Tickets are on sale NOW for our 18th Annual Spring Social presented by Hank's Hair of the Dog Saloon! Join us for our biggest celebration of the year at the Truman Little White House on Friday March 13th. VIP tickets include a Champagne Reception starting at 5:30pm before the main event, passed appetizers, a sneak peek at the silent auctions, and reserved seating.

On Saturday, March 7, the Key West Woman’s Club will host its annual fundraiser Diamonds are a Girls Best Friend!

 Enjoy an open bar, fully catered dinner, lively music by Skipper Kripitz & friends, and dancing while you shine in your diamonds!  

Join the community for a special evening celebrating the United States Marine Corps while supporting a worthy cause. This fundraiser, hosted in partnership with Neeley Family Distillery, promises an evening of camaraderie, fine spirits, and celebration.

Southernmost Beach Resort and Reggae Lou invite you to SoMo Roots, an afternoon of live music and island vibes taking place on Sunday, February 15, 2026. The festivities kick off at 1:00 PM.

The event features a dynamic lineup of live performances by Reggae Lou & The Kind Budz and Channel 3. While guests enjoy the beach party atmosphere, the event also serves as a fundraiser for the S.O.S. Foundation.

This Valentine’s day, you are invited to THE LOVE PARTY. 

Step inside of a weird wonderful world full of storytelling, surprises, games and good times. Your hostess Meme “spills the tea” and shares a UNIQLY* Key West Love Story: a journey through personal hell in paradise, only to find love and self-acceptance at the end of the road — Mile Zero!  Local audiences will recognize familiar locations and characters in this witty experimental play by local writer/director Chantal Pavageaux. 

*UNIQLY stands for:

Untitled Neurodivergent Illustrated Queer Love storY

Looking for an afternoon of breathtaking art and bold fashion?
Don't miss the Key West Woman's Club's Wearable Art Fashion Show 2026.

Experience the thrill of the runway, where high fashion meets high stakes. Witness the debut of one-of-a-kind, handcrafted creations from our city's most innovative local designers. As each unique piece is revealed on the catwalk, it becomes available for live auction. This is your chance to acquire a signature work of wearable art directly from the designer and take home an unforgettable piece of fashion history.

Your attendance also supports "Creativity in Design" scholarships for Key West High School students.

Step into an afternoon of island elegance as the Key West Woman’s Club revives its charming 1950s Tropical Luncheon tradition. Enjoy conversations with bestselling author Lucy Burdette, a preview of KWAHS’s Smithsonian-affiliated exhibit FOOD: Celebrating Conch Cuisine, and insights from curator Dr. Cori Convertito. Chef Martha Hubbard adds culinary flair to this celebration of the flavors and stories that define the Keys.

A delightful blend of history, culture, and island charm — all in the heart of Old Town.

Join us for Fighting For Laughs, Too — a night of powerhouse comedy featuring Sam Norton, Preston Gitlin, and headliner “The Reverend” Bob Levy, hosted by local veteran and comedian Petey Rancel. Building on last year’s sold-out success, this event delivers big laughs for an important cause. 

 All proceeds benefit AHERO, a 501(c)(3) organization dedicated to preventing Veteran and First Responder suicide through fellowship, outdoor adventures, and community support.

Your $50 general admission ticket directly helps fund AHERO trips here in Key West — creating healing connections and life-changing experiences for our nation’s heroes. Come laugh, support, and make a difference!

This Fringe Theater fundraiser is back by popular demand! These guys lit up the Armory last time they were in town (and sold out fast). Reverend Raven is as authentic as blues gets: original music in a classic blues style. You’ll want to get on that dance floor — we guarantee! This fundraiser includes open bar, buffet style food, incredible music, and all your Fringe friends!  

Mark your calendars for the second annual Key West Woman's Club Bougie Afternoon Tea Party on January 17th! This delightful event will benefit Take Stock In Children, with a $25,000 Monroe County scholarship to be awarded. 

 In addition to enjoying a lovely afternoon, there will be prizes for the most elegant attire, so bring your best bougie outfits, hats, shoes, and coats! Camille Russo Toler will provide charming musical entertainment while we sip tea and specialty cocktails. Don’t miss out—GET YOUR TICKETS NOW!!

MC Bill Hoebee.
Presentation by The United Cajun Navy.
Musical Director Larry Baeder,

 Musicians:
Mike Dennis, Rolando Rojas, David Feder, Toko Irie, Larry Smith, Joe Dallas, Skipper Kripitz, Claire Sawyer Caplan, Peter Diamond Ilacqua, Christine Cordone Smith, Camille Russo Toler, Maj Johnson, Larry Baeder, Bubba Lownotes, Ben Harrison, Terri White, Massai, Tim Marshall Curtis, CW Colt.

 Food provided by Yahman Jamaican Restaurant.

Get ready to "Get Freaky at the Tiki" as Looe Key Tiki presents its 1st Annual Christmas Tiki Olympics on Saturday, December 13th, starting at Noon. This festive and quirky competition requires teams of 4 to 6 players to compete in 5 rounds of funny Christmas games, plus one player from each team will participate in a separate chicken wing eating contest.

Join us for a sophisticated evening celebrating the birthday of the legendary actor and comedian, Sir Billy Connolly, with his wife, Lady Pamela Stephenson Connolly.

This exclusive gala is a fundraiser for the Key West International Dance Company (KWIDC). By securing your place, you are providing vital support for the artistic endeavors, community outreach, and educational programs that enrich the cultural fabric of Key West.

Your attendance helps ensure the future of professional dance in our vibrant community. Secure your tickets now for this memorable celebration of cinema, artistry, and philanthropy!

Do you have what it takes to be the smartest trivia team on stock island? Looking for a fun new holiday tradition? Bring your team to this one-of-a-kind holiday trivia & storytelling event! Family friendly! Everyone is welcome.

Details:
Teams of 6 or less. (2-6 players) Cost per team/table is $120. (100% of all money raised is used for the CFK HIGH SCHOOL students!)

$120 includes:
5 Rounds of Trivia plus a bonus round. Approx time should be about 1.5 hours.
A prize valuing at least $50 will be awarded after each round.
The 1st place winning team will receive a prize valued at over $300.
All tables will have light bites and non-alcoholic beverages served by our students.

Any other questions about our trivia fundraiser please contact Amy Andrade @ aandrade2010@live.com.