2023 Schedule of Events


Creatively Costume yourselves at all times at Fantasy Fest Events!

Schedule is subject to change and will be updated as our event partners update their event details with us for 2023.

Fantasy Fest 16oz. To-Go Cup

2023 Daily Diversions

# YOUR PICTURE WITH THE KING & QUEEN
Stop by Conch Republic Seafood Company and grab a selfie with our Fantasy Fest King & Queen! Open daily at 11:30AM for lunch and dinner! One of the best Happy Hours on the island. Every day from 4-7PM in the Bar & Patio. 631 Greene Street Be sure to tag us #conchfarm, #fantasyfest..you might win some cool Fantasy Fest prizes!

801 CABARET - Sushi & The 801 Girls
Come join The World Famous Sushi & The 801 Girls - October 20th -26th, and 29th. Shows are at 9PM and 11PM. The 801 Cabaret Drag Shows are the longest running shows in Key West . All guests must have a valid photo ID and MUST be at least 21 years old. Reservations are highly suggested for all shows so grab yours NOW!

BODY PAINTING BY CAPT. RON WOLEK
Join us at the HALLS OF DIVINE ART MUSEUM inside Willie’s Chicken Shack, located at 221 Duval St, Key West, FL. Capt. Ron is back with an exciting art and body painting gallery, featuring a talented team of local island painters and the renowned Reverend Gweko, "The Soundman from Hell." Prepare for ten nights of fantasy events and unbeatable body paint prices. Our body painting experience will unleash your inner party spirit on Duval St, Key West's vibrant hub. Notably, Capt Ron Wolek's clients achieved 2nd place at the Living Arts Festival last year, and you could be next! Mark your calendar: Capt Ron Wolek's & The Body Paint Gallery runs from October 19th to 28th, open from 12:00 pm to 11:00 pm. Capt Ron Wolek is celebrated for his work on hits like "Strange Things," "Walking Dead," "Vampire Diaries," and his role as the head makeup artist at "Disneyland." He has also contributed to cult classics like "Zombies! Zombies! Zombies!," "Yule Blood," and "Santa Stole My Dog!" For more info check out the website. captainronwolek.com or call 407-873-2237

FANTASTIC BODY PAINTING AND STUNNING SUNSETS: FEMME FATALE QUATRE BODY ART AT SUNSET PIER
Join our premier all girl team of body artists Femme Fatale Quatre Body Art, October 21-29 starting each day at 1 PM at Sunset Pier, 0 Duval Street. Our talented team has won many Fantasy Fest contests with their living art pieces and we want to make you our next canvas! From small body art pieces to full body’s we can help your imaginations run wild! Now booking appointments! Call or text 850-596-4065. Walkups available on most days! Prices start at $40 and up, see our Facebook page Femme Fatale Quatre Body Art for a full price listing. We will also have waterproof and sweat proof options available as well as a bling bar for all of you glitter junkies! Come join us at Sunset Pier for fantastic body art, sunsets, music, fun and food!! 0 Duval Street Sunset Pier

FANTASY FAÇADE COMPETITION sponsored by THE KEY WEST CHAMBER OF COMMERCE
Tour through historic key west and view the festively decorated homes and businesses who are competing for your votes! - This year, for the very first time, you are invited to choose a “Community Favorite”. The decorated digs that attract the most votes will score a special gift package of treats and services gifted by Key West Chamber of Commerce members. Polls will be open from Oct 24-29. Participating Facade Entries are found in the app Map! Entry form available HERE

FURY WATER ADVENTURES DISCOUNT
Save 10% off all Fury trips & 15% Off Fury Bike Rentals with promo code FANTASY. Book Online or visit the nearest authorized Fury Sales Booth. *Not valid with any other offer. One coupon per group. Blackouts and restrictions may apply. Limited Time Offer.

GET READY AT PARADISE TATTOO
Paradise Tattoo, your Fantasy Fest headquarters for Body painting, Tattoos, costumes and piercings. Located 627 Duval Street, call or stop in to make an appointment, open 7 days a week 10am-10pm 305-292-9110. Go to our website Paradisetattoo.com or check us out on Facebook

HAPPY HOUR AT ORCHID KEY INN BAR
Join us at our intimate poolside bar, offering a boutique wine list & mixologist designed craft cocktails. Find pleasure in our home-made infusions and fresh squeezed juices. We promise, it's worth the effort to find us. Bar Open daily from 12PM - 10PM. Happy hour 5-7PM.

KARAOKE PARTY!
Join us for a Karaoke party every night during Fantasy Fest week - 618 Duval Street- Stars Karaoke Club DJ Rico hosts the best Karaoke party in town! Doors open nightly at 8 pm till 2 am "Where it's ok to sing off Key in Key West!!

LUCY HAWK'S PHOTO OP
Take a selfie with Lucy Hawk's window ART! Hashtag it with #FantasyFest & #lucyhawkart for a chance to Win Parade VIP Passes! Location : Corner of Fleming & Duval -All Week Long - Hand cut paper originals that capture the 'essence' of life in Key West and the Florida Keys.

MEET & GREET WORLD-RENOWNED ARTIST SHAWN MACKEY AT OCEAN BLUE GALLERIES KEY WEST!
OCEAN BLUE GALLERIES brings you LIVE Artist Shows October 25th through 28th! Meet & greet SHAWN MACKEY, World-renowned for his unique fusion of Contemporary Realism and Abstract Expressionism, daily from open to close! Join us for a fabulous time at Ocean Blue Galleries Key West, located at 109 Duval Street.

MEET & GREET WORLD-RENOWNED ARTISTS AT WYLAND GALLERY KEY WEST!
Wyland Gallery Key West brings you LIVE Artist Shows with World-renowned Artists! Meet & greet World-renowned marine and wildlife artist WYLAND OCT 25-27 from 6pm to 10pm and enjoy special artist appearances ALL WEEK OCT 23-28 by Stephen Harlan, Steve Barton, and Stephen Muldoon -- open to close! Join us for a fabulous time at Wyland Gallery Key West, located at 623 Duval Street.

PHOTO OP FEST LETTERS ALL DAY & SUNSET HAPPY HOUR WITH CAPTAIN MORGAN COCKTAILS
Stop by the Opal Key Marina any time during the festival and take a selfie with our HUGE 'Fantasy Fest' Letters! Pop up to the Sunset Deck above Bistro 245 from 5pm to 8pm for our signature cocktail and stay for the breathtaking views of our gorgeous Key West sunsets. Try our special Captain Morgan Cocktail -SHIPWRECK PUNCH – in our Festival Souvenir Cup Opal Key Resort, 245 Front St.

THE ROCKY HORROR SHOW
The Rocky Horror Show - The Musical. Live on Stage- This wacky tacky musical comedy has played to standing room only houses for two seasons at the Waterfront. Returning to the playhouse for the 3rd time with some new cast members we're excited about. Show begins October 18 through 27th 2023! Starts at 8PM Click here and buy your tickets today! Waterfront Playhouse; 407 Wall St. 305-294-5015.

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Thursday, October 19, 2023

THE WAILERS CONCERT
Join us for a " Pre Fest" Concert! Rams Head Presents The Wailers at Key West Theater on Thursday October 19th. Doors open at 7:00P, show starts at 8:00P. Any Questions? Please email [email protected] Check out our website HERE for tickets.

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Friday, October 20, 2023

BAHAMA VILLAGE GOOMBAY FESTIVAL- A FAMILY FRIENDLY EVENT
This exuberant street party showcases island arts and crafts, music and food in the heart of Key West’s historic Bahama Village neighborhood. The festival’s main entertainment stage is located at the corner of Petronia and Emma Street and features nonstop musical entertainment ranging from reggae to soca. This is a family-friendly event. Noon to midnight; FREE. See the Goombay event Schedule HERE

GOOMBAY BASH OFF PETRONIA
Come join us at Rams Head Southernmost during Goombay! Live Music, specialty food & drinks, games & more! Enjoy our family friendly courtyard, rooftop terrace overlooking Petronia Street or dine at our outdoor patio right in the heart of the action.

