Experience worldly flavors and vibrant island vibes at the "Rum Around the World" event, hosted at Papa's Pilar Distillery in the heart of Key West. Taking place on May 30th, 2026, doors for this exclusive evening open at 6:00 PM. Guests will have the unique opportunity to sample a diverse selection of rums from various countries, proudly offered by the Foreign Liaison Officers' Association. Located at 201 Simonton Street, Key West, Florida, this gathering promises good company and a rich tasting experience at the home of the Hemingway Rum Company.

Join the Rotary Club of Key West on May 16, 2026, for Casino Night: Roaring ’20s Speakeasy! 🥂

Step back in time at the Beachside Resort for a night of blackjack, jazz, and specialty cocktails. All proceeds benefit local scholarships. 🎓 Dress your best for a chance to win prizes! Transport yourself back to the 1920s for a night of high-stakes fun and prohibition-style elegance! The Rotary Club of Key West invites you to our annual Casino Night gala. This year, we’re transforming the Beachside Resort into a secret Speakeasy where the jazz is hot, the drinks are cold, and the gaming is for a great cause.

In the words of a classic Howard Livingston song, “There’s still a lot of magic in Key West.” That magic will be on full display Saturday, April 11, when Howard and his Mile Marker 24 Band take audiences on a lively musical journey around the island city and the entire Florida Keys. The two-hour concert will showcase the band’s trop-rock melodies that capture the essence of saltwater days and rum-kissed nights — paired with visuals and stories to immerse listeners in a multi-sensory Keys experience.

Very special guests, surprises and Howard’s 1952 Johnson outboard motor “margarita machine” will add to the fun. The evening benefits the nonprofit Care Camps Foundation, funding special summer camps where kids diagnosed with cancer can find hope and happy times.

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.

Join us for one of Key West’s most anticipated foodie traditions! 🌴🍷
Taste of Key West returns for its 31st Annual Celebration, bringing together the island’s top restaurants, vintners, and beverage partners for an unforgettable open-air evening at Truman Waterfront.

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!

The doors of the Hemingway Home will swing open for an unforgettable event Thursday, March 19th, 2026. Top mocktail creators will gather to mix, mingle, and compete for the coveted title of “Master Mixologist 2026”. The food pairing highlights the key skills of pairing food to enhance the mocktail experience. 

Experience a truly authentic and unforgettable performance by Nashville’s own Analisa and John Gallo. This evening supports the local charities of the Sons and Daughters of Italy Key West Lodge.

• Schedule: Dinner at 5:30 PM | Show starts at 6:45 PM

• Admission: $50 (Includes dinner & one glass of wine)

"The Italian American Dream" show honors the story of the Italian immigrants of the early 1900s. It is a show for everyone, and highlights the themes of culture, family, sacrifice, and faith!

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.