January is a great time to visit Key West. Of course, I say that about every month. But, it’s right after the hustle and bustle of the Holiday Season and the crowds are a bit… less. Let’s explore Key West in January!
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Weather
It is probably a given fact, but Key West will be the warmest place in the Continental United States this month. That’s reason enough to plan a trip South, right? The average high temperature is around 74 degrees. With the low humidity, it will feel amazing, especially if you are coming in from the snowy North! Want to spend time in the water? The average water temperature is around 69 degrees, so it’s very doable in January.
Winter months up North are well… you know. But the best places to spend those months are someplace warm. Every morning you wake up to palm trees. Couldn’t ask for anything better than that.
The month of January offers great weather and a good time. Rainy days? Expect about 7 and about 2 inches of rain overall. See… it’s the perfect time to escape the cold. It won’t be long until the hot, humid summer months are here. Keep in mind, January is typically the coldest month. With the turn of the New Year, this is the best place to be, don’t you agree?
Best Sunset Cruises in Key West
See Dolphins! – Explore the coral reefs.
Driving down from Key Largo? Ultimate Road Trip to Key West
Hotels
Since it’s the last winter month in Key West, hotels can be hit or miss. Crowds, as I said, are a bit smaller, but expect to see a surge of people around holidays. Looking for great options? Check out one of our favorite resources Kayak.
Activities
Come to Key West in January to explore the beaches, or check out the many restaurants and bars on Island.
What Not to Miss when in Key West
Duval Street, in the heart of Old Town Key West, is a great place to take in all of the live music.
In the mood for Key Lime pie? Kermit’s is a great place to check out. All things Key Lime.
Feel like fresh seafood? Head over to the Conch Republic Seafood Company. Or, come for the Seafood Festival.
Want to explore Bahia Honda State Park? Check out Up the Keys.
Head down to the Southernmost Point and snap a pic. Your friends will be so jealous back home.
Want to explore the Dry Tortugas National Park? Plan ahead and book early. This is an in-demand tour and books up in advance. Check here for availability.
And then there is…
Fort Zachary Taylor State Park: First Day Hike – January 1
Join a park ranger for a guided First Day Hike through the park’s Tropical Hammock and Fort Moat trails, observing native vegetation and wildlife. Meet in the Fort parking lot in front of the cannon. The hike begins at 8 a.m. and lasts for one hour. Park entrance fee is required. 601 Howard England Way.
Studios of Key West Stories That Swing – Jazz on the Roof with Libby York – January 3
A regular at the top venues in New York, Chicago and Paris, celebrated vocalist Libby York presents the best of the Great American Songbook, and a few Bossa Nova gems, with her jazz quartet up on the roof at Hugh’s View. 5:30 p.m. Tickets $40. 533 Eaton St.
Studios of Key West: First Thursday Open House – January 4
During the First Thursday Open House event, the Studios keep the lights on late and throw the doors open to celebrate the newest work in its galleries. Stop in to say hello, relax with a glass of wine on the rooftop terrace, tour the third floor artist studios and see the just-installed exhibitions in the various galleries. 6 to 8 p.m. at 533 Eaton St.
The Studios of Key West: It’s in the Bag! – January 4- 25 2024
This colorful, irreverent exhibit conceived by writer Kevin Assam asks Key West artists to reimagine the “bags and baggage” they have schlepped, constructed, and embedded in their daily lives. Your favorite Key West creatives present inventive two and three-dimensional works inspired by the theme for one of the most fun exhibits this season. Find the exhibit in The Studios’ Zabar Lobby Gallery, 533 Eaton St.
The Studios of Key West: The State of our Nature – January 4 – 25, 2025
Kristen B. Grace’s photographs of native flora and fauna, plus Indigenous Floridian artworks are presented with Heather Dewar’s elegant captions telling stories of Florida’s evolution, survival, adventure and scientific discovery. The writer and photographer are co-authors of the Florida Book Award’s 2022 Gold Medal in Visual Arts winner, “All Things Beautiful.” The exhibition aims to highlight the importance of conserving Florida’s heritage in a state of environmental change. Find the exhibit in The Studios’ Zabar Project Gallery. 533 Eaton St.
Waterfront Playhouse: Joe Posa as Joan Rivers – January 4 – 6, 2024
Having performed alongside Joan Rivers on two separate occasions, Joe Posa was lovingly called by Ms. Rivers, her “favorite Joan Rivers Impersonator.” See his amazing performance at Waterfront Playhouse for three nights only. Showtime 8 p.m. 407 Wall St.