BARBIE'S PINK POOL PARTY FOR BREAST CANCER AWARENESS
Wear your Best Barbie or Ken pink costumes and join The Marker Key West Harbor Resort with DJ Tommy Tangie for a fun pool party that will also make you feel good! Along with great music, we’ll have a Barbie or Ken costume contest, Barbie pink pools, Barbie pink drink specials, pink food specials, and more – all to benefit Making Strides Against Breast Cancer in the Florida Keys… $10 donation – 4-7PM Tickets HERE

ROYAL CORONATION
Kick off Fantasy Fest at the Fun & Furryous Royal Coronation event to see who becomes the King & Queen of Fantasy Fest 2023! This fabulous 2-hour stage show includes entertainment by local celebrities and the candidates themselves! Tickets include reserved seating, a 3-course plated dinner and two votes for the candidates of your choice. General Admission Entry is FREE with open lawn space for self-seating. Cash bar for all. This evening is hosted at Key West's Coffee Butler Amphitheater. 6PM Doors, 7PM Show. Click HERE and get your tickets today. For more info, contact [email protected].

WITCHES IN THE HAMMOCK AT CRANE POINT
Join us at Crane Point for the annual Witches in the Hammock event! Take a lantern walk through the Hammock to someplace haunted and watch the Witches that live there dance for you around the fire pit. Have a little witches brew and ride back to the courtyard where the Pirates will be playing all kinds of pirate games including Walk the Plank. Casper’s house will also be open for a visit with the friendly ghost. A Halloween movie streaming under our new shade cover and amphitheater. Come have some popcorn, cider and join the haunted fun. Located in Marathon - 5550 Overseas Highway

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Saturday, October 21, 2023

BAHAMA VILLAGE GOOMBAY FESTIVAL- A FAMILY FRIENDLY EVENT
This exuberant street party showcases island arts and crafts, music and food in the heart of Key West’s historic Bahama Village neighborhood. The festival’s main entertainment stage is located at the corner of Petronia and Emma Street and features nonstop musical entertainment ranging from reggae to soca. This is a family-friendly event. Noon to midnight; FREE. See the Goombay event Schedule HERE

END OF PROHIBITION POOL PARTY
Hosted by the Gates Hotel at Rum Row! Dive into the Roaring 20s for a swanky bootleg pool party. A large party, because they’re so intimate (at small parties there isn’t any privacy). Come between 12pm-4pm for a pool party, blind pig eatery and tons of alcohol, because no good party started with a salad!

GOOMBAY BASH OFF PETRONIA
Come join us at Rams Head Southernmost during Goombay! Live Music, specialty food & drinks, games & more! Enjoy our family friendly courtyard, rooftop terrace overlooking Petronia Street or dine at our outdoor patio right in the heart of the action.

FLORIDA KEYS COUNCIL OF THE ARTS FANTASY FEST POSTER SIGNING PARTY
Come meet the winning 2023 Fantasy Fest poster designer, get your Official Fantasy Fest poster signed and pick up other 2023 Fantasy Fest T-Shirts and Swag! Swing by La Concha Hotel from 3 - 5pm. 430 Duval Street.

WITCHES IN THE HAMMOCK AT CRANE POINT
Join us at Crane Point for the annual Witches in the Hammock event! Take a lantern walk through the Hammock to someplace haunted and watch the Witches that live there dance for you around the fire pit. Have a little witches brew and ride back to the courtyard where the Pirates will be playing all kinds of pirate games including Walk the Plank. Casper’s house will also be open for a visit with the friendly ghost. A Halloween movie streaming under our new shade cover and amphitheater. Come have some popcorn, cider and join the haunted fun. Located in Marathon - 5550 Overseas Highway

THAT ARENA ROCK SHOW
FREE Concert at the Sunset Pier! The ultimate high energy and theatrical tribute to "Classic" Rock & Roll. Performing legendary rock anthems that rules the airwaves in the 70's & 80's. This show will take you on a trip back in time, turning Sunset Pier into an arena a night! Get your lighters out and your fist in the air. The Rock Show is more than just music - it's an experience. 7:00PM - 9:00PM Ocean Key Sunset Pier’s Live Cam

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Sunday, October 22, 2023

POST GOOMBAY BLOODY MARY BRUNCH
Come hangout with us at Rams Head Southernmost after Goombay for a post Goombay Bloody Mary Brunch. Join us all Goombay weekend for live music, food + drink specials, cornhole, ping pong & more! Live Music and Great Food & Drink Specials! Plus we have an amazing build your own Bloody Mary Bar!

ZOMBIE ZONE - A RED CARPET EVENT
Join us before the ride to walk the red carpet, show off your costume and dance with the dead! 12pm-6pm Free bike parking, live music, food & drink specials. Located at The Gates Hotel - 3820 N. Roosevelt Blvd.

ZOMBIE BIKE RIDE- A FAMILY FRIENDLY EVENT
Mark your calendars and get Zombie on your brains! The Rock & Roll costumed Halloween bike ride that attracted over 7500 bicycle enthusiasts at a time -is back! October 22, 2023 - Zombie returns for another wild run from East Martello to The Coffee Butler Amphitheater. . Join your newly awakened zombies as they gather at Zombieland in Fort East Martello at 2 PM for the newly expanded Kids Zone with bounce houses and more! Body painting, food vendors and full bar is on the grounds of the starting area 2-6 PM. Hop on your bike and join the thousands of costumed zombies at 6 PM when the zombie invasion heads down A1A to downtown Key West for the FREE Zombiefest Dance Party at the Coffee Butler Amphitheater presented by RamsHead. Register NOW, get our Zombie gear (tees and tanks), & check out all the zombified events.

ZOMBIELAND
Before the Ride! Join in the fun early as we gather at Zombieland in Fort East Martello starting at 2 PM for the newly-expanded Kids Zone with bounce houses and more! Body painting, food vendors and a full bar is on the grounds of the starting area 2-6 PM. Please check out our WEBSITE for more information. We hope to see you there.

RAMSHEAD PRESENTS ZOMBIEFEST OFFICIAL AFTER PARTY
Celebrate completing the wildest ride of the year with a DJ After Party at the Coffee Butler Amphitheater. FREE entry to the Official End of the Ride Event with DJ Sanaris, Food Vendors and Full Bar. If the ride's not for you, you can still be a part of the action and watch the Zombie Mob roll in. Amphitheater opens at 5pm. Check out the website for more information HERE

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Monday, October 23, 2023

MARGS & MAKERS
Enjoy snazzy margaritas while you meet multiple different local artists at this all female gallery. Browse artwork by 29 women while you sip & shop this fun pop up.Event 12-5PM 529 Southard Street

THE PERRY HOTEL & MARINA'S DUCK, DUCK, BOOZE POOL PARTY
Don’t miss the duckie takeover at The Perry Hotel! We’re kicking off Fantasy Fest with a pool party like you’ve never seen before – complete with a pool full of rubber duckies, beverage samples, and swag. Duck floats, duckie bathing suits, duckie tutus, and creativity are encouraged! This event is FREE and open to the public, 12pm-4pm. The Perry Hotel, 7011 Shrimp Road, 877-496-8712.

BEARD & MUSTACHE III - THE PHLOCKING PARROT HEAD EDITION presented by WILLIE'S CHICKEN SHACK
Build your Fantasy Fest Beards out of anything you can imagine or show up at Willie’s Chicken Shack with hair on your face to win prizes during the third annual Official Fantasy Fest Event; Wolek’s Famous Beard Championship. This year the contest is dedicated to the memory of Jimmy Buffett, and all mustache categories will benefit local charity “Nicky’s Celebration” in the tradition of partying with a purpose. Grow a stache for Jimmy! Beardsmen and Whiskerinas from all genders around the world are invited to compete. In the main event, Fantasy Fest & Capt Ron Wolek wants you to use your imagination and create the craziest beard contraption or decorate your own beard. Competition registration opens at 12:00pm for natural beards and mustaches. Registration for Fantasy Beards and Whiskerinas opens at 5:00pm. Register ahead online for only $5 at mustacheparlor.com. Day of entry fees are $20. Stage show begins at 6:00pm with awards at 8:00pm. All contestants must be judged prior to 6:00pm and present at 8:00pm to receive awards on stage. Victory celebration to commence immediately after awards with live music. Official mustache championship referees to determine the contest by National Beard and Mustache Competition standards. If you can't attend in-person on Monday Oct 23, you may enter online. Online contest winners will be announced during the 8:00pm Key West Show on Tikimanradio.com on October 30th. Contest is sponsored by Willie’s Chicken Shack Key West, Tiki Man Radio, William Ross Cigars, and MoustacheParlor.com. Event takes place at Willie’s Chicken Shack on 221 Duval St Key West, FL from 7:00pm-11:00pm.

