Step back in time to a sparkling 1960s Christmas Revue filled with laughter, harmony, and holiday heart.

Join Wanda, Gina, and Johnny as they host a nostalgic Christmas pageant bursting with classic retro charm, modern holiday hits re-imagined in vintage style, and heartfelt memories that feel like coming home. With shimmering harmonies, festive comedy, and a whole lot of tinsel, this merry trio leads the audience through stories of friendship, family, and the magic of believing —

 reminding us that the greatest gift of all is the people we share the season with.

Yin yoga is a slow-paced, meditative style of yoga where passive poses are held for a long duration, typically 3 to 5 minutes or longer. This practice targets deep connective tissues like ligaments, joints, and fascia, contrasting with more active styles that focus on muscles. The long holds encourage a state of stillness to increase flexibility, improve joint mobility, and foster a deeper mental and physical awareness. 

FREE!

Get your HO HO HO on with the Fringe, Tuesday Dec 16th, and enjoy live holiday music and a festive tour of the island’s holiday lights! Check-in begins at 7pm at the beautiful Gardens Hotel (526 Angela Street) where award-winning vocalist Claire Caplan and pianist Larry Smith will be the perfect prelude to the evening’s ride. (You might find inspiration to ‘jingle your bells’ on the dance floor at the Garden’s cash bar!) Then at 8:30pm it’s All Aboard the Holiday Train! Support Fringe Theater’s education and outreach programs by celebrating the holidays with friends! Tickets are $65.

Come feel the magic of the best jazz musicians in Key West! The Key West Jazz Allstars will wow you. Enjoy music and dancing. 

Featuring Terri White, Larry Baeder, Hal Howland, Bubba Lownotes, Tony Eitcher, and David Arndt.

Full Menu is available from Olive's Mediterranean Cafe.

 Parking Lot is at 201 Truman, enter lot off of Emma St, about a block away.

Part of the “Saints, Sinners & Scream Queens” Film Series
Sponsored by the Key West Film Festival
December 18 | 7:00 PM | $15 | Williams Hall

The most chaotic “Christmas movie” ever made. Terrorists, duct vents, Hans Gruber, and one barefoot cop who refuses to quit. A holiday classic by accident. Come celebrate the holidays the loud way.

Join us for an enchanted evening of decorated historic inns while enjoying light sweet or savory holiday treats and holiday cheer at each property. Visit each property, explore the unique architecture and history, and delight in holiday ambiance in a tropical setting. The tours are self-guided. Free trolley transportation will be provided between properties - but participants are welcome to bike, walk or use their own transportation.

Tickets can ONLY be picked up the night of the tour at the first property on the tour after 5:30pm ONLY (*Key West Butterfly & Nature Conservatory on the 19th)

 December 19th:   The properties on this night's tour are:

Key West Butterfly & Nature Conservatory* (1316 Duval St.)
The Southernmost House
Wicker Guest House
The Mermaid & The Alligator

Join the Key West Parrot Head Club on a Holiday Lights Trolley Tour! 

 We will meet at Salute restaurant at 4:30pm to check in and get your wrist band. One drink (beer or wine) is included. Additional beverages can be purchased at happy hour prices. At 6:00 will walk over to the White St pier parking lot to board the trolley/train.

See all the best decorations on our holiday tour as the locals decorate their historic Key West homes in a splendid cascade of lights and other decorative touches to see who can outdo the other in a friendly, holiday-inspired competition!

The trolley leaves at 6:30pm sharp! 

Yang yoga is the active, dynamic style of yoga that builds strength and stamina through flowing movements, unlike the passive, static poses of Yin yoga. It is characterized by rhythmic sequences that generate heat, such as those found in Vinyasa, Ashtanga, and Power Yoga, focusing on muscles and circulation to strengthen and lengthen them. 

FREE!

Join us for Christmas on the Keys, a joyful, high-spirited piano concert featuring the incredible James T. Slater—two-time Grammy-nominated, piano-playing, bilingual singer-songwriter of Bolivian American descent. Signed to BMG Music Publishing/Nashville, James will be performing hits recorded by legends from Carrie Underwood, and Kenny Chesney, to Tim McGraw and Willie Nelson, to Keith Urban and Enrique Iglesias...as well as songs off his latest album, Shrimp Boat Sessions, recorded LIVE on the piano at Jimmy Buffett's Shrimp Boat Studio here in Key West.

Get immersed in the deep sounds of Ian Maksin's soulful one-man-cello orchestra, paired and blended with his vibrant voice, as he explores a collection of traditional songs from different corners of the world: Japan, Finland, Bosnia, Iran, Ukraine, Armenia, India, Kyrgyzstan, and Medieval France and Spain, woven together with original instrumental works.

His latest release Lullaby for the World is an amazing multilingual journey in search of peace, healing and empowerment through music. It reflects the path of a true musical globetrotter, shaped by countless journeys across continents as a touring artist, along with mountaineering, flying airplanes, practicing meditation, and collaborating with local musicians in search of the mystical thread that connects all cultures. This album invites listeners into a space of presence, clarity, and emotional restoration.