Tennessee Williams Theatre: Stars of the New York City Ballet – January 5
This is a rare opportunity to see principal dancers from the New York City Ballet performing in Key West. It showcases ballets ranging from the classics to the most contemporary works of today. Tickets $35 to $135. Show at 8 p.m. 5901 College Rd.
Key West Theater: Chuck Cannon – January 5
Chuck Cannon is an American country music singer/songwriter. His compositions include hit singles for Toby Keith and John Michael Montgomery. He appears at Key West Theater as part of the Best of Key West Songrwriters Festival Series. Tickets range from $45 to $65. Doors open at 7 p.m., show at 8 p.m. 512 Eaton Street.
Studios of Key West: One Noble Journey – January 5
Actor and playwright Mike Wiley performs in the interactive, one-man show as Henry “Box Brown, a black slave who mails himself to freedom in a small crate. Audience members join Wiley on stage, becoming characters helping propel the historic action. Performance in Helmerich Theater at 8 p.m. Tickets $60 to $75. 533 Eaton St.
Studios of Key West Dar He: The Story of Emmett Till by Milke Wiley – January 6
Actor and playwright Mike Wiley, in his second of two one-man performances at Studios of Key West, portrays over 30 different characters in the tragic tale of Emmet Till. This riveting play chronicles the murder, trial and unbelievable confession of the men accused of Emmett Till’s lynching in 1955 Mississippi. Tickets for the performance in Helmerich Theater are $60 to $75. Showtime at 8 p.m. 533 Eaton St.
Pole Vault in Paradise Competition – January 6
Pole Vault in Paradise brings together pole vaulters of all ages to compete alongside pole vaulting elite athletes. Sponsored by the nonprofit Key West Track & Field Club, the event is staged at Key West High School’s track at The Backyard sports complex, 2100 Flagler Ave. The first flight of pole vaulters starts at 9 a.m. and continues throughout the day. Viewing is free.
The Studios of Key West: Getting Started with Encaustics – January 7
Transform your work with the luminosity of encaustics, also known as hot wax painting. This workshop offers tips for clarifying your idea, how-to’s for prepping the wax and surface, and tips for color, texture and embellishment possibilities. A brief slideshow of encaustics artwork will help inspire you and plan your steps to create. Class leader Cricket Desmarais is a local visual and performing artist who has taught workshops to all levels and ages. $195 per person, all supplies included. 10 a.m. to 2 p.m. in the Kat in the Hat Classroom. 533 Eaton St.
Tarpon/All That is Sacred Double Feature with Q&A – January 9
The iconic film 1974 documentary Tarpon, which chronicled Key West as a bohemian sportsman’s paradise on the verge of profound change, has been re-imagined into a new short film (with some old footage) called All That is Sacred. Captain Will Benson from the Lower Keys Guides Association and Arlo Haskell from Key West Literary Seminar will discuss the original iconic film and it’s impact that continues to inspire efforts to protect the natural beauty and cultural heritage of the Florida Keys. Showtime 6:30 p.m. Tickets $15. 416 Eaton St.
The Studios of Key West: David Wilcox in Concert – January 9 -10, 2024
Folk singer-songwriter David Wilcox’s lyrical insight is matched by a smooth baritone voice and virtuoso guitar playing, giving him a range and tenderness rare in folk music. More than twenty albums into a career spanning over 30 years of touring extensively around the U.S and world, he continues to deliver joy, inspiration and invention to his legions of fans. Tuesday night at 7 p.m. in Helmerich Theater; Wednesday night at 6 p.m. on the roof at Hugh’s View. Ticket prices vary. 533 Eaton St.
Fringe Theater: 5 Lesbians Eating a Quiche – January 10 – 20, 2024
A tasty recipe of hysterical laughs, sexual innuendos, and delicious discoveries are served up at the 1956 annual quiche breakfast of the Susan B. Anthony Society for the Sisters of Gertrude Stein. Winner of the 2021 New York International Fringe Festival. Tickets $45 to $60. Showtime 7 p.m. at the Armory, 600 White St.
Key West Kingfish Mayhem – January 11 – 14, 2024
Angling teams targeting kingfish can vie for mastery and substantial cash prizes during the 2024 Key West Kingfish Mayhem tournament. Slated for Thursday through Sunday, Jan. 11-14. The open division team that weighs in the heaviest kingfish, also known as king mackerel, is to take home a $10,000 first prize.