A GREEN PARROT BEATLES TRIBUTE
Well, Love, and Tony Baltimore, Chris Thomas, Hiram Garzaro, and Oren Polak, as they kick off Fantasy Week and re-create a Fab Four Show with "THE BEATLE BAND, All You Need is Love" at The Green Parrot with shows at 5:30 and 9 and 11 p.m. on Monday, October 23rd. Their past Beatle Tribute Shows had Parrot patrons swinging from the rafters as they danced, laughed, and sang-along to a set-list pulled from decades of Lennon-McCartny hits. And, let's not forget "It Was Fifty Years Ago Today...." so help us celebrate the 56th anniversary of the most famous and influential rock 'n' roll record ever made, Sgt. Pepper's Lonely Hearts Club Band! Tony and the boys will hit all the high-notes of the Beatles canon, from "All My Loving" to "The Ballad of John and Yoko", through Revolver/Rubber Soul territory to The White Album. Don't miss a beat! Be there as Billy Shears gets introduced and the British Invasion roars ashore! Those on Fantasy Fest's more interactive side may want to turn this into a Monday night "Sixties Dress-Up" dance party" , come as your favorite "Beatles Look-Alike" or come dressed in theme and help turn The Parrot into the 1967 summer of love!

HEROES & VILLAINS 5K & HOG ROAST BEACH PARTY!
Join us for the Fantasy Fest Monday Night Party in Key West dawning your best Super Hero or Villain gear! Capes, masks, and painted on costumes... let your Super self shine then get lei'd at the finish line before heading to the post race party on the beach at the Southernmost Beach Resort! The race begins at 6:00PM. Each 5K Participant will receive: Official race tank top, One FREE beer (21+) at the post race party, The only party where everyone gets lei'd. Come for the 5K, stay for the ALL YOU CAN EAT Hog Roast & Beach Party. Participants and spectators alike can grab a ticket and join in on the fun! Enjoy a selection of Hog, BBQ Chicken, Mac & Cheese, Couscous, Caribbean ColeSlaw, and CornBread. Hog Roast and Beach Party will be rockin from 5:30PM-8:00PM. Tickets are Limited to the Hog Roast! Register by using the link Click HERE register!

MARTINI MONDAY AT VIRGILIO'S
The Original MARTINI MONDAY is rocking the Fest. All Martinis are just $7.00. Live music, great food and, of course, did I mention, the best Martinis in Key West. Have a great Fantasy Fest everyone and we will see you there! GET EXCITED BABY! Virgilio's 524 Duval St.

KINKY CARNIVAL
Key West’s Original Fantasy Fest Kink Party in its 26th year! Ticket includes: 3 hour Open Bar from 8pm – 11pm, but the party goes until 1am! Interactive BDSM stations, Fetish rooms, Bondage and more! You can snag tickets from Friday, October 20th, through Sunday, October 22nd, between 1 pm and 9 pm. We're also selling tickets on Monday, the 23rd, starting at 1 p.m. and going strong all night. $50 | Cash Only No Kinky Costume | No Entry First Flight - 301 Whitehead Street.

SLOPPY JOE’S COMIC BOOK CAPE-ERS PARTY
Come dressed as your favorite “Caped” Superhero or Supervillain and party all day and night. Live music on stage all day! Dancing starts at 5:30pm, Turning The Tide on stage following contest, plus our house DJ will keep you dancing all night. To enter costume contest sign up next to stage at 8:15pm, contest on stage at 9:00pm. You may enter contest as an individual or as a group of 2-4 people (must be in costume). Prizes: 1st place $500 Sloppy Joe’s Gift Card; 2nd place $250 Sloppy Joe’s Gift Card; and third place $100 Sloppy Joe’s Gift Card. Other giveaways throughout the night. Sloppy Joe's 201 Duval Street.

TOPS OR BOTTOMS UNDERWEAR PARTY
Underwear party 10pm-4am. Private Underwear party - men's event. In the New Orleans House Garden & Pool Bar; 305-293-9800; 724 Duval St.; Bourbonstpub.com

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Tuesday, October 24, 2023

DANTE'S 4TH OF JULY PARTY!
Stars and Stripes rule the day! Celebrate in your best, most Patriotic Pool wear, make Uncle Sam and Betsy Ross jealous! Float and Frolic with Friends! Fantastic Food and Drink Specials from 11am to 5pm. $10 Cover Dante's Restaurant and Raw Bar, 951 Caroline St., 305-293-5123.

PIRATES AND PARROT HEADS POOL PARTY
Join us for our 2nd annual Pirates and Parrot Heads Pool Party at Margaritaville Beach House Key West! Tuesday, October 24th 1-5PM We will have a DJ, "chill & grill" food specials as well as beverage specials! 2001 S. Roosevelt Blvd. Looking forward to seeing you there!

COCKTAILS FOR ANIMAL TAILS! PRESENTED BY DIRTY MONKEY.
COCKTAILS FOR ANIMAL TAILS! LOCATION: Rick's Complex, 202 Duval St. 305-294-4857 TIME: 8PM-4AM. UNLIMITED DRINKS FROM 8-11PM - $40 ADMISSION! Party with a purpose for an official charity event that benefit the homeless animals of the Florida Keys SPCA. Time to get creative and dress up as your favorite animal for the costume contest with a $500 grand prize! Durty Harry’s complex transforms into an Animal Kingdom for this wild night. Purchase your pre-sale tickets now at FKSPCA.org under the Events tab and get early entry with an extra 30 minutes of open bar starting at 7:30pm. Warm up your tutus and get ready to party where the wild things are! For questions contact [email protected] or [email protected].

ROB BENTON, SUNSET BEACH BASH LIVE AT SOUTHERNMOST BEACH RESORT
A sunset beach concert not to be missed! New England based, Rob Benton has spent the last decade as both a solo artis, a member of the duo “key West Kings”, and lead guitarist performing alongside artists as diverse as Nelly, Lee Brice, Lansdowne, Skidrow, Everlast, LFO, New Kids On The Block, J. Geils Band, and many more! Rob also made an appearance on NBC’s “America’s Got Talent” television show, which earned him a contract with MGM Grand headlining a yearlong residency at Circus Circus Casino on the Las Vegas strip! A dynamic performer, Rob’s style is extremely unique. By combining percussion, looping, beat boxing, electrified rock, and hip-hop elements to his solo acoustic playing; he fills out his sound like a four-piece band. Whether playing original tracks from his own albums, “Dawn Meet Day” and KWK’s “Caroline Street” or covering one of the multitude of artists who have influenced him over the years, Rob makes every song his own. 6:30-9:30 FREE! Reserve your space HERE

TUTU TUESDAY PRE-PARTY
Mary Ellen's - pick up wristbands 5-6:30pm on Tuesday October 24. Parade steps off at 6:30pm, ending at the world's greatest TUTU party! Stops include: 22&Co, Shots & Giggles, Tiki House, and First Flight- we don't want any parched unicorns! $45 includes TUTU party ENTRY/WRISTBAND. YOU DO NOT NEED TO BUY TUTU PARTY ENTRY SEPARATELY. TICKET LINK HERE

PIRATES OF THE CONCH REPUBLIC: THE SEARCH FOR BODACIOUS BOOTY A BURLESQUE PARODY
Get set for a sexy, swashbuckling spectacular! “Pirates of the Conch Republic: The Search Bodacious Booty a Burlesque Parody”, follows the adventures of captain Jack as he braves the seas between the Caribbean and The Conch Republic in search of a bounty of bodacious booty. The show, staring all of your favorite Key West Burlesque performers, is an epic adventure with tails of treasure and salacious scallywags. Location - Key West Theater 512 Eaton Street Doors -7pm Show - 8pm Tickets - $45-$100 per person. For more information please visit the website HERE

TUTU TUESDAY RETURNS!
The one-of-a-kind Tutu Tuesday dance party returns for its annual celebration of all things silly on October 24th, 2023. The event, now in its 13th year, continually morphs its vibe and venues adding to the novelty of this singularly epic Key West dance party. FOLLOW THE YELLOW BRICK ROAD is the 2023 theme and the party takes over the Caroline Street district with nearly 20 DJ's, in 4 PREMIUM BARS in Downtown Key West. General Horseplay is the central hub as well as the wristband pickup location. Smokin' Tuna, First Flight Brewery and Hanks Hair of the Dog Saloon are all part of this year's event and each venue will have a variety of musical styles and unique set designs. One wristband gets you into ALL 4 VENUES! Tickets are $22 prior to the event date, $30 the day of the event and at the door. Get your tickets here: New DJ's, New Silly Tricks, More Venues and Even MORE WEIRD FUN! As always, and forever ... No Tutu, NO ENTRY!

