The Lodging Association of the Florida Keys and Key West

Keys Events

Florida Keys & Key West Events Information, Accommodations of the Florida Keys. Plan your Island vacation around an event or holiday.
Events calendar provided by

Events in the Florida Keys for January, 2020
Year: Month:  
December 31 to January 01,  in Key Largo
Sundowners Key Largo New Year's Eve Celebration
The back bay is the setting for the annual New Year's Eve fireworks extravaganza hosted by Sundowners, mile marker 104 bayside, with live music to accompany the night. Check website for details and to reserve seats for a special NYE dinner. Midnight fireworks to follow.
Contact: 305-451-5566

December 31 to January 01,  in Islamorada
New Year's Eve at Cheeca Lodge & Spa
For a casually elegant celebration, Cheeca Lodge & Spa, located at MM 82 oceanside, is planning live music and a midnight fireworks display over the Atlantic Ocean. Known for its renowned cuisine and beachside location, Cheeca is an ideal spot for revelers and romantics to ring in 2020. Call for more information about dining and reservations.
Contact: 305-664-4651, ext. 4580.

December 31 to January 01,  in Key West
New Year's Eve: Conch Shell Drop at Sloppy Joe's
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.

December 31 to January 01,  in Key West
New Year's Eve: Pirate Wench Drop at Schooner Wharf
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.

December 31 to January 01,  in Islamorada
New Year's Eve Celebrations in Islamorada
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 colorful large beach party with live music, beach barbecue, signature cocktails, performers and fireworks.
Contact: 305-664-0604

December 31 to January 01,  in Key West
New Year's Eve Dockside Bash on Schooner America 2.0
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.
Contact: 646-772-4880
Email: [email protected]

December 31 to January 01,  in Key West
New Year's Eve Shoe Drop Celebration
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: [email protected]

January 01,  in Key West
Polar Paddle Plunge
Plunge into a new decade! Blue Moon Kayak is honoring the tradition of cleansing the past year away and getting a refreshing start to 2020. What a better way than cleaning with purifying natural sea salt in the Gulf of Mexico. Start the year off right! $50 per person, departs from Sunset Marina, 5555 College Rd.

January 03,  in Key Largo
Orange Bowl Swim Classic
Hundreds of college swimmers from around the country, some who have pursued Olympic gold, are to meet and compete in a popular monthlong winter training session in Key Largo that culminates in the open-to-spectators event. Competition is to begin at 10 a.m. until noon. Free to watch, at Jacobs Aquatic Center, mile marker 99.6 oceanside. The sprint-style meet features several fast-paced swimming events.

January 03 to April 03,  in Key West
First Fridays on Fleming
Key West boutique owners in “The Fabulous 500 Block of Fleming Street” have kicked off a monthly First Fridays on Fleming 6-9 p.m. block party to encourage local buying. First Fridays on Fleming showcase boutiques, galleries and eateries in the 500 block of Fleming Street with events such as jewelry trunk shows, art openings, book signings, tastings and libations. Participants include The Roost Bar and Liquor Store, La Rubia Authentic Panama Hats, Key West Island Books, Key West Local Luxe Jewelry, Amanda Johnson Fine Art, Sea Store Antiques, Assortments Menswear, Island Antiques, Duck & Dolphin Antiques, Clemente’s Trolley Pizzaria, La Petite Grignote French Bakery, Thirsty Mermaid Seafood and Jean Pierre Klifa Resort Wear. First Fridays are scheduled Jan. 3, Feb. 7, March 6 and April 3.
Contact: 305-304-9001

January 03 to January 04,  in Islamorada
Fish for Holly Sailfish Tournament
Created to raise money for Florida Keys scholarships and domestic violence initiatives, this memorial tournament honors the late Holly Given, a Keys resident and avid angler. Participants are to gather at Whale Harbor Marina to compete for top male, female and junior angler awards as well as top offshore, bay boat and fun fish categories.

January 03 to January 05,  in Marathon
Conch Records Music Video Festival
Enjoy a totally 'Keys locals' event! Produced by Conch Records, the free-general-admission weekend features live performances of over 100 Florida Keys-based musicians, alongside the production of music videos with these talented performers: Blues Hall of Famers, guitar players, and superb musicians on the harmonica, fiddle, banjo, drummers, harp, sax, trumpet, trombone, bass, flute, keyboard, and much more. Multiple stages are to feature different genres, including Southern rock, folk/rock, trop rock, blues, country, alternative and others. Sales of event/musician tee-shirts help Keys nonprofit charities, including Marathon Wild Bird Center. Food and drink vendors, adult beverages. If you love local Keys music, stop by the Marathon Community Park, mile marker 49. Friday, 5-11pm, Sat., 11am - 11pm, Sunday 11am - 5 pm.
Contact: Cliff Rydell 305-587-9830
Email: [email protected]

January 04 to January 05,  in Key West
The Studios of Key West presents ‘Single Occupancies,’ an evening of Contemporary Opera Theatre Monologues
Performed by nationally renowned opera singers, "Single Occupancies" includes two world premiere pieces by Martin Hennessy and Stephen Kitsakos, and one regional premiere by Mark Campbell and Marisa Michelson. Scored for piano, cello, clarinet and double bass, and sung in English, the storylines are riveting, fresh and relevant. Each thirty-minute piece introduces a singularly unique character. Performances start at 8 p.m. Ticket prices range from $100 to $50, with discounts for Studios' members.
Contact: 305-296-0458

January 07 to January 09,  in Islamorada
Florida Keys Outfitters SailFly Tournament
This time of year the weather is ideal for a hot Atlantic sailfish bite. Enter for a chance to compete in one of the toughest and most exciting angling events of the year. For info visit and search “Sailfly entry” or visit the events tab.

