January is a great time, best 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.
January in Key West is the cure for winter weather woes—those cold months up north don’t stand a chance against the sunny days and warm weather vibes. With average temperatures lounging in the mid-70s (we’re not bragging, but we totally are), it’s no wonder this is peak season.
Tropical storms? Not a concern this time of year, so it’s a good idea to pack those flip-flops and ditch the parka. High season means you’ll be surrounded by fellow snowbirds flocking to paradise, but hey, more people to cheers at happy hour! One of the best things about January in Key West? While the rest of the country is shivering, you’re basking in island perfection. Winter weather? Never heard of her.
Key West 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, this time of year, 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 days and about 2 inches of rain overall. See… not the rainy season. 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 here.
Activities
Come to Key West in January to explore the beaches, and outdoor activities, 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 are these key events….
Truman Waterfront Farmers Market – Every Thursday – until September 25, 2025
Shop with a view every Thursday from 2 to 7 p.m. at the Truman Waterfront Farmers Market located on the harbor by the USCG Ingham Museum. Find great food options including ready-to-eat items, fresh Florida produce and other grocery items, along with gifts, home decor, art and more. Located at the corner of Southard Street and Weech Way.
Key West Art & Historical Society: Collecting Key West – The Works of Mario Sanchez – Until May 18, 2025
Mario Sanchez (1908-2005), a Key West native, is among this country’s finest and most-recognized folk artists. In hundreds of intricately painted wood carvings created in a lifelong labor of love, Sanchez has provided a better history of Key West in the first part of the 20th century than any annals or academic texts. His bas-relief carvings, or intaglios, are a visual feast filled with the music, smells and passion of Gato’s Village, the Cuban-American community of Key West where Sanchez spent much of his life. In the carvings, each person, chicken, dog and fish has its own singular expression, attitude and identity. The exhibit is on display at the Custom House Museum daily from 10 a.m. to 5 p.m. 281 Front St.
Red Barn Theatre: The Foreigner – until January 11, 2025
This very funny comedy is an American classic, winning the Best New American Play for 1985 by the Outer Critics Circle. Set at a rural Georgia fishing lodge, a pathologically shy man adopts a persona as a non-English speaking foreigner in an attempt to avoid conversation. Hilarity ensues as an outrageous group of characters reveal secrets and scandals. Shows at 7:30 p.m. 319 Duval St.
Waterfront Playhouse: Vagina Monologues – January 2-4, 2025
Featuring talented local voices, Waterfront Playhouse presents Eve Ensler’s groundbreaking show, “The Vagina Monologues.” The show is part of the theater’s Spotlight series. Shows at 8 p.m. 407 Wall St. at Mallory Square.
Studios of Key West: Jeffrey Cardenas – On the Reef – January 2 – 30, 2025
Key West resident Jeffrey Cardenas has traveled from Polynesia to the Mediterranean and Caribbean Sea, photographing vibrant coral reef ecosystems. His work reveals the beauty and essential role of coral reefs in supporting diverse marine life, prompting reflection on their significance and the urgent need for their conservation. 533 Eaton St.
Studios of Key West: First Thursday Open House – January 2
Studios of Key West invites all to visit during First Thursday Open House, where art, conversation and community come alive after hours. Wander through the galleries showcasing the newest exhibitions, sip drinks under the stars at the Hugh’s Rooftop terrace, and explore the creativity in the third-floor artist studios. Take in the vibrant energy, connect with fellow art lovers, and discover hidden gems at Books & Books. Mingle, marvel, or make memories!
Key Largo Library: First Friday Concert – Li’l Rev – January 3
First Friday Concerts are free and begin at 6 p.m. at the library in Tradewinds Shopping Plaza, MM 101.5. Lil’ Rev is a world-class entertainer and steward of vintage song and lore. Performing with ukulele, harmonica, mandolin, guitar and banjor, Rev has an unmatched reporteire of both traditional and original song, poetry, storytelling and humor.
