January in Key West (2023)

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 Holidays and the crowds are a bit… less. Let’s explore Key West in January!

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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 temperatures are 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. 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.

Best Sunset Cruises in Key West

See Dolphins! – Explore the coral reefs.

Driving down from Key Largo? Ultimate Road Trip to Key West


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.


Come to Key West in January to explore the beaches, or check out the many restaurants and bars on Island.

Key West Beaches

What Not to Miss when in Key West

Duval Street 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….

New Year’s Day Manatee Plunge at Postcard Inn’s Beach – Jan. 1

For a refreshing start to 2023 on New Year’s Day, put on a crazy outfit and jump in the ocean for the second annual Manatee Plunge at the Tiki Bar at Holiday Isle. The bar opens at 11 a.m. and the Manatee Plunge starts at 1 p.m. Registration is $10 per person and includes a free beer. Proceeds will be donated to Give Kids the World, an 89-acre, nonprofit resort in Central Florida that provides weeklong, cost-free vacations to children with life-threatening illnesses and their families.

Key West Artisan Market: The Hangover Edition – Jan. 1

Shop a curated outdoor market offering fine crafts and art from talented Florida Keys makers, wide variety of food & libations, local musicians & authors and outstanding ocean views as you work off that New Year’s eve celebration with craft made bloody mary’s and on the spot treatments from IV Hydration Stations Key West. From 10 a.m. to 2 p.m., Sonny McCoy Indigenous Park, 1801 White Street.

History Presentation – “Lighthouses, Reefs and Islands: Alligators at the Reef” – January 2

Historian Brad Bertelli will give a great talk at Islamorada Moose Lodge focusing on the history of the U.S. Schooner Alligator, its ties to piracy and how it left its name to Alligator Reef and the lighthouse. The event is open to the public with a requested donation of $5, and free for members of the Moose. Mile marker 81.5. Event begins at 6 p.m. The kitchen will be open.

Presidential Families Weekend – December 19, 2022 – Feb. 1, 2023

The Key West Harry S. Truman Foundation, in partnership with The Society of Presidential Descendants, is pleased to announce a series of special events.

Florida Keys History & Discovery Center: Special Exhiubit, Tribute to the Redbone Gallery – November 29, 2022 – January 8, 2023

As Redbone Gallery closes after 30 years, Florida Keys History & Discovery Center is showcasing the journey of Captain Gary, Susan and Nicole Ellis with a special exhibit highlighting their lives through Jan. 8. The remaining inventory of exceptional art is for sale in the upstairs gallery. Exhibit and artwork curated by Pasta Panteleo.

Red Barn Theatre: Dear Jack, Dear Louise – December 20, 2022 – Jan. 14, 2023

Ken Ludwig’s “Dear Jack, Dear Louise” opens the Red Barn Theatre’s 43rd season. Sparks fly and love blossoms from a world away when U.S. Army doctor, Jack, begins a correspondence with an aspiring actress, Louise during WWII. Winner of the Helen Hayes and Charles MacArthur Award for Best New Play of 2020. Order tickets online or at the box office. Showtime 8 p.m. 319 Duval Street.

Pole Vault in Paradise Competition – January 5 – 8, 2023

Pole Vault in Paradise brings together pole vaulters from ages 9 to 75 to compete alongside some of the best pole vaulting elites from around the country. Sponsored by the nonprofit Key West Track & Field Club, the event is to be staged at Higgs Beach, with the main event Saturday. Prize monies for male and female challengers are up for grabs, including additional prize money for any man or woman who breaks the island record. Pancake Breakfast from 8 am – 10 am. Admission Free. Pancake Breakfast tickets are sold onsite.

Florida Keys Celtic Festival – January 6 – 8, 2023

Celtic history, culture, food and music are to be celebrated by attendees at the 10th annual Florida Keys Celtic Festival, a favorite family event in the Middle Keys. The event opens Friday, Jan. 6 from 5 to 7 p.m for the free “Kilts in the Keys” celebration at Dockside Boot Key Harbor. During the weekend festival at Marathon Community Park at mile marker 49, enjoy Celtic rock and traditional musicians including Scottish band Albannach and the Screaming Orphans from Ireland. Enjoy Celtic merchandise, food, traditional sheep herding demonstrations and the Florida Police Pipe & Drum Corps. Tickets available online in advance for $10 per day or $15 for a two-day pass; or at the gate, $12 per day or $17 for a two-day pass.

