Holiday Store. Register online.

Contact: Claire Hiller at 305-809-5000
Email: claire.hiller@wesleyhouse.org
Key West /
December 10
Click to Enlarge
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! Holiday Bazaar inside the dog park features entertainment, food vendors, photos with Santa, gifts for that special person on your list 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.

Key West /
December 10
18
Click to Enlarge
Inspired by the unique and colorful environment of the Florida Keys, Clara and her young Prince encounter enchanted landscapes complete with snowy egrets on shimmering salt ponds, a wicked Rooster-King, an exquisite Sea-Star Fairy, and "underwater" sequences of almost unimaginable beauty. Local children, adults and community leaders are cast alongside a nationally-cast corps de ballet in this spectacularly crafted semi-annual production of a beloved classic. Shows held Dec. 10-11 & Dec. 14-18 at the Tennessee Williams Theatre. Purchase tickets online.

Contact: Box office 305-295-7676
Islamorada /
December 10
Click to Enlarge
An extra special holiday concert, to be held at the ICE amphitheater at Founders Park, mile marker 87 bayside. The family-friendly concert features traditional music of the holidays, and a sing-along with a special guest appearance from Santa Claus. Starts at 4 p.m.; free admission. All seats are outdoors, chairs and blankets recommended to bring. Presented by Keys Community Concert Band.

Contact: Donna Heiner 305-853-7294
Email: keyscommunityconcertband@yahoo.com
Key West /
December 10
Click to Enlarge
Lighted and decorated vessels from rowboats to tall ships proceed around Key West's Historic Seaport and harbor areas. 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.

Contact: 305-292-3302
Marathon /
December 10
A middle Keys holiday kick-off event; watch as dinghies, mega-yachts and anything in between turn the harbor into a sparkling procession along the parade route. Best viewing sites include Lazy Days South, Marathon Marina, Dockside Tropical Cafe and Burdine's Waterfront. Starts just after sunset, near 6 p.m.

Marathon /
December 11
Click to Enlarge
Christmas lights on outriggers, Santa's elves and brightly lit deck displays highlight the beautiful festivities during the Key Colony Beach Boat Parade. Set to begin at the 7th Street canal, the parade is open to all boats, and the route visits canals and cuts, and passes city hall three times. Great viewing spots include Sadowski Causeway at MM 53.5 and the dock area behind city hall and the post office. The public is welcome. An after-party is held with awards for captains and crews.

Key West /
December 11
Click to Enlarge
Devon Allman has toiled long and hard to establish his own musical identity, separate from his legendary dad, Gregg Allman. Royal Southern Brotherhood was formed during JazzFest in New Orleans. This unique quintet combines the vocal and musical talents of Devon, Mike Zito, and the legendary Cyril Neville with the veteran rhythm section of Charlie Wooton and Yonrico Scott. Their mixed sounds of funk, blues, rock and jazz proved to be a force to be reckoned with. Show starts 8 p.m.

Contact: 305.985.0433
Email: boxoffice@thekeywesttheater.com
Key West /
December 11
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.

Contact: 305-293-7300
Big Pine & the Lower Keys /
December 12
Annual Christmas Cantata
The Keys Chamber Orchestra and Lower Keys Community Choir will be performing their annual Christmas Cantata. This year's event will feature "Born a Savior, Born a King". All concerts are free. Performance at 7:30 p.m., Big Pine Key United Methodist Church, 280 Key Deer Blvd.

Key West /
December 13
January 7
Click to Enlarge
It's opening night for a new Broadway play called, The Golden Egg, and all of New York show biz has gathered for the opening night party to anxiously await the reviews. It's a celebration of theatre at its best...and theatre people behaving their not-so-best. All performances at 8 p.m., no shows 12/24 or 12/31.

Contact: 305-294-5015
Key West /
December 13
January 14
In 1904, in The Lapin Agile — a bar in Paris — a 10-person cast of wonderful characters hold an imagined meeting of the young Alfred Einstein and Pablo Picasso, mixing the sublime and the ridiculous.

Contact: 305-296-9911
Big Pine & the Lower Keys /
December 14
Annual Christmas Cantata
The Keys Chamber Orchestra and Lower Keys Community Choir will be performing their annual Christmas Cantata. This year's event will feature "Born a Savior, Born a King". All concerts are free. Performance at 7:30 p.m., at St. Peter Catholic Church, 31300 Overseas Hwy, on Big Pine Key.

Big Pine & the Lower Keys /
December 15
Annual Christmas Cantata
The Keys Chamber Orchestra and Lower Keys Community Choir will be performing their annual Christmas Cantata. This year's event will feature "Born a Savior, Born a King". All concerts are free. Performance at 7:30 p.m., Venture Out 701 Spanish Main Dr on Cudjoe Key.

Islamorada /
December 15
Showcasing the fine arts, music and culinary nuances of the Purple Isles, the Morada Way Arts & Cultural District features national and local artisans who are showcased in galleries at Morada Way between mile marker 81 and 82, as well as "culinary art" and live music from 6-9 p.m. A great pre-holiday celebration. Free admission. Art Walk is held the third Thursday of each month.

Email: Moradawaysusi@gmail.com
Key West /
December 16
Click to Enlarge
Enjoy an enchanted evening of decorated inns and a sampling of holiday treats and cheer at each property. From 6-8 p.m., tours are self guided. Participants are welcome to bike or use their own transportation. Call the Lodging Association for tickets.

