Calendar of Events
December 2018: Florida Keys Events
- Sponsored Event
- Jul 20, 2024 - Jul 20, 2024 Key West
- Hemingway 5k Sunset Run & Paddleboard Race
- Website Start of Paddle Board Race Higgs Beach & Start of 5K Southernmost Point
- Higgs Beach & Southernmost Point Key West FL 33040
- Key West Half Marathon E-mail
- View video
- Runners, walkers and paddleboard enthusiasts can test their skills and celebrate Ernest Hemingway’s sporting lifestyle Saturday, July 20th during the Hemingway 5k Sunset Run and Paddleboard Race. The athletic challenges are part of Hemingway Days!
- Buy tickets!
- Sponsored Event
- Apr 19, 2024 - Apr 28, 2024 Key West
- 42nd Annual Conch Republic Independence Celebration
- Website
- Party with Pirates, Admirals, Generals, Ambassadors & Island Royalty. 10 Days of FUN-Filled festivities for all ages! 20+ events at historic and unique venues in Key West. We Seceded… Where Others Failed!
- Sponsored Event
- Dec 04, 2023 - Aug 31, 2024 Key West
- Christopher Peterson's Eyecons at Birdcage Cabaret
- Website SideBar featuring the Birdcage Cabaret
- 504 Angela St. Key West FL 33040
- Birdcage Cabaret
- View video
- Christopher Peterson is a master of impersonations, both visually and vocally, and his comic timing is impeccable. The show is All Live, no lip-sync, and audiences will be thrilled with his many characterizations. Tickets available now!
- Buy tickets!
- Sponsored Event
- Jun 07, 2024 - Jun 09, 2024 The Lower Keys
- 31st Annual Dolphin Tournament Lower Keys Chamber of Commerce
- Website KOA Sugarloaf Key
- 251 State Rd 939 Summerland Key FL 33042
- Lower Keys Chamber of Commerce 305-872-2411 E-mail
- View video
- The 31st Annual Lower Keys Chamber of Commerce Dolphin Tournament is coming up June 7-9! Enter to win over $35,000 in cash & prizes. Friday the 7th is registration & appetizers at 5pm and Sunday the 9th is dinner & awards at 6pm. Largest Dolphin Wins!!!
- Buy tickets! Call now!
- Sponsored Event
- Mar 25, 2024 - Aug 13, 2024 Key Largo
- Fish & Friends Seminar
- Website REEF Environmental Education
- 98300 Overseas Hwy Key Largo FL 33037
- Amy Lee 305-852-0030 E-mail
- REEF Fish & Friends is a free, monthly community social and seminar series. Join us for light snacks and drinks plus an engaging, educational ocean-themed presentation. Seminars are live-streamed and recorded.
- Call now!
- Sponsored Event
- Jun 05, 2024 - Jun 09, 2024 Key West LGBTQ
- Key West Pride
- Website Key West Business Guild
- 808 Duval Street Key West FL 33040
- 305-294-4603 E-mail
- Celebrate PRIDE on a tropical island that is legendary for its laid-back style and its open and accepting atmosphere. Show us your pride, we will show you our Key West Pride!
- Buy tickets! Call now!
- Sponsored Event
- Apr 27, 2024 - Apr 27, 2024 Key Largo
- ART & SCIENCE FESTIVAL
- Website REEF Environmental Education
- 98300 Overseas Hwy Key Largo FL 33037
- Amy Lee 305-852-0030 E-mail
- Come see how the arts, science, and conservation are connected in our Florida Keys community and beyond! This family-friendly event includes hands-on activities, interactive displays, take-home art and science kits, and more!
- Call now!
- Sponsored Event
- Jul 17, 2024 - Jul 21, 2024 Key West Arts & Culture
- Sloppy Joe’s 43rd Annual Hemingway Look-Alike Contest
- Website Sloppy Joes
- 201 Duval Street Key West FL 33040
- 305-294-5717 E-mail
- Key West’s most iconic and whimsical tribute to one of the greatest literary figures of the 20th century, Ernest Hemingway. This event celebrates Hemingway’s life in Key West and enduring legacy in a way that’s as unique and spirited as the man himself.
