Key West Historic Seaport

25th Annual Key West Paddle Classic
2022-10-01 07:45 - 12:00 (America/New_York) | Higgs Beach, 100 Atlantic Blvd, Key West, FL, 33040, United States
Watersports enthusiasts on paddleboards and other self-propelled watercraft can race Key West on Saturday, Oct. 1, 2022 at the 25th annual Key West Paddle Classic!
The 12-mile distance race around Key West is open to paddlers on stand-up and prone paddleboards, outrigger canoes, surf skis, kayaks, row and dory boats. Participants can compete as individuals or in two-person, three-person, five-person and six-person teams as well as in relay teams of three.
Presented by the Florida Keys’ adventure tour company Lazy Dog, the race is a World Paddle Association national points event.
A kick-off party, packet pickup and late registration for racers is planned for 5 p.m. Friday, Sept. 30, at Salute! on Key West’s Higgs Beach, overlooking the Atlantic Ocean at 1000 Atlantic Blvd.
Saturday’s challenge begins with a participant check-in from 7:45 to 8:45 a.m. at Higgs Beach. A 9 a.m. racers meeting and a 9:15 a.m. Hawaiian Pule blessing are to precede the race’s staggered start times. The first wave of racers is to begin at 9:30 a.m. and the second wave at 10 a.m.
The 12-mile course takes competitors past island landmarks such as the Southernmost Point marker, Fort Zachary Taylor Historic State Park and Mallory Square, site of Key West’s nightly sunset celebration, before they reach the finish at Higgs Beach.
Participants can relax after the race at a 12:30 p.m. lunch hosted by Salute!, followed by an awards celebration. Entry fees for the renowned competition begin at $85 for individual participants and range from $160 to $360 for teams, depending on team size and division.
For more information and to register, click here or visit https://paddleguru.com/races/KeyWestPaddleClassic2022

Key West Fantasy Fest 2022
2022-10-20 - 2022-10-30
Key West Fantasy Fest is an exciting annual event that takes place in October. Every fall, the streets of Key West come to life for 10 days of unbelievable costumes, parades, and parties. Since its inception in 1979, The Key West Fantasy Fest has become one of the biggest events in Key West. People from all over the world come to Key West to explore their imaginations and celebrate creativity. Live your Fantasy in Key West!

2022 SCHEDULE OF EVENTS
DAILY DIVERSIONS
BODY PAINTING BY CAPTAIN RON WOLEK – Hard Rock Café, 313 Duval Street. 305-293-0230
FACES OF FANTASY FEST, OFFICIAL PORTRAITS BY TOM FLIP – Oct. 20-23. Portrait Studio location TBA. FREE
FAIRVILLA THE BEST PLACE IN TOWN FOR SEXY, FUN COSTUMES & ACCESSORIES – 11am – 12am 524 Front St. 305-292-0448
FANTASTIC BODY PAINTING & STUNNING SUNSETS: FEMME FATALE QUATRE BODY ART AT SUNSET PIER – All female body artists October 22-30. 1pm at Sunset Pier, 0 Duval St. Call or text 850-596-4065
FANTASY FAÇADE COMPETITION – Free to enter homes and businesses. Cash prizes! 305-295-9112
FURY WATER ADVENTURES DISCOUNT – 10% off select trips with promo code FANTASY. 855-831-5997
HAIR OF THE DOG AT ISLAND DOGS – Bottomless mimosas, huevos rancheros, breakfast pizza & more 10am-1pm. 505 Front St. 305-509-7136
KARAOKE! AT THE JAM PONY KARAOKE CLUB – 8pm-3am. Karaoke contests with prizes for the BEST and WORST Performers. 618 Duval St. 305-304-1188
SUNSET HAPPY HOUR WITH CAPTAIN MORGAN AT THE OPAL RESORT – 5-8pm. SHIPWRECK PUNCH in a Fantasy Fest Cup – $9 includes cup & $8 refills. 245 Front St. 305-294-4000
THE ROCKY HORROR SHOW – LIVE at WATERFRONT PLAYHOUSE – Starring Christopher Peterson. 10/14 – 28th.310 Wall St. 305-294-5015
HARRIET POTTER AND THE ENCHANTED TASSEL: A BURLESQUE PARODY – Join Auntie Harriett Potter on a salacious search for a magical, missing tassel. 10/25-28th. Key West Theater, 512 Eaton St. Doors -7pm Show – 8pm Tickets – $50-$125 pp.305-9850433
FRIDAY, OCTOBER 21, 2022
12pm-12am – BAHAMA VILLAGE GOOMBAY FESTIVAL- FAMILY FRIENDLY EVENT – Main Stage at the corner of Petronia and Front Streets. FREE
TBD – ROYAL CORONATION – Call 305-295-9112
7pm/ COSTUME CONTEST 9pm PIRATE BASH AT BOATHOUSE BAR & GRILL – More than $1,500 cash & prizes for best pirate & wench costumes. DJ Cory. 305-294-2640. 231 Margaret St. $10
SATURDAY, OCTOBER 22, 2022
12pm-12am – BAHAMA VILLAGE GOOMBAY FESTIVAL- FAMILY FRIENDLY EVENT – Main stage at the corner of Petronia and Fort Streets. FREE
7pm SMALLEST PARADE IN THE UNIVERSE – Design and build a float! All floats auctioned off at the end of the Parade. Floats exhibited for the month of October at the Studios of Key West, 535 Eaton Street. 305-296-0458
SUNDAY, OCTOBER 23, 2022
11am – 3pm LA TRATTORIA OCEANSIDE ZOMBIE BRUNCH – Zombie Brunch 2 blocks from Fort East Martello where Zombie Ride begins. All you can eat! Full Bar! 3593 S Roosevelt Blvd. 305-295-6789
1pm AFTER CHURCH POOL PARTY @ ISLAND HOUSE FOR MEN – Pool Boys, free shots, & giveaways! $40 cash/credit. Photo ID required. MEN ONLY. Includes lock & locker, towels, and resort privileges until Monday @4am 1129 Fleming St. 305-294-6284
2pm ZOMBIE BIKE RIDE PRE PARTY – FAMILY FRIENDLY –Gather at Zombieland in Fort East Martello, 3501 S Roosevelt BLVD, to get the blood flowing, bodies painted, and mid-afternoon snacks.
6pm ZOMBIE BIKE RIDE – A FAMILY FRIENDLY EVENT- Kicks off at Fort East Martello, 3501 S Roosevelt BLVD, and makes its way to Zombie Fest on Duval St.
MONDAY, OCTOBER 24, 2022
12pm-4pm PERRY HOTEL & MARINA’S DUCK, DUCK, BOOZE POOL PARTY – Pool of rubber duckies, beverage samples, swag, & DJ Buggy. FREE! 7011 Shrimp Rd. 305-296-1717
5:30pm, 9pm, & 11pm GREEN PARROT BEATLES TRIBUTE – Well, Love, and Tony Baltimore, Chris Thomas, Hiram Garzaro, and Oren Polak, re-create a Fab Four Show with “THE BEATLE BAND, All You Need is Love”. 601 Whitehead St. 305-294-6133
6pm HEROES AND VILLAINS RUN/WALK 5K – Race starts & ends at Southernmost Beach Resort parking lot, behind La Mer House, 506 South St. Free beer & snacks post-race. Happy Hour all night at Southernmost for runners; ½ off appetizers and $5 Beer, House Wine, & Well Drinks. 305-296-6577
MARTINI MONDAY AT VIRGILIO’S – Live music, food & the best Martinis for $7. 524 Duval St. 305-296-1075
8pm – 11pm FIRST FLIGHT’S KINKY CARNIVAL – 3hr Open Bar. Party until 1am! Tickets on sale Friday – Sunday, 12-9pm, 301 Whitehead St. No Pre-sales. $50, Cash Only. Kinky Costume Required.
8pm – 12am SLOPPY JOE’S COMIC BOOK CAPE-ERS – Dress as your favorite “Caped” Superhero or Supervillain. Whiskey Kiss on stage at 10pm, house DJ all night. Giveaways 8pm – 12am. 201 Duval St. 305-294-5717
10pm – 4am TOPS OR BOTTOMS UNDERWEAR PARTY at NEW ORLEANS HOUSE – Underwear party for Men. 724 Duval St. 305-293-9800
TUESDAY, OCTOBER 25, 2022
11am – 5pm DANTE’S 4TH OF JULY PARTY! – Food & Drink Specials, 951 Caroline St. 305-293-5123
7pm – 10pm COCKTAILS FOR ANIMAL TAILS! – Rick’s Complex, 202 Duval St. 305-294-4857. $40- All you can DRINK! Benefits the FL Keys SPCA. Wear your best animal ears & tails, fluff up your tutus and party like an animal! Costume contest with $500 grand prize!
7pm – 10pm ELECTRO LASER NIGHT POOL PARTY AT SOUTHERNMOST BEACH RESORT – DJ Aaron Moore & KW Lasers. Southernmost Beach Resort, 1319 Duval St. FREE
7pm ROCK THE TATAS CONTEST at HANKS’ HAIR OF THE DOG SALOON – Benefits Making Strides Against Breast Cancer. First place $500! DJ and special performances by Rob Benton & Friends. Doors open 5pm. Body Painting Artist on site! 409 Caroline St. 305-509-7758 $20 Cover/ $20 entry fee
8 pm CAPT. TONY’S PARTY IN PLAID – Wear naughty or nice plaid. 428 Greene St. 305-294-1838 FREE

