The Florida Keys & Key West

Calendar of Events

Current Florida Keys Events

  • Dec. 14, 2017 Location: Key West Category: Arts & Culture
  • South Florida Symphony presents a Soiree at Hemingway House
  • Website
  • Join the Symphony to commemorate its 20th season at the historical and beautiful Hemingway House. Immerse yourself in the writings of Hemingway as the Symphony brings to life four of his beloved stories in the four movements of the Tales of Hemingway concerto. From 6-8 p.m., at 907 Whitehead Street. Meet Grammy Award winners cellist Zuill Bailey and composer Michael Daugherty and the lead dancers of the Siudy Flamenco Dance Theater. Tickets $100 pp. Purchase tickets online.
  • Dec. 14, 2017 - Jan. 6, 2018 Location: Key West Category: Arts & Culture
  • Waterfront Playhouse presents: Inspecting Carol
  • 305-294-5015 Website
  • Grab a large helping of holiday cheer with this hilarious, madcap comedy! It's a cross between A Christmas Carol and Noises Off. Behind the scenes of a struggling theatre's annual slapdash production of A Christmas Carol, rehearsals are at a standstill. Tim is no longer Tiny, Scrooge wants to do the play in Spanish (Feliz Navidad), and their funding is on hold pending an inspection. This laugh out loud spoof makes for a night at the theatre that is anything but show business as usual. "Inspecting Carol" is a delightful mix of "A Christmas Carol," "Noises Off," "Waiting for Guffman."
  • Dec. 14, 2017 - Dec. 16, 2017 Location: Key West Category: Arts & Culture
  • Sugar Rum Cherry: A Burlesque Nutcracker
  • Christa Hunt 305.619.2862 Website
  • Put on your stockings and pull out your sugarplums for Key West Burlesque's "Sugar Rum Cherry: A Burlesque Nutcracker." This naughty holiday 2-act reverie features your favorite local performers, international burlesque superstars, and amazing aerial acrobats as they visit the land of libations. Doors open at 7:30 p.m., show starts at 8:00 p.m. Performance at Key West Theatre, 512 Eaton Street.
  • Dec. 15, 2017 Location: 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, priced at $30 per person.
  • Dec. 15, 2017 Location: Key West
  • RESCHEDULED: 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. 15, 2017 - Dec. 17, 2017 Location: Islamorada Category: Fishing
  • Islamorada Junior Sailfish Tournament
  • Tammie Gurgiolo 305-240-9337 Email
  • 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.
  • Dec. 16, 2017 Location: Key Largo
  • RESCHEDULED: Key Largo Holiday Lighted Boat Parade
  • Website
  • 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.
  • Dec. 16, 2017 Location: Key West Category: Arts & Culture
  • South Florida Symphony presents: Mozart Meets Hemingway & Siudy Flamenco Concert
  • 305-295-7676 Website
  • Zuill Bailey, cellist extraordinaire, returns to commemorate the 20th Anniversary of the South Florida Symphony Orchestra led by Founder|Music Director Sebrina Maria Alfonso. Bailey's rare combination of celebrated artistry, technical wizardry, and engaging personality has secured his place as one of the most sought after and active cellists today. Bailey performs the wondrous Tales of Hemingway concerto for cello and orchestra for which he won the Best Classical Instrument Solo Grammy Award in 2017. Pre-concert chat 7 p.m., performance at 7:30 p.m., Key West High School Auditorium, 2100 Flagler Avenue. Tickets available online.
  • Dec. 16, 2017 Location: Key West
  • Florida Keys Eco-Discover Center's Discovery Saturday: Dolphins in the Florida Keys
  • Register at 305-809-4750 Email
  • Discovery Saturday from 10-11 a.m. features guests from the Dolphin Research Center teaching children about the friendly and fascinating ocean mammal often seen in the waters of the Florida Keys. Space is limited. The Florida Keys Eco-Discover Center, operated by Florida Keys National Marine Sanctuary, hosts Discovery Saturday for children in kindergarten through fifth grade on the third Saturday of each month. Located in NOAA's Dr. Nancy Foster Florida Keys Environmental Complex on the Truman Annex waterfront in Key West, the Eco-Discovery Center features more than 6,000 square feet of interactive exhibits, which interpret the resources and management efforts of Florida Keys National Marine Sanctuary, two national parks, and four national wildlife refuges.