- Call now!
- Nov 15, 2018 - Dec 8, 2018 Marathon Arts & Culture
- Marathon Community Theater presents: Ken Ludwig's Leading Ladies
- 305-743-0994 Box Office Website
- The play is set in the late 1950's in and around York, PA. Leo Clark and Jack Gable, two down on their luck British actors performing their tired mash-up of "Scenes from Shakespeare", have been booed off the Elk and Moose Lodge circuit and are down to their last dollar. As they ride the train out of town, they read about a dying, elderly woman living nearby, who has been searching for her long-lost sister's children, Max and Steve, who have been raised in England, in hopes of leaving them her multi-million inheritance. Leo and Jack concoct a scheme to pass themselves off as her British nephews, and are surprised to learn that Max and Steve are actually Maxine and Stephanie! Forging ahead with their plans, they rapidly swap their men's attire for ladies' stylish finery. Tickets are $25 pp.
- Dec 1, 2018 Key Largo Arts & Culture
- Ninth Annual Light Up Key Largo
- 305-451-1414 Website
- Sponsored by the Key Largo Chamber of Commerce, holiday happenings with live music, decorations, food and drinks are to spark the holiday spirit, from 5-9 p.m. The annual tree lighting is to be at 8:30 p.m., events held at the Murray E. Nelson Government and Cultural Center, MM 102. Eggnog, caroling, holiday cookies and ornament making for stocking stuffers are guaranteed to get everyone in the festive mood.
- Dec 6, 2018 Key West
- Sixth Annual POSH Event
- 305-304-1232 Website
- The Paws Often Steal Hearts, or POSH, party is to be held at the Audubon House & Tropical Gardens, 205 Whitehead St., from 6-9 p.m., 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.
- Dec 7, 2018 The Lower Keys
- Stock Island Lighted Boat Parade
- Stock Island Lighted Boat Parade is a free event. Activities begin at 5 p.m., with the parade scheduled for 7 p.m., and an after-party at 9 p.m. Guests will delight in seeing the bright lights on everything from tri-masted schooners to dinghies to the shrimp boats that call Stock Island home. The boat parade is presented by Sunset Watersports with free viewing events at Stock Island Marina Village and Safe Harbor.
- Dec 7, 2018 Key West
- Holiday Historic Inn Tours
- 305-296-4959 Website
- Enjoy an enchanted evening to include trolley transportation between several participating inns, each decorated for the holidays. Treats and libations are offered at each inn. Event-goers also can provide their own transportation or bicycle to the inns. Contact the Lodging Association of the Florida Keys and Key West to purchase tickets.
- Dec 7, 2018 - Dec 16, 2018 Key West Arts & Culture
- Nutcracker Key West
- Box office 305-295-7676 Website
- 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 at the Tennessee Williams Theatre.
- Dec 7, 2018 - Dec 22, 2018 Key West
- Conch Tour Train Holiday Lights Tours
- 305-294-5161 Website
- During its annual holiday lights tours of the southernmost island in the continental United States, the Conch Train travels past decorated historic homes, buildings and neighborhoods. Tours are offered at multiple times with departures from Key West High School, 2100 Flagler Ave. TOUR DATES: Dec. 7, 15, 19, 21 and 22
- Dec 7, 2018 Key Largo
- First Friday MM 104 Block Party
- E-mail Website
- Join Key Largo's new monthly, free-admission block party along the Overseas Highway at mile marker 104 in Key Largo, presented by the Upper Keys Merchants Assoc. Held the first Friday of each month, rain or shine, from 6-10 p.m., stroll among artists, street bites, gifts, eateries and more. Park at any of the MM104 businesses and walk along the bayside bike pathway.