Key Largo Library: Special Saturday Concert Featuring Hungrytown – January 4
Concerts are free and begin at 6 p.m. at the library in Tradewinds Shopping Plaza, MM 101.5. Hungrytown is a true artistic hybrid, able to hold Celtic and Americana, ballads and psychedelia, sunshine and darkness, joy and despair — not only within the same album, but within the same song.
Pole Vault in Paradise – January 4
Pole Vault in Paradise is an all-comers pole vault competition taking place from 9 a.m. to 6 p.m. on Jan. 4 at Higgs Beach, 1000 Atlantic Ave. Participants compete in youth, masters and elite categories, with prize money for the elites. All pole vaulters are welcome and should register online. If you’re not a pole vaulter, bring a chair or beach towel and watch the competition. Admission is free and food and beverage sales support the Key West High School track team. The event is sanctioned by the USATF and is on the World Athletic Calendar.
Key West Literary Seminar: Writers’ Workshop Program – January 5 – 9, 2025
Writers at all stages of development have opportunities to explore the craft of writing at eight distinct workshops available through Key West Literary Seminar before the main seminar begins. Workshops available on the January 2025 program are: Small Miracles: An Exploration of the Short Story; Key West and the Queer Home; Paths Through the Labyrinth: Plot and Structure, Structure and Plot; The Poet as Chronicler of Our Times; Writing Into the Unknown; Developing the Young Adult Voice; Writing Poetry Alongside The Iliad; and The Intersection of Home, Memory and Imagery in Memoir.
Studios of Key West: Susan Werner & Jonatha Brooke in Concert – January 7 – 8, 2025
Join acclaimed folk rock artists Susan Werner and Jonatha Brooke for a night of innovative songwriting, captivating harmonies, and masterful musicianship. Jan. 7 at 7 p.m. in the Studio’s Helmerich Theater and Jan. 8 at 6 p.m. on the rooftop at Hugh’s View. 533 Eaton St.
Connections Project: A Mosaic of the Keys Grand Opening – January 8
This year’s Connections Project spotlights visual and performing artists throughout Monroe County at a series of pop-up events. Each venue will feature a mosaic of almost 100 unique canvases created by Keys artists along with performances by talented musicians. The opening event takes place at the Marathon Chamber After Hours members event at Berkshire Hathaway Keys Real Estate, 9141 Overseas Hwy., from 5:30 to 7:30 p.m.
Key West Literary Seminar: Family – January 9 – 12, 2025
The Key West Literary Seminar is a four-day literary celebration that explores a different theme each year. The 2025 seminar theme is “Family” — the one we’re born into, those we’ve later built or chosen, and the ones we’ve lost or found or run as far away from as possible. For “Family,” the seminar brings together writers who can help us understand how the ties that bind shape the stories we tell, the worlds we move through, and all the imagination’s possibilities for human connection. Featured writers include John Irving, Brando Skyhorse, Paul Harding, Nathan Hill, Dani Shapiro and many more. Programs take place at the historic San Carlos Institute, 516 Duval St.
Key West Art & Historical Society Historic Seaport Sail: Harry S. Truman in Key West – January 10
Enjoy a 2-hour Historic Harbor Tour with Truman Little White House docent Rick Warmbold on the S/V Argo Navis, talking about “Harry S. Truman’s Eleven Key West Visits.” The trips departs from the Historic Seaport docks at 0 Margaret St. at 10 a.m. and returns at 12 p.m. Passengers will enjoy Bloody Marys, mimosas, or non-alcoholic beverages along with lite breakfast fare as Warmbold dives into Truman’s eleven working vacations, and shares how Key West was not only a place for the President to recharge his batteries – he will tell you how things in Key West would shape the country and world. Book reservations online in advance.
Key West Outdoor Movies – January 10
Key West Outdoor Movies presents a family-friendly film (to be named) at the parade grounds at Fort East Martello, 3501 S. Roosevelt Blvd. The grounds open at 5 p.m. with free admission. Food and drink will be available for sale by vendors onsite, and there will be free popcorn and activities for all. Bring low chairs or a blanket. The movie starts at dusk.
