January is a great time… honestly, the best time of year… to visit Key West, Florida. And yes, I say that a lot. But hear me out. The month of January, the first month of the year, lands perfectly after the hustle of the holiday season, when the rest of the country is bundled up, and the island finally exhales.
While friends back home are scraping ice off windshields in colder climates, you’re stepping into an island paradise with palm trees, gentle ocean breezes, and that unmistakable feeling of a perfect escape.
January in Key West is a full-on winter getaway cure for the winter blues.
Key West Weather
Fun fact: Key West is often the warmest place in the continental United States during January, making it an ideal time to visit.
- Average high temperatures: mid-70s degrees Fahrenheit
- Average temperatures: mild, comfortable, and blissfully free of summer heat
- Humidity: low and lovely
- Rainfall: about 7 days total, roughly 2 inches
- Weather conditions: part of the dry season
- Tropical storms & hurricane season: not an issue this time of year
January is typically the coldest month in Key West, and that’s said with affection. Expect pleasant temperatures, warm weather, and evenings cool enough for a light sweater. Compared to the winter weather gripping the rest of the country, this is pure magic.
Water temps hover around the upper 60s, totally doable for water activities, water sports, and sunset swims in the Gulf of Mexico, thanks to the warming influence of the Gulf Stream.
Best Sunset Cruises in Key West
See Dolphins! – Explore the coral reefs.
Driving down from Key Largo? Ultimate Road Trip to Key West
Why January Is a Fantastic Time to Visit 🌊
This is high season and peak season, but crowds are calmer than late November through New Year’s. You’ll still feel the energy, just without the elbow-to-elbow chaos.
It’s a great time for:
- Outdoor activities
- Outdoor adventures
- Snorkeling near vibrant coral reefs
- Spotting sea turtles in their natural habitat
- A glass-bottom boat tour or dolphin encounter
- A classic sunset cruise
It’s also a perfect time to experience Key West at a relaxed pace, whether you’re here for a long weekend or checking off a bucket-list unforgettable experience.
January Events & Annual Happenings
January packs a surprising punch when it comes to events and culture:
- Key West Half Marathon
A high-energy multi-day event where runners chase the finish line through the southernmost city in the U.S. Stock up on carbs… or at least an energy drink. - Key West Literary Seminar
A beloved annual event celebrating writers like Tennessee Williams and Robert Frost, often hosted in historic venues supported by the Old Island Restoration Foundation. - Wine Festival
Because January deserves wine.
And while Fantasy Fest belongs to the fall, January still delivers its own brand of fun, from live entertainment to pop-up celebrations around town.
Best Things to Do in January
Explore Old Town & Duval Street
Duval Street, right in the heart of Old Town, is buzzing with live music, bars, restaurants, and the occasional unexpected drag show. It’s always a good time, especially in the winter season.
Mallory Square & Truman Waterfront Park
Catch the iconic sunset celebration at Mallory Square, then stroll over to Truman Waterfront Park for ocean views and evening breezes.
Historic Homes & Culture
- Ernest Hemingway Home
- Truman Little White House
- Charming historic homes scattered throughout Old Town
Eat Your Way Through the Island
January is peak season for food lovers:
- Key lime pie at Kermit’s
- Fresh seafood at Conch Republic Seafood Company
- Local favorites serving classic Key West food
Beach Days & Day Trips
- Plan ahead for Dry Tortugas National Park, one of the most in-demand tours in the Florida Keys
- Driving from Key Largo? Turn it into the ultimate road trip through the Florida Keys
Getting Here & Where to Stay
Flying in? Key West International Airport makes arrival easy, or you can road-trip from Fort Lauderdale or Key Largo.
Hotels can be hit or miss in January due to high season, but there are plenty of great options if you book early. Expect some holiday spillover crowds early in the month, then smoother sailing.
Final Thoughts: Is January the Best Time?
January checks every box:
- Idyllic weather
- Mild temperatures
- Fewer crowds than the holiday rush
- No summer heat, no tropical storms
- A true tropical escape during the winter months
Whether you’re escaping the cold, starting the new year somewhere warm, or simply craving a fantastic time, January in Key West delivers one of the most memorable Key West experiences of the year.
What Not to Miss when in Key West
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 are these key events….
Key West Literary Seminar (2026) – January 8 – 11, 2026
The Key West Literary Seminar is a world-renowned annual event that celebrates the art of storytelling in one of the most inspiring literary destinations in the world. Each January, authors, poets, journalists, playwrights, and passionate readers gather in Key West to share ideas, explore literary themes, and honor the island’s long tradition as a creative haven for writers.