CAPT. TONY'S PARTY IN PLAID
Experience a party that caters to all exotic lifestyles and fantasies. Whether you wear your naughty or nice plaid to attract old friends or to stimulate the new, this party is for you. Everyone is invited to this party for the ages that only the legendary Capt. Tony's can host. Great music and drinks, plaid costumes, exotic people. 428 Greene St. 305-294-1838. 8 PM; FREE.

WHAT'S UNDER YOUR TUTU?
Care to share what’s under your tutu?!? Join us at Sidebar at 9PM for tutu much fun! Contests, Prizes and more presented by the one and only, Beatrix Dixie! You won’t want to miss this party! $10 Cover

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Wednesday, October 25, 2023

SLOPPY JOE'S SLUMBER PARTY
Roll out of bed and head on over to Sloppy Joe’s Slumber Party. Be creative. Be goofy. But be dressed in a costume…will it be… a onesie, flannel jammies, boxers or your favorite lingerie. Create your outfit around Fantasy Fest Theme “Uniforms & Unicorns” (a costume you can wear all week). To enter costume contest sign up next to stage at 8:15pm, contest on stage at 9:00pm. You may enter contest as an individual or as a group of 2-4 people (must be in costume). Spend the day and night partying and dancing in comfort at Sloppy Joe’s. Prizes: 1st place $500 Sloppy Joe’s Gift Card; 2nd place $250 Sloppy Joe’s Gift Card; and 3rd place $100 Sloppy Joe’s Gift Card. Other giveaways throughout the night. Sloppy Joe’s 201 Duval Street.

LIVING ON THE EDGE POOL PARTY AT OCEANS EDGE RESORT AND MARINA!
If you’re not living on the edge, you’re taking up too much space! Don your style of the Fantasy Fest theme and take a trip uptown to party down with up-and-coming local band Reggae Lou and the Kind Budz, at the Fourth Annual Living on the Edge Fantasy Fest Pool Party at Oceans Edge Resort and Marina! Our bartenders will be mixing up Dulce Vida Tequila drink specials and Yellowfin Bar and Kitchen will be serving specialty bites poolside; Dulce Vida Tequila Tuna Nachos, Captain Morgan Mahi Tiradito Skewers and Ropa Viella Tacos ranging from $9-15 each. Games such as cornhole, ping pong, giant chess and connect four will be stationed poolside. This a 21+ Event. FREE ADMISSION 1-4PM at Oceans Edge Resort and Marina 5950 Peninsular Ave, Stock Island, Florida 33040. Oceans Edge Resort’s Live Crowd Cam

SOUTHERNMOST SCAVENGER HUNT'S 3rd ANNUAL FANTASY FEST BAR CRAWL
Come one, come all and do the 3rd Annual competitive Fantasy Fest Bar Crawl! Sponsored by Dulce Vida Organic Tequila. Grab your team of up to 6 people and see if your team has what it takes to bring home the grand First Place Prize! Prizes will be awarded to the TOP FIVE teams and include: 2023 Fantasy Fest swag, Dulce Vida Tequila and swag, shirts, coozies, free bar tabs, restaurant tabs, and much, much more! Each participant will receive a FREE Margarita and an exclusive Scavenger Hunt map featuring tons of drink coupons to use along the way. From world famous Sloppy Joe's to favorite local hideouts, you will enjoy the nightlife, hotspots, all while learning a thing or two about our unique island paradise and the bars in Key West! Earn the most points for your team to win and the reward could be yours! Each player must be 21 or older and you do not have to drink to participate. $45 per person includes the activity, the free drink, our exclusive scavenger hunt map with a value of over $160 and if you win you'll get a lot more! Check in starts at 2:00pm and the crawl begins at 2:30pm sharp and ends at 4:30pm. Awards and winners will be announced at 5:00 pm. Buy tickets HERE

ALOHA FROM MARGARITAVILLE
Come join us for a LUAU party at Margaritaville Cafe! We will be doing hula hoop contests from 6pm-7pm and pass the Limbo contest from 7pm-8pm. LUAU attire is a MUST! The events starts at 6pm - we will have drink specials, $10 Rum drinks specials and some amazing eats. Want to get your face painted to match our LUAU theme? We will have Body Painting by Pashur, Shannon and Emma all week. Stop by and make an appointment. Stay after and listing to the trio from Marshall Moorlock Band they will be playing from 8pm-11pm. This is a FREE event. We hope too see you there - 500 Duval Street

PET MASQUERADE
After more than 25 yrs, the emcee, owner and promoter of this event, Nancy D’Amato is retiring. So she wants this year’s Pet Masquerade to go out with a big woof, meow and squawk! You will see a carousel of frisky pets and playful owners performing for fame, fortune and prizes beginning at 6:30PM on the stage of the Key West Amphitheater at the Truman Waterfront Park! Think you and your furry, feathered or slithery friend have the purrfect outfit? 4 categories to enter including Junior-$25 each entry; benefits the Lower Keys Friends of Animals; Registration begins at 5 PM; Show starts at 6:30 PM; FREE to watch, plenty of FREE seats available or bring your blanket and lawn chair. Food and beverage available on site. 21 E. Quay Rd. For more information, visit our Facebook Page or email [email protected].

PIRATES OF THE CONCH REPUBLIC: THE SEARCH FOR BODACIOUS BOOTY A BURLESQUE PARODY
Get set for a sexy, swashbuckling spectacular! “Pirates of the Conch Republic: The Search Bodacious Booty a Burlesque Parody”, follows the adventures of captain Jack as he braves the seas between the Caribbean and The Conch Republic in search of a bounty of bodacious booty. The show, staring all of your favorite Key West Burlesque performers, is an epic adventure with tails of treasure and salacious scallywags. Location - Key West Theater 512 Eaton Street Doors -7pm Show - 8pm Tickets - $45-$100 per person. For more information please visit the website HERE

SMOKIN TUNA HOMEMADE BIKINI CONTEST
The Smokin’ Tuna Saloon is proud to present the 30th Anniversary of the Original Key West Homemade Bikini Contest. 8PM CONTEST Over $2,000 in cash & prizes. Creativity and attention to detail are the key elements to winning the 1st prize of $1000. Additional cash prizes for 2nd & 3rd place. Hosted by the World Famous Emcee and Local Celebrity Mr. Bill Hoebee and his celebrity judges. For contest entry ideas please see the gallery for pictures of previous years. Contest participation is $20. General Admission $20 Doors open at 7 PM, Event Starts @ 8pm. Purchase tickets HERE

WHARFSTOCK AT THE SCHOONER WHARF BAR
Travel back in time to the '60s, with Peace and Love Woodstock-style!. Feel the vibe with tie dye, flower power, and psychedelic colors in Schooner Wharf’s time capsule of the era. The sit-in starts at 7 PM. Prizes for sexiest Hippie Chick and Grooviest Dude -- judging at 8:30 PM. Groove to live music and dance to tunes reaching back in time from 'That Hippie Band' from 7-midnight, plus cold drinks and great galley fare. Cash prizes and gift certificates to the winners!. 202 William St.; 305-292-9520. No cover charge or entry fee to The Man. Schooner Wharf’s Live Stage Cam

