Habitat for Humanity of Key West and Lower Florida Keys provides affordable homeownership opportunities to low-income working families and critical home repairs to our community’s vulnerable elderly population. We are dedicated to empowerment, not entitlement, and bringing people together to build homes, communities, and hope. As a locally supported nonprofit the work we do is only made possible through support from the community. Proceeds from Habitat’s 2025 sold-out gala helped provide 9 families with affordable, safe homes to call their own, 5 senior household with critical home repairs allowing them to age in place, and 27 families with affordable rentals.

Our 2026 event will feature a delicious dinner, creative libations, and inspiring program, games, auctions, dancing and an all-around memorable evening. We invite you to attend, sponsor, and be recognized as we come together again in 2026 for a fun evening to change lives and build a better community.

Step back in time for an unforgettable evening of music and dance! Williams Hall proudly presents Swing Dance Night featuring the high-energy sounds of The Paradise Swing Band, directed by Joe Dallas.

 Joining him on stage will be Donna DeForrest, Mark Rose, Skipper Kripitz, and Tony Elitcher—keeping the dance floor alive with classic swing rhythms.

It’s a Celebration! The Fringe Board invites you to join us on March 23rd as we celebrate ten years with Rebecca Tomlinson as Fringe’s Managing Artistic Director. We’re celebrating the people, the shows, and the direction that has led Fringe Theater through its unprecedented growth. Join us for music, food, and memories!

Your ticket price includes the Ericson Holt Band, Food stations and hors d'oeuvres, Open Bar. We’ve memories to share and new memories to make!

Sponsored by William & Pattye Monroe, Blake Hunter & Murphy Davis, Dennis Beaver & Bert Whitt, Neal Ruchman & Melissa Jean McDaniel, The Gardens Hotel, Billy Cartledge & Jim Hall, and Janet & Charlie Bengel.

The iconic Vintners Dinner returns in 2026! “The ART of Tasting” is a chef-curated food and wine experience—an elegant evening of fine wines, delicious cuisine, and heartfelt community connection in beautiful, historic Williams Hall. Guests will enjoy a thoughtfully crafted multi-course tasting menu by Chefs John Corea and David Fuhrman, perfectly paired with exceptional wines presented by Pacific Southern Wine Company and Republic National Distributing Company. Erin McKenna hosts the evening of live music, Fine Wine & Cuisine, as we raise a glass to AH Monroe's four decades of compassion, innovation, and impact in the Keys. 

Join us for an artful evening of wine, cuisine, and community connection!

Join us for an exclusive first look at the Key West Cultural Center & Veterans Museum! We are opening our doors for a special Soft Opening event to share our vision with the community and gather your valuable feedback. Located at the historic William Weech American Legion Post 168, this evening is a celebration of local history, service, and the arts.

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.

Celebrate the magic of books, food, and community at the Friends of the Key West Library Gala—an unforgettable evening with a culinary legend.

Join us Monday, February 23, 2026, for the Friends of the Key West Library Fundraising Gala, featuring legendary food writer Ruth Reichl—author, critic, and culinary icon. Enjoy her exclusive interview, then mingle in the Palm Garden with delicious bites, tropical cocktails, and twinkling lights. Proceeds benefit the Key West Library—so come celebrate great books, great food, and our beloved little pink library!

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.

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.

Dress to Impress!

Dancing, DJ, Photo Booth, Desserts, and Refreshments

*For CFK Academy Students, Pre-approved Guests, & Monroe County School Students ONLY in grades 9-12

Contralto Vira Slywotzky and pianist David Sytkowski return to Williams Hall! The acclaimed duo joins forces with special guest Phillip Cole White to bring you the songs of America’s beloved musical theater composer and lyricist Stephen Sondheim and W. S. Gilbert and Arthur Sullivan, the incomparable craftsmen behind Great Britain’s great operetta tradition. From “Dirty Old Man” to “Send in the Clowns,” experience the giggles, grit and glory of the finest musical storytellers in the English language.

Doors open at 5:00 PM
Game starts at 6:30 PM
Location: Mac's Place, 1605 N. Roosevelt Blvd.

Tickets Include:
Two buffets open for the duration of the game
Open bar for the duration of the game, featuring:
Spirits: Concierge Vodka, Captain Morgan, Bacardi, Jim Beam, Jack Daniel’s, Tanqueray, Santoro Tequila
All draft and craft beers
Seltzers: High Noon, Surfside, Sun Cruiser, Good Boy Vodka Cocktails, & Sip Margs
Wines by the glass
Please note: Shots and shooters are not included.

Celebrate BIG GAME Sunday at The Marker Resort.
Enjoy a Tailgate Buffet and wine, draft beer, and premium well OPEN BAR.

Total ticket price is all inclusive of tax, gratuity, and fees.

Seating is first come, first served.

Celebrate Big Game Sunday at The Southernmost Beach Resort.
Enjoy an Unlimited Tailgate Buffet and Premium well/draft/wine OPEN BAR!!

Food only option available, too!

Total ticket price is all inclusive of tax, gratuity, and fees.

Seating is first come, first served.

Huge 10’ big screen!
 
Each ticket includes: One dinner (one plate of BBQ Ribs or Chicken, with Roll, Bake Beans, Cole Slaw, and Dessert); Viewing the Game on the BIG Screen; Raffles; Squares; and Prizes! Full bar and drink specials available for purchase. 
OPEN TO THE PUBLIC!

Tickets: $25 in advance, $30 at the door

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 a special evening with David Lowery, celebrated singer-songwriter and co-founder of the influential alt-rock bands Cracker and Camper Van Beethoven. Known for his sharp wit, distinctive voice, and genre-blending musical style, Lowery has written some of the most memorable rock tracks of the past three decades, including “Teen Angst (What the World Needs Now),” “Low,” “Euro-Trash Girl,” and “What the World Needs Now.”

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!