Wounded Warrior Project Soldier Ride– January 10 -11, 2025
The Wounded Warrior Project Solider Ride takes place in the Upper, Middle and Lower Keys Jan. 5 and 6. U.S. 1 will be open, but motorists are asked to be patient, use caution and be prepared for possible rolling lane shifts. The ride starts Friday at 8:30 a.m. departing Key Largo VFW, ending around 10:30 a.m. at Three Waters Resort. Riders will then be transported to Marathon, where they will depart from Marathon fire station and cross the 7 Mile Bridge between 1:30 and 2:30 p.m. Saturday, riders depart from NAS Key West at Boca Chica at 10:30 a.m., headed for Bayview Park in Key West. The public is invited to join the riders for a community ride from Bayview Park at 12:45 p.m. to historic military sites in Key West. Patriotic bike decorations are encouraged, along with a suggested donation of $20.
Classical Keys in the Keys – January 11
Enjoy an evening of classical piano music featuring piano virtuoso Frederic Chiu as he presents “Heart & Soul,” one of his signature Classical Smackdowns, where the audience votes for one of two legendary composers, round by round. The program has been performed around the world with the voting results captured for each venue. Doors open at 6 p.m. at Matecumbe Methodist Church, 81831 Overseas Hwy. VIP experience options available including cocktails and light bites at Kaiyo Grill & Sushi.
Florida Keys Celtic Festival – January 11 – 12, 2025
Experience the unique sights and sounds of the Scottish Highlands and the Emerald Isle in the heart of the Florida Keys. The resounding rhythms and “Bareknuckle Pipes and Drums” of Scottish band Albannach and the harmonies of Irish sisters, “The Screaming Orphans” headline the entertainment. Other highlights include bagpipers, Irish step dancers, a variety of highland athletic games, authentic Celtic food and vendors offering Tartan kilts along with jewelry, gifts, clothing and more. 10 a.m. to 7 p.m. Saturday; 11 a.m. to 5 p.m. Sunday. Kids age 12 and under get in free with paying adult. Marathon Community Park, MM 49 oceanside.
Lower Keys Guides Association: Get Trashed Cleanup– January 12
Join the Lower Keys Guides Association in keeping the Keys free of debris. Collect as much marine and coastal trash as you can to help the ocean and Florida Bay, then drop it off Sunday, Jan. 12 between 1 and 4 p.m. at Sugarloaf Marina, mile marker 17 bayside for free raffle tickets and swag. You do not need to be present to win raffle.
Impromptu Classical Concerts: Thomas Mesa & Greg Zelek – January 12
Cellist Thomas Mesa and organist Greg Zelek will present a special duo concert showcasing the historic pipe organ at St. Paul’s Episcopal church. Mr. Mesa has established himself as one of the most charismatic, innovative, and engaging performers of his generation, and is the recipient of the Sphinx Organization’s 2023 Medal of Excellence, its highest honor. Mr. Zelek is the Principal Organist of the Madison Symphony Orchestra and Curator of the Overture Concert Organ, where he regularly performs and oversees all the MSO’s organ programming. 4 p.m. at St. Paul’s, 401 Duval St.
Key West Artisan Market: Don’t Be Trashy! – January 12
Key West Artisan Market invites you to help keep our island clean and learn more about the efforts of Plogging the Keys and the Keep Key West Beautiful initiative. Find out how you can help and ways to be a part of the solution. Enjoy bloody’s, mimosas along with a full bar, coffee, smoothies, natural juices and cut fruit, multiple food trucks and stalls offering eat-here or take-away for snacking or a delicious meal. Shop a curated outdoor market offering fine crafts, art and jewelry from talented Florida Keys makers. Stock your pantry and fridge with fresh produce, artisan cheeses, local seafood, honey, pickles and so much more. Listen to awesome local musicians, meet local authors and support our featured charity. 10 a.m. to 2 p.m. 1801 White St.