11TH ANNUAL LUV2GLOW PARTY
Fantasy Fest’s official and longest running glow in the dark blacklight dance party is back for its 11th year!! Get your glowing costumes, paint, blinky lights/LEDS and UV reactive vibes flowing. We’re back at Rick’s Upstairs and the THEME is JUNGLE. Think jungle animals, reptiles, foliage and sexy vibes that would glow in a jungle setting. Incorporate that into your costumes and glow paint. NO GLOW NO ENTRY! 3 rooms of various styles of electronic music all night long, bumping electronic beats to move your glowing jungle feet. Featuring DJs: Jevne, (Minneapolis) Atnarko (Orlando) , Top Jimmy, Jimmy Jamz, Captain Ridiculous, Jameson & More TBA. Limited $30 Pre-Sale tickets available till 10/24/23. Purchase tickets at EVENTBRITE. $40 Cash only at the door. There will be a separate entrance for people who bought pre-sale tickets. 8PM-4AM 21+. For more info follow us at facebook.com/Luv2Glow or http://instagram.com/_luv2glow Please join us for some radical glowing self expression! Rick's & Durty Harry's Bar’s Live Cam

DESIRE MALE FETISH PARTY
Fetish Party 10pm-4am..Private Fetish party - men's event. In the New Orleans House Garden & Pool Bar.; 305-293-9800; 724 Duval St.; Bourbonstpub.com

PARTY LIKE A ROCK STAR COSTUME PARTY
Welcome to the Jungle!! Come dressed as your favorite Rockstar to enter our Best costume contest (cash prizes for best male/ female and group costumes) Rock out to all your favorite tunes from the 80"s .90"s and the 2000"s Big Dance floor. Rock the night away with three key west musical legends Ross Brown and Cayo Ritmo featuring Jeff Clark and Chris Toler 9 pm to 1 am Drink specials all night. NO COVER Located at KAYA Backyard Bar- 618 Duval Street. 10:00PM- 2:00AM

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Thursday, October 26, 2023

BERKSHIRE HATHAWAY PARADE OF HOMES MEGA OPEN HOUSE EVENT
Berkshire Hathaway Keys Real Estate | Knight & Gardner Realty invites you to their PARADE OF HOMES EVENT! Stop by any of their Open Houses and enter for a chance to win 4 tickets to their VIP viewing party on Duval Street!. Visit their website for a full list of our open houses & check their Facebook page. October 26th from 11-3pm.

UNICORNS AND TEQUILA POOL PARTY
Come dressed in your best unicorn costume and join us for an epic pool party with lots of tequila! Dance your tail off to our awesome DJ, enjoy glittering drink specials, take a ride on a unicorn, and if you dare...enter a Cock Fight (pool float)! Havana Cabana - 3420 N Roosevelt Blvd - 12PM - 4PM

SOUTHERNMOST SCAVENGER HUNT'S 3rd ANNUAL FANTASY FEST BAR CRAWL
Come one, come all and do the 3rd Annual competitive Fantasy Fest Bar Crawl! Sponsored by Dulce Vida Organic Tequila. Grab your team of up to 6 people and see if your team has what it takes to bring home the grand First Place Prize! Prizes will be awarded to the TOP FIVE teams and include: 2023 Fantasy Fest swag, Dulce Vida Tequila and swag, shirts, coozies, free bar tabs, restaurant tabs, and much, much more! Each participant will receive a FREE Margarita and an exclusive Scavenger Hunt map featuring tons of drink coupons to use along the way. From world famous Sloppy Joe's to favorite local hideouts, you will enjoy the nightlife, hotspots, all while learning a thing or two about our unique island paradise and the bars in Key West! Earn the most points for your team to win and the reward could be yours! Each player must be 21 or older and you do not have to drink to participate. $45 per person includes the activity, the free drink, our exclusive scavenger hunt map with a value of over $160 and if you win you'll get a lot more! Check in starts at 2:00pm and the crawl begins at 2:30pm sharp and ends at 4:30pm. Awards and winners will be announced at 5:00 pm. Buy tickets HERE

RED ELVISES POOL PARTY AT THE MARKER!
Get your swimsuit and come out to party with Red Elvises! This band has produced 12 studio albums, two live albums, a live concert DVD, and a Greatest Hits compilation. Some of their most notable film contributions include music and or performances in “Six String Samurai”, “Mail Order Bride”, “Armageddon”, “Skippy”, “Melrose Place”, “Fastlane”, “Penn and Teller’s Sin City Extravaganza”, “VH-1 Behind the Music”, and “MTV. No matter where they perform, Igor & Red Elvises always bring the party with them. FREE! 4-6PM Click HERE

ROCK ON WITH YOUR SMOCK ON!
Get ready to laugh and have a BLAST at our Fantasy Fest Paint N Sip! This is an exciting and fun-filled art class - one like you've never experienced before. Your ticket includes all the art, supplies & instruction you need to create your own masterpiece. Food & Drinks available for purchase. ARTISTIC EXPERIENCE IS NOT REQUIRED! Everyone is welcome! 4pm – 6pm, Located on Sunset Green (República Lounge at 24 North in case of rain) 3820 N Roosevelt Blvd Ticket Price: $40 per person. Click HERE for tickets.

DANTE'S 17TH ANNUAL HALOS & HORNS POOL PARTY
Whether you wear the halo of an ANGEL or prefer devilish HORNS, GET WET & WILD at Dante's for a chance to win BIG $$$! Free body painting, live music, great giveaways, fantastic food, drink specials and our one of a kind stage in the CENTER of the POOL! The party starts at noon and goes till 6 PM, pole dancing starts at 4:30 PM; Dante's Restaurant & Raw Bar, 951 Caroline Street next to the ferry terminal. 305-293-5123. $. Visit for more details danteskeywest.com.

GREEN PARROT
Who Dat? NOLA Funk Party with Colin Davis & Night People. Thursday 10/26. Sets at 5:30, 9:00 and 11:00 The Green Parrot has become legendary in particular for its solid reputation as THE Key West home of great live music while at the same time has long been favorably compared to many of the most famous live music venues of New Orleans. Compared not just for its live music but also for its air of celebration and as a far-flung bastion of New Orleans "Who Dat" culture and festivity and its joyful embrace of "Laissez les bon temps rouler" or "Let The Good Times Roll". Join us here with shows at 5:30, and 9 and 11pm for a very special night of New Orleans culture as Colin Davis & Night People lead us in a chant of "Who Dat" and turn our Key West intersection of Southard and Whitehead into the intersection of NOLA Funk and Soul! Colin Davis & Night People is fronted by New Orleans' bombshell vocalist Whitney Alouisious, and featuring Johnny Sketch sax-diva Sage Rouge, they're brimming with first-call NOLA sidemen ready to bring their brand of NOLA pop/soul to our island outpost. The Parrot as always is chock full of rich culture and vibrant costumes, so while costumes of any color combination are a part of any festive Mardi Gras party, purple, green and gold are the traditional Mardi Gras colors so we invite you to dress up accordingly as you come and help us stir the Gumbo at our New Orleans' "Who Dat" Party!

FANTASY FEST TRIVIA - SOUTHERNMOST BEACH RESORT
Bring all your favorite guys and ghouls for a one-of-a-kind TRIVIA experience. This spooky Fantasy Fest trivia features all the fun decorations of a proper Halloween Party, 6 great rounds of Trivia, Creepy drink specials, and the BEST part of all… all players in costume receive 5 bonus points! Reservations are a must; tables will fill fast! 6pm Sharp! FREE! Reserve your space HERE

80's DANCE PARTY!
Disco the night away to Funky beats! Hustle on over to La Concha - 430 Duval Street from 6:30PM- LATE. This Glittery Disco Themed Party is FREE to attend. Drink Specials & Food available to make sure your stayin' alive and feeling Groovy!

