Join us at our first stop for brunch to soak up the libations you're about to indulge in! Start your day with an included brunch buffet and, for a nominal additional fee, unlimited Bloody Marys and mimosas. Then, hop on the Old Town Trolley Tour and embark on the "Stroll Through Time Pub Roll," a spirited adventure through Key West's historic and vibrant bar scene. This unique event celebrates the island's rich cultural heritage while you enjoy specially curated Pride-themed drinks at each stop. Get ready to be transported back in time as you explore iconic bars outside of the Gayborhood, each offering a refreshing taste of Key West's lively atmosphere. Up for some COSPLAY? Come decked out in your favorite period attire, from Hippie to New Wave, to Grunge, get creative. Prizes will be awarded.

Hosted by local legends Tony 'Fat' Yaniz and Richie Gomez This special evening brings together a lineup of Key West locals sharing what it was like to grow up in the Conch Republic. Key West—1970s—Key West was a ghost town, dogs sleeping on Duval Street. The navy left town. The main occupations were shrimping and smuggling—maybe one in the same.. 50 cent draft beer at Sloppy’s. Sex and rock and roll at the Bull. And the Full Moon was THE late night spot. You’d find a smuggler and a DEA agent buying one another rounds. One day you’d be on a bike with bent rims and the next tooling around in a Porche 911…don’t you wish you were there? 

The ROSE (Recognition of Service Excellence) Awards recognizes Monroe County front line hospitality employees who demonstrate excellent customer service. These industry champions showcase the region’s commitment to creating an extraordinary visitor experience.

Be our guest on the evening of April 23 at 7:30 pm as we welcome back renowned singer, songwriter and virtuoso guitarist Anders Osborne to the storied Monkey Hut at Little Palm Island. This intimate and exclusive performance is only available to a limited number of guests.

We’re headed back to one of our favorite spots—the world-famous Standard Deluxe—for a special night inside the Little House! The evening kicks off with a set by the one and only B.B. Palmer, with Electric Blue Yonder as his backing band, followed by a full headline set from us to keep the party rolling. To make the night even sweeter... It’s B.B.’s Birthday! Let’s celebrate the man with music, love, and a whole lotta good energy.

CFK Academy at The College of the Florida Keys, is excited to invite you to A Roaring Good Time, Presented by the CFK Foundation. This year’s 2nd annual event will be hosted at the Tennessee Williams Theatre on Friday, April 18, 2025 6:00-8:30 p.m. We are planning a fun evening with food, cash bar, entertainment, auctions, and much more! Please join us to support our students.

Bringing back the elegance and charm of an afternoon high tea to celebrate the Key West Woman’s Club 110th Anniversary.  Enjoy from a fine selection of teas, finger sandwiches and delectable sweets, including scones, fruit tarts, and other extraordinary delights. 

Panel Moderator:  Dr. Roberta Isleib is a USA Today bestselling author and clinical psychologist.   She is also known as Lucy Burdette, author of The Key West Food Critic Mysteries and is a Key West Woman's Club member.  She has written 24 novels, including the latest The Key Lime Crime.  A Clue in the Crumbs, the 13th book in the series The Key West Food Critic Mysteries, won the Florida Book Award’s gold medal in popular fiction. Her series features a Key West food critic solving murders on the side. 

"After Party" at Hellings Curry Museum, home of the Key West Woman's Club.  

Open bar, appetizers and desserts from the new 2025 Key West Woman's Club Cookbook provided by the Key West Woman's Club.

Camille Toler & Friends will perform on the front porch. Appetizers from our Key West Woman's Club newly revised cookbook will be prepared for you by Key West Cooking School.

Darcy Cooke presents an intimate evening of 2 parts jazz favorites from the Great American Songbook along with 1 part well-loved cabaret tunes. Called a “swinging jazz singer…displaying versatility and a beautiful voice” by jazz journalist, Scott Yanow, Darcy’s “warm and inviting voice” exudes a depth of emotion that draws in and thrills her audiences. 

From Johnny Neebo’s Starlight Club, to the Bamboo Room, to the Hukilua, Coffee Butler entertained Key West since 1952. This special performance Memories of Coffee will include the amazing vocals of the King of Key West Soul - Robert Albury, Clayton Lopez and Mina Lopez-Martin, a young new voice of Claire Caplan. They will revive the classic soul sound of the Temptations, Smokey Robinson, and Aretha Franklin along with originals by Coffee Butler. Music Director Larry Baeder will lead the talented Soul of Key West Band.