January 08,  in Islamorada
Keys History & Discovery Center presents: Winter Lecture Series
This week’s topic, Saving our Reefs: Ambitious Efforts to Flip the Script, is to be presented by Sarah Fangman, Superintendent of the Florida Keys National Marine Sanctuary. Doors open at 5:30 p.m., with cash bar and snacks. Lecture is 6-7 p.m., including time for questions. Reservations should be made in advance. Lecture series runs October through May.
Contact: Reserve 305-922-2237
Email: [email protected]

January 08 to January 18,  in Key West
Fringe Theater presents: Talley's Folly
WWII is drawing to a close. In an abandoned boathouse, a Jewish immigrant woos a southern belle in this poignant romantic comedy. Can a new start really be found after so much loss? Performance 7 p.m., Back Room at the Key West Theater, 512 Eaton St. Fringe Theater is Key West's community-focused theater providing unique opportunities for people to see and do theater. 
Contact: 305-731-0581
Email: [email protected]

January 09 to January 19,  in Islamorada
‘Uncorked,’ the Key Largo Food and Wine Festival
Experience the fabulous restaurants of Islamorada, and don't miss the festival highlight at Postcard Inn Beach Resort & Marina scheduled for Saturday January 18, 2020. The Grand Tasting is a multi-sensory experience not to be missed. Area restaurants and wine experts will come together to present samples of their finest cuisine and world-class wines. Live music, celebrity chef appearances and cooking demos combine to serve up the recipe for a spectacular afternoon of tasting in the fabulous Florida Keys.

January 09 to January 12,  in Key West
Pole Vault in Paradise
Presented by Key West Track and Field Club, Pole Vault in Paradise is an all-comers pole vault competition with events spread across four days. Youth, College, Elite and Masters divisions. Pole vaulters from age 9 to 75 to compete alongside some of the best pole vaulting elites from around the country. Saturday’s activities are free admission. Enjoy food and drink vendors, and world class competition beginning at 9 a.m. at the beautiful Truman Waterfront Park. Bring your lawn chairs.
Contact: Steve Hanes 512-470-8076
Email: [email protected]

January 09 to January 19,  in Key Largo
Uncorked ... the Key Largo and Islamorada Food & Wine Festival
The 10-day food, wine and spirits showcase features dozens of savory events to please virtually every palate and budget, spread among numerous Upper Keys venues with fresh, locally sourced seafood and international-style dishes. The festival's outdoor 'A Grand Tasting,' is set for Saturday, Jan. 18 in Islamorada, at Postcard Inn. What better reason to 'Uncork' and unwind in the Florida Keys. For a complete events schedule, visit website.
Contact: 305-522-1300
Email: [email protected]

January 09 to January 12,  in Key West
38th Annual Key West Literary Seminar
The 2020 topic is "Reading Between the Lines, Sports & Literature." Literary aficionados from around the world are to gather to focus on writing that examines why sports matter so much and explores the roles sports play in social issues, personal transformation and cultural change.
Contact: 888-293-9291

January 10,  in Marathon
Dolphin Research Center to Welcome Wounded Warriors for Dolphin Swim
Dolphin Research Center (DRC) will welcome more than 40 military veterans from the Wounded Warrior Project’s annual Soldier Ride to enjoy a Dolphin Encounter dolphin swim free of charge during the annual Charles Evans Day for the Wounded Warrior Project. The group, along with caregivers and Wounded Warrior Project staff, is expected to arrive at DRC at 12 noon. Members of the public are invited to come earlier and join DRC staff and volunteers at 11:30 a.m. as they line up to give a heroes’ welcome to the participants. Admission to DRC is free for current members. Other visitors may pay general admission or become members with their donations when they get to DRC. Dolphin Research Center is located at 58901 Overseas Highway, mile marker 59, on Grassy Key.

January 11 to January 12,  in Marathon
The Florida Keys Celtic Festival
Some of America's most celebrated Celtic musical masters are to be featured at the Marathon Community Park, MM 49. The festival will also feature Irish and Scottish dancing, Highland athletics, Celtic merchandise, food and beverage booths and children's activities. Open Saturday 10AM to 7PM, Sunday 11AM to 5PM.

January 11 to January 12,  in Big Pine
16th Annual Nautical Expo
Admission and parking at this event are free, held at the Lower Keys Chamber of Commerce grounds, MM31, from 8AM to 2PM. Find steals and deals on everything imaginable for boating, fishing, diving and more, from dozens of vendors. Crafts, food and beverage, live music and entertainment round out the two-day event.
Contact: 305-872-2411
Email: [email protected]

January 11,  in Key West
Wounded Warrior Project Soldier Ride
This Solder Ride event kicks off the Wounded Warrior Project® (WWP) 2020 Soldier Ride season that will take warriors across the nation, visiting dozens of American cities. Soldier Ride begins at NAS KW at 10:30 a.m. and ends at 11:45 a.m., riding from Boca Chica Field at Naval Air Station, 12 miles to Bayview Park at 1320 Truman Ave., Key West. A welcome ceremony follows. Line the highway into Key West, North Roosevelt Blvd., they will then turn right on White Street, Left on Eaton Street, turn right on Simonton Street, Left on Front Street, Left on Duval Street to Truman Avenue, turning left on Truman ending in Bayview Park. Bring your friends and families, and business along the route have employees outside showing support to the 44 Wounded Warriors participating in this years ride.