PIRATES OF THE CONCH REPUBLIC: THE SEARCH FOR BODACIOUS BOOTY A BURLESQUE PARODY
Get set for a sexy, swashbuckling spectacular! “Pirates of the Conch Republic: The Search Bodacious Booty a Burlesque Parody”, follows the adventures of captain Jack as he braves the seas between the Caribbean and The Conch Republic in search of a bounty of bodacious booty. The show, staring all of your favorite Key West Burlesque performers, is an epic adventure with tails of treasure and salacious scallywags. Location - Key West Theater 512 Eaton Street Doors -7pm Show - 8pm Tickets - $45-$100 per person. For more information please visit the website HERE

ROCK THE TATAS CONTEST
Hanks’ Hair of the Dog Saloon presents Rock the Tatas Contest. Hosted by the "one and only" Elle! Join us in the fight against Breast Cancer October 26th. Contest starts at 7 PM at Hanks Hair of the Dog Saloon located at 409 Caroline St. First place prize $500! Additional cash prizes for second and third place. Live music by DJ EL Grace & special guest. Contest winner awarded starting at 9 PM. A portion of the proceeds benefiting Making Strides Against Breast Cancer. Doors open at 5pm, show starts at 7pm until late! Body Painting Artist on site if you want to fancy up your Tatas! Hanks Hair of the Dog Saloon 409 Caroline St. $20 tickets. No Contest Entry Fee. Buy your tickets HERE

40th ANNUAL HEADDRESS BALL
The Key West Business Guild proudly presents the 40th Anniversary Edition of the Headdress Ball, the premier LGBTQ+ event of the Fantasy Fest Celebration, presented on Thursday, October 26 2023, at the Coffee Butler Amphitheater, Truman Waterfront Park. Doors open at 6:30 and the show begins at 8:00 PM. La Te Da’s Randy Roberts opens the show and Laurie Thibaud of Aqua Idol Fame returns as the Emcee. WEOW’s Rudegirl oversees the music.. Twelve to Fifteen contestants will hit the stage to show their Headdress creations, judged from the shoulders up, and vie for the first prize of $3,000. Performances by some of Key West’s best local talent from over the years will again be featured. There is bar service and specialty wine, and food may be preordered delivered to your table. Tickets are $320 for a premium table of 4, $270 for a VIP table of 4, with Chair seating at $35 and General Admission (grass seating) at $30. Admission and food choices may be booked at: www.keystix.com or click on link HERE . Proceeds from the Headdress Ball go to promote Key West as a major LGBTQ+ destination worldwide. For more information and to enter the Headdress Contest go to gaykeywestfl.com/headdress-ball or call 305-294-4603. Sponsored by First Horizon Bank. Headdress entries will be displayed at a special exhibit at the Key West Museum of Art and History at 481 Front Street, Nov 10-Dec 3. Book early because this event always sells out.

FAT TUESDAY PINK PARTY
PARTY LIKE A FLOCK STAR! Wear your sexiest pink costume or pink body paint to the best Thursday night party for over a decade. Featuring live entertainment with premier DJs, Bubba’s Flavored Whiskey shots and High Noon bucket specials! Costume contest with a $500 bar tab for 1st place, $250 bar tab for 2nd place and $100 bar tab for 3rd place. 305 DUVAL STREET | THURSDAY 10/26; 8 PM - CLOSE

SLOPPY JOE'S 44th ANNUAL TOGA PARTY
Sloppy Joe’s Toga Party is “An ORIGINAL Fantasy Fest Event.” Get your toga ON and find out why we are “Still The Best Toga Party in Town!” Wear a traditional ancient Toga or dare to create your Toga using Fantasy Fest theme “Uniforms & Unicorns ” Live music on stage all day! Dancing starts at 5:30pm, M80 on stage after Toga contest, plus our house DJ make the party happen all night. Sign up for Toga Contest 8:15pm, contest on stage at 9:00pm. You may enter contest as an individual or as a group (a group is a minimum of 2 people and maximum of 4 people) must be in Toga(s). Prizes: 1st place $500 Sloppy Joe’s Gift Card; 2nd place $250 Sloppy Joe’s Gift Card; and 3rd place $100 Sloppy Joe’s Gift Card. Other giveaways throughout the night. Sloppy Joe’s 201 Duval Street. Sloppy Joe’s Live Stage Cam Sloppy Joe’s Live Bar Cam Sloppy Joe’s Live Crowd Cam

EXPOSED AT THE BOURBON ST. PUB ADULT ENTERTAINMENT COMPLEX 10PM-4AM (ALL WELCOMED)
10PM-4AM - Event Open to All! The most risqué party of Fantasy Fest! Play in the Poolside Foam Party! Dance the night away on 2 Dance Floors or Splash around in our Pool & Jacuzzi! Black Out & Black Light party inside, exotic dancers and FREE glow sticks! VIP tickets $75 cash advance sale, $85 day of event. CC sales fees will apply. Rain or Shine. Full access to the Bourbon St Pub and New Orleans House pool area, free clothes check. tickets will be on sale at the New Orleans House starting October 1st; open 8 AM-8 PM. Tickets available 305-293-9800; 724 Duval Street.; Doors will open, 9 PM ; Bourbonstpub.com

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Friday, October 27, 2023

FANTASY MARKET
Join your fellow revelers Friday, October 27 from 10 am to 3 pm at the Truman Waterfront Park for lots of great shopping, original local art, costumes & accessories, fun entertainment and of course serious eats & drinks. WIN BIG!!!!! All guests who spend $100 or more collectively at any of the Fantasy Market vendors can bring your receipts to redeem for a FREE vintage Fantasy Fest t-shirt (while supplies last) AND be entered to win 2 tix to our VIP Parade Suite at the La Concha hotel for the Saturday evening Bud Light Fantasy Fest Parade! BAM! Enjoy a live radio remote with Party 105.7 DJ spinning tunes, appearances by Fantasy Fest Royalty and score your official 2023 Fantasy Fest Merchandise. Vendors, makers, artists, crafters, photographers, jewelry, apparel, costumers, toys, non-profits, sponsors, culinary, food trucks and more will be set up in the grass at the picturesque Truman Waterfront Park overlooking the Atlantic Ocean. Find that perfect Keysie souvenir, get your picture with the Southernmost Inflatable Buoy, grab lunch and throw back a cocktail or two while you shop and support local. There will be huge shade tents, table and chairs, lounge areas and plenty of places to kick back and relax. All ages, accessible, pet friendly event. Metered parking (free with residential sticker), bike & scooter parking, located on the Free Duval Loop

BLOODY MARY PARTY & HOT DOG EATING CONTEST
Get ready for a hog-wild and bloody good time. Sponsored by lslamorada Brewery and Distillery featuring $6.00 Crooked Palm Seltzers and $6.00 Sandbar Sunday draft beer. Bloody bar opens at 10AM-1PM featuring Deep Eddy Vodka with $7.00 Bloody Mary's. But wait there's morel! We got the first annual "HOG"DOG EATING CONTEST. How many "hog"dogs can you down? Sign up at the door -- first 10 people gets a seat at the trough. The winner will SQUEAL with delight at their prize!! Contest time is 12 NOON. Of course, prizes for the best "hog"dog costume - WEINER TAKES ALL. No PULLED PORK going on here, it will be an OINKING GOOD TIMEII Yup we got a million of them. This is a FREE event. Hog's Breath Saloon, 400 Front Street, 305-296-4222

BOURBON ST. PUB'S POOL PARTY
Fantasy Fest 2023, Poolside dance party at Bourbon St Pub adult complex. Get your groove on while dancing and drinking! Live DJs, Boys, Beads and Booze, Drag Queens, games and MORE! Noon until 5 ish. $ cover charge w/FREE clothes check. Join the party at 724 Duval St. 305-293-9800 Bourbonstpub.com

COMPARSA AT THE SAN CARLOS STREET PARTY
The San Carlos Institute is bringing back their annual Street Party! Dance the night away and enjoy - Mojitos Bar, Cuban Music and dancing for those who are strong of heart! Noon - Midnight! 516 Duval St 305-294-3887 Free Entry.