- Dec 7, 2018 Key West Arts & Culture
- Rams Head Productions presents: Paula Poundstone
- Website
- With smart, observational humor and a legendary spontaneous interaction with the crowd, Paula Poundstone is one of our country's pre-eminent comedians. She improvises with a crowd like a Jazz musician, swinging in unexpected directions without a plan, without a net. There's a disarming ease in her craft, an immediate sense that she's so quick on her feet you need never worry about the possibility of something going wrong. Doors open 7 p.m., show starts 8 p.m., at Key West Theater, 512 Eaton St.
- Dec 8, 2018 Marathon
- Christmas By the Sea Boot Key Harbor Lighted Boat Parade
- 305-743-6575
- From dinghies to yachts, both power and sail boats welcome! Parade starts at 6 p.m. from the west end of Boot Key Harbor and slowly wind its way east into the harbor toward Sombrero Marina Dockside, back through the harbor and ending at Lazy Days South at Marathon Marina for a post-parade award party at approximately 8:30 p.m. Best viewing spots include Lazy Days South, Burdines Waterfront/Panchos Fuel Dock, Marathon Marina and Sombrero Marina Dockside. Prizes for best boat in each division.
- Dec 9, 2018 - Dec 22, 2018 Key West
- Old Town Trolley’s Holiday Lights and Sights Tours
- 305-296-6688 Website
- The popular green and orange trolleys, festively adorned with holiday lights, showcase Key West's best decorated historic neighborhoods, buildings and homes. TOUR DATES: Dec. 9, 15, 19, 21 and 22
- Dec 10, 2018 Islamorada Arts & Culture
- Celebrate the Life of Irving R. Eyster, Mr. History
- Barbara Edgar at 305-393-0940
- The posthumous celebration of the late Irving R. Eyster will be held at the Islamorada Moose Lodge. Hors d'oeuvres will be served starting at 5:30 p.m. followed by an audio visual presentation of Mr. Eyster's life, who would have been 100 years young on this day. A presentation is to show some of the most unusual and fascinating items ever found on our islands, and Eyster, a well-known historian and archaeologist, collected items and preserved them for future generations for over 60 years. Known as Mr. History, his knowledge was extensive. He excavated Indian Key in the 1970's, was the foremost authority on the island and was known as Mr. Indian Key. Presentation will include items from the early Indians, shipwrecks, diving, Flagler's Railway, Indian Key, lighthouses, maps, documents, and some rare and unusual items. Donation of $30 per person to honor and share the life of Mr. Eyster also helps the MHT. The evening will end with birthday cake to finish off the celebration.
- Dec 14, 2018 - Dec 21, 2018 Key West
- Chief Peachy-Poo’s Holiday Revue
- Tickets 305.294.0555 Website
- Deck the halls and jingle your balls, it's time for Chief Peachy-Poo's Holiday Revue! Key West's smallest strongman and drag-tastic super star, Chief Peach, hosts two evenings of holiday cheer. Peach is joined by the Conch Republic's Queen of Burlesque, Tatah DuJour, along with Nick Mazza, and the Key West Burlesque Dancers to celebrate the season. The show will feature festive weekly guest performers including Sofia Luna, Aurora Natrix, and Cheeky Derrière. Doors open at 7:30 p.m., show starts at 8 p.m. Show nights Dec. 14 & 21 at the Backroom at Sidebar 504 Angela St.
- Dec 14, 2018 Key West
- Holiday Historic Inn Tours
- 305-296-4959 Website
- Enjoy an enchanted evening to include trolley transportation between several participating inns, each decorated for the holidays. Treats and libations are offered at each inn. Event-goers also can provide their own transportation or bicycle to the inns. Contact the Lodging Association of the Florida Keys and Key West to purchase tickets.
- Dec 15, 2018 Islamorada Arts & Culture
- Keys Community Concert Band Holiday Suite Treats Concert
- Donna Heiner 305-853-7294 E-mail Website
- The family-friendly free-admission event, themed "Holiday Suite Treats," offers traditional and pops music performed by the Keys Community Concert Band, sing-alongs, stories and Santa as well as a children's ballet troupe performance and handbell ringers. Concert is to be held at 4 p.m., at the ICE Amphitheater at Founders Park, mile marker 87 bayside.
