
Masquerade Monday Wine Dinner
Step into an evening of mystery and elegance at our Bridgeton-inspired Masquerade Ball Wine Tasting Dinner featuring Juggernaut Wines. Dress the part in your favorite mask and costumes and enjoy a night where fine wine, exquisite food and live music and entertainment comes together. Savor a multi-course dinner paired with wine, while the music sets the mood for a magical night of intrigue and celebration.

Rum Revelation, A Cocktail Journey Ft. Captain Morgan
You will enjoy two rum Tastings of Captain Morgan White and Spiced Captain Morgan. Followed by two rum cocktail samples and two rum drinks that you personally make and enjoy. During this experience, you will learn the history of these rum drinks as well as a bit of background on Captain Morgan and what makes their rum so amazing. With this special Fantasy Fest Captain Morgan Cocktail Class, you will receive a swag bag filled with fun goodies to enjoy!

Rum Revelation, A Cocktail Journey Ft. Captain Morgan
You will enjoy two rum Tastings of Captain Morgan White and Spiced Captain Morgan. Followed by two rum cocktail samples and two rum drinks that you personally make and enjoy. During this experience, you will learn the history of these rum drinks as well as a bit of background on Captain Morgan and what makes their rum so amazing. With this special Fantasy Fest Captain Morgan Cocktail Class, you will receive a swag bag filled with fun goodies to enjoy!

Saturday Parade Viewing Party
Get ready for the most spectacular event of the year! Vinos on Duval invites you to a special viewing party for the legendary Fantasy Fest Parade.
Located directly on Duval Street, Vinos offers a perfect vantage point to take in all the elaborate floats, wild costumes, and electrifying energy of the parade. Join us on Saturday, October 25th, as Key West transforms into a vibrant playground of "Bedtime Stories & Magical Monsters."

Burgers & Buffett Tunes: A Tribute Show
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.

Burgers & Buffett Tunes: A Tribute Show
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.

Time to Talk Turkey!
Join us at The Key West Cooking Show for two special Thanksgiving-themed classes that bring holiday traditions to life—island style!
✨ Learn hands-on recipes and techniques to elevate your holiday table.
🍽️ From the perfect turkey to creative sides and desserts, we’ll show you how to add both classic and modern twists to your feast.

Burgers & Buffett Tunes: A Tribute Show
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.

Time to Talk Turkey!
Join us at The Key West Cooking Show for two special Thanksgiving-themed classes that bring holiday traditions to life—island style!
✨ Learn hands-on recipes and techniques to elevate your holiday table.
🍽️ From the perfect turkey to creative sides and desserts, we’ll show you how to add both classic and modern twists to your feast.

Thanksgiving at Key West Cooking Show
Celebrate Thanksgiving at The Key West Cooking Show!
Gather your crew and let us handle the cooking this year! Join us for a full Thanksgiving feast (buffet style) on the most delicious holiday of the year—because let’s be honest, Thanksgiving is all about the food (and so are we!).
📅 Two Seatings: 11:00 AM & 3:00 PM

Thanksgiving at Key West Cooking Show
Celebrate Thanksgiving at The Key West Cooking Show!
Gather your crew and let us handle the cooking this year! Join us for a full Thanksgiving feast (buffet style) on the most delicious holiday of the year—because let’s be honest, Thanksgiving is all about the food (and so are we!).
📅 Two Seatings: 11:00 AM & 3:00 PM

An Enchanted Evening in the Key West Gardens at Fort West Martello – Past, Present & Future
Join us for a very special evening amid a magical display of lights and tropical beauty as we honor 70 years of our beloved Key West Garden. Hear from some of our “keepers of the fort” as we celebrate the past, present and future in a visual display of lights, and garden history and as we share our exciting vision to continue to build on Key West Garden’s legacy.

Burgers & Buffett Tunes: A Tribute Show
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.

Burgers & Buffett Tunes: A Tribute Show
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.

Burgers & Buffett Tunes: A Tribute Show
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.

Burgers & Buffett Tunes: A Tribute Show
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.

The College of the Florida Keys 60th Anniversary Celebration
Toast to six decades of educational excellence at The College of the Florida Keys’ milestone 60th Anniversary Celebration, featuring fine dining, cocktails, historical exhibit, live music, and dancing in honor of the College's rich legacy and continued commitment to student success.