DAY AT SOUTHERNMOST PLAYBOY MANSION - BEACH BUNNY POOL PARTY BASH
We invite you to join us at The Southernmost Mansion On The Sea, Friday, October 27th - Noon to 5PM For the HOTTEST, MOST GLAM OCEANFRONT, ADULT ONLY, PLAYBOY BUNNY INFINITI POOL PARTY!!! Enjoy an all day pool pass, DJ Hazard, Drink Specials, and yes you can sunbathe topless as long as you wear your bunny ears. Admission: $25 1400 Duval Street, Key West 305-296-3141; NOON-5PM

BLOSSOM KEY WEST EDM DANCE PARTY AT THE AMPHITHEATER
People of Fantasy Festival, Welcome to Blossom Key West! Join us for an electrifying concert into the world of rhythm, harmony, and love at the Coffee Butler Amphitheater on October 27th. Let the sonic waves of frequency set you free as we unite together for a celebration of life and beauty. Do not forget to express your inner fantasies in costume on this night of pure organic alchemy! As the sun sets over the Gulf of Mexico, we will each find our own grooves that make us dance. It is almost time for new memories and vibrations to be created, let's make history! What are you waiting for....? For more information visit: blossomkeywest.com // Doors open at 4:00P, show starts at 5:00P. Questions? Please email [email protected] Ticket Link: HERE Coffee Butler Amphitheater - 21 East Quay Road Key West, FL 33040 - 305-985-0433 Ages: All Ages to Enter, 21 & Over to Drink Doors Open: 4:00 PM Show Starts: 5:00 PM

CAPTAIN MORGAN'S MASQUERADE MARCH
Join the crowd as they parade through Old Town with music and noisemakers! Thirst quenchers provided at selected guesthouses. Begins at the Old Town Wine & Spirits on Truman but revelers can join the mad march anywhere along the ONE route! Start marching at 5:30 PM; All welcome; FREE.

CAPTAIN MORGAN'S PIRATE PARTY
Celebrating the ocean and pirates that call it their home. Come dressed as a pirate or any marine creature to enter our costume party to win cash prizes. YO HO HO and a bottle of rum! Partial profits will be donated to the Sea Base Camp located right here in the Keys. Live music by The Jeff Clark band. Join us at the Backyard Bar Key West- at Kaya Island Eats 6:30PM-10:00PM. NO COVER and Bar open till 1AM.

AQUAPLEX'S POST MASQUERADE MARCH PARTY! DANCE & GLEE!
Gleefully boogie your way on down as we take over the entire Aquaplex compound! We've got multiple DJ's and delicious Captain Morgan Drink Specials! You don't want to miss this Exhilarating Party! 7PM

PIRATES OF THE CONCH REPUBLIC: THE SEARCH FOR BODACIOUS BOOTY A BURLESQUE PARODY
Get set for a sexy, swashbuckling spectacular! “Pirates of the Conch Republic: The Search Bodacious Booty a Burlesque Parody”, follows the adventures of captain Jack as he braves the seas between the Caribbean and The Conch Republic in search of a bounty of bodacious booty. The show, staring all of your favorite Key West Burlesque performers, is an epic adventure with tails of treasure and salacious scallywags. Location - Key West Theater 512 Eaton Street Doors -7pm Show - 8pm Tickets - $45-$100 per person. For more information please visit the website HERE

THE CRESCENT CITY PARTY WITH COLIN DAVIS & THE NIGHT PEOPLE
The party doesn't stop when the March ends. The Parrot will be buzzing once again with Colin Davis & Night People's classic New Orleans funk and soul music. The band takes its inspiration from Crescent City artists such as Allen Toussaint, Lee Dorsey, Dr. John, The Meters, Earl King, Willie Tee and many more. Colin Davis & Night People effortlessly infuse the work of these legendary NOLA artists with a passion and a style all their own. Let the marching turn into dancing as the night progresses to the corner of Southern and Whitehead. Sets at 7:00, 9:00, 11:00.

22nd ANNUAL LIVING ART EXPO
A showcase of the human form as a living canvas. Contestant entries are open to Female, Male or Group models competing for the title of Best Overall Living Art of Fantasy Fest 2023 and $2000 in cash and prizes. Best Overall wins $1000 in cash. FREE event. Front stage standing room and Sunset Pier table seating is all first come, first serve. Live DJ & MC Bill Hoebee on the Full Concert Stage with Catwalk. Party Starts at 7pm. Contest begins at 8pm. Contestant Registration - contact Sunset Pier 305-295-7047 or [email protected]. Ocean Key Sunset Pier's Cam

KINKY COUPLES PARTY HOSTED BY RUBBERDOLL!
The ONLY strictly Couples Only event. Join like-minded couples in the 801 Cabaret Bar overlooking Duval Street. A special performance by the world-renowned latex performer RubberDoll with Live Dark'n Dancing with New York DJ Lucas will be sure to get everyone in the mood for some serious playtime. Doors open ten minutes before showtime. Shows at 8:00pm and 11:00pm both Friday and Saturday - Check-in is at the Downstairs Bar. Private Area, Premium Open Bar, Clothes Check Couples Only! Come Together, Leave Together Re-Entry Not Permitted/Pre-Registration Required. NO EXTRA TICKETS WILL BE AVAILABLE WHEN THIS EVENT SELLS OUT! TICKETS CANNOT BE TRANSFERRED TO ANYONE ELSE! Friday $275 per couple Saturday $300 per couple Both Nights with Meet and Greet: $500 Contact Kitty with questions (305)783-4259 Buy Tickets Here

UNICORNS ONLY PARTY
Join us for the Biggest Unicorns Only party in Key West! On Friday, October 28th after the Masquerade March, you can wander down to our magically enchanted forest to find your fellow unicorns. We will have DJ Hazard spinning all night long! You must be a unicorn to enter. Unicorn kits will be available for purchase at the door. Party Starts at 8PM. We highly suggest that you purchase tickets in advance as this party has a limited number of unicorns allowed. Tickets: $35 includes 1 drink, pizza, and 20% of all ticket sales will go to the Key West Police Department Love Fund! Purchase tickets HERE

TIME 2 FLOAT - HORROR THEMED PARTY
Come dressed in your most horrifying costume! Look out for Dangerous Dancers and Killer Cocktails! Stay for the Costume Contest and Red Balloon Midnight special. Hosted & Performance by Beatrix Dixie! Party Starts at 9PM. Side Bar - 504 Angela St $20 Cover

ROCKHOUSE LIVE PRESENTS FANTASY LAND & COSTUME CONTEST
RockHouse Live , Key West's New Hot Spot - featuring two amazing floors with live music, titillating cocktails, a unique rock-n-roll vibe with a Key West twist, and the biggest and best outdoor roof deck on Duval overlooking the iconic corner of Duval & Greene, in the center of it all! Everyone has a self-expression Fantasy, and on this night, RHL brings your fantasies to life! Remember at festivals self-expression is encouraged. Don't be afraid to let your imagination run wild and create a unique costume that represents your personality and style. Have fun and let your creativity shine! Come dressed with your favorite costume from any era and realize your Fantasy! Prizes will be awarded at night, with the big contest at midnight and a $500 cash prize to the winner (must be present to enter) RockHouse Live will have live music starting at opening and will run all day on both of our amazing floors and our rooftop deck, to be an immersive experience, filled with energetic music by DJ MOSES, colorful visuals, and a feel-good atmosphere to have a memorable time. It's not just a party; it's a chance to be a part of a community and celebrate the joy of music and dance. Dress code: Bring your best costume - dare to bare! 135 Duval (corner of Greene & Duval); 305.394.1110; 10:30 PM; $150 for reserved seating overlooking Duval and Greene; just $20 for our second floor deck/DJ/Party! Tickets available HERE

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Saturday, October 28, 2023

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 Noon until 5pm at New Orleans House! Clothing Optional. $ cover charge w/FREE clothes check 724 Duval St 305-294-9800

SAN CARLOS STREET PARTY
The San Carlos Institute is bringing back their annual Street Party! Dance the night away and enjoy - Mojitos Bar, Cuban Music and dancing for those who are strong of heart! Noon - Midnight! 516 Duval St 305-294-3887 Free Entry. -

SOUTHERNMOST SCAVENGER HUNT'S 3rd ANNUAL FANTASY FEST BAR CRAWL
Come one, come all and do the 3rd Annual competitive Fantasy Fest Bar Crawl! Sponsored by Dulce Vida Organic Tequila. Grab your team of up to 6 people and see if your team has what it takes to bring home the grand First Place Prize! Prizes will be awarded to the TOP FIVE teams and include: 2023 Fantasy Fest swag, Dulce Vida Tequila and swag, shirts, coozies, free bar tabs, restaurant tabs, and much, much more! Each participant will receive a FREE Margarita and an exclusive Scavenger Hunt map featuring tons of drink coupons to use along the way. From world famous Sloppy Joe's to favorite local hideouts, you will enjoy the nightlife, hotspots, all while learning a thing or two about our unique island paradise and the bars in Key West! Earn the most points for your team to win and the reward could be yours! Each player must be 21 or older and you do not have to drink to participate. $45 per person includes the activity, the free drink, our exclusive scavenger hunt map with a value of over $160 and if you win you'll get a lot more! Check in starts at 2:00pm and the crawl begins at 2:30pm sharp and ends at 4:30pm. Awards and winners will be announced at 5:00 pm. Buy tickets HERE