Founded in 1983, the seminar features a four-day program of readings, lectures, and panel discussions led by some of today’s most acclaimed voices in literature. The event has hosted legendary authors such as Margaret Atwood, Colson Whitehead, Jamaica Kincaid, and George Saunders — all contributing to its reputation as one of the premier literary gatherings in the United States.
Beyond the main seminar, the organization offers a weeklong series of writers’ workshops, giving emerging authors the chance to refine their craft under the guidance of distinguished faculty. Participants also enjoy a range of community events, book signings, and cultural programs that weave together the island’s historic charm with its vibrant literary legacy.
The Key West Literary Seminar continues to foster creativity through year-round initiatives, including the Young Writers Studio, Scholarship Program, and Audio Archives, which preserve decades of readings and talks for public access. Visitors can also take part in the Key West Literary Walking Tour, exploring the homes and haunts of iconic authors like Ernest Hemingway, Tennessee Williams, and Elizabeth Bishop.
Combining intellectual depth with tropical allure, the Key West Literary Seminar offers an unforgettable experience where literature, history, and island beauty come together — inspiring readers and writers alike to keep the spirit of storytelling alive in the Florida Keys.
Florida Keys Wounded Warrior Project: Soldier Ride 2026 – January 9 – 10
Join the Wounded Warrior Project’s Soldier Rides in the Florida Keys Jan. 9–10: scenic, inspiring cycling events from Key Largo to Islamorada, Marathon to Big Pine, and a Key West welcome ceremony with a guided community ride. Cheer veterans, savor island vistas, support heroes, and expect rolling lane shifts on U.S.1—arrive early.
Mile 0 Fest (2026) – January 27 – 31
Experience Mile 0 Fest in the stunning Florida Keys! Enjoy five days of top Texas Red Dirt & Americana music, beachfront parties, and unforgettable sunsets in Key West. Join fellow music lovers for an epic festival getaway filled with live performances, island vibes, and endless fun.
In addition to the music, attendees can enjoy a variety of fun activities, such as Live Music Sails, Pool Parties & more! The festival takes advantage of Key West’s natural beauty and laid-back island vibe, providing a unique and unforgettable experience for music fans and vacationers alike. Join us for five days (or longer!) of incredible music, breathtaking scenery, and unforgettable memories at Mile 0 Fest.
Mile 0 Fest utilizes the Coffee Butler/Truman Waterfront Park Amphitheater, a beautifully designed facility on the Gulf side of the island. This boutique venue offers an unparalleled view from every conceivable spot – whether it is a VIP tent or a blanket spread out on the grassy hill, every ticket level is sure to thrill.
The Amphitheater hosts all evening shows during the festival. Daytime VIP Parties and other events are scattered around the island at hotels, piers, bars, boats, & beaches.
Morada Way Third Thursday Art Walk
Dates: Third Thursday of each month from 6 to 9pm
Experience the vibrant Morada Way Arts & Cultural District Art Walk in the Florida Keys! Enjoy local art, live music, delicious food, and unique shops along a lively, walkable corridor. Join us for an unforgettable evening celebrating creativity and community in paradise.
THE QUEENS OF COUNTRY: PATSY! DOLLY! LORETTA! – January 7 – 10, 2025
Christine Mild will return to the Barn with her latest musical special event, “The Queens of Country: Patsy! Dolly! Loretta!”. The show will have only four performances, January 7-10, 2026. Pianist Jim Rice will once again lead a terrific country band to back Christine up. Limited tickets will be available, and Christine always sells out, so grab your seats as soon as they go on sale later this summer.
Starring:
Christine Mild
Jim Rice, Musical Director & Piano
Edel Rodriguez: WORM: A Cuban American Odyssey – January 8 – 29, 2026
WORM: A Cuban American Odyssey
The Studios of Key West presents WORM: A Cuban American Odyssey, an exhibition by internationally acclaimed artist and illustrator Edel Rodriguez, on view January 8–29, 2026, in the Sanger Gallery. Featuring original drawings from Rodriguez’s graphic memoir Worm, along with new paintings, posters, political illustrations, and personal artifacts, the exhibition traces his journey from Cold War Cuba to Key West via the 1980 Mariel boatlift, exploring themes of migration, identity, and freedom.