WEDNESDAY, OCTOBER 26, 2022
12pm – 3pm LIVING ON THE EDGE POOL PARTY AT OCEANS EDGE RESORT AND MARINA – Key West’s favorite band, the DurtBags, Dulce Vida tequila specials & games. Havana Nights Pig Roast $25 plus tax and gratuity. 21+ Event. 5950 Peninsular Ave FREE
1pm – 4pm SPLASH DANCE AT THE MARKER KEY WEST HARBOR RESORT – Pool Party featuring PATRICK & THE SWAYZEES! 200 William St. 855-485-9291 FREE
5pm – 8pm HUMPDAY POOL PARTY @ ISLAND HOUSE FOR MEN – Half-Price Drinks! $40 cash/credit. Photo ID required. MEN ONLY. Admission includes lock & locker, towels, and resort privileges until Thursday @ 4am. 1129 Fleming St. 305-294-6284
5pm Reg./ 6:30pm PET MASQUERADE at Key West Amphitheater in Truman Waterfront Park – 4 categories $25 each entry benefits the Lower Keys Friends of Animals. FREE to watch, seats available or bring a blanket or lawn chair. NO COOLERS. Food & Bev available. 21 E. Quay Rd. petmasquerade@gmail.com
8pm SMOKIN TUNA HOMEMADE BIKINI CONTEST – 7pm VIP MEET AND GREET; 8pm CONTEST Over $2,000 in cash & prizes. VIP open bar and appetizers. Hosted by Bill Hoebee and celebrity judges. VIP $50. Contest participation & general admission $20. 4 Charles St. 305-517-6350
7pm WHARFSTOCK AT THE SCHOONER WHARF BAR – Peace and Love Woodstock-style! Prizes for sexiest Hippie Chick and Grooviest Dude — judging at 8:30 PM. Live music from Raven Cooper and the Hippies, cold drinks & great galley fare. Cash & prizes to the winners! 202 William St. 305-292-9520. NO COVER
8pm – 4am 9TH ANNUAL LUV2GLOW DANCE PARTY – DJ’s Jevne, Top Jimmy & Herb Javier. Paint up, wear glowing costumes and blinky & LED lights welcomed. NO GLOW NO ENTRY $20 cover, INCLUDES 1 FREE Dulce Vida Cocktail. 21+. Body painter at the door. Rick’s Upstairs open air club, 202 Duval St. 305-296-5513
10pm – 4am DESIRE MALE FETISH PARTY – MEN ONLY Fetish Party! New Orleans House Garden & Pool Bar. 724 Duval St. 305-293-9800
THURSDAY, OCTOBER 27, 2022
11am – 3pm BERKSHIRE HATHAWAY PARADE OF HOMES MEGA OPEN HOUSE EVENT – Open Houses with chances to win a Night on the Town Gift Basket with certificates to favorite island spots. 305-928-8370
11am – 1pm NAUGHTY BIKE RIDE – Body painting, libations and music! Some bikes and Pedicabs on hand. Registration and Pre-Party @ 803 Duval St. parking lot. Music by DJ Lucas. Open bloody Mary & Mimosa Bar! 1pm ride kicks off to Irish Kevin’s with free admission.
12pm – 6pm DANTE’S HALOS & HORNS POOL PARTY – Free body painting, live music, giveaways, food, drink specials and the CENTER POOL STAGE! 951 Caroline St. 305-293-5123 $
4pm SOUTHERNMOST SCAVENGER HUNT’S BAR CRAWL – Teams up to 5 people vying for the Grand Prize! Participants receive map with 2-4-1 drink coupons valid anytime! 21+, $30 pp. Conch Republic Seafood Company, 631 Greene St. 305-294-4403
8pm HEADDRESS BALL – Doors open 6:30pm at Coffee Butler Amphitheater in Truman Waterfront Park. Tom Luna emcees with Rude Girl from WEOW 92.7 radio. The Aquanettes open the show and will be joined by Christopher Peterson and the cast of the Waterfront Playhouse’s Rocky Horror Picture Show and surprise guest entertainment! Over fifteen contestants parade Headdresses vying for the $3,000 1st prize. Premium table and lawn seating. 305-294-4603
8pm WHITE PARTY @ RICK’S DURTY HARRY’S ENERTAINMENT COMPLEX – DJs in two venues. The island’s best rock band, The DurtBags, in Durty Harry’s. Enjoy secret fantasies with the lovely Red Garter ladies. Glow off under the black lights. 202 Duval St. 305-296-5513
8pm PATRICK & THE SWAYZEES LIVE FROM THE LAWN AT SLOPPY JOE’S DOCKSIDE – Playing surf rock to doo wop, rockabilly to beach music. 7001 Shrimp Rd. 877-496-8712 FREE
8pm SLOPPY JOE’S TOGA PARTY – Limited Togas available for $10. Juliano Brother on stage 10pm, DJ all night. Giveaways 8pm-12am. 201 Duval St. 305-294-5717
9pm – Close FAT TUESDAY PINK PARTY – Flocking Fabulous Rosé Daiquiris, DJ Gyver, costume contest with $500 bar tab for 1st place, $250 2nd and $100 3rd. All cover charges donated to the American Cancer Society – Making Strides Against Breast Cancer of the Florida Keys. 305 Duval St. 305-296-9373 $
10pm – 4am EXPOSED AT THE BOURBON ST. PUB ADULT ENTERTAINMENT COMPLEX – All WELCOME Foam Party, 2 Dance Floors, pool & jacuzzi! Black Out & Black Light party inside with FREE glow sticks! VIP All Access $50. (VIP includes Main Bar, Garden & Pool Bar and Foam Party) tickets on sale at the New Orleans House 10/1. General Admission $20 (Access to the Main Bar only) Tickets at the door, 724 Duval St. 305-293-9800
