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.
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Events in the Florida Keys for January, 2021
Year: Month:  
November 30 to January 01,  in Key West
2020 Harbor Walk of Lights
The “Harbor Walk of Lights” stretches along the seawall past Greene St, William St, and Margaret St. to the K.W. Ferry Terminal. A nautical theme honors the maritime history of the Key West waterfront. The harborwalk area in the Key West Historic Seaport is to glimmer with holiday displays from Elizabeth to Grinnell streets throughout the season, all themed to celebrate the island city’s maritime heritage. Elements include tens of thousands of lights, dozens of lighted palm trees, a lobster trap holiday tree, a nautically decorated pine and a tree adorned with fishing buoys that resemble giant ornaments.

January 05 to January 07,  in Islamorada
Islamorada Sailfly Tournament
This time of year the weather is ideal for a hot Atlantic sailfish bite. Enter for a chance to compete in a tough yet exciting angling event to kick off the year.
Contact: Randy Towe 305-394-2667
Email: [email protected]

January 05 to March 30,  in Key West
Figure Drawing: Virtual Classes with Lothar Speer
The Key West Art Center is happy to have Lothar Speer return as a figure drawing instructor on Zoom as a virtual art instructor. Lothar studied at The National Academy of The Fine Arts, Vienna, where he received The Johannes Fueger Medal, a European distinction in the field of figure drawing. This workshop is an introduction to this powerful tradition for artists of all levels. Lothar has been teaching the figure for over three decades and delights in adjusting his feedback to each student's level and needs. The principles learned here are universal and can be applied to any subject matter and develop skill which is the prerequisite for powerful personal artistic expression. Classes are held Tuesdays, from 10 a.m. to 12:30 p.m. Visit KWAC website for more information.

January 06,  in Key West
A Virtual Happy Hour with the Historian
In 2022, the island of Key West will be celebrating its bicentennial. In observing this milestone, this talk will be an abbreviated history of Key West from its founding in 1822 through to the present day. A swift canter through the island’s history – approached decade by decade – demonstrates how it has taken on many different identities and functions. Presented by Key West Art & Historical Society. Event from 4-5 p.m.

January 07 to December 23,  in Marathon
Marathon Community Theater presents: The Vagina Monologues
An Obie Award-winning whirlwind tour of a forbidden zone. THE VAGINA MONOLOGUES by Eve Ensler, introduces a wildly divergent gathering of female voices, including a six-year-old girl, a septuagenarian New Yorker, a vagina workshop participant, a woman who witnessed her best friend give birth, a Bosnian survivor of rape, and a feminist happy to have found a man who “liked to look at it.” Performances Thursday, Friday and Saturday evening shows at 8:00 pm with a 3:00 pm matinee offered on Sunday, January 17. Tickets $25 pp.

January 08 to January 09,  in Islamorada
Fish for Holly Sailfish Tournament
Created to raise monies for Keys scholarships and domestic violence initiatives, this memorial tournament honors the late Holly Given, a Keys resident and avid angler. Headquartered out of Whale Harbor Marina, participants are to compete for top male, female and junior angler awards as well top offshore, bay boat, and fun fish categories.
Contact: Annie Hagen 305-304-1762

January 09,  in Big Pine
Stock Island Art Stroll
Experience Stock Island's unique art scene and creative culture, tour Stock Island's best art studios from 11am - 5pm. Start at The Perry Hotel with featured artist Jasmine Jones, who creates her artwork using a combination of alcohol inks, acrylic paint and resin layers to create a body of work with a greater depth than traditional two dimensional paintings.. Make a day of it and treat yourself to lunch at Salty Oyster, dinner at Matt's Stock Island, relax in the hammock gardens, and more!

January 13,  in Key West
The Studios of Key West presents: Livingston Taylor
Part of TSKW's Old Town, New Folk music series. Described as “equal parts Mark Twain, college professor, and musical icon,” Livingston delights audiences with his charm, upbeat storytelling and vast repertoire musical genres – including folk, pop, gospel and jazz. Tickets for this virtual concert are $25, $22 for TSKW members. Starts 8 p.m.

January 13,  in Islamorada
Keys History & Discovery Center Presents…History in Images: Dry Tortugas National Park
Join a live virtual lecture, from 6-7 p.m. (ET), presented by James A. Kushlan and Kirsten Hines. You’ll hear about the lighthouse built in 1826, the nation’s most ambitious masonry fortification Fort Jefferson and its role in the Civil War, and Dr. Samuel Mudd and the other Lincoln conspirators imprisoned there. You’ll see images of its waters, coral reefs and aquatic life, which remain among the most biologically intact in the American tropics. Lecture is free for members and $5 for non-members. Register in advance.

January 14 to January 17,  in Key West
Key West Kingfish Mayhem
Headquartered at Stock Island Marina Village, this four-species event enhances what was formerly a king mackerel tournament by adding tuna, mahi and wahoo. Anglers are to vie for cash prizes.
Contact: Jimmy Wickett 954-605-8284
Email: [email protected]

January 15 to January 16,  in Key West
61st 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 1 to 5 p.m. each day. Proceeds benefit the foundation's Oldest House Museum, grant and scholarship programs. For each tour, the number of visitors allowed inside each home will be limited, masks will be required and hand sanitizers will be provided. Reservations for tour time slots are required and tickets must be purchased in advance.
Contact: 305-294-9501
Email: [email protected]

January 16,  in Key West
Native Plants for Sale at the Key West Tropical Forest
The plant nursery at the Key West Tropical Forest & Botanical Garden will be offering native trees, shrubs, vegetables and vines for sale from 9 a.m. to noon. More than 150 species of plants are available with plants that attract birds and butterflies, in one- to 10-gallon pots.  Key West Tropical Forest members receive a 15 percent discount.  The Garden is a 501 (c) 3 non-profit corporation and all proceeds directly benefit the Garden’s conservation program. Face masks are required and social distancing protocol will be strictly followed.  The Garden is located at 5210 College Road on Stock Island. 