Opening Reception: Thursday, January 8, 6–8pm
Free Gallery Talk with the Artist: Friday, January 9, 5pm
Location: The Studios of Key West, 533 Eaton Street
Admission: Free
Ben Harrison at Key West Theater – various dates
Show Dates:
Jan 8, 21
Feb 5, 17
March 5, 25
IRREVERENT, FUNNY, and FULL OF KEY WEST, Ben is the author of the musicals UNDYING LOVE, EL ISLEÑO: The Untold Key West Story, and CLOUDS OVER THE SUNSHINE INN. Back on stage, this will be his third year performing at the Key West Theatre. He and his wife Helen own Harrison Gallery on White Street.
THE ODD COUPLE at Marathon Community Theater
JANUARY 8, 9, 10 @ 8:00PM
JANUARY 15, 16, 17 @ 8:00 PM
JANUARY 18 @ 3:00 PM-SUNDAY MATINEE
JANUARY 22, 23, 24 @ 8:00PM
JANUARY 25 @ 3:00PM -SUNDAY MATINEE
JANUARY. 29, 30, 31 @ 8:00PM
This classic comedy opens on a friendly card game in the untidy apartment of divorced Oscar Madison. And if the mess is any indication, it’s no wonder that his wife left him. Late to arrive is Felix Ungar, who has just been separated from his wife. Fastidious, depressed, and none too tense, Felix seems suicidal, but as the action unfolds, Oscar
Fish for Holly Sailfish Tournament (2026) – January 9 – 11
. Created to raise money for Keys scholarships and domestic violence initiatives, this memorial tournament honors the late Holly Given, a Keys resident and avid angler. Participants gather at the Islander Resort to compete for overall angler and top male, female and junior angler awards as well top boat and fun fish prizes.
RAMS HEAD PRESENTS: ROBYN SCHALL’S HOLIDAY EXTRAVAGANZA TOUR
Experience holiday magic in the Florida Keys! Don’t miss Robyn Schall’s Holiday Extravaganza at the Key West Theater on Janurary 9. Enjoy an evening of laughter and festive cheer with this acclaimed comedian in a vibrant island setting. Book your tickets now for a memorable night!
Exhibit Runs January 9, 2026 – February 15, 2026
Analogous
Old Cameras. New Work.
An Experiment in Analog Photography by Key West Artists Michael Marrero and Mark Hedden
The title of the show, and therefore its concept, is something of a play on words. Michael Marrero and Mark Hedden are two Key West photographers with similar interests but different approaches. Their work is comparable in many aspects and intentions, but distinct in approach and execution, a.k.a. analogous. But within that word there is another word – analog – a term that is used to describe pre-digital photographic techniques, ones that rely on chemicals reacting to light. The show was partly inspired by the work of A.V. Rabenau, an itinerant photographer who worked in the Keys 1910 shooting on glass plate negatives. The images, which contained a deeply impressive sense of depth and clarity, were first exhibited at the Key West Art & Historical Society’s Key West Museum of Art & History more than a century later.
Analagous is also a response to digital imagery that can be created using software like Photoshop and the still nascent array of AI applications. With the (relatively) easily attained perfection of digital imagery, the unique and unpredictable artifacts and imperfections, such as scratches, grain, and uncontrolled lighting are not flaws but assets, reminding us that beauty can be found in the unexpected.
RAMS HEAD PRESENTS: GIVEN TO FLY: A TRIBUTE TO PEARL JAM – January 10
Given to Fly recreates the power and passion of Pearl Jam’s iconic sound and live show. Fronted by Bob Donahue, with his rich and resonant voice that’s strikingly similar to Eddie Vedder’s, Given to Fly is made up of talented, veteran musicians that deliver the vibe, energy, and electricity of Pearl Jam… on classic hits, deep cuts, and new material. Given to Fly is a Pearl Jam tribute for Pearl Jam’s most die-hard fans.
Florida Keys Celtic Festival – January 10 -11, 2026
Experience the vibrant Florida Keys Celtic Festival! Enjoy lively Celtic music, thrilling Highland games, authentic food, and family-friendly fun in a stunning island setting. Celebrate Celtic culture with world-class performers and unique vendors—don’t miss this unforgettable Keys tradition!
Whiskers at Sunset – January 10
Set sail from Marathon on a magical sunset cruise with Island Girls Excursions to support Forgotten Felines of the Florida Keys. Soak in golden skies, calm waters and island breezes while you mingle with fellow travelers—an effortless, scenic evening perfect for leisure seekers wanting authentic Florida Keys sunset vibes.