Florida Keys Concert Association: Boilermaker Jazz Band – January 13 – 14, 2025
The 55th season for Florida Keys Concert Association includes six concerts, each taking place in two locations. The first concert features the Boilermaker Jazz Band from Pittsburgh, that has been performing swing and hot jazz worldwide for over 30 years. Shows begin at 7:30 p.m. On Monday, Jan. 13, the band plays at Marathon High School, 350 Sombrero Beach Rd., and on Tuesday, Jan. 14 the show is at Coral Shores High School, 89901 Old Hwy.
Key Largo Library: Eco Voices & Art – January 13
Join a representative from the Florida Keys Wild Bird Rehabilitation Center at 11 a.m. to learn all about the unique birds of the Florida Keys, the center’s role in rescuing them and how you can help local bird populations. From 1 to 4:30 p.m., artist Gloria Avner leads a batik workshop to create amazing images of birds. The library is located at Tradewinds Plaza, mile marker 101.5.
Key West Library Speaker Series: Mondays at 6 p.m. – January 13 -17, 2025
Authors in the Key West Library Speakers series appear on Mondays, January through March. January’s featured speakers are: January 13: Ayana Mathis, author of The Unsettled (Knopf, 2023), named a New York Times and Washington Post Notable Book of 2023. January 20: Jimin Han, author of The Apology, named best book of the summer by the Los Angeles Times, Vanity Fair and others. January 27: Cathy Salustri in conversation with David Sloan – Salute is author of Florida Spectacular: Extraordinary Places and Exceptional Lives. Free to attend and no registration required. Talks take place in the library’s Palm Garden, 700 Fleming St. at 6 p.m.
Key West Theater: Bitch Trouble – January 14
Writer performer Alice Johnson Boher takes you on a coming-of-age roller coaster ride of the giddy highs and codependent lows of best friendship. Told in three chronological tales, Bitch Trouble charts Alice from friendless youngster in a lame southern subdivision all the way to one-half of an iconic friend duo in the shadows of Hollywood. Performance takes place in the theater’s Back Stage Listening Room. Doors open 6 p.m.; show 7 p.m. 512 Eaton St.
Fringe Theater: I Love You, You’re Perfect, Now Change – January 14 – 25, 2025
A hilarious and insightful musical exploration of the epic truths and challenges of modern love and romance. Nightly showtimes 7 p.m. at Key West Armory, 600 White Street.
Studios of Key West: Dom Flemons, the American Songster in Concert – January 14 – 15, 2025
Preservationist, storyteller and multi-instrumentalist Dom Flemons’ repertoire covers over 100 years of early American popular music. He performs Jan. 14 at 7 p.m. at the Studios’ Helmerich Theater and Jan. 15 at 6 p.m. on the Hugh’s View rooftop. 533 Eaton St.
Islamorada Fishing Club Captain’s Cup Sailfish Tournament – January 14 -15, 2025
Presented by the Islamorada Fishing Club, this is the second leg of the Florida Keys Gold Cup Series, with a field of up to 25 boat teams of elite sport fishermen. A total cash payout for a full field at the IFC Captain’s Cup Sailfish Tournament could reach $25,000. Kick off is Jan. 14 with one day of fishing on Jan. 15, with the awards ceremony immediately after at the Islamorada Fishing Club.
Key West Kingfish Mayhem – January 15 – 19, 2025
Angling teams targeting kingfish can vie for mastery and substantial cash prizes during the 2025 Key West Kingfish Mayhem tournament. The open division team that weighs in the heaviest kingfish, also known as king mackerel, is to take home a $75,000 first prize with $35,000 and $20,000 going to the second and third place teams, respectively. The tournament is headquartered at The Perry Hotel & Marina.
History of Diving Museum: Art Exhibit – Fintastic Fish of Florida – January 15 – April 16, 2025
The History of Diving Museum’s latest featured exhibit, “Dive Into Art: Fintastic Fish of Florida” is on display through April 16. The exhibit features artistic creations from students across the Keys, as well as from the Art Guild of the Purple Isles. These works focus on the diverse fish of the Florida coast, along with sustainable fishing, aquaculture, and conservation.
