“2025 A Fresh Start: Unmissable Events This January”

Delight in January's Wonders: Events, Happenings and Seasonal Magic in Key West!

Key West is a special place to enjoy the holiday season. During the holidays, Key West lights up with fun festivities and offers a unique atmosphere to celebrate this exciting time of year. Key West is the perfect place for you and yours to gather and create very special holiday memories!

01/01/2025 to 01/25/2025


January 02-04,2025 : Waterfront Playhouse: Vagina Monologues

The Vagina Monologues(Spotlight Series)

Starting off the new year will be our second Spotlight series production; a show that the New York Times at the end of the 1990’s called “probably the most important piece of political theatre of the last decade” and again in a 2018 article reiterated “No recent hour of theatre has had a greater impact worldwide”. Featuring talented local voices, we are proud to present Eve Ensler’s “The Vagina Monologues”.

Buy Tickets : https://www.waterfrontplayhouse.org/shows/the-vagina-monologues-spotlight-series/#/productions-view

January 04,2025 :Pole Vault in Paradise

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.

January 2th, 2025 , Higgs Beach

Pole Vault in Paradise Competition
$75 Early Registration thru Dec 14
$100 Late Registration after Dec 14

January 3, 2025 , Higgs Beach

PV Clinic 10AM
Open Practice 1PM-5PM
Registration Open 1PM-5PM

January 4th, 2025 – Saturday, Higgs Beach

Pole Vault in Paradise Competition

8:00am

Runway Opens

9:00am

First flights begin
Times and Flights posted when entries close

*Prize Money. 

Prize Money for the Open Men and Women’s Divisions

1st Place: $1500

2nd Place: $1000

 3rd Place: $500

There is a $5,000 prize pool for the Men and a $5,000 prize pool for the women for breaking the Island Record.   As an example:  All men breaking the Island Record will share the $5,000 prize.  One record breaker would receive $5,000.   If two men break the record then each gets $2,500.   Separate pool for the women.

*Island Records. The Men’s record of 5.72 is shared by Tray Oates and Austin Miller in 2024. The Women’s record of 4.57m is shared by Katerina Stefanidi and Anicka Newell in 2024.

January 05-09, 2025: Key West Literary Seminar: Writers’ Workshop Program

Every year we offer eight to ten workshops, each with its own focus and application requirements. Workshops meet in-person for three hours a day for four days. Enrollment is typically limited to twelve participants per workshop to ensure individual attention.

Advanced workshops require a writing sample as part of the application; All Levels workshops are open to writers at any level and require only a cover letter for consideration. The registration fee for all workshops is $675.

Note that the Workshop Program is separate and distinct from the Seminar. This year the workshops end at noon on Thursday, January 9. The Seminar kicks off that same day with an evening keynote address. You can therefore participate in a workshop and still attend the full Seminar if you wish. Alternately, to cap off the workshop experience, students may purchase a separate ticket for only the Seminar Keynote only.

Spaces are reserved in each workshop for fellowship recipients, who receive full fee waivers ($675 value) to the workshop of their choice, as well as financial assistance to offset lodging costs, as needed. If you would like to apply for a fellowship and your preferred workshop is listed as full, please do not be deterred. https://www.kwls.org/writers_workshops/

January 07-08,2025: Studios of Key West: Susan Werner & Jonatha Brooke in Concert

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.

Over the course of her twenty five year career, Susan Werner has earned a reputation as “one of the most innovative songwriters working today” (Chicago Tribune). With formidable chops on guitar (she began playing at age 5) and piano (she was a guest on Marian McPartland’s Piano Jazz), along with a graduate degree in voice performance, her shows are a one-woman master class in musicianship. Although best known as an acoustic songwriter that came up through coffeehouses and folk festivals, the Chicago-based artist has written songs in the style of Gershwin and Cole Porter (I Can’t Be New, 2004), gospel music (The Gospel Truth, 2007), traditional Cuban “son” (An American In Havana, 2016), and New Orleans junk piano (NOLA, 2019). In 2014 she composed the music and lyrics to the musical theater score Bull Durham, The Musical (MGM). Her songs have been recorded by Tom Jones, Michael Feinstein, and Shemekia Copeland, and her latest recording of originals, The Birds of Florida, took flight in 2022.

Jonatha Brooke is an acclaimed American folk rock singer-songwriter and guitarist from Massachusetts. Combining elements of folk, rock, and pop with poignant lyrics and complex harmonies, Brooke’s music has captivated audiences since the late 1980s. Her career began at Amherst College with Jennifer Kimball as the duo “The Story,” gaining attention for their witty wordplay and lush harmonies. They released two albums before Brooke pursued a solo career in 1994. Brooke’s solo debut, Plumb (1995), showcased her distinctive soprano and intricate songwriting. Despite industry challenges, she thrived independently, founding Bad Dog Records and releasing Jonatha Brooke Live (1999). Her albums, like Steady Pull (2001) and Careful What You Wish For (2007), reflect her evolution as an artist, marked by collaborations with renowned musicians and contributions to soundtracks, including Disney’s Return to Never Land. Brooke’s work often draws comparisons to Joni Mitchell and other 90s folk-rock talents. Her more recent projects include My Mother Has 4 Noses (2014), an off-Broadway play and album, and Midnight. Hallelujah. (2016). She continues to innovate and inspire, living in Minneapolis and producing music that resonates deeply with her audience.

Old Town New Folk is underwritten by Nick and Lorie Howley, with additional support from Doug and Sherri Montgomery, John and Marilyn Rintamaki, Nell Smets, and Michael Blades and Kathy Kilroy. Series sponsored by Blue Heaven

January 10,2025: Key West Art & Historical Society Historic Seaport Sail: Harry S. Truman in Key West

Two 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’

On Friday, January 10, Warmbold will lead an illuminating morning seafaring excursion presented by Key West Art & Historical Society aboard the luxury catamaran SV Argo Navis, departing from the dock at 0 Margaret Street at 10:00 a.m. and returning at 12:00 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.  Truman’s staff said they got more done in Key West than in DC due to the peace and lack of distractions.  The Presidents never truly had a day off – there are 175 days of his working holiday to explore.

This project is sponsored in part by S/V Argo Navis.

  • Date: January 10
  • Time: 10:00am – 12:00pm
  • Cost: $85.00 – $95.00
  • Location: S/V Argo Navis

January 13,2025: Key West Music Awards

  • Date Mon, January 13, 2025
  • Time 8:00 PMDoors7:00 PM
  • Ages 21 & Over
  • Venue Key West Theater