January 11 to January 29,  in Key Largo
2020 Upper Keys Members Art Show: Small Works, Flora and Fauna
An opening reception will be held Saturday, Jan. 11, from 1–4 p.m. at the Key Largo Library, 101485 Overseas Hwy. The public is invited, refreshments will be served, and there is ample free parking. This Upper Keys Arts Council Member's Show at Key Largo Library supports the Art in Public Buildings program which offers an alternate space for artists to display their work. The exhibition will remain on display through January 29, 2020.

January 11 to April 11,  in Big Pine
Stock Island Arts District's Second Saturday Art Stroll
A new Stock Island Arts District encompasses Collections Key West at Safe Harbor Marina, The Art Shack at 6404 Front St., The Shops at the Perry Hotel, The Studios at Stock Island Marina Village and Washed Up Studios. Each spot offers a variety of eclectic shops and working studios with multiple artists and disciplines from sculptures to woodworking, mosaics to screen printing, soaps to fabric art along with several retail and gallery buying opportunities. There's a few stand-alone studios that will be open for viewing, as well, including Yodanis Studios. ‘Stroll' at leisure from 11AM to 4PM between the studios. Some artists will offer drawings for great prizes and delicious food & beverages. It's free to attend and free to park. Guests can look for the bright pink 'Arts District' banners flying proud at each location and follow the route on the mobile map 

January 12,  in Key West
Impromptu Classical Concerts presents: Blake Pouliot
Blake Pouliot, violinist, has quickly become one of Canada’s most celebrated and promising young artists. He was the Grand Prize winner of the 2016 Orchestra Symphonique de Montréal Manulife Competition while featured on a number of television and radio broadcasts across North America including CBC Radio and NPR’s Performance Today. All Impromptu Classical Concerts are at 4:00 PM at St. Paul’s Episcopal Church, 401 Duval St. in Old Town.

January 12,  in Key West
Rams Head Presents Key West: Grace Potter with Devon Gilfillian
An acclaimed songwriter and electrifying performer, Potter has commanded stages around the world. Her voice has paired with Kenny Chesney in hits such as "You and Tequila" and "Wild Child." Sunset Green Event Lawn is a multipurpose event space located between 24 North Hotel and The Gates Hotel. Tickets can be purchased online or visiting the Key West Theater box office at 512 Eaton St.

January 12,  in Key West
Visit the Family-Friendly Sheriff's Animal Farm
Looking for a fun place to take the kids? The Sheriff's Animal Farm is open 1 - 3 p.m. Bring the family and come visit the animals at the farm, including miniature horses, a cow, pigs, goats, bunnies, alligators, tropical birds, Kinkajous, Sloths, a Lemur, Kramer the Emu, a family of Patagonian Cavys, a skunk, an opossum, tortoises and turtles, snakes and many more. It is free of charge, but donations are welcomed because that is how the farm is sustained. The farm is located just off of College Road, on Stock Island, at the Sheriff's Office Headquarters complex. Open the second and fourth Sundays of the month.
Contact: Farmer Jeanne Selander 305-293-7300

January 12,  in Key West
Key West Artisan Market: Gone to the Dogs! Edition
From 10 am to 2 pm at Clarence H. Higgs Memorial Beach. Meet volunteers of Florida Keys SPCA and maybe a pup or two! Bring your well-behaved four legged friends - the market is always pet friendly and right next to the dog park! Florida Keys SPCA, The Center for Animal Welfare & Education, is dedicated to promoting the humane treatment of all animals through compassionate care, adoption, education, population control and humane law enforcement. Donations toward their mission will be welcome and appreciated. The market is conveniently located close to the free West Martello Tower botanical gardens, White Street Pier and of course, the alluring Atlantic ocean.

January 13,  in Key West
Friends of the Key West Library 2020 Speaker Series
The first speaker in the acclaimed and popular Monday evening lecture series is Rowan Ricardo Phillips, author of The Circuit: A Tennis Odyssey, winner of the 2019 PEN/ESPN Award for Literary Sports Writing. Lecture takes place at the Tropic Cinema on Eaton St. at 6 p.m.  Seating starts at 5:40 on a first come, first served basis. Admission to the lectures is free. 

January 14,  in Key West
Rams Head Presents: Sinbad at Key West Theater
Actor and comedian Sinbad has had audiences laughing for over three decades. His storytelling style of comedy is profound without being profane. Sinbad has recently appeared on Disney’s “Planes,” “Comedy Bang Bang,” “The Eric Andre Show,” FX Television series “It’s Always Sunny in Philadelphia” and NBC’s “Celebrity Apprentice”. Sinbad produced and starred in his own WE TV’s reality show, SINBAD: It’s Just family.” He has done six, one-hour comedy specials in his long comedy career, four on HBO and the last two on Comedy Central…and he’s not stopping anytime soon! Shows at 6:30 p.m. & 9 p.m.

January 15,  in Key West
South Florida Symphony presents Masterworks I: Beethoven, Mahler, Barber
Enjoy two powerful, strikingly beautiful and inspiring musical masterpieces: Bruckner’s dynamic Symphony No. 6, and the U.S Premiere of Borenstein’s glorious Concerto for Violin and Orchestra, featuring accomplished violinist Irmina Trynkos; along with the world premiere of Nardi’s Upon An Ocean. Performance 7:30 p.m., Tennessee Williams Theatre, 5901 College Rd.