History of Diving Museum – January 15
Join Jill Kuehnert and Michaela Peterson of REEF — Reef Environmental Education Foundation —as they present actions you can take to help save Keys coral reefs. The free 7 p.m. presentation explains that small steps, like learning about marine life or contributing an hour to citizen science, can truly add up to impactful, lasting change for our oceans. Come early to see the History of Diving Museum’s new featured exhibit, Dive Into Art: Fintastic Fish of Florida on its opening day. See incredible creations by students across the Keys, as well as by the Art Guild of the Purple Isles.
College of the Florida Keys VIP Series: Galapagos Fishes with Dr. Jack Stein Grove – January 15 -16, 2025
The College of the Florida Keys’ kicks off the 2025 CFK VIP Series with Jan. 15 at the Upper Keys Center in Key Largo and January 16 at Tennessee Williams Theatre. Both events start at 7 p.m. The topic by speaker Dr. Jack Stein Grove is ‘Galapagos Fishes, From the Shore to the Abyss & From Darwin to DNA.’ Tickets are $5 at the door; admission is free for CFK and Monroe County School District students.
27th Annual Key West Half Marathon & Runfest Weekend – January 16 -19, 2025
Enjoy a weekend filled with running and camaraderie including 5k, 8k, 10k and half marathon races. Participants can also sign up for the Papa’s Pilar Rum Stroll and the Beach N’ Beer Mile, and celebrate with recovery and farewell parties.
Marathon Community Theater: Always a Bridesmaid – January 16 – February 8, 2025
This comedy follows four Southern high school friends who vow serve as bridesmaids in each other’s weddings, no matter what. Fast forward to 30 years later, they are still determined to honor their vow and navigate the challenges of love and marriage as bridesmaids through multiple weddings. Showtimes at 8 p.m. 5101 Overseas Hwy.
Morada Way Third Thursday Art Walk – January 16
The Morada Way Arts & Cultural District’s Third Thursday Art Walk in Islamorada is the organization’s landmark, monthly event. This Thursday, enjoy a holiday-flavored edition of the art walk with Keys-inspired fine artists, vendors, residents, and visitors congregating on Morada Way in Islamorada. Enjoy a relaxing evening from 6-9 p.m. perusing local fine art, imbibing local craft beer and wine and listening to music, in the area between mile markers 81 and 82 at 151 Morada Way.
Baygrass Bluegrass Festival – January 16 -20, 2025
This year’s festival includes three days of music in the Morada Way Arts and Cultural District in the beer garden at Florida Keys Brewing Co., 81611 Old Hwy., from Friday, Jan. 17 through Sunday, Jan. 19; then concluding with an afternoon concert on Monday, Jan. 20 at the amphitheater at Founders Park, mile marker 87 bayside. Free admission to both venues, but there is a $10 parking charge on Monday at Founders Park.
Weinerpalooza – January 18
Key West’s annual Dachshund Parade takes place Saturday, Jan. 18. All parade revelers are to gather at 11:30 a.m. in front of Customs House, 281 Front St., for a group portrait followed by the parade at 12 noon. Tails wag all along the parade route that ends at Hank’s Hair of the Dog Saloon. All doggies are welcome and pet costumes are encouraged. Enjoy drink specials, raffles to benefit the Friends of Luci Fund and live entertainment.
Art Under the Oaks – January 18
Explore original arts and crafts at booths spread under the towering oak trees in the San Pedro Church Gardens, MM 89.5 from 9 a.m. to 4 p.m. There will be live music, specialty and international food booths and trucks, and homemade goodies in the bake sale. Parking available at Plantation Key School.
South Florida Symphony: Candide – January 19
South Florida Symphony opens the Key West season with performs Leonard Bernstein’s satirical Candide – a thrilling blend of outrageous humor, poignant storytelling and unforgettable music that follows the optimistic Candide on a globetrotting adventure of love and self-discovery. This version features the orchestra, a dynamic cast of actor-vocalists, minimal sets and costumes and a chorus performing together on stage.