Save Our First Responders 5K Sponsored By Shatterproof FHE Health – January 10
Join us in Key West for the Save Our First Responders 5K! Enjoy a scenic run or walk through paradise while supporting our local heroes. Perfect for leisure travelers, this event blends fitness, fun, and community spirit in the beautiful Florida Keys. Register now and make a difference!
HISTORIC KEY WEST CEMETERY STROLL – January 11
Join the Historic Key West Cemetery Stroll on Sunday, Jan 11, 2026. Small-group, 90-minute guided tours depart 9:30, 9:50 & 10:10 AM with first-person monologues at notable gravesites like Capt. Willard Gomez and Los Martires de Cuba. Reserve: call/text (305) 304-1453. $20 donation suggested.
2026 Concert Season Preview Party
Experience the Florida Keys 2026 Season Preview Party — Monday, Jan 12, 5–7 PM at the Florida Keys History & Discovery Center in Islamorada. Free admission; cash bar. Meet artists, see video/audio highlights, and mingle—preview world‑class concerts in paradise.
Friends of the Library Speaker Series
Escape to Key West for a free Speaker Series with New York Times bestselling author Nicholas Boggs on Jan 12, 2026, 6–7pm at Key West Library. Presented by the Key West Literary Seminar, Boggs—author of Baldwin: A Love Story—shares illuminating biographical insights. Gates 5:30; first-come seating; rain plan indoors.
Los Lobos at Key West Theater – January 13
It’s a matter of time. 50 years to be exact. And in that time Los Lobos have created an unprecedented body of work, a legacy of greatness.
Christine Andreas (with Martin Silvestri) at The Studios of Key West – January 13
Experience Broadway‑caliber magic in Key West: two‑time Tony nominee Christine Andreas, with Grammy‑nominated composer Martin Silvestri, performs an intimate Spotlight Cabaret curated by Randy Roberts—perfect for an elegant night while visiting the Keys. Tue, Jan 13, 7PM at Helmerich Theater.
Anchors & Atolls – The life and adventures of a 20th Century naturalist in the Tropical Pacific – January 14
Discover CFK’s VIP Series—evening talks and performances featuring local and regional speakers. Join “Anchors & Atolls” with marine biologist Dr. Jack Stein Grove for atoll science, sea‑rise stories and a thrilling anchor recovery—Jan 14 (Key Largo) & Jan 15 (Key West). $5 at door; students free.
5th Annual Key West Chick Fest – January 14 – 18, 2026
Join the ultimate girls’ getaway at Key West Chick Fest, January 14-18, 2026! Enjoy live music, beach parties, island adventures, and exclusive events with Erica Sunshine Lee. Experience the vibrant spirit of the Florida Keys—sun, fun, and unforgettable memories await!
Waterfront Playhouse Presents: Tuesdays With Morrie (Spotlight Series)
Jan 15, 2026 – Jan 17, 2026
A moving adaptation of Mitch Albom’s bestselling memoir, this play follows the touching reunion between a busy journalist and his former professor, Morrie Schwartz, who is facing ALS with heart, humor, and wisdom. An unforgettable drama that celebrates what truly matters.
Scott Kirby- 35 Years of Songs & Stories w/ Caffeine Carl at Key West Theater – January 15
Singer, songwriter, guitarist, storyteller, traveler and road warrior are all words that aptly describe Scott Kirby. Finishing songs while driving through the Italian countryside, performing 100 plus live shows throughout the US and Canada, touring Ireland with 50 fans in tow, and recording his tenth album in Nashville, all keep the barnacles off this modern-day troubadour.
History of Weather Forecasting in the Florida Keys – January 15
Join meteorologist Jonathan Rizzo on Thursday, January 15 for “A History of Weather Forecasting in the Florida Keys,” part of the Key West Art & Historical Society’s Distinguished Speaker Series. Held 6–7 p.m. at the Tropic Cinema (416 Eaton St., Key West), the talk will trace the evolution of weather observing and forecasting in the Keys—from the early U.S. Lighthouse Board and Signal Corps offices to today’s National Weather Service. Through historic photographs and firsthand anecdotes, Rizzo will share how early forecasters predicted extreme conditions in this uniquely challenging region and how those advances shaped life in the islands. Tickets are $13 for KWAHS members and $17 for non-members (available online or at the door); reserve at [kwahs.org/whats-on](http://kwahs.org/whats-on).