10:30pm IRISH KEVIN’S 80’s PARTY – Full 80’s band! 211 Duval St. 305-292-1262 $
FRIDAY, OCTOBER 28, 2022
12pm – 5pm BOWTIES & BIRTHDAY SUITS at ISLAND HOUSE RESORT FOR MEN – All-male, clothing-optional pool party! Admission includes Bowtie and resort privileges until 4am Saturday. Music, go-go boys, and free shots. Locks & lockers provided while they last and free clothes-check. $40 cash/credit. Men 18+ Only *PHOTO ID REQUIRED FOR ALL ENTRANTS* 1129 Fleming St. 305-294-6284
12pm – 5pm SOUTHERNMOST PLAYBOY MANSION’S BEACH BUNNY POOL PARTY BASH – OCEANFRONT, ADULTS ONLY! All day pool pass, DJ Hazard, Drink Specials, and topless sunbathing with bunny ears on. $25. 1400 Duval St. 305-296-3141
3pm -5pm FLORIDA KEYS COUNCIL OF THE ARTS FANTASY FEST POSTER SIGNING PARTY – Carrie Disrud, winner of 2022 Fantasy Fest Poster Creator Contest, signs for attendees. 2020 poster designer Pashur will also be present to sign his winning poster. Posters and Fantasy Fest Swag for Sale! WINO at the La Concha Hotel, 430 Duval St. 305-280-0208
5:30pm MASQUERADE MARCH – Parade through Old Town with music and noisemakers! Thirst quenchers provided at select guesthouses. Begins at Frances Street entrance to cemetery, but revelers can join anywhere along the ONE route! FREE
7:30pm MASQUERADE MARCH AFTER-PARTY at THE GREEN PARROT – “Sooner or later, you always wind up at The Green Parrot”. 601 Whitehead St. 305-294-6133
8pm LIVING ART EXPO – Female, Male and Groups compete for title of Best Overall Living Art of Fantasy Fest 2022 and $3000 in cash & prizes. FREE General Admission. VIP Backstage and Stage-front tickets available. Doors open at 7pm. Sunset Pier, 0 Duval St. 305-295-7047 or rlevering@oceankey.com
9pm & 11pm KINKY COUPLES ONLY PARTY HOSTED BY RUBBERDOLL! – World-renowned latex performer RubberDoll with Live Dark’n Dancing with New York DJ Lucas. Open Bar, Clothes Check, Private Area. Pre-Registration Required. Friday $275 per couple/$50 Single Ladies. Saturday $300 per couple/$50 Single Ladies. Both Nights with Meet and Greet: $500. Contact Jim 305-304-2400
10:30pm ROCKHOUSE LIVE PRESENTS THE INAUGURAL ROCK-N-ROLL FANTASY AND COSTUME CONTEST – Two floors with live music and the biggest outdoor roof deck on Duval! Prizes awarded all night. Rock & Roll costume contest at 12am, $500 cash prize. 135 Duval, 305-440-3263; $100 admission; $150 reserved seating.
SATURDAY, OCTOBER 29, 2022
12pm – 5pm BOURBON ST. PUB POOL PARTY – Live DJ. Clothing Optional. 724 Duval St. 305-294-9354
12pm – 12am SAN CARLOS INSTITUTE BLOCK PARTY – Mojitos Bar, Cuban Music Fest and dancing! 516 Duval St 305-294-3887 FREE
1pm – 4pm !SUENALO! LIVE ON THE BEACH AT SOUTHERNMOST RESORT – SUÉNALO, an amazing, 7-piece Latin funk band from Miami performs. Cash bar featuring Froze and Sangria by Cupcake Wines and Beso Del Sol. 1319 Duval St. 305-296-6577 $25 – $60
5:30pm – 9pm SSP GIRLS ROCK! SUNSET PIER OCEAN KEY RESORT & SPA – The women of Sunset Pier take the stage for a concert in support of Mote Marine Lab, portion of proceeds benefit Florida’s Coral Reef. FREE! 0 Duval St. 305-296-7701
6pm BOURBON ST. PUB’S VIP BALCONY BASH PARADE VIEWING – Grand Balcony of the New Orleans House. Open bar & catered buffet. Private entrance and restrooms. Free bag of beads to toss to the crowd below! Tickets $200. Only 150 tickets available starting 10/1 at the New Orleans House, 724 Duval St. 305-293-9800
6pm BEST PARADE VIEWING AT THE HARD ROCK CAFÉ , 313 DUVAL – For priority seating contact Kelly at keywest.gm@hardrock.com or 305-293-0230
6pm FANTASY FEST PARADE GRAND BALCONY VIEWING PARTY – Open Bar, Light Hors d ’Oeuvres and beads to throw. 801 Bourbon Bar – 801 Duval St. 305-294-4737
7pm BUD LIGHT FANTASY FEST PARADE – Duval Street Parade features glittering floats, spectacular costumes and dazzling dancing groups! FREE
SUNDAY, OCTOBER 30, 2022
12pm -5 pm CHILDREN’S DAY – A family event featuring food, rides, games, arts & crafts and a costume contest for children located at Bayview Park, Truman Ave & Eisenhower Dr. 305-292-8912
2pm – 5pm HANGOVER REHAB POOL PARTY AT THE MARKER KEY WEST HARBOR RESORT – Dulce Vida Tequila and Booze Bandage to the rescue! Food & drink specials, live music and free Booze Bandages for the first 50 guests! 200 William St. 855-485-9291 FREE!
4pm – 8pm “THE FAT LADY SINGS” TEA DANCE at LA TE DA – DJ Rude Girl provides the music for the very last hoorah! 1125 Duval St. 305-296-6706 $5

