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.

Join us to celebrate the end of Songwriters Festival with a Southern-style brunch at Williams Hall's Unity Table before the "Sunday Songs: Music & Mimosas"

Brunch includes exclusive balcony seating for the show.

Get ready to shell-ebrate 44 years of independence at the Conch-Tail Party, Dinner & Sunset Toast!

Join the fun on April 21 from 6:00 PM to 9:00 PM at the legendary Sunset Pier for an evening of harborside dining and island tradition. You’ll be mingling with Admirals, Generals, and local legends while enjoying live tunes from Reggae Lou and Sir CW Colt.

Between the official 21 Conch Shell Salute and the sunset toast, it’s the most festive way to honor the Republic.
Grab your tickets for $50 before the price jumps to $60 after April 10.

Stand at ease and prepare for a sovereign celebration like no other!

As part of the 44th Annual Conch Republic Independence Celebration, we invite you to the official Military Muster. This is your exclusive opportunity to rub elbows with the "High Command" from all seven prestigious branches of our military forces—all decked out in their finest full regalia. In true Conch Republic fashion, we fight our battles with humor, heart, and a side of conch fritters.
Whether you are a long-time citizen or a newly arrived "alien," come share in the community spirit as we defend our borders from "Key to Shining Key." 

Admission to this community event is $20 plus a potluck donation to share with your fellow patriots.

Celebrate the spirited independence of the Conch Republic with the ultimate Old Town stroll! As part of the 44th Anniversary celebration, the annual Conch Crawl invites you to experience the best of Key West’s legendary bar scene while supporting a great cause.

The Lineup
Your ticket grants you access to nine of Old Town’s most famous establishments: 801 Bourbon Bar, Mango’s, Hank’s Hair of the Dog, Kaya’s Backyard Bar, Doc’s on Duval, Irish Kevin’s Bar, Rick’s Downstairs Bar, Salty Frog’s Bar & Grill - Plus, stay for the official After Party!

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.

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 an exclusive, guided journey through the world of premium agave spirits. Hosted at HiNote—the intimate cocktail lounge located upstairs at General Horseplay—this event offers a deep dive into the craft and heritage of Tequila Ocho.

Your evening begins with a refreshing welcome cocktail followed by a curated tasting of four specialty pours. From 7:00 PM to 9:00 PM, guests will enjoy an educational session led by industry experts, exploring the unique "single estate" philosophy that defines Tequila Ocho. After the formal tasting concludes, the bar will remain open until late, allowing you to settle in and enjoy the atmosphere of one of Key West's most hidden gems.

Join us for a special literary evening featuring Lucy Burdette, USA Today bestselling author of the beloved Key West Food Critic mystery series. Enjoy a live reading of one of Lucy’s short stories by local creative and actress Erin McKenna, followed by dinner prepared by Chef Martha and conversation celebrating storytelling and 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!

Comedy Key West is happy to be bringing back the first show paying tribute to the funny side of the life and works of Ernest Hemingway. A few blocks down the street from the famed Hemingway House, where he lived and wrote for nine years, and around the corner from his legendary watering hole Sloppy Joe’s, comedian James Scott Patterson takes us on an hourlong tour of Hemingway’s childhood, writing career, adventuring, and, of course, drinking days. The humor ranges from the tragic-comic (it is Ernest Hemingway after all) to the witty, wild, and difficult to believe. The show is a happy hour celebration from 5:30 to 6:30 including a complimentary glass of Hemingway’s favorite wine (Valpolicella) with your ticket.