January 15 to March 18,  in Islamorada
History of Diving Museum NEW Featured Exhibit: Dive Into Art, The Beauty of Recycling
Visitors to the museum can enjoy this new Featured Exhibit's opening reception and ribbon cutting Jan. 15 from 5:30 to 6:30 pm. The museum's regularly scheduled 'Immerse Yourself!' free lecture series is to follow at 7 p.m. 'Dive Into Art, The Beauty of Recycling' is a creative combination of marine and nautical themed artwork created by members of the Purple Isles Art Guild, along with sculptures made from repurposed materials by Keys school children. Exhibit is to be on display through March 18.

January 15,  in Islamorada
History of Diving Museum Immerse Yourself! Lecture Series: Recycling Tires of Osborne Reef
Since the 1970s, the Osborne Reef off of Fort Lauderdale collected more than 1.3 million tires to create an artificial reef to attract wildlife. Sadly, it had the opposite effect and is now a rubber cemetery polluting the sea floor. Join Commercial Diver Services Corporation owner Geno Gargiulo as he talks about how his company has helped clean Osborne Reef and how you can aid in that process. Lecture series is free; begins 7 p.m., mile marker 82.9, following 5:30 - 6:30 p.m. ribbon cutting of new Featured Exhibit, 'Dive Into Art, the Beauty of Recycling.'

January 15,  in Key Largo
Delicate Balance of Nature Lecture Series: Owls of the Keys
Jordan Budnik, Executive Director of the Florida Keys Wild Bird Center, will introduce the variety of owl species that live in the Florida Keys, from the quirky burrowing owl to the massive great horned owl. She will offer tips to identify them by sight, sound, and behavior, as well as how we can protect them for future generations. Informative lectures are held at the John Pennekamp Coral Reef State Park visitor center and aquarium, mile marker 102.5 oceanside, from 7:30 – 8:30 p.m. Park gates open at 7 p.m. for all lectures. There is no charge to enter the park to attend lectures. Visitors are urged to arrive on time to assure seating in the auditorium.
Email: [email protected]

January 15 to January 20,  in Key West
22nd Annual Key West Half Marathon & 5k Run
Recognized by Runners World magazine as one of the 10 great half-marathons of the winter season, the race follows a 13.1-mile course that includes Old Town Key West and the scenic waterfront. The race typically attracts American and international runners to compete in Key West's balmy January climate. Named as one of the United States' leading winter half marathons, Best Destination Half Marathons and Bucket List Best Half Marathons, is ranked among 13 must-do U.S. half-marathons by
Contact: Barbara Wright 305-240-0727
Email: [email protected]

January 16 to February 01,  in Key West
Waterfront Playhouse presents: Glass
Two legendary figures of the American Theatre, Tennessee Williams and actress Laurette Taylor, meet backstage before the opening night of The Glass Menagerie in Chicago to exchange best wishes. When an unopened bottle of scotch is discovered in her dressing room, sparks ignite as they are both challenged to face down a common demon. Showtimes 8 p.m.

January 16 to February 08,  in Marathon
Marathon Community Theater presents: Four Old Broads
In this laugh-out-loud comedy, retired burlesque queen Beatrice Shelton desperately needs a vacation--and a Sassy Seniors Cruise may be just the ticket if she can convince her best friend, Eaddy Mae Clayton, to stop praying and join her. Unfortunately, things haven’t been pleasant at Magnolia Place Assisted Living since Nurse Pat Jones was hired. A mystery unfolds, hilarity ensues at a Miss Magnolia Senior Citizen Pageant. Will the four old broads make it to their cruise ship? Show dates online; showtimes 8 p.m.; Sunday matinee 3 p.m.

January 16 to January 19,  in Key West
Key West Kingfish Mayhem
Big fish, big money! Come fish for some of the largest kingfish in Florida Keys waters in this tournament. Fishing headquartered at Stock Island Marina. First prize could earn $15,000 cash, based on a 50-boat field.
Contact: Jimmy Wickett 954-605-8284
Email: [email protected]

January 16,  in Islamorada
Morada Way Arts & Cultural District presents: Third Thursday Art Walk
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 - formerly named Industrial Road - as well as "culinary art" and live music from 6-9 p.m. Free admission. Art Walk is held the third Thursday of each month. This month is to feature Coral Restoration Foundation, and you can purchase a reusable cup for your drink as you stroll through Art Walk. And you'll be supporting the reduction of plastic consumption in the Florida Keys!

January 16,  in Key West
Studios of Key West presents Carrie Newcomer
Part of TSKW Old Town New Folk Series. Carrie Newcomer is a singer-songwriter, poet and author at the intersection of folk, Americana and progressive spirituality. She’s described as a “prairie mystic” by the Boston Globe and one who asks “all the right questions” by Rolling Stone. Tickets $60 Preferred, $45 General ($10 discount for members - advance only). Showtime 8 p.m., 533 Eaton St.

January 17 to January 19,  in Islamorada
8th Annual Baygrass Bluegrass & Craft Beer Festival
Flavorful traditional bluegrass, old-time, “soulgrass” and Americana singing bands are to attract thousands of music lovers The three-day jam features satellite events at local spots and culminates in an all-day main event in a waterfront setting. Friday includes a weekend warmup with traditional square dancing; Saturday features live music popups, performing musicians and craft beer; Sunday at Founders Park, MM 87 bayside on Plantation Key, the weekend’s main event is as much a craft beer festival as a musical one, with several Florida breweries “on tap.”