Reef Relief Under-The-Sea Party
2022-10-24 12:00 - 18:00 | Dante’s Key West, 955 Caroline Street, Key West, FL, 33040, United States
Reef Relief will be hosting an “Under the Sea Party” fundraiser at Dante’s Key West Pool Bar and Restaurant sponsored by Ocean Vodka, on Monday, October 24 from 12:00 PM- 6:00 PM.
The Under the Sea Party will host a DJ playing great tunes, various raffle prizes, and most importantly a costume contest.
The attendee with the best ocean themed costume will be voted by party guests and will win a prize. Prizes can include alcohol, restaurant, and bar gift cards, IV hydration treatments, and even gift cards to local transportation companies! Proceeds from this event will benefit Reef Relief to help fund our various programs geared towards ocean conservation education and outreach.
Come have a great time, party by the pool, wear your best costume, listen to great music, all while helping support coral reef conservation or visit the Reef Relief Facebook event page. The location is at 951 Caroline Street, Key West, Florida. Must be 21 or older to participate.
Call 305-294-3100 or email reefrelief@gmail.com with any questions.
Contact: Dora DeMaria, Education Director
Reef Relief 305-294-3100
reefrelief@gmail.com

Wharfstock at Schooner Wharf Bar - Key West Historic Seaport
2022-10-26 15:00 - 19:30 | Schooner Wharf Bar, 202 William St, Key West, FL, 33040, United States
7pm WHARFSTOCK AT THE SCHOONER WHARF BAR – Peace and Love Woodstock-style!
Prizes for sexiest Hippie Chick and Grooviest Dude — judging at 8:30 PM. Live music from Raven Cooper and the Hippies, cold drinks & great galley fare. Cash & prizes to the winners! 202 William St. 305-292-9520. NO COVER!
Tune in and drop IN for our annual transformation to Wharfstock! Join us for a week of peace, love, and music–Woodstock style! We will be getting groovy with tie-dye and flower power fun on Wednesday, October 26th for Costume Night at Schooner Wharf Bar.
Hippie chicks and groovy dudes don your bell bottoms, love beads, headbands & join in. Groove to live music by Raven Cooper and The Hippies, a group of local peace-lovin’ musicians, reaching back in time for favorites by Woodstock legends. The fun starts at 7:00 p.m.
Enter our Annual Walk On Costume Competition October 29 after the Parade Saturday, October 29. Costumes eligible. No cover No entry fee
We will be decorated all week with our Wharfstock vibe! So drop in to the scene and step back in time — wear your favorite tie-dye and tune in for amazing music, psychedelic décor, cold drinks and great food. Schooner Wharf Bar, 202 William St. For more information, call (305) 292-9520 or visit Schoonerwharf.com or Facebook.

Lighting of the 2022 Harbor Walk of Lights at Key West Historic Seaport
2022-11-23 17:00 - 22:00 | Harbor Walk of Lights – 16′ Nautical Christmas Tree at the foot of Williams St.
LOCATION: The Harbor Walk plaza at Greene and Elizabeth St. for the best view. Enjoy creative holiday displays and thousands of lights honoring Key West’s maritime history.
The Key West “Harbor Walk of Lights” traditional main features will light up that night, including the 20’ Fishing Buoy Tree, a 16’ Nautical Christmas Tree and the original Key West Lobster Trap Tree.
Walk along the water’s edge for a merry infusion of colorful lights and nautical holiday displays. See light sculptures of ship’s anchors, tropical birds, tropical fish, a flock of pink flamingos, jolly pelicans, merry manatees, animated sea turtles and dancing dolphins, and even a festive moray eel, all under brightly lit holiday palm trees!
And with thousands of ADDITIONAL lights this year around the Historic Seaport, the 2022 Key West “Harbor Walk of Lights” is promised to be a real holiday treat!

2022 Pet Pictures with Santa™ – Hosted by The All Animal Clinic
2022-12-04 | Harbor Walk of Lights – 16′ Nautical Christmas Tree at the foot of Williams St.
2022 Pet Pictures with Santa™ – Hosted by The All Animal Clinic
Professional photos by Mary Martin
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 Rob O’Neal.
Professional high resolution photos are $20 (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

2022 Annual Tree Trimming and Toys for Tots and Angels Just 4 Kids Drive
2022-12-05 18:00 - 23:30 | Schooner Wharf Bar, 202 William St, Key West, FL, 33040, United States
Annual Tree Trimming and Toys for Tots and Angels Just 4 Kids Drive
Rock Around Our Christmas Tree! Schooner Wharf Bar Tree Trimming Party is Sunday, Dec. 4th starting at 6:00 p.m.
Schooner Wharf Bar will share warm season’s greetings and plenty of holiday “spirits” at its annual Tree Trimming Party and toy drive beginning at 6 p.m. on Sunday, Dec. 5th.
Maritime merry makers will deck the halls and make dreams come true at the popular waterfront winter wonderland. Ornaments will be entered in a contest and prizes will be awarded
for the Most Original, Most Nautical and 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.
Share the holiday spirit and visit our Mercantile Shop for holiday gift giving and you can also get photographer Rob O’Neal’s 2021 calendar here!
Twenty-two years ago the Schooner Wharf Breakfast Club initiated a Toy Drive on Tree Trimming Day, benefiting Toys for Tots, Angels–Just for Kids and Boys and Girls Club of the
Florida Keys. Each of Santa’s helpers who donates an unwrapped gift to one (or all!) of these worthwhile causes will also receive a free holiday drink from Schooner Wharf Bar.
Favorite local musicians will be playing Holiday Tunes, Reggae, Classic and Current favorites with the island sound of to round out the festivities. Come make our tree yours! Happy Holidays from the crew of Schooner Wharf Bar and Galley!
For more information, call (305) 292-9520 or visit Schoonerwharf.com or like them on Facebook.

