14th Annual FRLA Wine on the Water
Wine on the Water is a signature fundraising events hosted by the Florida Restaurant & Lodging Association Monroe Chapter. The experience is designed as an elegant sunset cruise with live music featuring A five-course pairing menu with five wine varietals prepared by a local celebrity chef showcasing the creativity and talent of the Florida Keys culinary community.
Ghost Stories from the Gardens
Just in time for Halloween, join Island Tales for a creepy garden ghost tour.
This will be an enthralling evening filled with ghost tales and spooky legends led by 5-star rated tour guide Amy Andrade. Learn about haunted lighthouses, murder, betrayal, diseases, natural disasters, and ghosts that haunt the Florida Keys.
All proceeds will benefit the CFK Academy students.
Ghost Stories from the Gardens
Just in time for Halloween, join Island Tales for a creepy garden ghost tour.
This will be an enthralling evening filled with ghost tales and spooky legends led by 5-star rated tour guide Amy Andrade. Learn about haunted lighthouses, murder, betrayal, diseases, natural disasters, and ghosts that haunt the Florida Keys.
All proceeds will benefit the CFK Academy students.
Lost Women, Found Art Gallery Trolley Tour
Celebrate the creativity and impact of women in the arts on this inspiring trolley tour of Key West’s women-owned and women-managed galleries. In honor of this year’s Lost Women in the Arts theme, you’ll visit a curated selection of local galleries, meet the artists and gallery owners behind them, and discover the stories, talent, and vision that continue to shape Key West’s vibrant arts community. Each gallery stop includes a complimentary beverage, giving you the chance to sip, socialize, and enjoy each unique space while learning about the featured artists and their work. Whether you’re an avid art collector or simply looking for a fun afternoon exploring Key West’s creative scene, this tour offers an engaging and memorable Womenfest experience.
Paint the Town Proud Pub Roll
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!
Rum Around the World
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.
Walk with a Doc: Gut Check – What’s Normal and What’s Not
Take a step toward better health at our next Walk with a Doc event!
This month, we are focusing on digestive wellness with a special presentation and community walk designed to educate, exercise, and empower.
Join guest speaker Michael P. Klitenick, MD FACS, for an informative talk titled "Gut Check: What's Normal and What's Not." Dr. Klitenick will walk through common digestive issues, highlighting what symptoms to watch for and providing guidance on when it is time to seek professional care.
FREE!
Sunshine at the Sandbar with a Sunset
Kick Off Songwriters Week on the Water with Erica "Sunshine" Lee! ☀️🎤
Get ready for the ultimate private concert experience! We’re hitting the waves for 6 hours of sun, music, and good vibes. Catch a live 1-hour performance by Erica "Sunshine" Lee while we cruise.
Conch Crawl Pub Stroll
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!
Soft Opening: Key West Cultural Center & Veterans Museum
Join us for an exclusive first look at the Key West Cultural Center & Veterans Museum! We are opening our doors for a special Soft Opening event to share our vision with the community and gather your valuable feedback. Located at the historic William Weech American Legion Post 168, this evening is a celebration of local history, service, and the arts.
Holiday Lights Trolley Tour
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!
Holiday Historic Inn Tour
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
Holiday Lights Train Ride
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.
Holiday Historic Inn Tour
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 (*Gardens Hotel on the 12th)
December 12th: The properties on this night's tour are:
Gardens Hotel* (526 Angela St.)
Island City House Hotel
Key West Cooking Show
Lighthouse Hotel
Pride Brunch and "Stroll Through Time" Pub Roll
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.
Holiday Lights Trolley Tour
Join the Key West Parrot Head Club on a Holiday Lights Trolley Tour!
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!
Holiday Train Ride
It's our first fundraiser of the season and a crowd favorite! Check-in at 7pm at the beautiful Gardens Hotel and enjoy a tasty beverage at the Garden's cash bar while you catch up with your Fringe friends and enjoy the live holiday music. Then at 8pm it's All Aboard our Holiday Train for a festive ride about town to see the holiday lights of Key West. Pickup and Return at the Gardens Hotel, 526 Angela Street. Tickets: $60.
Holiday Historic Inn Tour
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 encouraged to bike, walk or use their own transportation.
Holiday Historic Inn Tour
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 encouraged to bike, walk or use their own transportation.