Key West Fantasy Fest 2025
2025-10-17 - 2025-10-26
Key West Fantasy Fest 2025 – October 17-26, 2025!
Fantasy Fest Background: Fantasy Fest is an annual 10-day party in paradise for grown-ups. Started in 1979 by a small group of Key West locals, the party was created to bring visitors to the island in what was a typically quiet, but beautiful season. It worked. Fantasy Fest has grown every year since its inception and is now the wildest extravaganza around! Fun-loving revelers from around the globe bring their creativity and imaginations as they descend upon Key West each year in October for 10 days filled with costuming, parades, libations, and excitement!
Check out the full schedule here: https://fantasyfest.com/schedule/

2025 Daily Diversions

# YOUR PICTURE WITH THE KING & QUEEN SCULPTURE
Stop by the Chamber of Commerce and snap a selfie with our Fantasy Fest King & Queen Sculpture! While you’re there, grab some Official Fantasy Fest SWAG! Be sure to tag #Keywestchamber and #fantasyfest for a chance to win some cool Fantasy Fest prizes! 510 Greene Street | Open Daily | 9-5PM.

“Q-RATED” A 20 YEAR EXHIBITION RETROSPECTIVE BY QMITCH
On display October 2-30, 2025 The Studios of Key West – 533 Eaton St Gallery Hours: Tues – Sat, 10am-4pm Free to visit! Mitchell “Qmitch” Jones’s “Q-Rated” is a dynamic exhibition honoring twenty years of bold fashion, costume, and design. By blending unique textiles, sketches, and playful creations, the exhibition showcases his influence as a drag icon, designer, and community supporter. With a mix of fun, texture, and storytelling, this show offers an intimate glimpse into his impact and influence in the world of art and festivities in Key West. More info click HERE .

801 CABARET – Sushi & The 801 Girls
Come join The World Famous Sushi & The 801 Girls – October 17th -23th and 26th. 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 your NOW! Doors at 8pm. No shows Oct 24 & 25. Located at 801 Bourbon Bar – 801 Duval Street – 9pm & 11pm

FANTASTIC BODY ART AND STUNNING SUNSETS AT SUNSET PIER
Join our premier, all girl, award winning team of body artists Femme Fatale Body Art, October 17-25 starting each day at 1 PM at Sunset Pier, 0 Duval Street. Our talented team wants to make YOU our next canvas! From small body art pieces (starting at just $60) to full body’s we can help your imaginations run wild! And we have waterproof and sweat proof options available! Book direct please by texting Amanda our body art team leader at 850-596-4065! Come join us at Sunset Pier for fantastic body art, sunsets, music, fun and food!! 0 Duval Street Sunset Pier – find us just inside the parking garage area!

FANTASY FACADE sponsored by HAUNTED KEY WEST
This year the Facade is sponsored by Haunted Key West. Tap into your Halloween horror spirit and creep out your crib to win cash awards and spooktacular prizes this Fantasy Fest! Open to all businesses and residents in Key West and Stock Island, this spine-chilling contest offers a $1000 cash grand prize for the best Spooktacular Showstopper. Additional prizes will be awarded for Creepiest Concept, Bloodiest Horror Scene, Best Fantasy Fest Theme Integration, and the coveted Great Pumpkin Award. Final day to register Mon Oct 13; judging Mon. Oct 20. 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 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. Promotion valid 10/16/25 – 10/31/25.

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.

IVs IN THE KEYS
Happy Fantasy Fest! As Key West’s Original Medical Spa, we’re here to meet your hydration needs. Fantasy Fest Special: Mobile Service Fee waived for groups of 5 or more. An additional 10 % discount for parties of 10 or more. Please call for after-hour appointments 305-395-8245.

KARAOKE PARTY!
Karaoke Lounge @ The Key West Empourium | 618 Duval St | 8PM-2AM Join us for a Karaoke party every night during Fantasy Fest week. 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!!”