31st Annual Schooner Wharf Bar Lighted Boat Parade
2022-12-10 20:00 - 23:30 | Key West Historic Seaport
31st Annual Schooner Wharf Lighted Boat Parade 2022
Mistletoe goes on the mast and running lights will twinkle in the appropriate red and green holiday colors for the 31st Annual Schooner Wharf Bar & Galley Lighted Boat Parade, Saturday, December 10th. The parade begins at 8:00 p.m. but the festivities start early on the Harbor Walk of Lights Bight Before Christmas Celebration. The elementary students with the Bahama Village Steel Pan Band entertain with calypso Christmas music at 6:00 pm. Followed by a group of the island’s favorite musicians playing classic holiday tunes mixed with contemporary songs and classics.
The community family-friendly parade begins in the Historic Seaport and makes a close pass in front of Schooner Wharf Bar and the judge’s stand for the best view of our creative mariner’s efforts. The variety is amazing and endless as dolphins and other aquatic creatures leap out of the sea to dazzle us all. Past years have had Huge Conch Shells, Candy Canes, Grinch’s, Messages of Peace on Earth and Support Our Troops, Sea Monsters, as well as Santa’s sleigh pulled by dolphins. Vessels range from classic Schooners with Christmas trees on the mast, small fishing vessels with dancing seahorses, to kayaks and dinghies decked out in their holiday best!
Dinghies, kayaks, ships and schooners all are eligible to share in Key West’s version of Christmas and to compete for boatloads of prizes with a FREE RAFFLE for all participating boats. Adding to the Wonderland excitement are multi-screens showcasing the dazzling display of the island’s imaginative boaters and their ingenuity in past parades on the Harborwalk, the sails of tall ships and in Schooner Wharf nightly.
The Harbor Walk of Lights becomes the island’s holiday headquarters, and the parade is a must- see event in Key West, where we don’t need snow to make our holidays bright. Join the fun of
this awesome show of lights and creativity brought to you by Schooner Wharf Bar & Galley and the island’s imaginative and resourceful holiday spirited mariners.
For more info, call 305-292-9520 or visit www.SchoonerWharf.com and or www.KeyWestChristmas.org. To enter your boat call or stop by Schooner Wharf Bar.

Reef Relief Winter Party Fundraiser
2022-12-17 13:00 - 15:00 | Hyatt Centric Key West, 601 Front Street, Key West, FL, 33040, United States
HYATT CENTRIC KEY WEST RINGS IN THE HOLIDAY SEASON WITH
WINTER BEACH PARTY BENEFITTING REEF RELIEF
100% of the proceeds from the event’s raffle will aid in Reef Relief’s mission of improving and protecting Key West’s coral reef ecosystem.
There’s a 100% chance of snow in Key West this holiday season as the Hyatt Centric Resort & Spa announces its can’t-miss wintertime bash benefitting Reef Relief. Locals and tourists alike will enjoy spirited festivities including handcrafted cocktails, live music, a snow machine, raffles, and an appearance from Santa, amongst a backdrop of unforgettable oceanfront views. The featured holiday cocktails will include Homemade Eggnog, Boozy Snow Cones and Peppermint Espresso Martinis made with local Keys Coffee.
100% of the proceeds from the raffle will benefit Reef Relief, a nonprofit membership organization in Key West focused on the rigorous science to understand, educate, and strengthen community-based efforts and strategies to protect the coral reef ecosystems. “We are so excited to celebrate the most wonderful time of the year at the Hyatt Centric.
We encourage everyone to come join us and help support Reef Relief. Proceeds from the raffle will directly fund our 2023 programs,” said Reef Relief Education Director Dora DeMaria. The winter holiday parties will be held on Saturday, December 17, and Saturday, December 24, from 1pm to 3pm at Blue Mojito Bar and Grill located at 601 Front St.
About Reef Relief
Reef Relief improves and protects our coral reef ecosystem through education, advocacy, and
grassroots community efforts. They have a wide variety of programs educating the public about
coral reefs and encouraging community action, including school programs, their Coral Camp for
kids, organized clean-ups, stenciling storm drains to discourage dumping, as well as policy work
with their straw and sunscreen campaigns. To learn more about Reef Relief visit reefrelief.org.
For more information, contact:
Baily Floyd | Bais Creative & Public Relations
E: Bailey@baiscreative.com
C: 863-266-7277

Ring in 2023 - New Years Eve Celebration at Schooner Wharf
2022-12-31 11:30 - 2023-01-01 02:00 | Schooner Wharf Bar, 202 William St, Key West, FL, 33040, United States
Celebrate with Schooner Wharf this New Year’s Eve for our annual original tradition of The Lowering of the Pirate Wench! Evalena will once again descend from the towering mast of America 2.0 to welcome in the new year with all you!
The festivities start at early with 15 hours of live music starting with Michael McCloud at 11:30am, followed by a popular local band soon to be announced.
Headliners are brought back from Chicago by popular demand, it’s the eclectic and energetic Sushi Roll, who will bring you dancin’ well into the new year!
Featuring live music, party favors, champagne, cannon blasts and a dramatic descent into 2023 at the Key West Historic Seaport!

17th Annual Florida Keys Seafood Festival
2023-01-14 - 2023-01-15 | Bayview Park, 1400 Truman Avenue, Key West, 33040
17th Annual Florida Keys Seafood Festival – January 14-15, 2023
The 17th Annual Florida Keys Seafood Festival is Saturday, January 14th from 11:00 a.m. to 8:00 p.m. AND Sunday, January 15th from 11:00 a.m. to 5:00 p.m., at Bayview Park, Key West.

There is a $10 admission charge per person for adults, good for both days, which enters that person into a raffle for $250 worth of seafood. Children under 12 are admitted free! Proceeds benefit sustainable fisheries management programs and youth scholarships.
Learn more and check out the entertainment schedule at https://www.floridakeysseafoodfestival.com/
ASSOCIATION: 305-743-0294 | FESTIVAL DIRECTOR: 305-619-0039

Email: flkeysseafoodfestival@gmail.com
PO Box 501404 | Marathon, FL 33050-1404

The Southernmost Regatta powered by Sailing Inc.
2023-01-16 - 2023-01-20
The Southernmost Regatta offers 5 consecutive days of high-quality racing on the picturesque blue waters of Key West, FL. The event is open to One Design and ORC Racing / Cruising Keelboats.
Their plan is to provide a two races a day on two course, a One Design Course and an ORC Course. They will also offer one distance race a day for ORC cruisers.
For more information, contact Regatta Chairman: Martin Kullman at martin.kullman@thesailinginc.com or (727) 560-0164.

#MeetUsatMile0

Please call (305) 294-1124 to pre-register well in advance of your arrival to Key West. Official paperwork must be completed by the owner of the vessel and payment received prior to launch.
Located on Stock Island at 7281 Shrimp Road, Robbie’s is just minutes from downtown Key West and the Key West International Airport in the heart of Key West’s commercial maritime district. Robbie’s is a full service commercial waterfront marina consisting of nearly 25 land and water based acres with Ocean-side deep water access that will accommodate some of the largest commercial vessels and motor yachts.