Key West International Dance Company – “LAMBADA IS DEAD: LONG LIVE LAMBADA!”
January 15, 16, 17, 20, 21, 22, 23, 24
This popular show – that wowed audiences in our inaugural season – returns in 2026. With
stunning dance numbers, thrilling music by Gil Semedo and narration by Kirby Myers, this
show traces the rise, fall, and rebirth of a dance craze that swept the world in the 80’s. It is
also the story of Master Braz Dos Santos – the world’s most famous lambada dancer. All the
dancers are nationally and internationally known – drawing fans, students and other
aficionados to see them wherever they perform.
Jan 16, 2026 – Jan 18, 2026
The Southernmost Youth Regatta, held January 16–18, 2025, is the youth component of the renowned Southernmost Regatta — a weeklong celebration of competitive sailing in Key West, Florida.
Hosted by the Key West Community Sailing Center, this two-day youth regatta brings together junior sailors from across the region to compete in one of the most iconic sailing venues in the United States. The event features the Optimist (Green Fleet and RWB), ILCA (4 & 6), and 420 class.
Set in the warm, turquoise waters off Key West, the regatta offers excellent racing conditions and the chance for young sailors to be part of a high-profile sailing festival alongside top-level adult competition.
In the spirit of the Southernmost Regatta, this youth event emphasizes great racing, sportsmanship, and community, with social events and awards rounding out the experience.
Join us at the Southernmost point of the continental U.S. for a youth regatta that’s as fun as it is competitive.
RAMS HEAD PRESENTS: ASLEEP AT THE WHEEL – January 15
Experience legendary Western swing with Asleep at the Wheel live at Key West Theater! Don’t miss this unforgettable night of music and fun in the heart of the Florida Keys. Perfect for leisure travelers seeking great entertainment and island vibes. Book your tickets now!
Kash’d Out at Key West Theater – January 16
Get ready for an electrifying night of reggae and rock as Kash’d Out brings their high-energy live show to the Florida Keys! Known for their clever lyrics, infectious grooves, and signature island sound, this Florida-based band has toured with icons like Pepper, The Expendables, and Collie Buddz. Signed to Pepper’s LAW Records, Kash’d Out made waves with their debut album The Hookup and their latest release Butter, showcasing their evolving sound and undeniable originality. Expect a feel-good mix of reggae, rock, and sunshine vibes that will have you moving from the first note to the last. Don’t miss this powerhouse band that’s redefining modern reggae—live and full of Keys energy!
Beats on the Bay – The 13th Annual Baygrass Bluegrass at Founders Park – January 16 – 19
Experience the Baygrass Bluegrass Festival in the Florida Keys! Enjoy live bluegrass music, local food, craft beer, and family-friendly fun in a stunning bayside setting. Celebrate island vibes and great tunes—don’t miss this unique event in the heart of Islamorada!
Jimmy Buffett’s Coral Reefer Band – January 16
Jimmy Buffett’s Coral Reefer Band – Keepin’ the Party Going For over five decades, Jimmy Buffett and The Coral Reefer Band created the soundtrack to endless summers, salty breezes, and carefree good times. What began in 1973, evolved into one of the most beloved live acts in American music history. Though the legendary Jimmy Buffett passed away in 2023, he left a clear message to“keep the party going.” And that’s exactly what The Coral Reefer Band continues to do—with their heart and soul.
Martina Bevis & Friends at Tennessee Williams Theater – January 16
Prague Conservatory of Music trained guitarist, Martina Bevis, returns to the Tennessee Williams Theatre. Join her along with her special guests to experience music from an artist who has mastered her instrument.
Rams Head Presents: The Brit Pack: The Ultimate British Music Experience – January 17
Experience the ultimate British music journey in the Florida Keys! Rams Head presents The Brit Pack, delivering iconic hits from legendary UK artists. Enjoy an unforgettable night of classic rock and pop in a vibrant island setting. Don’t miss this must-see event for music lovers!
A Taste of Thailand: Dinner and a Show at Grimal Grove – January 17
Grimal Grove invites you to take a step into Thailand. Featuring a curated menu by Big Pine Key resident, private chef and celebrated Thai culinary instructor Yupha Kuhn. Chef Yupha values the ability of a home style meal to bring people together. Her meals are prepared with love and served with a smile. Alongside traditional Thai fare, Kai Whitcomb of Thai dance Miami will present Traditional Thai folk and line dancing.