Cooking with Salt and Pepa
A flavorful fundraiser for Floyd “Pepa” Jenkins, candidate for Fantasy Fest King 2025, benefiting the Florida Keys SPCA 🐾
👨🍳 Featuring:
Chef Joey Bove (“Salt”)
Floyd Jenkins (“Pepa”)
Resident Chef Karl from the Key West Cooking School

A Seat at the Table: Modern Manners for Young Diners
Inspired by the timeless teachings of Emily Post, this special event invites preteens and teens to rediscover the value of meaningful connection over a shared meal. Before cell phones and today’s shiny distractions, dinnertime was a chance to connect, communicate, and show consideration. “A Seat at the Table” helps bring those values back to life.

No Power, No Problem: Hurricane Life in the Keys
Join us for No Power, No Problem, an unforgettable night of true tales, dark humor, and island resilience, hosted by legendary Conch and local historian Tony “Fats” Yaniz. From Hurricane Donna to Irma and everything in between, we’ll hear first-person accounts of what it’s like to ride out nature’s fury in the southernmost city—where survival is just as much about community as it is about prep.

"You CAN Sit With Us" Drag Brunch
Join us for a fabulous Drag Brunch on Sunday, September 7, from 12–3 PM, with dazzling performances starting at 1 PM! Enjoy a vibrant afternoon of entertainment, laughter, and a delicious buffet featuring shrimp bisque, French toast with berries, eggs, bacon, sausage, home fries, cured salmon, benedicts, jerk chicken with yellow rice, croissants, fresh fruit, salad, and sweet treats like flan and key lime pie. Grab your friends, sip something bubbly, and get ready for a Sunday full of glam and good vibes!

Brewfest/ Green Parrot Bar Charity Bingo to Benefit the Key West Sunrise Rotary's Scholarship Fund
A final effort to raise more money for a good cause at the Green Parrot. Play bingo for the Sunrise Rotary. All proceeds will be donated to the Key West Sunrise Rotary's scholarship fund for local Key West students. Beer & drink specials, prizes. tons of fun, and more!

Four Course Beer Pairing Dinner
Get ready to indulge in some of the best food you've ever tasted. Matt's Stock Island Kitchen & Bar and Key West local Cayo Hueso Brewing are teaming up for a beer pairing dinner and offer a variety of delicious options that will satisfy any craving.

3 Daughters Brewing Drink & Draw
3 Daughters Brewing is challenging you to chug one of their beers and and attempt to draw a randomly selected item/ person/ or place. 3 participants at a time will then be judged to see who moves on to the next round to win a 3 Daughters Brewing bar tab!

Key West Brewfest Grand Tasting Event 2025
Key West BrewFest is an island wide festival hosted by the Key West Sunrise Rotary of the Conch Republic and the Southernmost Beach Resort. This is a 100% nonprofit, charitable event, to raise money for local student’s scholarships.

Backyard Olympics: Brewfest Edition
Sunset Green Event Lawn comes alive as you'll go for gold with their Backyard Olympics: Brewfest Edition! Beer Pong Relays, Flip Cup, Blind Taste Tests and more... Das Boot!

Pizza & Pints Pool Party at Lighthouse Hotel
Dive into deliciousness with live entertainment, signature gluten-free beer and Clemente’s legendary pizza – available in both gluten-free and classic styles.

Pineapple Pool Party & Belly Flop Contest
Brought to you by Islamorada Brewing & Distillery, the Pineapple Pool comes alive with a DJ, beer samples, swag, and a belly flop contest that will leave you sore from either participating or from laughing at those who do!

Grilled Cheese & Beer Pairing with Pub Style Trivia with a Twist!
Paired with brews from FL Keys Brewing, enjoy 4 different gourmet grilled cheese sandwiches, sure to please the palate - all while testing your team's knowledge with Pub Style Trivia!
Pool Floatie Chug & Race
Who wants to be the Pool Floatie Chug & Race Champ?! Chug a beer and race to one end of the pool, then chug another one and race back to the finish line to claim the checkered flag!

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.

Key West 1970s
Hosted by local legends Tony 'Fat' Yaniz and Richie Gomez This special evening brings together a lineup of Key West locals sharing what it was like to grow up in the Conch Republic. Key West—1970s—Key West was a ghost town, dogs sleeping on Duval Street. The navy left town. The main occupations were shrimping and smuggling—maybe one in the same.. 50 cent draft beer at Sloppy’s. Sex and rock and roll at the Bull. And the Full Moon was THE late night spot. You’d find a smuggler and a DEA agent buying one another rounds. One day you’d be on a bike with bent rims and the next tooling around in a Porche 911…don’t you wish you were there?

3nd Annual FRLA Monroe R.O.S.E Awards
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.