Florida Keys Concert Association: Famous Opera Highlights – January 20 -21, 2025
The 55th season for Florida Keys Concert Association includes six concerts, each taking place in two locations. The second concert features Chelea Duo, Soprano and Joe Luis Maldonado, Barton with pianist Benedicte Jourdois, offering an evening of spine-tingling music including arias and duets from Carmen, La Traviata, The Barber of Seville and Carousel. Shows begin at 7:30 p.m. On Monday, Jan. 20, they perform at Marathon High School, 350 Sombrero Beach Rd., and on Tuesday, Jan. 21, the show is at Coral Shores High School, 89901 Old Hwy.
The Southernmost Regatta – January 20 – 25, 2025
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.
Kelly McGillis Classic International Flag Football Championship – January 21 – 27, 2025
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.
Mile 0 Fest – January 21 – 25, 2025
Mile 0 Festival is a premier music festival that celebrates Red Dirt and Americana music. Artists includes the Red Clay Strays, Randy Rogers Band, Shane Smith & the Saints, Steve Earle, Reckless Kelly, Kaitlin Butts and many more. A variety of passes that include lodging are available along with event-only passes.
Key West Theater: Ben Harrison – January 21
Ben Harrison is a playwright, lyricist and composer who is also an entertainer. What makes his live performances so enjoyable is that, at his core, he is a barroom guitar player/singer/songwriter who somehow manages to blend history, musical theater, Key West and humor into unusual stories that are mostly true. Key West Theater’s Backstage Listening Room. Doors at 6 p.m.; show at 7 p.m. 512 Eaton Street.
Connections Project: A Mosaic of the Keys Pop-Up at Cheeca Lodge – January 21
The Florida Keys Council of the Arts Connections Project spotlights visual and performing artists throughout Monroe County at a series of pop-up events. View this year’s artful mosaic of almost 100 unique canvases created by Keys artists along with performances by talented musicians at the Islamorada Chamber of Commerce’s Members After Hours event at Cheeca Lodge, 81800 Overseas Highway oceanside beginning at 5:30 p.m.
Key West Theater: Melissa Etheridge– January 22
Don’t miss the legendary Melissa Etheridge on the Key West stop of her 2025 tour. Known for her confessional lyrics and raspy, smoky vocals, Etheridge has remained one of America’s favorite female singer-songwriters for more than two decades. Doors at 7 p.m.; show at 8 p.m. 512 Eaton Street.
Waterfront Playhouse: The Angel Next Door – January 22 – February 8, 2025
The wonderfully funny script by Paul Slade Smith captures the joy and wit of 1940s screwball comedies. Brace yourself for what a critic called “a perfect storm of comedic chaos, irresistible charm and rapid-fire banter.” Showtimes 8 p.m. plus a 2 p.m. matinee on Feb. 1. 407 Wall St. at Mallory Square.
Key West Theater: Jon McLaughlin & Eric Hutchinson– January 23
Acclaimed guitarist Jon McLaughlin and singer-songwriter Eric Hutchinson perform together, bringing a blend of collaborative moments with both playing on each other’s songs as well as each of them being on stage solo. Doors open at 7 p.m.; Show at 8 p.m. 512 Eaton St.
Walk on White Third Thursday Art Walk – January 23
Explore an array of arts-focused offerings at more than 20 locations showcasing the works of painters, photographers, sculptors, ceramic and mixed media artists, and artisan jewelry makers at this monthly third Thursday event from 6 to 9 p.m. Take in views of beautiful island architecture, exhibit openings, creative demonstrations, musical, literary and performance offerings and complimentary libations. White Street between Southard and United Streets.
Everglades National Park Flamingo Campground: Two Nights Under the Stars – January 24 – 26, 2025
Join the Alliance for Florida’s National Parks for an unforgettable weekend adventure. Activities include a tour of the historic Nike missile base inside the park, stargazing, kayaking, yoga, hikes, campfires, storytelling and more. Each campsite includes a picnic table and a fire ring. Bring your own tent, sleeping gear and personal supplies. Rooms may also be available at Flamingo Lodge. Tickets required to participate in the weekend programming.