Contact: 305-296-4959
Islamorada /
December 16
18
Islamorada Junior Sailfish Tournament
Recreation for teens in the Florida Keys can mean learning from experienced local captains and mates to tie a bimini or rig ballyhoo. One weekend each year anglers aged 16 and younger can apply such lessons in this competition. A maximum of six anglers is allowed per boat. Proceeds aid the Montessori Island School.

Contact: Tammie Gurgiolo 305-240-9337
Email: fishnbully@msn.com
Key Largo /
December 17
Click to Enlarge
Blackwater Sound is to shimmer as decorated boats parade along the shoreline in celebration of the holiday season; 55-foot yachts to single-person kayaks are to set sail at 7:30 p.m. The best viewing and libations are to be found at Sundowners, Jimmy Johnson's Big Chill, Senor Frijoles, the Marriott Key Largo Bay Resort and Caribbean Club, MM 103-104. Awards after-party at Sundowners, at 10 p.m.

Big Pine & the Lower Keys /
December 17
Lower Keys Lighted Boat Parade
All boats are welcome to enter the Pine Channel Causeway parade including deep-sea cruisers, dinghies, kayaks and canoes. Santa and Mrs. Claus are expected to arrive and hand out candy to the kids. The best recommended viewing is from Kiki's Sandbar, 183 Barry Ave. on Little Torch Key. Parade begins at 7 p.m. Saturday evening.

Contact: Steve Estes 305-923-5370
Email: bigpinenews@aol.com
Marathon /
December 18
Annual Christmas Cantata
The Keys Chamber Orchestra and Lower Keys Community Choir will be performing their annual Christmas Cantata. This year's event will feature "Born a Savior, Born a King". All concerts are free. Performance at 7:30 p.m., at San Pablo Catholic Church 550 122nd St Ocean.

Key West /
December 20
30
Click to Enlarge
Female impersonator extraordinaire brings a one man, all live tribute to some famous and infamous women of stage and screen. A Key West tradition for 18 years. Join Randy for an evening with "Bette Midler", "Cher", and Randy's signature lounge act. Hilarious comedy, gorgeous costumes, and voice that never fails to thrill! Open your eyes and mind and let yourself go with Randy Roberts LIVE! The NY Times calls him "Delicious ,..at the top of his game, ...truly talented", and you'll call yourself lucky to catch Randy Roberts LIVE! Visit website for show dates.

Contact: 305-296-6706
Email: bookings@randyroberts.net
Key West /
December 20
24
Click to Enlarge
Feeling the tropical island holiday blues? We've got just the antidote! It's 1970 and Lillian Baxter is staging her comeback with a Christmas show. Oy Vey! Tinsel flies in this very entertaining "one woman" show. Written by and starring John Vessels as Lillian Baxter with Jay Schwandt on piano. "This is an extreme dose of whatever it is your holiday spirit is missing!" Performances at 7 p.m., at Little Room Jazz Club at 821 Duval Street.

Contact: 305-731-0581
Key West /
December 21
Inaugural Holiday Concert & Bazaar at Custom House Museum
Click to Enlarge
The event, from 5-9 p.m., will feature Key West's finest artisans, musicians and choirs, along with a spectacular holiday light show. 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. Open and free to the public.

Contact: 305-295-6616
Email: scowles@kwahs.org
Islamorada /
December 21
Click to Enlarge
A free lecture series held at the museum, located at MM 82.9, every third Wednesday of the month at 7 p.m. Adventurers from treasure hunters to aquanauts help tell the story of mankind's attempts to explore, understand and venture under the sea. The evening lectures are informal, informative and provide a valuable educational resource at the museum, an acclaimed facility dedicated to the collection, preservation and display of relics and artifacts related to diving and its heritage.

Contact: 305-664-9737
Key West /
December 27
28
Presented by the Old Island Restoration Foundation, the annual self-guided tours showcase festively dressed Key West homes and gardens. December tours are from 4-7 p.m., both evenings. Transportation between homes is NOT included. Tickets are $30. Proceeds benefit the Old Island Restoration Foundation's museums, collection and education, grant and scholarship programs.

Contact: 305-294-9501
Key West /
December 31
Click to Enlarge
The arrival of 2017 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.

Islamorada /
December 31
Revelers in the Upper Keys' Islamorada can ring in the new year with midnight fireworks on the Atlantic Ocean beach at the luxurious Cheeca Lodge & Spa, located at mile marker (MM) 82 oceanside. Attractions include live music, dancing on the beach and a gourmet dinner.

Contact: 305-517-4447
Key West /
December 31
Click to Enlarge
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 2017. Scallywags in attendance can expect live music all day, dancing and festivities at the Schooner Wharf Bar, 202 William St.

Key West /
December 31
Click to Enlarge
At the Ocean Key Resort & Spa, 0 Duval St. on Key West Harbor, plans call for a huge replica of a Key lime wedge to splash down into a larger-than-life margarita glass as crowds welcome 2017 on the property's Sunset Pier. The free event features live entertainment by local favorites the E'Claires and Happy Dog, followed by the Robert Albury Band.

Contact: 305-296-7701
Key Largo /
December 31
Click to Enlarge
The back bay is the setting for the annual New Year's Eve fireworks extravaganza hosted by Sundowners, Jimmy Johnson's Big Chill, Senor Frijoles, Cactus Jacks, Gus' Grille at the Marriott Key Largo Beach Resort and the Caribbean Club, MM 103-104. Check website for details.

Contact: 305-451-4502
Key West /
December 31
Key West Dachshund Walk
Click to Enlarge
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.

Email: keywestdachshundwalk@gmail.com
Key West /
December 31
Click to Enlarge
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.

Email: schroedkw@aol.com

Back to Top