Wrap up an unforgettable Womenfest at our fabulous all-welcome Closing Drag Brunch, hosted by Hugh Janus! Enjoy spectacular drag performances, a special performance by our Queen Mother, Claire Brummell, delicious food, and nonstop laughter as some of Key West's most talented entertainers take the stage throughout the afternoon. Indulge in an abundant brunch buffet including flan and Key lime pie.

Take control of your financial future—without the complicated jargon. Join financial consultant Teo Masters for How Money Works, an engaging, easy-to-understand conversation about saving, investing, getting out of debt, planning for retirement, protecting your income, and discovering your Financial Independence Number (FIN). Whether you’re just getting started or want to make smarter moves with the money you already have, you’ll leave with practical knowledge you can put to work right away. Come curious, leave empowered—and take the first step toward making your money work for you.

Acclaimed musician, actor, and Buffett historian Caleb Hogan appears in-costume as the man himself in a show blending live music, storytelling, humor, and of course...Cheeseburgers! Enjoy a journey back in time to a place where artists and misfits lived the eclectic Bohemian dream, and our favorite "grandson of a sailor" roamed the land.
Part lunch theater, part tribute concert, and part educational adventure, Burgers & Buffett Tunes is a one-of-a-kind musical celebration of the songs, spirit, and the island where the legend began. This show is a MUST-SEE for all Buffett fans, music enthusiasts, or anyone looking for Key West’s most entertaining lunch experience.

Acclaimed musician, actor, and Buffett historian Caleb Hogan appears in-costume as the man himself in a show blending live music, storytelling, humor, and of course...Cheeseburgers! Enjoy a journey back in time to a place where artists and misfits lived the eclectic Bohemian dream, and our favorite "grandson of a sailor" roamed the land.
Part lunch theater, part tribute concert, and part educational adventure, Burgers & Buffett Tunes is a one-of-a-kind musical celebration of the songs, spirit, and the island where the legend began. This show is a MUST-SEE for all Buffett fans, music enthusiasts, or anyone looking for Key West’s most entertaining lunch experience.

Join us for an exclusive masterclass diving deep into the rich histories, distinct production styles, and complex flavor profiles of world-class rums. Featuring two iconic brands—Diplomático Rum and Worthy Park Estate—this immersive event offers a side-by-side exploration of Venezuelan and Jamaican rum-making traditions.

Join us for our second installment of Drink & Think's local lecture series at Rick's brand new Old Sailor Bar! Yvonne Jefferson, owner of iWitness: True Crime Tours, will take you through some of Key West's most notorious, and lesser known, true crime stories.

Official Lobsterfest Event!

Lobster roll eating contest… $30 to enter. Comes with 1 lobster roll – the fastest to finish it completely, wins!

Get ready to test your knowledge at the Key West Lobsterfest, featuring an evening of Pub Style Trivia with a Lobster Twist. For $50 per person, attendees can enjoy the competitive atmosphere along with a fresh lobster roll and a drink included with their entry. Not Hungry? For $25 per person, attendees can enjoy the competitive atmosphere along with a drink only included with their entry.

Join Salty Chef Catering for an unforgettable evening of flavor, culture, and giving back at The Spain Tables — a Salty Chef Experience benefiting our local Marine Corps unit. Set at The Studios of Key West, this charity event brings together Spanish-inspired cuisine, live music, cocktails, and great people, all in support of the men and women who serve. A portion of proceeds goes directly to a local Marine Corps unit, helping support their mission, families, and community outreach.

This is the inaugural presentation in our newly formed lecture series featuring local experts across different industries. The topic is AI: The Good, The Bad, and The Ugly.

 Presented by Marlene Kolodziej, CTO and IT Director of the Monroe County School District and Computer Science Adjunct Professor at College of the Florida Keys.

Acclaimed musician, actor, and Buffett historian Caleb Hogan appears in-costume as the man himself in a show blending live music, storytelling, humor, and of course...Cheeseburgers! Enjoy a journey back in time to a place where artists and misfits lived the eclectic Bohemian dream, and our favorite "grandson of a sailor" roamed the land.
Part lunch theater, part tribute concert, and part educational adventure, Burgers & Buffett Tunes is a one-of-a-kind musical celebration of the songs, spirit, and the island where the legend began. This show is a MUST-SEE for all Buffett fans, music enthusiasts, or anyone looking for Key West’s most entertaining lunch experience.

Get ready for a little friendly competition! Join us on Sunday, July 26th from 4:00 PM – 9:00 PM as our talented bartenders go head-to-head in the ultimate summer showdown: The Horseplay Punch Classic.

They’re mixing up their best large-format concoctions, and you get to be the judge.

Tuesday, July 14 • Tasting 6:30 PM • Film 8 PM

Join sommelier Daniel McCurdy for a special wine tasting before the film exploring the wines of the central coast. No merlot will be served. Lite bites from Chef Martha.

A movie that launched a thousand wine clubs and nearly destroyed the reputation of merlot forever. Funny, moving, and proof that middle-aged existential crises can occasionally be entertaining.

Join us on the Old Town Trolley Tour for the "Paint the Town Proud Pub Roll", an exciting adventure outside Key West's historic and vibrant Gayborhood. This unique event celebrates the island's LGBTQ+ cultural heritage while you enjoy specially curated Pride-themed drinks at each stop. Be sure to dress in your favorite color of the rainbow to win best dressed! We'll kick off the tour at Bobby's Monkey Bar, where you can enjoy delicious breakfast bites and a welcome drink. A cash bar is also available for mimosas, Bloody Marys, or any other drinks you might want to have before the tour begins!

Join us at Tropicado Mojito Bar at La Concha Hotel for an immersive, hands-on mojito experience in the heart of Key West!

Shake, “slap”, and sip your way through the art of crafting the perfect mojito as you explore Papa’s rum, fresh ingredients, and the vibrant spirit of Havana. This interactive class is a must-do for cocktail enthusiasts, curious beginners, and anyone looking to elevate their island experience.

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 Sons and Daughters of Italy, Key West Lodge, for an evening of wine, music, and celebration as we mark our 47th anniversary on Wednesday, May 20, 2026. We invite you to Grand Vin Wine Bar at 1107 Duval Street from 5:30 PM to 7:30 PM for an Italian wine tasting paired with delicious antipasto and, of course, birthday cake.

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.