Old Island Restoration Foundation: January Home Tours – January 24 – 25, 2025
Key West is home to what is considered the largest predominantly wooden historic district in the United States. One weekend a month, from January through March, five distinctive homes and their gardens open, revealing a range of architectural gems, eclectic art, transformed cigar-makers cottages, shipbuilders’ craft, re-imagined Victorian mansions, and the stories behind the facades. Home tour tickets provide entry to 5 homes at your self-guided pace during the Friday-Saturday tour dates. All tickets for sale online. Your receipt will be your ticket to enter the home. If you prefer to have a physical ticket, you can pick one up at the Oldest House Museum gift shop, 322 Duval St., the week before the tour date.
Coconut Cove Resort & Marina: Roaring for Rescues – January 24
Enjoy an elegant, 1920s-style event from 6 to 10 p.m. at the 6th annual Roaring for Rescues benefit for the Upper Keys Humane Society. Enjoy dancing to live music by Retro Rebel, dinner, entertainment, raffles, a silent auction and more. Mile marker 84.8 oceanside.
Island Boat Show – January 24 – 26, 2025
Billed as the Florida Keys’ premier boat show, Island Boat Show is held on the grounds of Island Community Church in Islamorada. Planned attractions include top boat brands and dealers, large silent auction, food and drink vendors, and nautical merchandise for the entire family. The show is open Friday from 1 to 5 p.m.; Saturday from 10 a.m. to 5 p.m.; and Sunday from 10 a.m. to 3 p.m., mile marker 83.4 bayside.
Tropic Cinema: Movies Under the Stars – War Games – January 25
Don’t miss the monthly free Movies Under the Stars screening – this month, the movie is War Games. The film will be presented free for all, outdoors on Eaton Street. Bring chairs or blankets for seating. Concessions are to be available in the theater lobby. The film begins a half hour after sunset. 416 Eaton St.
21st annual Big Pine & the Lower Keys Nautical Expo – January 25 -26, 2025
Find steals and deals on everything imaginable for boating, fishing, diving and more, from over 100 vendors. You’ll also find clothing, jewelry, arts and crafts, food and beverages, and live music during the two-day event. Admission and parking are free at the Lower Keys Chamber of Commerce grounds, mile marker 31 on Big Pine Key, Saturday from 8 a.m. to 4 p.m. and Sunday 8 a.m. to 2 p.m.
Connections Project: A Mosaic of the Keys Pop-Up at Lower Keys Nautical Expo – January 25
The Florida Keys Council of the Arts Connections Project spotlights visual and performing artists throughout Monroe County at a series of pop-up events. View this year’s mosaic of almost 100 unique canvases created by Keys artists along with performances by talented musicians at the Lower Keys Chamber’s Nautical Market, 8 a.m. to 4 p.m. at 31020 Overseas Hwy.
Pops in the Park: Afternoon Delight & Pet Parade– January 25
The Florida Keys Community Concert Band’s Jan. 25 free Pops in the Park performance, themed “Afternoon Delight,” is to be filled with upbeat animal-themed music along with other classic and pop favorites. Bring your pets to strut their stuff in the annual pet parade during the performance. Animal Care Coalition will bring adorable adoptable pets to the performance. 4 p.m. at the amphitheater at Founders Park, mile marker 87 bayside.
Key West Cemetery Tour – January 26
Historic Florida Keys Foundation holds its first Key West Cemetery tours of the season on Sunday, Jan. 26 at 9:30, 9:50 and 10:10 a.m. Groups of visitors will be escorted to the grave sites of Juana Borrero Pierra, William Curry, George Adderly, May Douglas, Hilda Russel and the USS Maine Monument. The 90-minute tour will cover about one mile – wear comfortable shoes. A donation of $20 to the foundation is appreciated. Reservations are required. Email hfkf@bellsouth.net or call 305-304-1453.
Sheriff’s Animal Farm Open House – January 26
Visit the family-friendly Monroe County Sheriff’s Animal Farm, open the second and fourth Sundays of each month from 1 to 3 p.m. Animals include a capybara, possum, sloths, goats, birds and many more. Visits are free of charge, but donations of cash or fresh produce are always welcomed. Stock Island Detention Center, 5501 College Rd.