This open-air event promises an assortment of beverages and palate-pleasing small plates.  Local Restaurants and Vintners Present the perfect Taste of Key West at our 30th Annual Celebration!

A.H. Monroe & Republic National Distributing Company bring the community together for Cuisine, Craft Beer & Fine Wines!  Cheers!

This reading of two short plays written by Tennessee Williams is presented in partnership with the Fringe Theater, Key West Arts & Historical Society and Williams Hall as part of the annual month-long Tennessee William Festival. Directed by Wende Shoer with readers Wayne Dapser, Jim Argoudelis, Merle Dimbath, Jim Speake, Wayne LaRue Smith, Nancy 3 Hoffman, Alana Thurston, Samantha Laskey, and Thomas Masat.

We are "painting" a garden. Canvases can be painted separately or as a group. So much fun! 

 One of a kind painting events- Paint the Tale!

Join us for a unique and immersive experience where you'll transform a classic cigar box into a personalized work of art. Sara "Pie" Butler, renowned for her vibrant and whimsical style, will guide you through the painting process, sharing her techniques and inspiring your creativity. No prior painting experience is necessary – just bring your enthusiasm and a willingness to explore your inner artist.

It's the "luck" of the IRISH! Paint to stories of luck and superstition! 

One of a kind painting event- Paint the Tale!

Tickets are on sale NOW for our 17th 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 14th. 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.

Take a trip down memory lane with a special brunch honoring the beloved Dennis Pharmacy. Enjoy a menu inspired by its iconic comfort food, accompanied by the soulful sounds of conch singer Carmen Rodriguez and pianist James King.

For years, the iconic grounds at 907 Whitehead Street have been the backdrop for some unforgettable events—celebrations with a drink in hand. But here’s the twist: this event is about raising a glass that won’t leave you feeling foggy the next day. It’s the rise of mocktails! Those delicious drinks that deliver all the flavor without the buzz.

This Fringe fundraiser embraces the old fashion supper club as its inspiration — then givees it a modern twist! Open bar. A buffet that features classic Americana cuisine. Captivating music of Key West songbird Carmen Rodriguez with Larry Smith, Skipper Kripitz, and Tim Mayer. You’ll need your dancing shoes for this one! It's delicious fun. A night of revelry. And it raises funds for the Fringe! Street Parking

Join contralto Vira Slywotzky and pianist David Sytkowski for An Evening of Sea Songs. From Puccini to Sondheim, this concert/cabaret is a musical celebration of life above, below and beside the waves. 

On Saturday, March 1, the Key West Woman’s Club will host its’ annual fundraiser Denim to Diamonds!

Enjoy cocktails, scrumptious hors d’oeuvres, decadent desserts, lively music by Jerico and dancing while you shine in your denim or diamonds!

Get ready, Key West! The legendary Wearable Art Fashion Show is making a spectacular comeback on February 15th at the Hellings Curry Museum, home of the Key West Woman’s Club.

This electrifying afternoon will feature bold, one-of-a-kind designs in three categories: Tropical Couture, Creative Costume, and Eleanor’s Up-cycle—where donated garments are transformed into runway masterpieces. Bid live on these stunning creations and cheer on your favorites as designers compete for top honors!

Celebrate Big Game Sunday at The Southernmost Beach Resort.
Enjoy an Unlimited Tailgate Food Station and Well/Draft/Wine OPEN BAR!!

Food only option available, too!

Tickets Include:

Two buffets open for the duration of the game

Open bar for the duration of the game

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.

Vendor Village Marketplace to take place at the Duval Street Pocket Park, where Duval meets the Atlantic 2/8/25 from 12 noon – 6pm, featuring local artisans, crafts, candles, art, jewelry & more. FREE!

Saturday, 2/8 we’ll have 4 LIVE reggae bands on the beach, with a DJ to get the party started!

Party starts at 3pm. Bring your beach chair, your flip flops and your sunscreen and be ready to be Irie, Mon!

Vocalist Libby York, who the New York Times calls "a jazz singer of cool composure and artful subtlety" presents an evening of timeless classic songs by the great Johnny Mercer. York's been praised as a storyteller  "... spotlights her membership in a generation of jazz singers...including Sandy Stewart, Mary Stallings and Carol Sloane...who could wrap themselves around  a lyric and, with a deep dive, tell a powerful story." NYC Jazz Record. Her latest album "DreamLand" (Origin Records) was among Downbeat Magazine's best of the Year. www.libbyyork.com