A Pirate Looks Back - Jimmy Buffett 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.
Hush Money
This fresh, fabulous new drag show is hosted by winner of Best in Drag at the 2026 Bubba Awards in Key West, Beatrix Dixie. HUSH MONEY dives headfirst into a deliciously naughty world of fame, fortune and temptation.
Expect brand-new material, iconic drag classics, killer looks, comedy, glamour, and unforgettable performances from some of the best drag talent Key West has to offer. One minute you’ll be laughing, the next you’ll be gagging—and you may leave knowing a few things you probably weren’t supposed to hear.
Stack & Lew's Fright Night Party
Get ready for a spooktacular Halloween night with Stack & Lew! Join us at General Horseplay for pumpkin carving, live entertainment, and a costume contest with a cash prize.
Coast is Clear Music & Arts Festival
The Coast Is Clear Music & Arts Festival is back this December 4-6 with a weekend-long series of cultural events to celebrate the official end of Atlantic Hurricane Season. Held at venues throughout Bahama Village in Key West, the festival includes a mix of ticketed live-music shows as well as plenty of free music & events, including the Petronia Street Block Party which takes place all day (10am-10pm) on Saturday, December 5.
Bourbon St Pub's VIP Balcony Bash
Join us for one of the best views of the Fantasy Fest parade on Duval St. from the Grand Balcony of the New Orleans House, 724 Duval St. Don't deal with the crowds! VIP high-end open bar and catered buffet/Mangoes Restaurant-no need to go anywhere else. Bags of beads to toss to the crowd below! MC'd by John "Ma" Evans. Private entrance and restrooms.
Don't miss this opportunity for a great vantage point to see the parade and a fantastic party.
New Orleans House Pool Party
Soaking Wet Pool Party / Parade day.
Come splash around in the pool or jacuzzi while listening to music to get you hyped with live DJ and pool games.
Join us 12 Noon until 5pm at New Orleans House! Clothing Optional.
Kinky Couples Party hosted by Rubberdoll!
The ONLY event exclusively for couples.
Join like-minded couples in the Cabaret Bar overlooking Duval Street. A special performance by the world-renowned latex entertainer RubberDoll, including Live Dark'n Dancing. Live DJ will be sure to get everyone in the mood for some serious playtime!
Bourbon St Pub's Afternoon Pool Party
Fantasy Fest 2026, Poolside Dance Party / Street Fair T Dance at the Bourbon St Pub Adult Complex.
Get your groove on while dancing and drinking at the Duval Street T Dance or Poolside at the Bourbon St Pub! Live DJs, Boys, Beads and Booze, Drag Queens, games and MORE! 12 noon until 5-ish.
Exposed
10PM-4AM - Event Open to All! The most risqué party of Fantasy Fest! Voyeur/Exhibition areas throughout! Play in the Poolside Foam Party!
Dance the night away w/DJ Gyvers/outdoor Laser Light show, Splash around in our Pool & Jacuzzi! Black Out & Black Light party inside, TheTazzle.com will be there adding some extra excitement with fun giveaways of OXJOK and more!
Desire Male Fetish Party
Fetish Party 10PM - 4AM.
Private Fetish party - For the Men, Fetish attire encouraged. Live DJ, Exhibition areas, Bring out the Gear!
Free clothes check w/ $30 door cover.
Tops or Bottoms Underwear Party
Underwear party 10PM - 4AM.
Private Underwear party - For the Men, You must lose one or the other or both!
Free clothes check w/ $20 door cover.
A Pirate Looks Back - Jimmy Buffett 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.
Afterlife: the Awakening
Step into the forbidden garden of desire at Bourbon Street Pub. This one-night experience transforms the Garden into a realm of aerial burlesque performed over the pool, voyeur shower stations, and sensual performances that ignite every sense.
Guests will wander through seductive zones designed to tempt and tease, leading up to electrifying stage shows and free-flowing encounters that set the tone for the week ahead. This isn’t just a party — it’s the erotic heartbeat of Fantasy Fest.
Hush Money
This fresh, fabulous new drag show is hosted by winner of Best in Drag at the 2026 Bubba Awards in Key West, Beatrix Dixie. HUSH MONEY dives headfirst into a deliciously naughty world of fame, fortune and temptation.
Expect brand-new material, iconic drag classics, killer looks, comedy, glamour, and unforgettable performances from some of the best drag talent Key West has to offer. One minute you’ll be laughing, the next you’ll be gagging—and you may leave knowing a few things you probably weren’t supposed to hear.
Aqua Idol at the Legion
Starting Tuesday, September 8th join us for the Royal AQUA IDOL season! Every Tuesday, September 8th - October 13th, our group of singers will battle it out through song to become the winner of Aqua Idol for their King or Queen candidate to benefit the animals of the FKSPCA!
You can help your singer of choice and their King or Queen candidate win by donating dollars to their buckets and all proceeds will directly benefit animals! If you're looking for a fun event for a fantastic cause look no further! We look forward to seeing you there!
FREE!
A Pirate Looks Back - Jimmy Buffett 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.
Hush Money
This fresh, fabulous new drag show is hosted by winner of Best in Drag at the 2026 Bubba Awards in Key West, Beatrix Dixie. HUSH MONEY dives headfirst into a deliciously naughty world of fame, fortune and temptation.
Expect brand-new material, iconic drag classics, killer looks, comedy, glamour, and unforgettable performances from some of the best drag talent Key West has to offer. One minute you’ll be laughing, the next you’ll be gagging—and you may leave knowing a few things you probably weren’t supposed to hear.