LOST. LUST. PIXIE DUST: A RETURN TO NEVERLAND
Show Dates are : October 17, 18, 20, 21, 22, 23. Doors at 7PM | Show starts at 7:30PM. Think a naughty thought and take flight… Second star to the right and straight into temptation! There’s a place with pirates pouring drinks, mermaids singing from the shadows, and longing, laughter, and misplaced memories tangle together in a bedtime story no one’s dared to tell. Lost. Lust. Dust: A Neverland Cabaret is an immersive experience of circus, burlesque, and comedy – electric with mischief and aching with delight. Starring internationally renowned performers, the show brings to life the forgotten corners of Neverland— where innocence is lost, lust is found, and imagination becomes the most seductive magic of all. Guided by a glitter-drenched and dangerous Tinkerbell, you’ll enter a world built for grown-ups who find that forgetting was the tragedy. But remembering? That’s the real adventure. Key West Theater | 512 Eaton Street | Tickets available at keywesttheater.com

PHOTO OP FEST LETTERS ALL DAY
Stop by Conch Republic Seafood Company and snap a selfie with our Fantasy Fest Letters! 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.

POT STOP SELFIE CONTEST AT THE GREEEN HOUSE LOCATIONS
Stop in one of our stores, grab some of our fun props and snap a selfie for a chance to win a Grand Prize valued at over $500. Shop the largest Cannabis selection in all of South Florida with 9 dispensary locations in the Florida Keys Full-Strength THC Products – No Medical Card Needed – 21 and Over – Money Back Guaranteed. Please toke responsibility. Stop on By and “Stay High.” Key West Locations – 211 Duval St., 532 Duval St., and 431 Front St. “The Mothership” 3128 N Roosevelt see more locations on the website HERE

SLOPPY JOE’S HANGOVER HEADQUARTERS
Hungover? We have the cure! Head to Sloppy Joe’s Bar…Your Hangover Headquarters! Our perfect remedies include Deep Eddy Vodka Cocktails & Bloody Mary’s, Dolce Vida Frozen Margaritas, live entertainment & giveaways throughout the morning. Let the cold drinks, air conditioning & live music ease you back to the festivities. The kitchen opens at 10am to help fuel the day. Whether you are nursing your glitter-covered self in sunglasses or dressed for the next party, you will fit right in! Skip the morning-after regret, and let us be your Hangover Heroes. Trust us, this is one hangover cure you’ll want to remember! All week long 9am- RECOVERY! Sloppy Joe’s 201 Duval Street. #STILLTHEBESTPARTYINTOWN

THE ROCKY HORROR SHOW
The cult classic returns! The Waterfront Playhouse is thrilled to present our 5th annual production of The Rocky Horror Show — just in time to celebrate the 50th Anniversary of the legendary film that started a global phenomenon. Oct 15-24, 2025, 8pm. Read More →

Key West Powerboat Races - Race World OffShore
2025-11-05 - 2025-11-09
WAYS TO WATCH LIVE!
Key West, FL – November 5th, 7th, & 9th, 2025

Race World Offshore is gearing up to deliver an unforgettable week of offshore powerboat racing in Key West on November 2nd – 9th, 2025. Fans don’t have to be at the waterfront to catch the action, as the event will be streaming live across multiple platforms. From the roar of the engines to the thrill of the finish line, every moment will be brought directly to fans through exciting live coverage.
Supporters can follow the action on Race World Offshore’s official Facebook and YouTube channels and on the XINSURANCE Sports YouTube channel, all completely FREE OF CHARGE!

Sponsored in part by one of our very own Key West Historic Seaport tenants, Fury Watersports!

Bight Before Christmas Lighting of The Bight: Key West Harbor Walk of Lights 2025
2025-11-26 17:00 - 23:00 (America/New_York) | At the 16’ Nautical Christmas Tree on the Harbor Walk of Lights at William St.
Wednesday, Nov. 26 – Free
The Lighting of the 2025 “Harbor Walk of Lights”
at the Key West Historic Seaport
Main Harbor Walk Lighting at the 2025 “Fishing Buoy Christmas Tree”
Lights come on at 6:00pm – holiday music starts at 5:00pm – Greene and Elizabeth St. plaza.
Santa and Mrs Clause will be making a NICE list and passing out treats!
SECOND lighting of the 2025 “Lobster Trap Christmas Tree”
Lights come on at 7:00pm, holiday music starts at 6:00pm – Margaret St. plaza (Old Lands End Village).
There will be holiday cookies and candy canes for the children!
Enjoy creative holiday displays and thousands of lights honoring the “Maritime History of Key West”.
With 3 blocks of sparkling holiday lights and displays around the Key West Bight Marina and Historic Seaport, the 2025 Key West “Harbor Walk of Lights” is destined to bring miles of holiday smiles to our One Human Family of visitors and locals alike.
Harbor Walk of Lights is on every night from Thanksgiving eve through New Year’s eve!
Please join us at the “Lighting of the Harbor Walk” to kickoff the “Cheryl Cates Toy Drive”.
Bring a toy, or toys will be available at the “Imagination Station” table to purchase and donate.
ALSO, be there for a special announcement from the Cheryl Cates Toy Drive.