Movies Under the Stars: School of Rock
Catch a free, family-friendly “Movies Under the Stars” screening of the 2003 comedy School of Rock at Tropic Cinema in Key West. Enjoy laughs, heart and classic rock tunes under the sky – perfect for leisure travelers and families. Bring the whole family for singalongs, feel-good music and island-style fun. Sat, Jan 17 • 6:15–8:15 PM. Free!
Bougie Afternoon Tea Party – January 17
Indulge in elegance at the Bougie Afternoon Tea Party in Key West! Savor gourmet teas, decadent treats, and live entertainment in a chic setting. Perfect for leisure travelers seeking a unique, upscale experience in the Florida Keys. Reserve your spot for an unforgettable afternoon!
Art Under the Oaks – January 17
Art Under the Oaks is a beloved annual tradition held beneath the beautiful oak trees on the grounds of San Pedro Church in Islamorada. This vibrant arts and crafts festival has brought the community together each January to celebrate local creativity with handmade goods, fine art, live music, food vendors, and family-friendly activities. Visitors can enjoy everything from children’s crafts and face painting to specialty foods and raffle prizes—all in a warm, welcoming atmosphere. Whether you’re a shopper, artist, or simply looking for a fun day out, this event offers something special for everyone.
28th Annual Key West Half Marathon & Runfest – January 17 – 18
Experience the excitement of the Key West Half Marathon! Run through stunning oceanfront views, lively streets, and historic landmarks in the heart of the Florida Keys. Enjoy live music, local food, and a festive island atmosphere—perfect for leisure travelers seeking fun and adventure.
Yevgeny Kutik at Tennessee Williams Theater – January 18
With a “dark-hued tone and razor-sharp technique” (The New York Times), violinist Yevgeny Kutik has captivated audiences worldwide with an old-world sound that communicates a modern intellect. Praised for his technical precision and virtuosity, he is lauded for his poetic and imaginative interpretations of standard works as well as rarely heard and newly composed repertoire.
Friends of Key West Library Speaker Series: Robert Fieseler
Author Robert W. Fieseler joins the Friends of the Library Speaker Series on January 19th. He will speak about his book, American Scare: Florida’s Hidden Cold War on Black and Queer Lives, a history of how Black activists and gay teachers were targeted by a legislative inquest in Florida in the 1950s and how the story was recovered and revealed after authorities tried to hide it.
The Southernmost Regatta – January 19 – 24
Experience the thrill of The Southernmost Regatta in the stunning Florida Keys! Enjoy world-class sailing, vibrant parties, and breathtaking ocean views. Whether you’re a seasoned sailor or a leisure traveler, this unforgettable event blends excitement, relaxation, and island charm.
Islamorada Fishing Club Captain’s Cup Sailfish Tournament – January 20 -21
Presented by the Islamorada Fishing Club, the event is the second leg of the three-pronged Florida Keys Gold Cup Sailfish Championship trifecta, attracting teams of elite sport fishermen. A total winner-take-all cash payout for a full field at the IFC Sailfish Tournament could reach $25,000
Kelly McGillis Classic – January 20 -26
Join the 2026 Kelly McGillis Classic in the beautiful Florida Keys! Enjoy exciting women’s and girls’ flag football tournaments, beachside fun, and vibrant local culture. Perfect for leisure travelers seeking sun, sports, and unforgettable memories. Don’t miss this unique event!
Truman Music Series: Key West Jazz Society Presents: The Heart Starters – January 20
Experience a swinging night at the Key West Harry S. Truman Little White House with The Heart‑Starters! Live on the North Lawn, this Truman-era tribute revives American Songbook favorites with clarinet, trombone, sax, piano and drums. Gates 5:15pm, show 6–8pm. Retro tropical attire suggested. General-admission seating—book tables or seats early.
AT THE WEDDING at Red Barn Theater
Jan 20 – Feb 14, 2026
Shows: Tuesdays-Saturdays at 7:30pm
Patrons will be cordially invited to a Northern California wedding and meet Carlo, an agent of comedic chaos, as she attempts to make it through the night without drinking too much, talking too much, or trying to win back the bride.
Rams Head Presents: Rumours ATL: A Fleetwood Mac Tribute – January 21
Experience the magic of Fleetwood Mac with Rumours ATL, the ultimate tribute band, live at the Key West Theater! Enjoy iconic hits, vibrant energy, and unforgettable performances in the heart of the Florida Keys. Don’t miss this night of classic rock nostalgia and island vibes!