January 17 to January 18,  in Key West
60th Annual Key West Home Tours
Tour elegant and unique private homes of Key West, ranging from exquisite restorations to creative renovations, and the interior design that complements each. January tours are offered 3 to 7 pm each day. Transportation between homes is available via Conch Train for $45 each, seating is limited. Tickets without transportation are $35 in advance and $45 on tour days. Proceeds benefit the foundation's Oldest House Museum, grant and scholarship programs.
Contact: 305-294-9501
Email: [email protected]

January 18 to January 19,  in Key West
15th Annual Florida Keys Seafood Festival
A family-friendly event with local fresh Keys seafood, drinks, marine-related crafts, youth activities, and live music. $5 admission per person; hours open from 11 a.m. - 8 p.m. on Saturday; 11 a.m. to 5 p.m. on Sunday, at Bayview Park, Truman Avenue and Jose Marti Drive.
Email: [email protected]

January 18,  in Key West
Florida Keys Eco-Discover Center's Discovery Saturday: Forts and Cannons
Kids in kindergarten through fifth grade are invited to join the free, fun-filled Discovery Saturday at the Florida Keys Eco-Discovery Center from 10-11 a.m., hosted by Fort Zachary Taylor State Park, a prime birdwatching location. Children will learn how migrating birds rely on the rich resources of the island chain during their seasonal journeys. 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.

January 18,  in Key West
Early Music Key West Presents: Dances and Divisions, A Wind Player's Delight
Priscilla and Grant will present a program of medieval and renaissance music that highlights the versatility of the wind player. From lively estampies to virtuosic recorder solos by Jacob van Eyck to Playford dance tunes, we will take a journey through the many styles of solo wind playing. Performance 7 p.m., at The Parish Hall at St. Paul’s Episcopal Church, 401 Duval St. Admission $30, $15 for students in advance, online. At the door, cash only.

January 18,  in Islamorada
Free Outdoor Pops-in-the-Park Band Concert: What a Wonderful World
Florida Keys Community Concert Band continues its 2020 season at Islamorada Founders Park, Bayside, MM 87, Plantation Key. Performances are outdoors; no chairs provided. Starts at 4:00 p.m. Admission free for all concerts. 'What a Wonderful World' celebrates the beauty of our planet with international music, song and dance.

January 18,  in Key West
Mile Zero Fights
The Key West boxing tradition that dates back to Ernest Hemingway is to be celebrated, when aficionados can watch 11 fights in an open-air waterfront setting at the island’s East Quay Wall at 301 E. Quay Road. The evening’s anticipated highlights include a three-round boxing match between Scott Diaz and Jude Brogli, a five-round kickboxing challenge pitting Gabriel Alvarez against Chase Brooks and a three-round MMA competition between Oscar Lacayo and Chris Gonzalez.

January 19 to January 25,  in Key West
Tara Mandala Key West presents: Tibetan Monks' 2020 Sacred Arts Tour
Tara Mandala Key West meditation group and St. Paul’s Episcopal Church invite the public to help celebrate at the church’s 401 Duval St. location on the corner of Eaton St. The seven-day Tibetan festival will be led by eight visiting Tibetan monks from the Drepung Gomang Monastery—students of H.H. Dalai Lama— and includes noontime dharma talks, a Tibetan Marketplace, classes in the Tibetan Arts, varying music and dance demonstrations of Tibetan culture, and the monks' week-long creation of a Medicine Buddha sand mandala for world healing. The tour aims to spread the message of peace, loving kindness, wisdom, and compassion while sharing their traditional Tibetan arts and culture.
Email: [email protected]

January 20 to January 21,  in Islamorada
31st Annual Al Flutie Over the Hill Rip-Off Sailfish Tournament
Dubbed “almost too much fun for old guys to handle,” the tournament is locally referred to as the Flutie, welcomes anglers age 50 and over. Proceeds benefit "Catch the Cure" for Cystic Fibrosis and the Monroe Association for ReMARCable Citizens, providing life services to Monroe County's adult intellectually disabled residents.

January 20,  in Islamorada
Matecumbe Historical Trust presents: Fortunes Made and Lost in the Florida Keys
The free presentation is to be held at Island Community Church, 83250 Overseas Hwy, at 6:30 P.M. The audio visual presentation is from the late Irving Eyster archives, and will show many of the industries and businesses from the past going back to the early 1800’s through today. Many fortunes were made and lost in the Florida Keys.  Indians had trade here long ago.  Stories include the wreckers, the salt industry, the tobacco factories in Key West, pineapple farming, coconuts and turtles, sponges and the building of what are many of today’s subdivisions.  These industries brought millions of dollars to company owners and employed hundreds.  Presentation is free and open to the public.  

January 21 to April 24,  in Key West
LaTeDa presents: Randy Roberts Live!
The Randy Roberts Show is an all live, multi-media tribute to some of the world’s most loved performers. Randy’s uncanny impersonations of Cher and Bette Midler have kept him in the spotlight for the past twenty years. His roster of famous and infamous ladies also includes: Mae West (a perennial favorite), Joan Crawford, Carol Channing, Ann Miller, Phyllis Diller and a bevy of original ladies. He closes every show with a mini-lounge act, allowing him the chance to get up close and personal with his audience. Showtimes and tickets online.

January 21,  in Big Pine
Outstanding in the Field Dinner
The table will be set on a historic dock surrounded by fishing boats that ply Gulf waters for conch, pink shrimp, spiny lobster, yellowtail, hogfish, and a fresh catch of countless other types of seafood. The day, the first day of kingfish season, starts in Safe Harbor with a reception on the Fishbusterz dock with host fisherwoman, Colleen Quirk. Guests will be shuttled to the Bama Shrimp Dock, where the meal will be prepared by a trio of chefs known for doing great things with the Florida Keys’ ocean harvest. Guest chefs include Martin Liz of Lost Kitchen Supper Club, Stock Island’s Jose Izquierdo of Hogfish Bar & Grill, Jose "Angel" Castro of Roostica, Key West.