20th Annual Pet Pictures with Santa™ – Hosted by The All Animal Clinic
2025-12-04 18:00 - 20:00
Thursday, December 4 – FREE to attend
6:00pm – 8:00pm
2025 Pet Pictures with Santa™ – Hosted by The All Animal Clinic
Professional photos by Rob O’Neal – $25 (cash only) to benefit our local Boys & Girls Club.
LOCATION: At the 16’ Nautical Christmas Tree on the Harbor Walk of Lights at William St.
The “Pet Pictures with Santa” event always raises money for the Boys & Girls Club of Key West, Please continue to support them all year by donating at bgckeywest.org.
Thank you for supporting the Boys and Girls Club and our lower Keys Children.
DONATE

HOSTED BY: All Animal Clinic of Key West
Dr. Lisa Bramson DVM
Santa is back at the Historic Seaport this year to take a break in Key West and to get a photo with you and your entire brood, whether they include the dog, the cat, the rooster or even the kids. Santa will be waiting to get a great holiday photo with you and the entire family – and early enough for your custom Holiday card!

All photo sales to benefit The Boys & Girls Club of the Keys.
All participating pets and kids will receive goodies and treats including Holiday pet bandanas, doggie treats and toys, coupons for the Clinic.
FREE to attend! Photos by famous photographer Mary Martin.
Professional high resolution photos are $25 (cash only please – ATM on site) will be available online.
Additional cash donations happily accepted for the Boys & Girls Club of the Keys.

Graciously Hosted by:
All Animal Clinic – Dr. Lisa Bramson DVM
5450 MacDonald Ave Ste 13
Key West, Fl (Stock Island)
305-294-5255

Services for your family pet include:

Medicine, Cancer, Cardiology, Ultrasound, Surgery, Therapy, In House Lab, Endoscopy, Dentistry, Hospice, Digital X-Ray & Pain management
Board Certified Radiologist, Cardiologist & Ophthalmologist Available
Emergency On Call Care Available 24 hours a day
Open 7 days a week
Boarding & Grooming Available

All Animal Clinic is an AAHA (American Animal Hospital Association) accredited full service veterinary hospital that has been serving Key West pets for over 20 years.
All Animal Clinic is the only AAHA certified hospital in the lower keys.
BBB (Better Business Bureau) accredited.

2025 Key West City “Hometown Holiday Parade”
2025-12-06 18:30 - 20:30
Saturday, December 6 – FREE
2025 Key West City “Hometown Holiday Parade”
Starts at 6:30pm
LOCATION: Parade starts on Truman Ave. (at White St.) then proceeds to Duval St., then down Duval St. ending at Eaton St. The most charming hometown parade you’ll ever see with holiday floats, and tons of kids (of all ages). Of course Santa will make a guest appearance!

Schooner Wharf Bar 2025 Tree Trimming Party and Toy Drive
2025-12-07 18:00 - 21:00
Sunday, December 7 – FREE to Attend
Schooner Wharf Bar 2025 Tree Trimming Party and Toy Drive
Starting at 6:00PM
LOCATION: Schooner Wharf Bar and Galley On the Harbor Walk of Lights at William St.
Maritime merry makers will deck the halls and make dreams come true at the popular waterfront winter wonderland. Great PRIZES for the Best Handmade Ornaments that are:

Most Original
Most Nautical
Most Popular with the holiday crowd

All tree trimmers will be treated to a free holiday cocktail — egg nog, hot apple jack or Swedish Glogg.
Then step into Santa’s southernmost workshop at Schooner Wharf. Share the holiday spirit, as local artists and authors sign and sell ORIGINAL WORKS for HOLIDAY GIFT GIVING.
Bring a donation for the “Cheryl Cates Memorial Toy Drive” by Angles Just 4 Kids!
Each of Santa’s helpers who donates an unwrapped gift will also receive a free holiday drink from Schooner Wharf Bar.
Some of our favorite local musicians will be playing Holiday Tunes, Reggae, and Calypso with the island sound of Steel Drums to round out the festivities.