- Dec 15, 2018 Key West
- Rudolph Red Nose Run
- Website
- Don your festive holiday running attire, affix your ruby-red nose, and join in the 11th Annual 5K Rudolph Red Nose Run, Saturday Dec. 15, starting and ending at the Southernmost Beach Café. Race day check-in starts at 7 a.m. with an 8 a.m. start. After the race, enjoy refreshments, fun, prizes and a huge silent auction.
- Dec 15, 2018 Key West
- Maser Gardener Speaker Series at Key West Botanical Garden
- 305-296-1504 Website
- The Key West Botanical Garden Society presents Master Gardener, Michelle Leonard-Mularz to begin its 6-month Speaker Series. Held at 1:30 p.m. in the Toppino Nature Chapel. Michelle will speak on "Gardening in the Keys and the Master Gardener Program." Admission is free for members, $5 for non-members. All proceeds directly benefit the Garden's conservation program. The Garden is located at 5210 College Road, Stock Island.
- Dec 19, 2018 Islamorada Arts & Culture
- History of Diving Museum presents: Immerse Yourself Free Speaker Series
- 305-664-9737 Website
- The History of Diving Museum presents the annual presentation series that spotlights a new topic the third Wednesday of each month, at 7 p.m. Exhibits and museum store stay open late (normal museum admission applies).
- Dec 27, 2018 - Dec 31, 2018 Key West Arts & Culture
- Fringe Theater presents: Terri White’s Blue Evening
- Rebecca Tomlinson 305-587-8961 Website
- Broadway star Terri White shares her personal journey to Broadway and back again. The evening intersperses personal stories and show tunes, triumphs and challenges. Accompanied by Pianist Megan Clay. Little Room Jazz Club, 821 Duval Street. Show starts 7 p.m.
- Dec 29, 2018 Key West Arts & Culture
- JJ Grey Returns to Key West with Full Band, JJ Grey & Mofro
- E-mail Website
- From the days of playing greasy local juke joints to headlining major festivals, JJ Grey remains an unfet-tered, blissful performer, singing with a blue-collared spirit over the bone-deep grooves of his composi-tions. His presence before an audience is something startling and immediate, at times a funk rave-up, other times a sort of mass-absolution for the mortal weaknesses that make him and his audience human. When you see JJ Grey and his band Mofro live—and you truly, absolutely must—the man is fearless.
- Dec 30, 2018 Key West
- GLO on the Beach
- Starting at 6 p.m., a free event with DJ music, food and beverages available for purchase; complimentary "glo" items and face painting for kids; stay for the fireworks show that starts at 9 p.m. Held at Marriott Beachside Hotel 3841 N. Roosevelt Blvd.
- Dec 30, 2018 Key West
- Key West Artisan Market
- Website
- Browse among culinary, textile, jewelry, wood, artists & crafters, curiosities, live music, craft beer, wine and art and food concessions. From 10 a.m. to 2 p.m., at a NEW location this year, at Higgs Beach. Bring your own bags. A fantastic, family-friendly, free event.
- Dec 31, 2018 Key West
- Great Gatsby NYE 2019
- Website
- Dress to impress in your best Gatsby-era outfits! Enjoy bottomless champagne, live music and DJ performances, passed hors d'oeuvres and chef-manned food stations; tickets are $99 per person. From 8 p.m. to 1 a.m., at First Flight Brewery, 301 Whitehead St.
- Dec 31, 2018 The Florida Keys
- TEST EVENT
- Dec 31, 2018 Key West
- New Year's Eve Rock the Tuna Celebration
- Ring in the New Year at Smokin' Tuna Saloon, 4 Charles St. A $10 cover includes champagne and party favors at midnight, live entertainment and the Tuna drops at midnight.