January 21,  in Key West
Fourth Annual Conch Revival Picnic
The Key West Art & Historical Society, Great Events Catering, and Isle Cook Key West team up to present the fourth annual Conch Revival Picnic, an informal Conch heritage dinner prepared by acclaimed chefs Martha Hubbard and Dave Furman featuring a variety of classic Key West/Conch recipes set to take place, from 6- p.m. on the grounds of the Key West Lighthouse & Keeper’s Quarters. Tickets —$45 for Members, $55 for Non-members, kids under 12 are free.

January 21 to January 27,  in Key West
29th Annual Kelly McGillis Classic International Flag Football Championship
Women and girls from around the world are to meet on the playing field for hard-fought sporting action. Each year, nearly 30 teams from across the United States, Mexico, Central America, Sweden and India participate.
Contact: 305-896-8678
Email: [email protected]

January 22,  in Key Largo
Delicate Balance of Nature Lecture Series: Lionfish, A Tasty Bite
Invasive lionfish have made a big impact on Western Atlantic coral reefs. Dr. Alli Candelmo, Invasive Species Program Manager at Reef Environmental Education Foundation (REEF), will discuss programs that several organizations have employed to reduce the effect of lionfish. Current and future research to understand and manage this species will also be covered. Informative lectures are held at the John Pennekamp Coral Reef State Park visitor center and aquarium, mile marker 102.5 oceanside, from 7:30 – 8:30 p.m. Park gates open at 7 p.m. for all lectures. There is no charge to enter the park to attend lectures. Visitors are urged to arrive on time to assure seating in the auditorium.
Email: [email protected]

January 22,  in Islamorada
Keys History & Discovery Center presents: Winter Lecture Series
This week’s topic, Restoring the Keys Flats Fishery, is to be presented by Dr. Ross Boucek, Bonefish & Tarpon Trust. Doors open at 5:30 p.m., with cash bar and snacks. Lecture is 6-7 p.m., including time for questions. Reservations should be made in advance. Lecture series runs October through May.
Contact: Reserve 305-922-2237
Email: [email protected]

January 22,  in Key West
Tropic Cinema presents 'Kalachakra: The Enlightenment,' a Special Event
A group of Tibetan Monks from the Drepung Gomang Monastery have visited Key West for a stop on the Sacred Art Tour -- public is invited to meet them at the Tropic for a Tibetan Reception and the showing of an inspiring movie of the Tibetan people, their rituals, and their culture. A reception from 6:30-7 p.m. with tea and cookies is followed by a screening of ‘Kalachakra: The Enlightenment’ with a Q&A session with the monks. Admission $20 per person

January 22 to April 28,  in Key West
LaTeDa presents: Christopher Peterson's EyeCons Cabaret
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 characterizations 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 and even Lady GaGa. Christopher transforms himself from icon to icon right in front of your eyes aided by his magic closet on stage. Showtimes and tickets online.

January 23,  in Key West
Rat Pack Together Again at Key West Theater
A toast to the original Rat Pack, ‘Rat Pack Together Again,’ takes you on a musical journey featuring the greatest hits from the legendary Frank Sinatra, Dean Martin, and Sammy Davis Jr. This production will treat you to Sinatra classics including, ‘Come Fly With Me,’ ‘My Way,’ and ‘New York...’ Dino with great songs like, ‘Everybody Loves Somebody,’ and ‘That's Amore!’ ...and from the dynamic Sammy Davis Jr., ‘Mr. Bojangles’ and Candy Man.’ After watching these performers, you will leave the show feeling as though The Rat Pack is still going strong after all these years. Show Starts 8 p.m., Key West Theater, 512 Eaton St. Tickets available online.

January 24 to January 26,  in Marathon
Island Boat Show & Festival
Come enjoy a great show with loads of the top boat brands , auction items, food, vendors featuring a variety of merchandise, great fishing seminars presented by local captains... all at a very reasonable $10 admission. The show is to take place 1-5 p.m. Friday, 10 a.m. to 5 p.m. Saturday and 10 a.m. to 3 p.m. Sunday. Venue at Hawks Cay Resort.
Contact: Bob Phelps 239-691-3290

January 24 to January 26,  in Islamorada
Cheeca Lodge Presidential Sailfish Tournament
Second in the Gold Cup series. Anglers put 20-pound line and light-tackle skills to the test during the two-day challenge against the high-flying acrobatic fish, known for tail-walking the waves. Only circle hooks can be used. "The Presidential" typically awards sophisticated sculpture trophies to top anglers who release the most sailfish.
Contact: Lisa Thornhill 305-517-4512
Email: [email protected]

January 25,  in Islamorada
Matecumbe Historical Trust presents 'Historical Trolley Tour Through Time'
Enjoy an enlightening trolley ride through time. Guided trolley tours depart at 10 a.m. from the Whale Harbor Restaurant. The one-hour, colorful and much acclaimed historical tours feature 29 points of interest on the islands of Islamorada. Tickets may be purchased on site or call in advance. Adults are $20, children six and under are free.
Contact: Barbara Edgar 305-393-0940

January 25 to January 26,  in Key West
35th Annual Key West Craft Show
The Key West Craft Show is a two day juried outdoor craft festival. This nationally recognized Craft Show brings over 100 fine and skilled craft artists to this beautiful historic area of Key West. Tens of thousands of attendees browse and buy among juried artisans and crafters who gather to display their talents at this popular outdoor festival on lower Whitehead Street in historic Old Town Key West.
Contact: 305-294-1243
Email: [email protected]

January 25,  in Marathon
Fourth Annual Coconut Crawl
The Key Colony Beach Community Association's hilarious pub crawl is back! Every stop on the pub crawl is located within Key Colony Beach and the fun includes a poker run, food, prizes (best hand, best costume and best team spirit) and an award ceremony. The event begins at 1:30 p.m. and concludes at 6 p.m. Registration is $30 for members of the KCB Community Association, and $35 for nonmembers. Register for the crawl at the Key Colony Beach Post Office between the hours of 11 a.m. and 1 p.m. on the following days: Tuesday, Jan. 14; Saturday, Jan. 18; Tuesday, Jan. 21; and Thursday, Jan. 23. Participants can also register the day of the event at the KCB Post Office tiki hut.