Annual Schooner Wharf Knot & Shot Contest 2023
2023-01-18 - 2023-01-20
Annual Schooner Wharf Knot & Shot Contest 2023

Get “Tied Up” at Schooner Wharf Bar Wednesday, January 18th , Thursday, January 19th and Friday, January 20th!
Key West wouldn’t be Key West without sailors, rum and ropes at Schooner Wharf. Watch what happens when all four combine on the docks at 8 PM!
This is a unique SWB home-spun and also world-famous competition among sailors, testing the skills of drinking a shot, tying a bowline, lassoing a piling, and drinking a beer. Lots of fun to be
in and to watch! Last year’s champion was Sean Pierson with a time of 00:08:28.
For more information, please call (305) 292-9520 or visit https://SchoonerWharf.com/23knot.htm.
Come tie one on!

2023 Key West Food and Wine Festival
2023-01-25 - 2023-01-29
Save the Date! January 25-29, 2023
Key West Food and Wine Festival – 1075 Duval Street, Key West, Florida 33040, United States

Did you know? The Key West Food & Wine Fest was named #1 Best Wine Fest in 2022!
Purchase tickets here: https://keywestfoodandwinefestival.com/buy-tickets-now
Questions? Contact Dolce Events & Marketing | Email: dolce@dolceeventsandmarketing.com

2023 Original Painting by Carrie Disrud

2023 Annual Schooner Wharf Bar Wrecker’s Cup Race Series
2023-01-29 13:00 - 17:00 | Schooner Wharf Bar, 202 William St, Key West, FL, 33040, United States
The much anticipated first race of the Schooner Wharf Bar Wrecker’s Cup Race Series is scheduled for Sunday, January 29 at 1:00 p.m. The course is 7 miles from Key West Harbor to Sand Key, re-enacting the ancient wrecking tradition of Key West…a series of ruthless one way races to the reef to claim the booty.

Get Your Heart on 5K to Benefit Reef Relief
2023-02-11 08:00 - 11:00 | 1327 Duval St Key West, FL US 33040
Grab your favorite partner and get your heart thumping at this year’s Get Your Heart On 5k presented by Southernmost Point Bar, Feb. 11 at 8 a.m. Costumes are encouraged in this run to support Reef Relief.
There’s more than one way to break a sweat this Valentine’s! Grab your favorite partner and get your heart thumping at this years Get Your Heart On 5K presented by Southernmost Point Bar, February 11, 2023, at 8 AM. Come hard, grab your medal, and finish strong at our post race after party! All participants 21+ will receive one free Mimosa or Tito’s Bloody Mary. Clothing optional – not quite – but costumes are encourage to heighten the race experience!
The race starts at 8 a.m. at 1327 Duval Street.
$34.99 to sign up, and there is a virtual option as well! For more information, visit https://runsignup.com/Race/FL/KeyWest/GetYourHeartOn5K

23rd Annual Schooner Wharf Open Air Art & Music Affair
2023-03-04 | Schooner Wharf Bar, 202 William St, Key West, FL, 33040, United States
Call To Artists: The 23 rd Annual Schooner Wharf Open Air Art & Music Affair is scheduled for Saturday, March 4th, 2023. Open to artists of all mediums, including but not limited to painting, printmaking, sculpture, drawing, carving, photography and mixed media.
A colorful waterfront setting, arts and crafts by skilled Florida Keys artisans and tunes by talented local and visiting musicians are top attractions at the Annual Schooner Wharf Open Air Art & Music Affair. The event is set for 9:30 to midnight, Saturday, March 4th, in Key West’s Historic Seaport.
This eclectic festival highlights the creative talents of the free-spirited artists of Key West. The Old-Town Historic Seaport provides the perfect backdrop, with the traditional tall ships along the boardwalk, and the ocean breeze wafting through Schooner Wharf Bar, “A last little piece of old Key West”.
This one of a kind show features award winning local and national artists and crafters whose work isn’t shown anywhere else. Negotiate directly with the designers, or watch as they create a custom piece for you. Enjoy many personal demonstrations of technique, including glass bead blowing, jewelry making, and painting “En plein air.”
-All original artists are encouraged to apply. Space is limited. For more information go to schoonerwharf.com/23artaffair.htm.
-For applications or questions, stop in for a cold one or send e-mail to swartaffair@yahoo.com , or call Capt. Carl at (305) 304-2275.

41st Annual Conch Republic Independence Celebration
2023-04-21 - 2023-04-30
41st Annual Conch Republic Independence Celebration

MORE DETAILS COMING SOON! :-)
The Conch Republic was born on April 23, 1982, in response to a United States Border Patrol Blockade of the Florida Keys. Since the United States insisted on treating the Keys like a foreign country, Mayor Dennis Wardlow seceded from Union. Today we stand proudly as a community of who have “Sovereign State Of Mind” and as the “People who seceded where others have failed.”

Questions? Feel free to contact them at Office.of.the.Conch.Republic@gmail.com or call (305) 304-2400 or visit their website at https://conchrepublic.com/.

41st Annual Schooner Wharf Kick Off Party - Conch Republic Independence Celebration
2023-04-21 19:00 - 23:30 | Schooner Wharf Bar, 202 William St, Key West, FL, 33040, United States
KICK-OFF PARTY AND CONCH SHELL BLOWING CONTEST
PARTY HEADQUARTERS of the CONCH REPUBLIC INDEPENDENCE CELEBRATION!

Schooner Wharf Kick-Off Party is the start of the Conch Republic Independence Celebration on Friday, April 21st! The festivities kick off at 7 p.m. with the popular local Myles Mancuso Band. Their original style of music is a unique blend of Roots Americana and R&B. Truly a musical experience you don’t want to miss! Definitely bring your dancing shoes!
Listen to how it all happened! Conch Republic Prime Minister Dennis Wardlow will be on stage recounting the story of the events that led to our secession, as can only be told by the mayor who spearheaded our secession in 1982! We seceded from the United States, surrendered, and demanded foreign aid (we are still waiting on that!)
There will be a special presentation to longtime local performer/songwriter and Schooner Wharf staple Michael McCloud. Our Prime Minister and Secretary General of the State of the Conch Republic, Captain James R. Gilleran will honor Michael as the Official Troubadour of the Conch Republic.
Compete in the Annual Schooner Wharf Conch Shell Blowing Contest, there is no entry fee – anyone can enter. Bring your own conch shell or one will be provided, with 1st, 2nd, and 3rd Place Prizes for the longest, loudest and most musical blow. Prizes are Water adventures, bottles of rum, Schooner Wharf Bar tabs, tees and caps, Conch Republic flags, etc. “We succeeded where others failed!” Long Live the Conch Republic!