The Music of ABBA at Tennessee Williams Theater – January 21
A fun colorful family show, all the way from Sweden!
With hits like Mamma Mia, Waterloo, Fernando and Dancing Queen, ABBA, Sweden’s biggest music export group ever, made their way into the hearts of people all around the world.
We will give you the closest ABBA experience you’ll ever going to get with some of the most experienced and talented musicians and singers from Sweden in a tribute that will bring you down memory lane through stunning, mirroring images of their stage costumes, hairstyles, and voices.
You will be dancing in the aisles, singing along to your favorite ABBA song and we assure you, this will be a night you’ll never forget.
Jan 21 – Jan 31
Don’t miss the concert-style revival of 70 Girls 70, the delightfully irreverent Kander & Ebb musical running January 21–31. This “joyously imperfect and irresistibly funny” tale follows a group of senior citizens who turn to life on the edge—committing a few harmless crimes to save their homes. Bursting with charm, wit, and classic show tunes, this feel-good performance reminds us that age is just a number when it comes to adventure. Featuring a talented ensemble led by Karen Grant, Jim Speake, Camille Toler, Barbara Mundy, and Andrew Theede, with narration by Glenda Donovan and Jim Argoudelis.
Honoring America’s First Ladies: Two-Night Series at the Harry S. Truman Little White House
The Harry S. Truman Little White House will host a two-night series on January 23–24, 2026, honoring the legacy and influence of America’s First Ladies, presented in partnership with America250. Guests will enjoy insightful conversations with leading scholars and historians, including the co-authors of Remember the First Ladies and Clifton Truman Daniel, grandson of President and First Lady Harry and Bess Truman. Through expert dialogue, personal stories, and historical perspectives, the series will illuminate the pivotal roles First Ladies have played in shaping the presidency and the nation. Tickets are $40 for Foundation members and $60 for non-members, with a cash bar available; details and reservations can be found at [trumanlittlewhitehouse.org/foundation/events](http://trumanlittlewhitehouse.org/foundation/events).
The Young Dubliners: The HOT TODDY Tour at Key West Theater – January 23
Experience an unforgettable night in the Florida Keys! Catch The Young Dubliners live at the Key West Theater on January 23. Enjoy high-energy Celtic rock in an intimate setting—perfect for leisure travelers seeking unique entertainment and vibrant local culture. Don’t miss out!
Island Boat Show 2026 – January 23 – 25
Experience the Island Boat Show in the beautiful Florida Keys! Explore top boat brands, enjoy waterfront views, live music, delicious food, and family-friendly fun!
Darcy Cooke Celebrates Great Women of Song: Timeless Voices, Unforgettable Music at Williams Hall
Spend an elegant evening in Key West: Darcy Cooke’s tribute to the Great Women of Song—timeless vocals honoring Billie Holiday, Judy Garland, Barbra Streisand and more—at Williams Hall on Jan 23, 2026 (8 PM). Optional 3-course dinner by Chef Martha Hubbard at 6 PM. Perfect for couples and travelers seeking island charm.
22nd Annual Nautical Expo – January 24 – 25
The Lower Keys Chamber of Commerce welcomes you to one of our biggest events with over 100 vendors who showcase a variety of nautical items.
Boating, fishing, diving, snorkeling, watersports, home and office decor, arts & crafts, clothing, jewelry and so much more that makes Florida Keys Living GREAT!
Paradise Big Band at Tennessee Williams Theater – January 25
Under the baton of Joe Dallas Jr, the band remains a truly “local” organization consisting of professional and semi-professional musicians from the Lower Keys and primarily 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
South Florida Symphony Orchestra: Sibelius’ Symphony No. 2 & Ravel’s Piano Concertoat Tennessee Williams Theater – January 24
Rhythmic drive meets lyrical beauty in this exhilarating South Florida Symphony program brimming with wit and brilliance when Ravel’s bluesy and spirited Piano Concerto in G major with SFSO fan-favorite Svetlana Smolina at the keys, joins the windswept glory of Sibelius’ Symphony No. 2. Based on a melody by a 16th century composer, Vaughan Williams’ haunting Fantasia on a Theme by Thomas Tallis opens the sparkling evening of music, led by Key West native, Maestra Sebrina Alfonso.
Tickets on sale now from $35.