January 25,  in Islamorada
33rd Annual George Poveromo's Saltwater Sportsman National Seminar Series
The Seminar Series featuring George Poveromo along with teams of top national and regional angling authorities follows a “No Holds Barred” format that requires experts to reveal their prime fishing spots, the best times to fish them and the best baits and lures to use! Attendees receive five hours of fishing instruction, plus chances to win prizes and a Florida Keys fishing trip. Staged at Coral Shores High School Performing Arts Center, mile marker 89.9 in Tavernier, 9 a.m. to 3 p.m.

January 25,  in Key Largo
Native Plant Day 2020 at John Pennekamp Coral Reef State Park
From 9 a.m. to 1 p.m, enjoy a native plant giveaway, plant identification, informative talks about insects in Keys gardens and their benefits, stroll nature trails and two butterfly garden tours, children's activities, and more. Event admission is free with park entry fee. John Pennekamp Coral Reef State Park is located at mile marker 102.5 oceanside.
Contact: Elena Muratori 305-676-3786

January 26,  in Key West
Cow Key Channel Waterway Clean up
Paddle with a purpose! Join the Blue Moon Crew from 3-5 p.m., helping beautify the Keys’ waterways. Blue Moon Kayak Key West has adopted Cow Key Channel and encourages volunteers to help keep the waters crystal clear. Make an impact on your vacation by looking closely in the water, in the mangroves and on the beaches. Everyone can make a difference by picking up one, two, three or more pieces of plastic. Participants are educated on the different types of debris, how long each takes to decompose in the Keys’ natural environment and what impacts they have on local flora and fauna. Free kayak rentals for the first 10 signups!

January 26,  in Key West
Key West Artisan Market: Food & Wine Edition
Enjoy wine and spirit sampling and bottle and case pricing to stock your cellar. Enjoy a full bar, multiple food trucks and stalls and shop a curated outdoor market offering fine crafts, art and jewelry from talented Florida Keys makers. Listen to awesome local musicians, from 10 am to 2 pm at Clarence H. Higgs Memorial Beach. The market is conveniently located close to the free West Martello Tower botanical gardens, White Street Pier and of course, the alluring Atlantic ocean.

January 26 to October 08,  in Key West
Impromptu Classical Concerts presents: Trio Gaspard
Trio Gaspard, whose members are from Germany, Greece and the UK, is one of the most sought-after trios of its generation. Jonian Ilias Kadesha (violin), Vashti Hunter (cello) and Nicholas Rimmer (piano) have been invited to perform regularly at major international concert halls like Wigmore Hall and the Berlin Philharmonie. They have been winners of three major international competitions since their inception in 2010. All Impromptu Classical Concerts are at 4:00 PM at St. Paul’s Episcopal Church, 401 Duval St. in Old Town.

January 26,  in Marathon
Banana Bay Bazaar
The Banana Bay Bazaar is a premier art and culture event held the last Sunday of every month at the infamous sunset bar, The Pointe. This outdoor, fully immersive experience will showcase diverse arts and local vendors bringing together some of the best attractions to give attendees a wonderful taste of The Florida Keys. Celebrate the afternoon with live local music, food trucks and drinks offered at The Pointe, from noon to 5 p.m., inside Banana Bay Resort, mile marker 45.9 bayside.  

January 26,  in Key West
26th Annual Key West Master Chefs Classic
Local restaurants vie for top honors in appetizer, entrée and dessert categories. Attendees sample the culinary treats while judges pick the winners. The show is held from 4-7 p.m. at the Margaritaville Resort & Marina pier, 245 Front St. Event proceeds benefit the nonprofit Monroe Association for ReMARCable Citizens.
Contact: 305-294-9526, ext 25

January 26 to February 02,  in Key West
Key West Food & Wine Festival
Top chefs and restaurateurs display culinary creativity and the Keys' indigenous cuisine in a flavorful schedule of events for food lovers. Highlights include the lively "Old Town Uncorked," neighborhood wine strolls, food and wine pairings, intriguing seminars, winemaker dinner series and a grand tasting.
Contact: 800-474-4319
Email: [email protected]

January 26,  in Key West
Visit the Family-Friendly Sheriff's Animal Farm
Open between 1 - 3 p.m., the Sheriff's Animal Farm invites you to bring the family and visit the animals at the farm, including horses, a cow, pigs, goats, bunnies, alligators, tropical birds, a Kinkajou, Sloths, a Lemur, Kramer the Emu, a family of Patagonian Cavys, tortoises and turtles, snakes and many more. The farm is located just off of College Road, on Stock Island, at the Sheriff's Office Headquarters complex. The Animal Farm is open every second and fourth Sundays of the month. The Animal Farm is always free, but donations are appreciated!
Contact: Farmer Jeanne Selander 305-293-7300