Market on the Green – January 7

Held the first Saturday of every month from 10 a.m.- 2 p.m., visitors and residents are invited to browse and shop amazing local artisans. The monthly market is located at the Sunset Green Event Lawn, at Key West’s 24 North Hotel, 3820 N. Roosevelt Boulevard.

Pancake Breakfast – Higgs Beach – January 7

8 am – 10 am in support of the Key West High School Track Team and the Mays Sands Montessori School. Pancake Booth is located near the African Cemetery and at the Pole Vault in Paradise competition. Unlimited pancakes and one mimosa (adults only) are included. $20 Adults, $10 Children Tickets at the website and on the day of the event.

Friends of the Key West Library Book Sale – January 7

Monthly used book sale from 10 a.m. to 1 p.m. in the garden at the library, located at 700 Fleming Street. In celebration of the Friends’ 50th Anniversary year, those who join as a new member of the Friends of the Key West Library for $25 or more will receive one book free.

Sheriff’s Animal Farm Open House – January 8

Looking for a fun place to take the kids? The Sheriff’s Animal Farm is open 1 – 3 p.m. Come visit the animals at the farm, including miniature horses, a steer, pigs, goats, bunnies, alligators, tropical birds, kinkajous, a lemur, an alpaca, a skunk, a prairie dog, tortoises and turtles, snakes and many more. It is free of charge, but donations are welcomed because that is how the farm is sustained. The farm is located just off of College Road on Stock Island, at the Sheriff’s Office Headquarters complex. Open the second and fourth Sundays of the month.

Key West Kingfish Mayem – January 12 – 15, 2023

This is the first tournament of the five-leg Kingfish Mayhem Pro Series. In the winter, Key West is the staging ground for King Mackerel before they start their annual migration in the Gulf. Big fish from the 50-70 lb. range are common in these areas, which creates an exciting and competitive environment at the weigh-in. This event has been enhanced by adding tuna, mahi, and wahoo, for a four-species tournament. Teams from all around travel to join this world-class event for their shot at claiming King of Key West!

Key West Literary Seminar – January 12 – 15, 2023

Each year, the Key West Literary Seminar features a particular theme. “Singing America,” the 40th seminar, will center on Black American experiences through poetry, fiction, biography, and history. From slavery and Reconstruction to the Harlem Renaissance, the civil rights movement, today, and into the future. All presentations take place at Coffee Butler Amphitheater, 21 Quay Road, within Truman Waterfront Park. Selected portions of the seminar are free-of-charge and open to the public. Find information and registration online.

Old Island Restoration Foundation’s 63rd Annual Key West Home Tours – January 13 – 14, 2023

Enjoy tours of beautiful and historic Key West homes and gardens. Your ticket purchase supports the ongoing mission of preserving and promoting Key West’s unique architecture, culture and history. Tickets purchased online in advance are $45 for members, $55 for non-members and $60 at the door. Visit the website or call 305-294-9501.

25th Annual Key West Half Marathon & 5k Run – January 13 – 15, 2023

Recognized by Runners World magazine as one of the 10 great half-marathons of the winter season, the 2023 25th anniversary race follows a 13.1-mile course that includes Old Town Key West and the scenic waterfront. The race typically attracts American and international runners to compete in Key West’s balmy January climate. Ranked among 13 must-do U.S. half-marathons by Competitor.com.

Baygrass Bluegrass in the Beer Garden – January 13 – 15, 2023

Island Community Entertainment (ICE) and Florida Keys Brewing Co. are keeping the spirit of Baygrass Bluegrass Festival alive. Enjoy three days of music blending the best of traditional bluegrass with the next generation of bluegrass and some interesting variations of the genre. This year’s festival is free to attend (no tickets required) in the beer garden, courtesy of ICE. Music kicks off Friday night with Grandpas Cough Medicine, then continues through the weekend, ending Sunday night with headliner The Grass is Dead. Find the full entertainment lineup and schedule on the website.

Paws for a Cause Dog Walk on Old Seven – January 14

Enjoy a lovely walk with your dog on the iconic Old Seven Mile Bridge to Pigeon Key to support the Domestic Abuse Shelter of Monroe County. A light breakfast will be served on Pigeon Key, then take a leisurely stroll back. Every walker that raises donations of $100 or more will have the $25 registration fee waived. The person that collects the most money will win a two-night stay at Isla Bella Resort. If you don’t have a dog, you can borrow a dog from the SPCA. Expect to see turtles, manatee, dolphins or rays on the walk.