Impromptu Classical Concerts: Simone Porter – January 26
Violinist Simone Porter has been recognized as an emerging artist of impassioned energy, interpretive integrity, and vibrant communication. In the past few years, she has debuted with the New York Philharmonic, the Philadelphia Orchestra, and the Los Angeles Philharmonic. Born in 1996, Simone made her professional solo debut at age 10 with the Seattle Symphony and her international debut with the Royal Philharmonic Orchestra in London at age 13. 4 p.m. at St. Paul’s, 401 Duval St.
Florida Keys Concert Association: Fred Moyer, Pianist – January 27 -28, 2025
The 55th season for Florida Keys Concert Association includes a selection of concerts, each taking place in two locations. The third concert in the series features Frederick Moyer. During more than thirty years as a full-time concert virtuoso, Moyer has appeared as piano soloist with numerous world-renowned orchestras in all parts of the globe. A consummate communicator and educator, he is one of the concert association’s favorite artists and is returning with his magnificent performances of classical music. Shows begin at 7:30 p.m. On Monday, Jan. 27, he plays at Marathon High School, 350 Sombrero Beach Rd., and on Tuesday, Jan. 28, the show is at Coral Shores High School, 89901 Old Hwy.
Connections Project: A Mosaic of the Keys Pop-Up at The Hale Gallery – January 27
The Florida Keys Council of the Arts Connections Project spotlights visual and performing artists throughout Monroe County at a series of pop-up events. View this year’s mosaic of almost 100 unique canvases created by Keys artists along with performances by talented musicians at The Hale Gallery at Ocean Sotheby’s Realty, 81800 Overseas Highway bayside beginning at 5:30 p.m.
Winter Star Party – January 27 – February 2, 2025
Astronomers and astrophotographers from around the globe gather in the Lower Florida Keys to enjoy 180-degree viewing of the Southern Cross and other constellations, comets and stars during the Winter Star Party.
Red Barn Theatre: Ms Holmes & Ms Watson, Apt. 2B – January 28 – February 22, 2025
Fast-paced and wildly entertaining, this take on Sir Arthur Conan Doyle’s famous sleuth and sidekick re-examines the classic adventure stories you love through a bold new female lens. Shows at 7:30 p.m. 319 Duval St.
Registration Opens for 7 Mile Bridge Run – January 28
Registration opens on Tuesday, January 28, 2025 beginning at 6 a.m. Anyone can register on this date, but race organizers are only able to accept 1,500 entries and the field fills very quickly. Sometimes the registration is filled within minutes, so please be online and ready. You must show a PHOTO ID when picking up your bib number that matches the same address you used to register.
Cirque Ma’Ceo by Cavallo Equestrian Arts – January 29 – February 2, 2025
Experience the magic with this emotionally charging, up close and personal experience. Step into the exclusive, custom designed Italian Big Top theater and settle back in brand-new, state of the art seating. The world of Ma’Ceo is proud to showcase mesmerizing acrobatic feats, aerial dancing, and exotic horses. Come feast your senses on the beauty and mystery through the adventure of Cirque Ma’Ceo. Showtimes vary. San Pablo Catholic Church, 550 122 Street Ocean.
Key West Theater: Ben Harrison – January 29
Ben Harrison is a playwright, lyricist and composer who is also an entertainer. What makes his live performances so enjoyable is that, at his core, he is a barroom guitar player/singer/songwriter who somehow manages to blend history, musical theater, Key West and humor into unusual stories that are mostly true. Key West Theater’s Backstage Listening Room. Doors at 6 p.m.; show at 7 p.m. 512 Eaton Street.
Coffee Butler Amphitheater: Chicago – January 31
Hailed as one of the most important bands in music since the dawn of the rock and roll era, the legendary rock and roll band with horns, Chicago, came in as the highest charting American band in Billboard Magazine’s Top 125 Artists Of All Time. And, Chicago is the first American rock band to chart Top 40 albums in six consecutive decades. Doors open at 6:30 p.m.; show at 8 p.m. 21 Quay Rd.