Schooner Appledore Lighted Boat Parade Party
2025-12-13 19:30 - 21:30
Saturday, Dec. 13
Schooner Appledore Lighted Boat Parade Party
7:30pm – 9:30pm
Be a participant in the 2025 The Lighted Parade aboard the Schooner Appledore II Parade Boat!
Trip Includes: Premium beer, boutique wines, wines and soft drinks. Very Limited Seating!

The 34th Annual Schooner Wharf Bar/Absolut Vodka Lighted Boat Parade
2025-12-13 20:00 - 23:00
The 34th Annual Schooner Wharf Bar/Absolut Vodka Lighted Boat Parade sails into the holiday season on Dec. 13th.
Key West’s Historic Seaport has been transformed into a warm winter wonderland, as the annual Lighted Boat Parade sails through the Key West Bight and Harbor on Dec. 13th, bringing maritime merriment to the harbor.
This year marks the 34th anniversary of the Schooner Wharf Bar/Absolut Vodka Lighted Boat Parade, a must-see holiday event in the tropics. Vessels of all shapes and sizes deck their hulls, and string lights in their rigging to twinkle through the night sky over Key West Bight and Key West Harbor. Schooner Wharf Bar is the holiday headquarters with festivities starting at 6 p.m. when Christmas takes on the sounds of the islands with the Bahama Village Music Program House of Pan Steel Band tapping out holiday favorites on steel drums.
Followed by the best music this island has to offer, adding to the festivities. Come early for the best viewing spots and take a stroll along the Harbor Walk of Lights while watching the brightly lit boats, captains and crews add their final decorations for the parade.
The 34th Annual Schooner Wharf Bar/Absolut Vodka Lighted Boat Parade begins at 8 p.m., when the vessels in the harbor begin their festive procession past the judging stand at Schooner Wharf to compete for bragging rights and $40,000 in prizes with a free raffle for boat entries.
Captains should register for the parade by Thursday, Dec. 11th but entries will be accepted as late as the day of the parade. A Captains Meeting will take place Thursday, Dec. 11th at 8 p.m. in the Sail Loft of Schooner Wharf and an Awards Ceremony Sunday at 8:00 p.m. For more information, or to register for the parade, call 305-292-9520.

2025 “Holiday Classic Car Show” & Toy Drive
2025-12-21 11:00 - 15:00 | Conch Republic Seafood Company parking lot – on the Harbor Walk of Lights at Greene St.
Sunday, December 21
The Florida Keys Southernmost Car Club presents
2025 “Holiday Classic Car Show” & Toy Drive
FREE • 11:00am – 3:00pm
LOCATION: Conch Republic Seafood Company parking lot – on the Harbor Walk of Lights at Greene St.
TOY DRIVE: Please bring an unwrapped toy for Monroe County Domestic Abuse Shelter.
VOTE for the “Peoples Choice” award for: BEST sports car, pick up, engine, interior, original & custom, pre & post 1950, Best in Show.
See classic cars from every era decked out for the holidays!
Run by the Florida Keys Southernmost Car Club, honoring founder Dick Moody.
Non-member cars may enter same day FREE with an unwrapped toy!

Lowering of the Pirate Wench at Midnight at Schooner Wharf Bar!
2025-12-31 17:00 - 2026-01-01 00:00
Lowering of the Pirate Wench at Midnight!
LOCATION: Schooner Wharf Bar and Galley On the Harbor Walk of Lights at William St.
Great Food, Holiday Drinks and LIVE Music!
Party starts early in the day with 3 Local and National Acts. Party Favors – Champagne & Fun
The Unique Schooner Wharf Bar’s Seaport Tradition!