A Pirate Looks Back - Jimmy Buffett 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.
Aqua Idol at the Legion
Starting Tuesday, September 8th join us for the Royal AQUA IDOL season! Every Tuesday, September 8th - October 13th, our group of singers will battle it out through song to become the winner of Aqua Idol for their King or Queen candidate to benefit the animals of the FKSPCA!
You can help your singer of choice and their King or Queen candidate win by donating dollars to their buckets and all proceeds will directly benefit animals! If you're looking for a fun event for a fantastic cause look no further! We look forward to seeing you there!
FREE!
Aqua Idol at the Legion
Starting Tuesday, September 8th join us for the Royal AQUA IDOL season! Every Tuesday, September 8th - October 13th, our group of singers will battle it out through song to become the winner of Aqua Idol for their King or Queen candidate to benefit the animals of the FKSPCA!
You can help your singer of choice and their King or Queen candidate win by donating dollars to their buckets and all proceeds will directly benefit animals! If you're looking for a fun event for a fantastic cause look no further! We look forward to seeing you there!
FREE!
Hush Money
This fresh, fabulous new drag show is hosted by winner of Best in Drag at the 2026 Bubba Awards in Key West, Beatrix Dixie. HUSH MONEY dives headfirst into a deliciously naughty world of fame, fortune and temptation.
Expect brand-new material, iconic drag classics, killer looks, comedy, glamour, and unforgettable performances from some of the best drag talent Key West has to offer. One minute you’ll be laughing, the next you’ll be gagging—and you may leave knowing a few things you probably weren’t supposed to hear.
Aqua Idol at the Legion
Starting Tuesday, September 8th join us for the Royal AQUA IDOL season! Every Tuesday, September 8th - October 13th, our group of singers will battle it out through song to become the winner of Aqua Idol for their King or Queen candidate to benefit the animals of the FKSPCA!
You can help your singer of choice and their King or Queen candidate win by donating dollars to their buckets and all proceeds will directly benefit animals! If you're looking for a fun event for a fantastic cause look no further! We look forward to seeing you there!
FREE!
Hush Money
This fresh, fabulous new drag show is hosted by winner of Best in Drag at the 2026 Bubba Awards in Key West, Beatrix Dixie. HUSH MONEY dives headfirst into a deliciously naughty world of fame, fortune and temptation.
Expect brand-new material, iconic drag classics, killer looks, comedy, glamour, and unforgettable performances from some of the best drag talent Key West has to offer. One minute you’ll be laughing, the next you’ll be gagging—and you may leave knowing a few things you probably weren’t supposed to hear.
Aqua Idol at the Legion
Starting Tuesday, September 8th join us for the Royal AQUA IDOL season! Every Tuesday, September 8th - October 13th, our group of singers will battle it out through song to become the winner of Aqua Idol for their King or Queen candidate to benefit the animals of the FKSPCA!
You can help your singer of choice and their King or Queen candidate win by donating dollars to their buckets and all proceeds will directly benefit animals! If you're looking for a fun event for a fantastic cause look no further! We look forward to seeing you there!
FREE!
Aqua Idol at the Legion
Starting Tuesday, September 8th join us for the Royal AQUA IDOL season! Every Tuesday, September 8th - October 13th, our group of singers will battle it out through song to become the winner of Aqua Idol for their King or Queen candidate to benefit the animals of the FKSPCA!
You can help your singer of choice and their King or Queen candidate win by donating dollars to their buckets and all proceeds will directly benefit animals! If you're looking for a fun event for a fantastic cause look no further! We look forward to seeing you there!
FREE!
Roger Bartlett & Emily Randle
Often referred to as "Coral Reefer #1," Roger Bartlett was Jimmy Buffett's first guitar player and was the foundation of the Coral Reefer Band. Roger joined Jimmy on the hit "Come Monday," and returned to help in the production of the album Volcano.
Maddie Rean in Concert
Raised in the rural heart of South Carolina, Maddie Rean brings a little bit of rock, a whole lot of country grit, and a voice you won’t soon forget. Rooted in classic and Southern rock, country, blues, and a touch of rap, Maddie has created a sound all her own—bold, soulful, rebellious, and unmistakably Southern.
Maddie first caught national attention when her original song “Whiskey and Women” exploded on social media, earning more than 700,000 views and helping grow her following to more than 90,000 fans. Since then, she has taken her infectious live energy to stages across the East Coast and Midwest, sharing bills with artists including Morgan Wade, Riley Green, Parmalee, Lauren Alaina, Lonestar, Edwin McCain, David Nail, Ashland Craft, and more.
A Pirate Looks Back - Jimmy Buffett 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.
A Pirate Looks Back - Jimmy Buffett 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.
Best of Key West Jazz Concert Series
Best of Key West Jazz Concert Series
Featuring Key West Jazz All Stars & More: Larry Baeder, Joe Dallas, Terri White, Jeff Dalton & Mark Rose
Doors Always Open at 6:00
Dinner Always Available from Olive's Mediterranean Cafe
FREE Parking Available at 201 Truman Avenue
Suggested Donation: Fundraiser Proceeds Benefit William Weech American Legion Post 168 and the Key West Cultural Center & Veterans Museum (501.c.3)
FREE!
A Pirate Looks Back - Jimmy Buffett 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.
A Pirate Looks Back - Jimmy Buffett 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.
A Pirate Looks Back - Jimmy Buffett 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.
A Pirate Looks Back - Jimmy Buffett 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.