Vaughan Williams | Fantasia on a Theme by Thomas Tallis
Ravel | Piano Concerto in G major
with Svetlana Smolina, piano
Sibelius | Symphony No. 2
Kouzov Duo at Marathon High School PAC – January 26
Experience an elegant evening in the Florida Keys: the Kouzov Duo—prize‑winning cellist Dmitry Kouzov and pianist Yulia Federoseeva Kousova—perform beloved works by Beethoven, Schumann, Tchaikovsky, Rachmaninoff and Rostropovich. Jan 26, 7:30 PM at Marathon High School PAC—perfect for a cultured night on your Keys getaway.
Library Speaker Series: Sarah Stewart Taylor – January 26
Join bestselling mystery author Sarah Stewart Taylor at Key West Library on Jan 26, 6:00 PM for a free Speaker Series talk. Creator of the Sweeney St. George and Maggie D’arcy novels, and nominee for the Dashiell Hammett and Sue Grafton awards, she’ll discuss her new 1960s Vermont thriller Hunter’s Heart Ridge. First-come seating.
The Yuck Show: The Science of Slime in Key West! at Tennessee Williams Theater. January 27
Experience The Yuck Show: The Science of Slime at Key West’s Tennessee Williams Theatre! Perfect for families and curious minds, this interactive event blends science and fun with hands-on slime experiments and hilarious entertainment. Don’t miss this unique, messy adventure in the Florida Keys!
Dolphin Sunset Celebration – January 28
Join the Dolphin Research Center’s Dolphin Sunset Celebration in the Florida Keys: exclusive after-hours access, intimate dolphin interactions with jello feedings, expert Q&A on behavior and conservation, and a champagne sunset toast over the Gulf. Includes next‑day admission, one‑year membership and limited monthly spots.
Food and Wine Festival Key West – January 28 – February 1, 2026
Key West
Jan 28, 2026 – Feb 1, 2026
Experience the Key West Food & Wine Festival in the beautiful Florida Keys! Savor world-class cuisine, fine wines, and vibrant island culture with tastings, dinners, and lively events. Join fellow food and wine lovers for an unforgettable celebration in paradise.
Truman Literary Series – “Whistle-Stop Politics” by Edward Segal – January 29
Escape to Key West for the Truman Literary Series: Edward Segal presents Whistle-Stop Politics—a lively, image-rich look at how campaign trains shaped American elections. Join us Jan 29 at Williams Hall for storytelling, Q&A and a post-talk book signing—perfect for curious travelers.
Waterfront Playhouse – Almost, Maine (Mainstage Series)
Jan 29, 2026 – Feb 14, 2026
This whimsical and heartfelt series of vignettes explores the joys and sorrows of love in a mythical town in northern Maine. The New York Daily News wrote: “Almost, Maine’s charm is real. It packs wit, earns its laughs, and, like love, surprises you.”
Petals and Pearls Gala – January 30
Celebrate the 90th Anniversary Gala at Key West Garden Club’s “Petals & Pearls” event! Enjoy an enchanting evening of live music, gourmet cuisine, and lush tropical beauty in the historic West Martello Tower. Experience the magic of the Florida Keys—an unforgettable night awaits!
Key West Tropical Forest & Botanical Garden turns 90 – January 30
Discover paradise at the Key West Tropical Forest & Botanical Garden! Explore lush trails, vibrant native plants, and unique wildlife in the heart of the Florida Keys. Perfect for nature lovers and families, this hidden gem offers a serene escape and unforgettable experiences. Plan your visit today!
Bronson Arroyo – Coming Home! Concert – January 31
Spend a magical Key West evening with local star and former MLB Bronson Arroyo—an intimate solo acoustic concert in the lush gardens of the Oldest House. Proceeds support Key West Conch Baseball and the Oldest House Museum & Gardens. Tickets: General & VIP (pre-show soundcheck, Q&A, signed ball, swag).
Wrong and Strong by Juliet Gray at Williams Hall – January 31
Join Juliet Gray for the world-premiere reading of Wrong & Strong — an hourlong blend of theater and memoir packed with heart, humor and oddball tales (Burt Reynolds, a moon-bound cat, and a longing to belong). Jan 31, 6PM at Williams Hall, Key West. Tickets $15; proceeds support local programs.
Beers, Boats & Banjo’s – Nashville in the Keys – January 31
4th Annual Beers, Boats & Banjos — Nashville in the Keys at Kiki’s Sandbar & Grille on 1/31/26. Live country from Josh Melton, Jason Blaine, Mark Burke & more, boatside fun, cold brews; music starts 11AM.