Key West Literary Seminar: Florida – The State We’re In – January 11 -14, 2024
Readers and writers gather every January for this festive four-day literary celebration. This year’s theme is: “Florida: The State We’re In.” Attendees will find a cast of novelists, poets, historians, humorists, and cultural critics who know the Sunshine State better than anybody. Featured authors include Dave Barry, Carl Hiaasen, Craig Pittman, Diane Roberts, Campbell McGrath and others. Most seminar events take place at Coffee Butler Amphitheater at Truman Waterfront Park, 21 Quay Road. Tickets are available for the full seminar program. Sunday afternoon events from 1:30 p.m. to 5 p.m. are free and open to the public.
Key West Home Tours – January 12 – 13, 2024
The Old Island Restoration Foundation’s Key West Home Tours are among America’s oldest and longest-running, dating from 1960. This 64th series features self-guided tours of several Key West homes and gardens. Home Tour tickets provide entry to 5 homes at your self-guided pace, between 1-4 p.m. during the Friday-Saturday tour. $55 per person. Addresses of featured homes are to be provided when tickets are purchased.
18th Annual Florida Keys Seafood Festival – January 13 – 14, 2024
Bring the whole family for the freshest seafood caught, cleaned, prepared and served by local fishermen, along with live music both days, plus a kids eco-discovery zone and great shopping and art. Hours on Saturday are 11 a.m. to 7 p.m., and Sunday 11 a.m. to 5 p.m. $10 admission is good for both days and includes entry in a raffle for $250 worth of seafood. The festival takes place at Bayview Park, 1320 Truman Ave.
Sunset Green: Cool Down & Recover Pool Party – January 14
Key West Half Marathon and 5k race participants and the public are invited to a free Cool Down & Recover pool party at the Sunset Green Event Lawn, 3820 N. Roosevelt Blvd. from 4 to 6 p.m. Enjoy live music and drink specials and cool down in the pool.
26th Annual Key West Half Marathon & Runfest – January 14
Recognized by Runners World magazine as one of the 10 great half-marathons of the winter season, the 2024 race follows a 13.1-mile course that includes the Southernmost Point, Duval Street, Smathers Beach and more. The race typically attracts American and international runners to compete in Key West’s balmy January climate. Other events include the 5k along with the Rum Stroll and Beach N’ Beer Mile events.
The Southernmost Regatta – January 15 – 19, 2024
Top sailing teams from around the world compete in the azure waters off Key West, showcasing colorful sails and avid sportsmanship during five consecutive days of racing. Competition is open to One Design and ORC Racing / Cruising Keelboats. Spectators can watch the races from various waterfront venues, mingle with sailors and view sailboats at the Galleon Resort’s marina, 617 Front Street, after each day’s races.
Rokisland Fest – January 17- 20, 2024
More than 20 of the best and most iconic rock bands and performers bring their massive hits to the Southernmost City in the U.S. for four days of unforgettable songs, sun & sand at RokIsland Fest. The lineup includes Bret Michaels, Styx, Stone Temple Pilots, Night Ranger, Don Felder and many more. Multi-day passes with and without rooms and VIP experiences are available, with most performances at Truman Waterfront Park, 21 Quay Rd.
Red Barn Theatre: This One’s for the Girls – The Women of Country Music – January 17 – 20, 2024
Christine Mild returns with a new show featuring the best of women who sing country . . . their stories and their incredible music. She sold out her Patsy Cline show last season so don’t miss this one! Starring Christine Mild with Musical Direction by Jim Rice, Gary Rivenson on bass and Gary McDonald on drums. Tickets $75. Showtime 8 p.m. 319 Duval Street.
Key West Art & Historical Society: Happy Hour with the Historian – January 18
Join historian Dr. Cori Convertito for a talk that explores the diversity of work historically done along the Key West waterfront, including shipbuilding, wrecking, sponging, turtling and shrimping. Important questions will be addressed about how the waterfront has changed over time, the reasons for these changes, and implications for the future. $15 ticket includes one glass of wine, beer or a soft drink. 5 to 6 p.m. at Comedy Key West, 218 Whitehead St.