Schooner Wharf Entertainment Schedule May 3-9, 2023
2023-05-03 - 2023-05-09
SCHOONER WHARF ENTERTAINMENT
May 3 – May 9, 2023
Raven Cooper
Wednesday, May 3 – 7:00 – 11:00 pm
Monday, May 8 – Noon – 5:00 pm
Talented and charismatic entertainer/singer with a five-octave range.
*****
Tony Baltimore
Wednesday, May 3- Noon – 5:00 pm
Classic rock, funk, pop and originals. A great acoustic show!
*****
Thursday – all day: Songwriters Showcase
*****
Tony Baltimore
Friday, May 5 – Noon – 5:00 pm
Classic rock, funk, pop and originals. A great acoustic show!
*****
Rolando Rojas Duo
Friday, May 5 – 7:00-11:30 pm
R&B, funk, soul and reggae.
*****
Kristen Kearns Duo
Saturday, May 6 – Noon-5:00 pm
A great acoustic show with oldies and current favorites
*****
Raven Cooper Band
Saturday, May 6 – 7:00 – 11:00 pm
Talented and charismatic entertainer/singer with a five-octave range.
*****
Jillian Todd
Sunday, May 7 – Noon – 5:00 pm
Solo acoustic guitar with a rich, vibrant voice covering oldies favorites
*****
Christopher Dean Duo
Sunday, May 7 – 7:00 pm – 11:00 pm
A great diverse band playing jazz, folk, country, r&b and pop
*****
Joe the Show
Monday, May 8- 7:00 – 11:00 pm
Entertainer with great showmanship with current and classic favorites
****
Jillian Todd
Tuesday, May 9- Noon – 5:00 pm
Acoustic guitar, Americana and oldies.
*****
Jesse Wagner
Tuesday, May 9 – 7:00 – 11:00 pm
Great acoustic artist covering jam bands and oldies favorites
*****Frank Everhart Jr. Wednesday thru Sunday for up close and personal magic – 7 pm

Annual Schooner Wharf Minimal Regatta
2023-05-28 13:00 - 21:00 | Schooner Wharf Bar, 202 William St, Key West, FL, 33040, United States
Annual Schooner Wharf Minimal Regatta
May 28, 2023
Pick up your entry form at Schooner Wharf Bar today!
To register and pay online, please click here

Calling All Ship Wrights
Minimal Regatta Construction Rules
1. One sheet of 4′ x 8′ x 1/4″ plywood
2. Two 2″x 4″ 8′
3. One pound of fasteners
4. One roll of 2″ x 60 yard duct tape
5. No caulking or adhesives – Epoxy paint is permitted
6. Painting of boats is optional
7. Oars/Paddles must be made out of these materials
There are two categories of “Minimal Vessels” Kayak/Canoe Design & Open Design
Competitors will win prizes in each design group for Fastest – 1st, 2nd & 3rd Place, Most Creative Designs – 1st & 2nd Place, Best Paint Jobs, Best Costumed Entries, Sportsmanship Awards, and Sinker Awards
The $20 entry fee will benefit our local VFW Post 3911 Veteran’s Relief fund for Monroe County.
Boats made of thin plywood and duct tape don’t sound very seaworthy, but they’re the only vessels allowed in the 31st annual Schooner Wharf Minimal Regatta, expected to provide maximum merriment for spectators Sunday, May 28.
The wacky Memorial Day Weekend regatta takes place off the Schooner Wharf Bar, 202 William St., in the Key West Historic Seaport. A vessel inspection is set for 12:30 p.m. Sunday, with the first heat around 1:30 p.m.
Each team can use only the most minimal materials to build its boat — just a single sheet of 4-by-8-foot plywood, two 8-foot-long two-by-fours, a roll of duct tape and a pound of fasteners. Calking and adhesives are forbidden, though epoxy paint is permitted.
Teams are charged with keeping their homemade craft afloat long enough to complete a short course. Up to six members are allowed per team, and at least one “designated passenger” must crew the vessel throughout the regatta.
Costumes and themed entries are encouraged, and many boats end up being more scenic than seaworthy. Entries in past regattas have included alligators, spaceships, guitars, wine bottles and replicas of schooners, shrimp boats, pirate vessels and paddle boats! Costumes have ranged from the crew of Gilligan’s Island, the Adams family, Spock and Star Trek, Batman & the Joker, Barbie and her Dream House, Banana Splits and Red Hot Chili Peppers and Popeye!
Multiple prizes are to be awarded in categories including fastest boat, most creative designs, best paint jobs, sportsmanship and best costumed entries. In addition, organizers plan to present the disheartening “sinker” awards to the hapless teams unable to stay above water.
As well as regatta action, Schooner Wharf Bar also plans to host its traditional Memorial Day weekend barbecue. Ya Gotta Regatta!
Event information: 305-292-9520

Key West Pride 2023
2023-06-07 - 2023-06-11
Celebrate PRIDE on a tropical island that is legendary for its laid-back style and its open and accepting atmosphere. Whether you’re looking to party with friends, travel with family, or get lost in the magic of our tropical island, rediscover Key West and discover how one island’s One Human Family philosophy has created one of the most integrated and unique communities in the world. Show us your pride, we will show you our Key West Pride!
ALL EVENTS ARE 21 YEARS OF AGE AND UP UNLESS NOTED OTHERWISE

Daily Activities

Museums: Key West Butterfly Conservatory, Little White House, Key West Aquarium, Mel Fisher Maritime Museum, Key West Firehouse Museum, Key West Light House, Key West Ship Wreck Museum, Audubon House, Oldest House, and Garden Museum, USCGC Ingham Museum, Tennessee Williams Museum, Hemingway House
Land Activities: Key West Food Tours, Fort Zachary State Park, West Martello Tower, A & M Scooter Rental, KW Tropical Forest and Botanical Garden, Key West Cemetery, Key West Adventures, Papa’s Pilar Rum Distillery, Ghost Hunt, Old Town Trolley Tours, Conch Tour Train, Haunted Key West, Ghosts and Mysteries, Ghosts and Gravestones, D’vine Wine Gallery, Key West Wildlife Center, Key Lime Bike Tour
Water Activities: Blu Q, Classic Harbor Lines, Cruisin’ Tikis, Danger Charters, Fish N Chicks, Fury, Island Vibe Charters, Java Cat, Jolly Rover II, Key West Eco Tours, Key West Sailing Center, Key West Snorkeling. Land Boat Charters, Off the Charts, Schooner America, Sunset Sail Key West, Sunset Watersports, SV Argo Navis, Yankee Freedom III

For the full schedule of events, visit https://gaykeywestfl.com/pride/!