January 17,  in Key West
23rd 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 COVID-19 safety protocols are to be in place.
Contact: Barbara Wright 305-240-0727
Email: [email protected]

January 19 to January 20,  in Islamorada
IFC Sailfish Tournament
Presented by the Islamorada Fishing Club, the event this year is the second leg of the three-pronged Florida Keys Gold Cup Championship series. It typically draws a field of up to 30 boat teams of elite sport fishermen. A total cash payout for a full field at the IFC Sailfish Tournament could reach $30,000.
Contact: IFC 305-664-4735

January 21,  in Islamorada
Morada Way Art Walk
From 6-9 p.m., stroll among outdoor artisans. Presented by Morada Way Arts & Cultural District, a non-profit organization in the heart of Islamorada between mile marker 81 and 82, comprised of Morada Way Clay, Jessica Ann Art, Rum Brush, Limelight Studio/Gallery, and other creative partners. Admission is free, social distancing protocols are to be in place.

January 21 to January 22,  in Key West
Key West Art Center and Gallery presents: Online Art Class with Priscilla Coote
Key West artist Priscilla Coote "takes" students to Bahia Honda State Park via video, where she paints from the water using her Amphibious Easel. She explains how she chooses the subject matter and all the considerations that go into painting on the scene in an active environment. Then students join her in the studio to paint along as she interprets her plein air painting into a finished studio work. Students will be sharing what they create for a positive, personalized experience. Medium can be oils or acrylics. This is an ideal opportunity to learn from a wonderful instructor whose work is collected worldwide. Classes are from 9:30 a.m. to 12:30 a.m. each day. Visit KWAC website for class fees and information.

January 22,  in Big Pine
LIVE on the Lawn at The Perry Hotel: Ciara Rae
Join The Perry for another exclusive concert on the new Barrel House event lawn featuring Ciara Rae, a country/southern rock artist from Nashville! This exclusive performance will be limited to 100 guests - please reserve your chair or blanket space on the lawn for up to 4 guests using the link. In the interest of social distancing, reservations are required and tickets must be purchased in advance. *Due to hosting it outdoors, this event is dependent on weather. Performance starts at 8 p.m.

January 22 to January 24,  in Islamorada
Cheeca Lodge Presidential Sailfish Tournament
The Presidential is one of the most prestigious offshore tournaments in the Florida Keys, and serves as the third and final leg of the three-pronged Florida Keys Gold Cup Championship.
Contact: Liz Hill 305-451-5094

January 22 to January 24,  in Marathon
Island Boat Show
Boating and watersports aficionados can browse among top boat brands at the event, staged at Hawks Cay Resort, mile marker 61 on Duck Key. Boat brands and vendors expected to be featured in the open-air show include Worldcat, Contender, Robalo, Sailfish, Cobia, Twin Vee, Hell’s Bay Boatworks, Stingray, Wellcraft, Bob Hewes, Century and Grady White. The show is to take place 1-5 p.m. Friday, 9 a.m. to 5 p.m. Saturday and 9 a.m. to 3 p.m. Sunday.

January 27 to January 31,  in Key West
Key West Food and Wine Festival
Adventurous aficionados of fine food and vintages can explore creative cuisine, premium wines and unique events in a subtropical island setting during the annual celebration. Whet your appetite for island-style excellence, showcasing local chefs’ culinary flair and favorite indigenous ingredients, intriguing libations and distinctive Florida Keys atmosphere. Ticket sales available online.
Email: [email protected]

January 27,  in Islamorada
Keys History & Discovery Center Presents: Florida Bay & the Everglades, An Ecological Update
Join a live virtual lecture from 6-7 p.m., presented by Dr. Steven Davis of The Everglades Foundation, for an update about the Everglades and its ecology. Established as a national park in 1947, the Everglades is home to more than 70 threatened or endangered species and one out of every three Floridians relies on the Everglades for their water supply. Named the River of Grass by Marjory Stoneman Douglas the same year the park was established, the effort to conserve the Everglades has been ongoing for many decades. Lecture is free for members; $5 for non-members. Register in advance.

January 28 to January 30,  in Big Pine
NEW DATES: Sugarloaf Showdown
Postponed from Nov. 2020. Angling teams are to pit their skills against the Lower Florida Keys’ wiliest in-water inhabitants. Presented by the Lower Keys Guides Association, the tournament raises money for the Florida Keys Guides Trust Foundation. The foundation provides funds to assist fishing guides who are recovering from an illness or injury. According to tournament organizers, participants are to follow Monroe County COVID-19 health safety protocols throughout, including social distancing and wearing facial coverings when appropriate.

January 28 to February 03,  in Key West
Sundance Film Festival 2021 Satellite Screens: Tropic Cinema
This year, Sundance Film Festival is doing things differently by bringing the Fest to Key West audiences with a Sundance Satellite screen in the local community, at the Tropic Cinema, 416 Eaton St. Offered digitally via a custom-designed online platform alongside drive-ins, independent art-houses and a network of local community partnerships in select cities, the Utah festival's characteristics remain the same: celebrating independent film, visionary artists, unique perspectives, and adventurous audiences.

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]

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