South Florida Symphony: Brahms, Bach, Montgomery & Price – January 20
South Florida Symphony Orchestra kicks off its 26th Key West Season with the works of two trailblazing composers: Florence Price, the first African American female to have a work premiered by a major U.S. orchestra, and Jessie Montgomery, one of today’s most compelling composers. The stage comes alive as virtuoso pianist Awadagin Pratt presents Montgomery’s latest piano concerto alongside another Symphony premiere, Bach’s Keyboard Concerto No. 4. All of this is anchored by Brahms’ lyrically beautiful Symphony No. 1. Tickets start at $25. Tennessee Williams Theatre, 5901 College Rd. Curtain time is 7:30 p.m.
Tennessee Wiliams Theatre: Paradise Big Band – January 21
Under the baton of Joe Dallas Jr, the band consists of professional and semi-professional musicians from the Lower Keys and Key West. In the interest of enhancing both solo and ensemble performances, the band regularly features outstanding guest artists from New England, New York City and Pittsburgh. Tickets $30 and $40. Showtime 8 p.m. 5901 College Rd.
Kelly McGilis Classic – January 22 -29, 2024
Women from countries far and wide will be descending upon Key West for the 32nd annual flag football competition with teams participating from USA, Morocco, Spain, Mexico, Sweden, Pakistan, Mexico, Honduras and El Salvador. Kelly McGillis will serve as grand Marshall for the players’ parade from the historic seaport down Duval Street on Thursday, Jan. 25. Game activities throughout the weekend Jan. 26-28 are free for the public to attend at Wicker Field Sports Complex on Kennedy Drive off Flagler Ave.
Key West Food & Wine Festival – January 23 – 28, 2024
The festival includes over 20 unique events taking place across the southernmost island city, including waterfront wine tastings, winemaker/chef collaborations, local events that present an authentic taste of Key West, and an amazing grand tasting event. The theme for 2024 is España, celebrating the wine and culture of Spain and Spain’s impact on Key West. Events celebrate the food and wines of Spain along with renowned Spanish artists, and one event themed around Ernest Hemingway’s time spent in Spain. Online ticket sales have closed. Call 800-474-4319 to inquire about availability.
Mile 0 Fest – January 23 – 27, 2024
With a carefully curated line-up of well-known and up-and-coming artists, Mile 0 Fest offers an unforgettable music experience. The event’s “Mile 0” moniker refers to Key West’s location at “mile 0” of U.S. 1. Single day passes are available. Talent includes Morgan Wade, Tanner Usery, the Randy Rogers Band and many more.
Tennessee Wiliams Theatre: The Midtown Men – January 24
The Midtown Men Tenth Anniversary Tour reunites stars from the Original Broadway Cast of the smash hit musical, Jersey Boys. Highlighted with their own high octane arrangements, slick moves and one of a kind repartee, the group’s all new concert features even more iconic 60s music from The Beatles, The Beach Boys, Chicago, Elvis, The Temptations, The 4 Seasons and more. Tickets $35 to $155. Showtime 8 p.m. 5901 College Rd.
Tennessee Wiliams Theatre: Puppy Pals, Live! – January 26
As seen on “America’s Got Talent,” Puppy Pals is coming to town. It’s 60 minutes of Dogs Gone Wild and Humans Gone Crazy! There will be a special meet and greet after the show with your favorite Puppy Pals for photos and ‘paw’ shakes. Tickets $25 to $95. Showtime 7 p.m. 5901 College Rd.
Artisan Market: Food & Wine Edition – January 28
Shop a curated outdoor market displaying delicious culinary creations, fine crafts, art and jewelry from talented Florida Keys makers. Listen to awesome local musicians, meet talented local authors and support the market’s featured charity. In honor of the Key West Food and Wine Festival, you may sip on some great wines while you shop, or visit our full bar. The market is open 10 a.m to 2 p.m. every Sunday through April in Sonny McCoy Indigenous Park, 1881 White St.
Tennessee Williams Theatre: Ann Frank, Words from the Shadows – January 29
The Imperfect Dancers Company presents this inspirational tribute to a young woman’s life and her spiritual strength during one of the darkest moments in the 20th century. Tickets $35 to $155. Showtime 8 p.m. 5901 College Rd.
Monday & Tuesday Evening Glow Hours at Hugh’s Rooftop – Until March 5, 2024
The Studios of Key West’s Hugh’s Rooftop offers the best views in town and an ideal spot to catch the sunset and a drink on Monday and Tuesday evenings from 5 to 7 p.m. through March 5. The bar is open and admission is free. Capacity is limited, so come early. 533 Eaton Street.