January 27,  in Marathon
Florida Keys Concert Association presents: Rising Star Concert
Each year the Florida Keys Concert Association presents a “Rising Star” in the classical music field.  Meet Pianist Youlan Ji, born in 1999 in Beijing, China.  At the age of four, she began studying the piano with her mother, and between the ages of nine and twelve, continued her piano studies with Professor Yuan Ling at the Affiliated Middle School of Central Conservatory of Music at Beijing.  In 2012, Youlan moved to New York to attend the Juilliard School’s Pre-College Division, where she continues to study with Yoheved Kaplinsky. Performance at Marathon High School Performing Arts Center. Performance 7:30 p.m. Tickets online.
Contact: (305) 289-1110 or (216) 408-6546

January 27 to January 30,  in Islamorada
Tibetan Monks' 2020 Sacred Arts Tour, Upper Keys
Tibetan Buddhist monks from the Drepung Gomang Monastery return to the Upper Keys to share their ancient cultural teachings, artistic expressions and unique vocal chants with sacred instruments. A series of events include a Tibetan marketplace with handcrafted items.

January 28,  in Key West
Tropic Cinema presents: Babette's Feast, with Master Sommelier Doug Frost
Meet Doug Frost, one of only three people in the world to have achieved Master Sommelier and Master of Wine distinctions, for a special screening of Gabriel Axel’s Oscar-winning 1987 masterpiece, ‘Babette’s Feast.’ The film is lauded as one of the most sumptuous all-time cinematic celebrations of food and wine. Doug will introduce the event and discuss the featured wines and their context. And, throughout the screening, attendees have the opportunity to taste similar wines to those being featured on screen. Tickets online.

January 28,  in Islamorada
Florida Keys Concert Association presents: Rising Star Concert
Each year the Florida Keys Concert Association presents a “Rising Star” in the classical music field.  Meet Pianist Youlan Ji, born in 1999 in Beijing, China.  At the age of four, she began studying the piano with her mother, and between the ages of nine and twelve, continued her piano studies with Professor Yuan Ling at the Affiliated Middle School of Central Conservatory of Music at Beijing.  In 2012, Youlan moved to New York to attend the Juilliard School’s Pre-College Division, where she continues to study with Yoheved Kaplinsky. Performance at Island Community Church. Performance 7:30 p.m. Tickets online.

January 28 to February 01,  in Key West
Third Annual Mile 0 Fest Key West
Mile 0 Fest Key West is a "must see" music festival in the burgeoning Red Dirt & Americana music scene. Take in big shows at Truman Waterfront Park Amphitheatre, a state-of-the-art facility located blocks off the hopping streets of Duval, or get into a stripped down acoustic set with your favorite band leader at one of the theaters or bars off Duval. Many activities and memorable experiences await.

January 28,  in Key West
Old Island Restoration Foundation Lecture Series presents: The Architecture of Key West
Key West is the largest historical district of wooden structures on the US Department of the Interior’s National Register of Historic Places. The charm of Old Town can be attributed to the eclectic mix of over 3,000 wooden buildings constructed throughout the 19-Century; some of which were built in the Bahamas and brought to Key West. In her presentation, art historian Snow Philip will discuss the wide variety of styles and influences that led to Key West’s unique architectural fusion. Snow lives between Key West and Venice, Italy and currently gives presentations to Road Scholar tours on the subject of Architecture. Gates open at 6:00 PM. Admission: $25, OIRF members $15. Water and soft drinks will be available for sale. Held at The Garden at the Oldest House Museum, 322 Duval St. Tickets available online.

January 28 to February 08,  in Key West
The Studios of Key West presents: Prime Time
This new musical follows a female TV executive in the 1970s fighting to keep her variety show afloat, her star husband in check and temptation at bay. Under the direction of Murphy Davis, the script takes off, propelled by commanding performances and a whiff of classic TV nostalgia. Shows Tue-Sat Jan 28-Feb 1 & Feb 4-8, 8 p.m.

January 29 to January 30,  in Islamorada
IFC Sailfish Tournament
Presented by the Islamorada Fishing Club, the event is the last leg this year of the three-pronged Florida Keys Gold Cup Championship series and typically draws a field of up to 30 boat teams of elite sport fishermen. Kickoff is 1/29 and fishing day is 1/30. A total cash payout for a full field at the IFC Sailfish Tournament could reach $30,000.

January 30 to February 01,  in Key West
Cuda Bowl
Shallow water flats anglers and guides are invited to hook-up and fight their barracuda rivals. Event is to be headquartered at Hurricane Hole Marina, Stock Island. Prizes and trophies are to be awarded for top angler and guide in light tackle spin and fly divisions.
Contact: Loren Rea 305-360-6969
Email: [email protected]

January 30,  in Big Pine
Pop and Pour, at the Perry Hotel
In a small class setting at the Perry Hotel’s Salty Oyster,from 7-9 p.m., learn step-by-step, tips and tricks from artist Jasmine Jones for creating your very own 10x10 canvas masterpiece, ready to hang. It’s a twist on paint-and-sip, the newest fluid art craze, ‘alcohol inks.’ Space limited, reserve online.

January 31 to February 01,  in Islamorada
Swamp Guides Ball
Sponsored by the Florida Keys Fishing Guides Association, this all-release event offers team and individual awards to anglers for bonefish, redfish and snook. Anglers fish the shallows of the Florida Keys and the saltwater fringes of the Everglades. Social events are to be headquartered at the Lorelei Restaurant & Cabana Bar.

The Lodging Association of the Florida Keys and Key West
818 White St.
Suite 8
Key West, FL 33040
  305-296-4959 phone
305-296-1408 fax
[email protected]

© The Lodging Association of the Florida Keys and Key West. All rights reserved.
Design & Hosting by