  • Dec. 17, 2017 Location: Key West Category: Arts & Culture
  • Keys Love Festival
  • Elmira Leto 305-434-6564 Email Website
  • Featuring a wide variety of talented local favorites on the City of Key West Amphitheater stage, at the Truman Waterfront from 12 noon-6pm, an all-star lineup of local musical icons includes Howard Livingston, Caffeine Carl & the Buzz, Clayton Lopez, Coffee Butler and many other well-known musicians takes the stage to make this a special day and an authentic Florida Keys event. Laid back, relaxed and in true island style, you're asked to bring your lawn chairs and blankets for seating on the lawn. Soak up the sun for the afternoon, with final performances taking the stage under our glorious Key West sunset. Admission is free with donations of any amount greatly appreciated upon entrance, being made to support the children, families and individuals of the Florida Keys through KeysStrong.org. The funds raised will provide much needed aide and support to individuals throughout Monroe County who have been affected by Hurricane Irma.The concert will be broadcast live on Facebook Live at KeysStrong.org's official Facebook page.
  • Dec. 17, 2017 Location: Islamorada
  • Santa Claus & His Carolers Come to Town!
  • From 5:30 p.m. to 9:19 p.m., Santa is en route with Season's Greetings between Lower Matecumbe and Plantation Shores! Bring new unwrapped toys to the parade for a donation to Toys for Tots.
  • Dec. 21, 2017 Location: Key West Category: Arts & Culture
  • Second Annual Holiday Concert & Bazaar at Custom House Museum
  • 305-295-6616 Website
  • Key West Art & Historical Society is to host this second annual event, from 5-9 p.m. at the historic Custom House Museum, to feature Key West's finest artisans, musicians and choirs, along with a spectacular holiday light show. Highlights of the evening gathering are to include performances by musicians and choirs, local artisans showcasing their wares, a light show and "selfies" with Santa. Open and free to the public.
  • Dec. 21, 2017 - Dec. 31, 2017 Location: Key West Category: Arts & Culture
  • Fringe Theater presents: An Evening with Lillian Baxter- ALL NEW!
  • 305-731-0581 Website
  • Back by popular demand! John Vessels and Jay Schwandt bring Lillian Baxter back to Key West in this all-new "one woman" show. Lillian Baxter is sweet, funny, and capable of knocking your socks off when she belts out a song! Cabaret comedy with beautiful renditions of the American songbook. Enjoy an upbeat show about life just left of the spotlight. Limited Seating. Shows 12/21-24, 12/26-31 at Little Room Jazz Club. 821 Duval Street. House opens at 6 p.m. Show at 7 p.m.
  • Dec. 27, 2017 - Dec. 28, 2017 Location: Key West
  • 58th Annual Key West House & Garden Tours
  • 305-294-9501 Website
  • Presented by the Old Island Restoration Foundation, the annual self-guided tours from 3-7 p.m. each day showcase festively dressed Key West homes and gardens. Tickets are $30 in advance, $35 day-of-tour. Proceeds benefit the foundation's museum and programs.
  • Dec. 31, 2017 Location: Key West
  • New Year's Eve: Conch Shell Drop at Sloppy Joe's
  • Website
  • The arrival of 2018 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, 2017 Location: Islamorada
  • New Year's Eve Celebrations in Islamorada
  • Website
  • Revelers in the Upper Keys' Islamorada can ring in the new year with midnight fireworks on the beach at Morada Bay Beach Café at MM 81.6 bayside, who is to host a large beach party with live music, beach barbecue, signature cocktails, performers and fireworks.
  • Dec. 31, 2017 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, 2017 Location: Key Largo
  • New Year's Eve Fireworks on Blackwater Sound
  • 305-451-4502 Website
  • 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.
  • Dec. 31, 2017 Location: Key West
  • New Year's Eve Dockside Bash on Schooner America 2.0
  • 646-772-4880 Email Website
  • Enjoy a front-row seat for the famous "Lowering of the Wench" at Schooner Wharf Bar! This special adults-only event features complimentary beer, wine, champagne, well drinks, soda, and water and delicious hot and cold hors d' oeuvres! From 9:30 PM- 12:30 AM; tickets for purchase are limited so reserve early.
  • Dec. 31, 2017 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.
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