Yin yoga is a slow-paced, meditative style of yoga where passive poses are held for a long duration, typically 3 to 5 minutes or longer. This practice targets deep connective tissues like ligaments, joints, and fascia, contrasting with more active styles that focus on muscles. The long holds encourage a state of stillness to increase flexibility, improve joint mobility, and foster a deeper mental and physical awareness. 

FREE!

Yang yoga is the active, dynamic style of yoga that builds strength and stamina through flowing movements, unlike the passive, static poses of Yin yoga. It is characterized by rhythmic sequences that generate heat, such as those found in Vinyasa, Ashtanga, and Power Yoga, focusing on muscles and circulation to strengthen and lengthen them. 

FREE!

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!!

Yin yoga is a slow-paced, meditative style of yoga where passive poses are held for a long duration, typically 3 to 5 minutes or longer. This practice targets deep connective tissues like ligaments, joints, and fascia, contrasting with more active styles that focus on muscles. The long holds encourage a state of stillness to increase flexibility, improve joint mobility, and foster a deeper mental and physical awareness. 

FREE!

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. With a love of jazz and a background in theater, Darcy is a master of song interpretation and an engaging storyteller who effortlessly guides and charms audiences through an evening of pure entertainment.

Yang yoga is the active, dynamic style of yoga that builds strength and stamina through flowing movements, unlike the passive, static poses of Yin yoga. It is characterized by rhythmic sequences that generate heat, such as those found in Vinyasa, Ashtanga, and Power Yoga, focusing on muscles and circulation to strengthen and lengthen them. 

FREE!

Yin yoga is a slow-paced, meditative style of yoga where passive poses are held for a long duration, typically 3 to 5 minutes or longer. This practice targets deep connective tissues like ligaments, joints, and fascia, contrasting with more active styles that focus on muscles. The long holds encourage a state of stillness to increase flexibility, improve joint mobility, and foster a deeper mental and physical awareness. 

FREE!

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!

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.

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.

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.

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.

Yang yoga is the active, dynamic style of yoga that builds strength and stamina through flowing movements, unlike the passive, static poses of Yin yoga. It is characterized by rhythmic sequences that generate heat, such as those found in Vinyasa, Ashtanga, and Power Yoga, focusing on muscles and circulation to strengthen and lengthen them. 

FREE!

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.

Yin yoga is a slow-paced, meditative style of yoga where passive poses are held for a long duration, typically 3 to 5 minutes or longer. This practice targets deep connective tissues like ligaments, joints, and fascia, contrasting with more active styles that focus on muscles. The long holds encourage a state of stillness to increase flexibility, improve joint mobility, and foster a deeper mental and physical awareness. 

FREE!

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!

Yang yoga is the active, dynamic style of yoga that builds strength and stamina through flowing movements, unlike the passive, static poses of Yin yoga. It is characterized by rhythmic sequences that generate heat, such as those found in Vinyasa, Ashtanga, and Power Yoga, focusing on muscles and circulation to strengthen and lengthen them. 

FREE!

Yin yoga is a slow-paced, meditative style of yoga where passive poses are held for a long duration, typically 3 to 5 minutes or longer. This practice targets deep connective tissues like ligaments, joints, and fascia, contrasting with more active styles that focus on muscles. The long holds encourage a state of stillness to increase flexibility, improve joint mobility, and foster a deeper mental and physical awareness. 

FREE!

Yang yoga is the active, dynamic style of yoga that builds strength and stamina through flowing movements, unlike the passive, static poses of Yin yoga. It is characterized by rhythmic sequences that generate heat, such as those found in Vinyasa, Ashtanga, and Power Yoga, focusing on muscles and circulation to strengthen and lengthen them. 

FREE!

Yin yoga is a slow-paced, meditative style of yoga where passive poses are held for a long duration, typically 3 to 5 minutes or longer. This practice targets deep connective tissues like ligaments, joints, and fascia, contrasting with more active styles that focus on muscles. The long holds encourage a state of stillness to increase flexibility, improve joint mobility, and foster a deeper mental and physical awareness. 

FREE!

Yang yoga is the active, dynamic style of yoga that builds strength and stamina through flowing movements, unlike the passive, static poses of Yin yoga. It is characterized by rhythmic sequences that generate heat, such as those found in Vinyasa, Ashtanga, and Power Yoga, focusing on muscles and circulation to strengthen and lengthen them. 

FREE!

Little-known short plays by Tennessee Williams that boldly explore sexuality, identity, and longing. Presented in partnership with the Tennessee Williams Festival at Williams Hall. Directed by Dominic Paolillo. Cast: Kitty Clements, Cassidy Timms, Aramis Ikatu, Phillip Cole, Todd Glenn, Jim Speake, Trey Forsyth, Diane May, Chris Massicotte, Kathy Russ, Mariah Woessner, Davis Stack, Barbara Mundy.

Venue: Williams Hall, 729 Fleming St.

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.

Sponsorship opportunities available.