17th Annual Florida Keys Seafood Festival – January 14 – 15, 2023

Bring the whole family for the freshest seafood caught, cleaned, prepared and served by local fishermen. This event is a fundraiser for the Florida Keys Commercial Fishermen’s Association FKCFA and goes to support sustainable fishing programs, marine restoration projects and college scholarships. A $10 admission is good for BOTH Saturday and Sunday and the festival is to be held at Bayview Park. 1320 Truman Avenue, Key West.

Big Pine and Lower Keys Nautical Expo – January 14

The LKCC welcomes you to one of the biggest events with over 100 vendors. Fun for the whole family and includes an array of nautical pieces and so much more.

The Southernmost Regatta – January 16 – 20, 2023

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 2023

Staged at the Truman Waterfront Park Amphitheater, the world’s greatest rock bands descend upon the island of Key West for this 4-day music festival in paradise. Single- and multi-day passes available. Performers include Styx, Tesla, Loverboy, Vince Neil, 38 Special, Queensryche, Stryper, Quiet Riot and more.

Sheriff’s Animal Farm Open House – January 22

Looking for a fun place to take the kids? The Sheriff’s Animal Farm is open 1 – 3 p.m. Come visit the animals at the farm, including miniature horses, a steer, pigs, goats, bunnies, alligators, tropical birds, kinkajous, a lemur, an alpaca, a skunk, a prairie dog, tortoises and turtles, snakes and many more. It is free of charge, but donations are welcomed because that is how the farm is sustained. The farm is located just off of College Road on Stock Island, at the Sheriff’s Office Headquarters complex. Open the second and fourth Sundays of the month.

Kelly McGillis Classic – January 24 – 30, 2023

Women from countries far and wide will be descending upon Key West for flag football competition, fun and learning. It is anticipated this event is to represent the most international countries, and organizers have hosted teams from USA, Morocco, Spain, Mexico, India, Jamaica, Honduras, El Salvador, and Sweden.

Mile 0 Fest Key West – January 24 – 20, 2023

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

Key West Food and Wine Festival – January 25 – 29, 2023

The 2023 Key West Food & Wine Festival celebrates the flavors, vintages and culture of Argentina at multiple events across the southernmost island city. Events include the Carnival de Buenos Aires gaucho parade and vintner dinner, a Last Tango in Cayo Hueso Brunch and the festival highlight SLaM grand tasting where guests can sample vintages from every wine region in Argentina. Tickets to individual events are going fast – purchase online at KeyWestFoodandWineFestival.com

38th Annual Key West Craft Show – January 28 – 29 2023

The Key West Craft Show is a two day juried outdoor craft festival. This nationally recognized Craft Show brings over 100 fine and skilled craft artists to this beautiful historic area of Key West. Tens of thousands of attendees browse and buy among juried artisans and crafters who gather to display their talents at this popular outdoor festival on lower Whitehead Street in historic Old Town Key West.

Spanish Fly Music Festival – January 29

Presented by the Jose Wejebe Memorial Foundation, enjoy a family-friendly day of music and activities, auctions and raffles, from 1-6 p.m. at Boondock’s Grille and Draft House, mile marker 27.5 on Ramrod Key. Live musical lineup includes Brian Roberts and Gunner and the Grizzly Boys.

Key Western Fest – January 31 – Feb. 4, 2023

More than 20 of the very best classic country bands bring their massive hits to the Southernmost City in the U.S. for a week of unforgettable songs, sun & sand. Take in the warm sunshine and tunes during the day at the island’s iconic bars, snag a bite from one of the renowned restaurants, leave your troubles on land during a live-music sail on a comfy catamaran, and then sing your heart out under the stars at night at the Truman Waterfront Amphitheater, 21 Quay Rd, Key West. Passes and packages available online.

Red Barn Theatre: Flaming Guns of the Purple Sage – January 31 – Feb. 25, 2023

Be ready to take a wild and crazy ride into the classic mash-up spoof of a Western-Horror “B” movie with Jane Martin’s hilarious “Flaming Guns of the Purple Sage.” Big 8, a rodeo competitor, is facing foreclosure on the Wyoming ranch where she rehabilitates injured rodeo cowboys. The arrival of a shocking woman named Shedevil and a one-eyed Ukrainian biker named Black Dog leads to violence and horror in this satire of pulp western writers like Zane Grey. Order tickets online or at the box office. Showtime 8 p.m. 319 Duval Street.

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