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. Don't deal with the crowds! VIP high-end open bar and catered buffet-no need to go anywhere else. Private entrance and restrooms. Free bag of beads to toss to the crowd below! MC'd by John "Ma" Evans. Don't miss this opportunity for a great vantage point to see the parade and a fantastic party. VIP Tickets $200. No reserved spaces, first come, first served. Only 150 tickets available! Tickets on sale October 1 at the New Orleans House 305-293-9800 724 Duval Street open 8 AM-8 PM or keystix.com. ; 724 Duval Street $$ doors at 6pm

FIRST FLIGHT PARADE VIEWING PARTY
Enjoy all the parade Extravagance from the comfort of First flight Island Restaurant & Brewery. Saturday, October 28, 2023, 6-9 pm (5:30pm check-in) ALL Tickets include: Signature Dinner Buffet and 3-hour Open Bar! 3 Ticket Options: $125++ Sidewalk Chair ticket: Seating is First come, First serve. Guests are asked to check in with the hostess and receive a name card for the sidewalk chair. Then we would like to invite you to enjoy your meal, open seating, family style in the Canopy Garden! This will allow everyone to enjoy cocktails, food, and festivities for about an hour and then 7 pm is PARADE time!!! $150++ Indoors Table ticket: Reserved table seating for you and your friends, inside our air-conditioned dining room with the doors open for the parade view. Also, includes a designated porch for standing. $150++ Downstairs Porch Chair ticket: Front porch seating area just up from the sidewalk! Very Limited! Click HERE for tickets.

MANGOES PARADE PARTY
Join us a step above Duval with all the comforts of home for one of the most epic parties of the year. Mangoes Private Parade Party offers an elevated patio for street spectating, incredible drink specials, an air-conditioned dining option, and a special parade party dinner menu for purchase. After the parade, stay and enjoy live entertainment by island legend piano player Dave Bootle! Pre-purchase your tickets starting for $50 for presale and $60 on the event day at the door. Doors open 6PM Parade to start at 7PM Tickets grant you access to the private event and include a complimentary welcome drink, access to the entire ground floor of the restaurant and bar area, air-conditioned bathrooms, and an air-conditioned dining room. Come early to get your seat or stand upfront and enjoy people and parade-watching on the world-famous Duval street. Buy tickets HERE

PARADE VIEWING AT THE HARD ROCK CAFÉ
Join us and experience "Uniforms & Unicorns" for the best viewing of the Fantasy Fest parade on Duval St. Hard Rock Cafe will be grilling up a Fantasy Fest exclusive menu. Priority seats still remain but we sell out early every year so let us know today! Contact Kelly at [email protected] for VIP red carpet treatment. 313 Duval Street, 305-293-0230. Doors open at 6 PM!

PARADE VIEWING DINNER PARTY
The Hellings Curry Museum (319 Duval Street) will be hosting a grand Fantasy Fest Parade Viewing Dinner Party! We invite you to dress in royal uniform, adding an air of nautical elegance to the event. Enjoy a magical evening seated in a beautiful courtyard at a decorated table enjoying your three-course meal, fabulous parade view and two complimentary cocktails. This fun event will sell out so be sure to buy your seats early. All proceeds go to preserving and restoring the Hellings Curry Museum. Information about this event HERE

BUD LIGHT FANTASY FEST PARADE
Join 70,000 exuberant partygoers as this year’s Bud Light Fantasy Fest parade rolls down Duval Street. Featuring glittering floats, spectacular costumes and dazzling dancing groups! It doesn’t get any wilder than this! Parade steps off at 7 PM; FREE. Sloppy Joe's Live Crowd Cam Live Duval Street Cam Rick’s and Durty Harry’s Cam Wicker Guesthouse Cam

PARADE VIEWING PARTY AT LA TE DA
Join the Fun at La Te Da - Street side for a front row view with our favorite MC Rude Girl - from WEOW 92.7 who will be on hand to celebrate with you and announce all the fabulous floats, and walking groups in the Bud Light Fantasy Fest Parade!

BLUE PARTY AT THE BACK BAR
What’s your favorite color? Well on this night , it’s definitely Blue! Come dressed all in blue and enjoy one of key wests biggest and best live music venues . An all star band with The Newtons, Toko Irie and many other musical guests. This is a dance party like no other. Live music , cash prizes for the best Blue costume, and no cover charge. Party starts at 8PM and goes all night! 618 Duval St

KINKY COUPLES PARTY HOSTED BY RUBBERDOLL!
The ONLY strictly Couples Only event. Join like-minded couples in the 801 Cabaret Bar overlooking Duval Street. A special performance by the world-renowned latex performer RubberDoll with Live Dark'n Dancing with New York DJ Lucas will be sure to get everyone in the mood for some serious playtime. Doors open ten minutes before showtime. Shows at 8:00pm and 11:00pm both Friday and Saturday - Check-in is at the Downstairs Bar. Private Area, Premium Open Bar, Clothes Check Couples Only! Come Together, Leave Together Re-Entry Not Permitted/Pre-Registration Required. NO EXTRA TICKETS WILL BE AVAILABLE WHEN THIS EVENT SELLS OUT! TICKETS CANNOT BE TRANSFERRED TO ANYONE ELSE! Friday $275 per couple Saturday $300 per couple Both Nights with Meet and Greet: $500 Contact Kitty with questions (305)783-4259 Buy Tickets Here

SAVE A UNICORN, RIDE A COWBOY!
Saddle up and ride over to Side Bar after the Bud Light Fantasy Fest Parade! All cowboys, cowgirls and unicorns are welcome at this Ho Down – hosted by Elle Taylor! DJ Honey Davenport will be spinning the tunes all night long. Party starts at 9PM. $5 Cover

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Sunday, October 29, 2023

CHILDREN'S DAY
A family event featuring food, rides, games, arts and crafts and a costume contest for children located at Bayview Park. Truman Ave. and Eisenhower Dr.; Noon to 5 PM; 305-292-8912.

HANGOVER POOL PARTY AT SOMO'S PINEAPPLE POOL
We'll have plenty of food and drink specials, and a live DJ spinning all your favorites, along with free Booze Bandages for the first 50 guests, to bring you back to life! Deep Eddy’s Bloody Mary specials. Sunday, 10/29, 1-4pm Southernmost Beach Resort’s Pineapple Pool. FREE! Reserve your space HERE

REGGAE REHAB POOL PARTY AT THE MARKER w/REGGAE BY CHANNEL 3
Feeling hungover after your long week of debauchery? Captain Morgan and Booze Bandage to the rescue! We'll have plenty of food and drink specials, live reggae music by Channel 3, along with free Booze Bandages for the first 50 guests, to help bring you back to life! Sunday, 10/29, 2-5pm The Marker Key West Harbor Resort, 200 William St. 2-5pm FREE! Reserve your space HERE

“THE FAT LADY SINGS” TEA DANCE
As the saying goes, “It ain’t over ‘til the fat lady sings.” Everyone will be at La Te Da from 4 PM to 8 PM for the last official event of Fantasy Fest 2023. DJ Rude Girl provides the music for the very last hoorah! La Te Da - Hotel, Restaurant, Cabaret and Bars, 1125 Duval St.; 305-296-6706; $5.

DRAG QUEEN BINGO
Drag Queen Bingo @ Marathon Community Theatre Join us for Drag Queen Bingo @ The Marathon Community Theatre 5101 Overseas Hwy, Come see Rocky Horror star JJ Mills. Bingo starts at... Doors and concessions open @ 4pm Bingo starts @ 5pm! 18+ event - ID Required at the door.

THE SUN SETS ON FANTASY FEST WITH REGGAE LOU & THE KIND BUDS and THE SKALLYWAGZ!
Join us on the Sunset Pier - Sunday, October 29th, 2023, for Fantasy Fest Close - Out Concert featuring....Reggae Lou & The Kind Buds and The Skallywagz! Now that Fantasy Fest is over, wind down and chill on the water at Sunset Pier. Show starts at 5:00 PM. FREE

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