Anders Osborne
Be our guest on the evening of April 23 at 7:30 pm as we welcome back renowned singer, songwriter and virtuoso guitarist Anders Osborne to the storied Monkey Hut at Little Palm Island. This intimate and exclusive performance is only available to a limited number of guests.

Electric Blue Yonder + B.B. Palmer – Live at the Little House
We’re headed back to one of our favorite spots—the world-famous Standard Deluxe—for a special night inside the Little House! The evening kicks off with a set by the one and only B.B. Palmer, with Electric Blue Yonder as his backing band, followed by a full headline set from us to keep the party rolling. To make the night even sweeter... It’s B.B.’s Birthday! Let’s celebrate the man with music, love, and a whole lotta good energy.

A Roaring Good Time Speakeasy!
CFK Academy at The College of the Florida Keys, is excited to invite you to A Roaring Good Time, Presented by the CFK Foundation. This year’s 2nd annual event will be hosted at the Tennessee Williams Theatre on Friday, April 18, 2025 6:00-8:30 p.m. We are planning a fun evening with food, cash bar, entertainment, auctions, and much more! Please join us to support our students.

Key West Historic Days: High Tea of Years Gone By
Bringing back the elegance and charm of an afternoon high tea to celebrate the Key West Woman’s Club 110th Anniversary. Enjoy from a fine selection of teas, finger sandwiches and delectable sweets, including scones, fruit tarts, and other extraordinary delights.

Key West Historic Days: Flavors of the Past
Panel Moderator: Dr. Roberta Isleib is a USA Today bestselling author and clinical psychologist. She is also known as Lucy Burdette, author of The Key West Food Critic Mysteries and is a Key West Woman's Club member. She has written 24 novels, including the latest The Key Lime Crime. A Clue in the Crumbs, the 13th book in the series The Key West Food Critic Mysteries, won the Florida Book Award’s gold medal in popular fiction. Her series features a Key West food critic solving murders on the side.

Key West Historic Days: “Echoes of the Island” Panel & “After Party”
"After Party" at Hellings Curry Museum, home of the Key West Woman's Club.
Open bar, appetizers and desserts from the new 2025 Key West Woman's Club Cookbook provided by the Key West Woman's Club.

Key West Historic Days: WOMEN GET THINGS DONE
Camille Toler & Friends will perform on the front porch. Appetizers from our Key West Woman's Club newly revised cookbook will be prepared for you by Key West Cooking School.

Darcy Cooke: “Jazz, Cabaret, & Cocktails”
Darcy Cooke presents an intimate evening of 2 parts jazz favorites from the Great American Songbook along with 1 part well-loved cabaret tunes. 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.

Memories of Coffee
From Johnny Neebo’s Starlight Club, to the Bamboo Room, to the Hukilua, Coffee Butler entertained Key West since 1952. This special performance Memories of Coffee will include the amazing vocals of the King of Key West Soul - Robert Albury, Clayton Lopez and Mina Lopez-Martin, a young new voice of Claire Caplan. They will revive the classic soul sound of the Temptations, Smokey Robinson, and Aretha Franklin along with originals by Coffee Butler. Music Director Larry Baeder will lead the talented Soul of Key West Band.

Taste of Key West
This open-air event promises an assortment of beverages and palate-pleasing small plates. Local Restaurants and Vintners Present the perfect Taste of Key West at our 30th Annual Celebration!
A.H. Monroe & Republic National Distributing Company bring the community together for Cuisine, Craft Beer & Fine Wines! Cheers!

Tennessee’s Men, a reading in two acts
This reading of two short plays written by Tennessee Williams is presented in partnership with the Fringe Theater, Key West Arts & Historical Society and Williams Hall as part of the annual month-long Tennessee William Festival. Directed by Wende Shoer with readers Wayne Dapser, Jim Argoudelis, Merle Dimbath, Jim Speake, Wayne LaRue Smith, Nancy 3 Hoffman, Alana Thurston, Samantha Laskey, and Thomas Masat.

Sip n' Paint: Celebrate Spring, Island Style!
We are "painting" a garden. Canvases can be painted separately or as a group. So much fun!
One of a kind painting events- Paint the Tale!

Cigar Box Paint, Sip & Storytelling Party
Join us for a unique and immersive experience where you'll transform a classic cigar box into a personalized work of art. Sara "Pie" Butler, renowned for her vibrant and whimsical style, will guide you through the painting process, sharing her techniques and inspiring your creativity. No prior painting experience is necessary – just bring your enthusiasm and a willingness to explore your inner artist.

Sip n' Paint: Celebrate the Luck of the Irish!
It's the "luck" of the IRISH! Paint to stories of luck and superstition!
One of a kind painting event- Paint the Tale!