Key Lime Festival 2023
2023-06-30 - 2023-07-04
Welcome to the Key Lime Festival: America’s Favorite Citrus Celebration! In the Florida Keys, they like to celebrate the things that make our islands unique. Citrus, eccentrics, people & pie. The celebrations are fun, odd & unforgettable, so come on down to the birthplace of Key Lime Pie for a little taste and you’ll see what they mean. Love & Limes!
2023 is shaping up to be the best Key Lime Festival yet. With fuve days of culinary events for every taste, including favorites from past years like the Key Lime Cocktail Sip & Stroll and Key Lime Pie Hop and new favorites for Key Lime lovers! They’ve also added a few intimate culinary events for their VIP Key Lime lovers!
Most of the events will sell out, so make sure to get your tickets and stay up to date on how to register for any and all of the 2023 events!
305-295-9112 | keylimefest@gmail.com

Mel Fisher Days 2023
2023-07-15 16:00 - 23:59 | Schooner Wharf Bar, 202 William St, Key West, FL, 33040, United States
ALL NET PROFITS OF THESE EVENTS GO TO CHARITIES: Michael Abt Jr. Have a Heart Foundation and Wesley House Family Services

Location: Schooner Wharf at Historic Key West Seaport

Date: Saturday, July 15, 2023

Time: 4pm until ??

– Mel Fisher’s Crew Reunion at Schooner Wharf- meet and exchange scuttlebutt with current and past crew members

– X Marks the Spot – Treasure Cupcakes- win Authentic Treasure if you get the lucky cupcake

– 50/50 raffle – You never know, you could be the lucky winner of Big Booty

– Live Music

– Mel Fisher Lifetime Achievement Award Presentation- top secret winner

– Mel Fisher Trivia

– Live onstage auctions

– Huge Silent Auction . ONLINE ONLY CLICK HERE TO VIEW AUCTION (June 15 thru Midnight July 15)

– Author Author- Book signing of the newly published Today’s the Day – The Mel Fisher Story; by Mel Fisher with Wendy Tucker

Select Event T Shirts, Books, and Cupcakes available for purchase at the Event.

ALL NET PROFITS OF THESE EVENTS GO TO CHARITIES

Michael Abt Jr. Have a Heart Foundation and Wesley House Family Services

2023 Hemingway Days
2023-07-18 - 2023-07-23
Hemingway Days to Honor Ernest in Key West July 18-23, 2023
Ernest Hemingway look-alikes, writers, anglers, and fans of the late author’s work are to gather in Key West Tuesday through Sunday, July 18-23, 2023, for the annual Hemingway Days celebration. The festival honors the legacy of the American literary giant who lived and wrote on the island for most of the 1930s.
Scores of stocky, bearded men resembling Ernest are to compete in the annual Hemingway® Look-Alike Contest at Sloppy Joe’s Bar, 201 Duval St., a frequent hangout for the legendary writer during his Key West years.
Other festival events include prose and poetry readings, the wacky “Running of the Bulls,” presentations on Ernest and his influence, a commemoration of the 124th anniversary of his July 21 birth, a museum exhibit of rare Hemingway memorabilia, a three-day marlin tournament recalling his passion for deep-sea angling, a street fair celebrating Key West’s lively spirit, a 5k run and paddleboard race that salute Hemingway’s sporting interests, a walking tour, and the announcement of the winner of the Lorian Hemingway Short Story Competition coordinated by Ernest’s author granddaughter.
Ernest Hemingway wrote many of his best-known works in the second-story studio that adjoins his former Key West home — now a museum — at 907 Whitehead St. Among them were “Death in the Afternoon,” “For Whom the Bell Tolls,” “The Snows of Kilimanjaro” and “The Short Happy Life of Francis Macomber.” Hemingway even used Depression-era Key West as the setting for his widely acclaimed novel “To Have and Have Not.”
Both his literary prowess and his exuberant Key West lifestyle are commemorated during Hemingway Days.

Key West BrewFest
2023-08-31 - 2023-09-04
Beer-pairing Dinners, Pool Parties, Bingo, a Belly Flop Contest, and of course, the Signature Event featuring specialty beers, held on Saturday, September 2, 2023!
Tickets on Sale Now!
Thursday, August 31, 2023

5pm – 9pm Havana Cabana Throwback Thursday Kick-Off Pool Party with Vera Cruz

Friday, September 1, 2023:

1 pm – 4 pm – Southernmost Beach Resort: Pineapple Pool Party & Belly Flop Contest, Sponsored by Islamorada Brewery & Distillery
7 pm – Southernmost Beach Resort – FIVE STATION BEER Pairing Dinner with FL Keys Brewing Co.! – Tickets here.

Saturday, September 2, 2023:

BrewFest Signature Tasting Festival at South Beach

3 pm – 5 pm – VIP Hours (Tickets $100)
5 pm – 8 pm – General Admission (Tickets $45)

Sunday, September 3, 2023:

1 pm – 4 pm The Marker – Reggae Rehab Pool Party with Channel 3 and South Beach Brewing.
1pm – 4pm – Ocean’s Edge – Pool Party with Waterfront Brewery
6 pm – Matt’s Stock Island Kitchen & Bar – Beer Pairing Dinner with Cayo Hueso Brewing Co.

Monday, September 4, 2023

7 pm The Green Parrot – Bingo! with lots of beer prizes!

Womenfest Key West 2023
2023-09-06 - 2023-09-10
For decades, Key West’s Womenfest (5-day celebration) has attracted thousands of lesbians, transwomen, and allies to what is arguably the premier LGBTQ+ vacation destination in the country. Womenfest has a simple goal: to celebrate ALL women! Key West Womenfest offers a wide range of activities for those who want to socialize, feel comfortable being themselves, soak up some sun, then party and dance the night away. Since its introduction over 20 years ago, Key West Womenfest has grown to become a standard for celebrating women ranging from all ages 21 and over. Couples, singles, and those in between are all welcome! Join them annually in September to immerse yourself in what is dubbed the HOTTEST party for women in the Florida Keys!

Daily Activities

Museums: Ernest Hemingway, Key West Butterfly Conservatory, Little White House, Key West Aquarium, Mel Fisher Maritime Museum, Key West Firehouse Museum, Key West Light House, Key West Ship Wreck Museum, Audubon House, Oldest House and Garden Museum, USCGC Ingham Museum, Tennessee Williams Exhibit.
Land Activities: Key West Food Tours, Up the Keys Eco Tour, Fort Zachary State Park, West Martello Tower, A & M Scooter Rental, Key West Tropical Forest and Botanical Garden, Key West Cemetery, Key West Adventures, Papa’s Pilar Rum Distillery, Ghost Hunt, Old Town Trolley Tours, Conch Tour Train, Haunted Key West, Ghosts and Mysteries, Ghosts and Gravestones, D’vine Wine Gallery, Perky’s Key West Excursions.
Water Activities: Argo Navis, Blu Q, Classic Harbor Lines, Cruisin’ Tikis, Danger Charters, Fish N Chicks, Fury, Island Vibe Charters, Island Vibe Charters, Java Cat, Jolly Rover II, Key West Eco Tours, Key West Sailing Center, Key West Snorkeling. Land Boat Charters, Off the Charts, Schooner America, Sunset Sail Key West, Sunset Watersports, SV Argo Navis, Yankee Freedom.
For more information, visit https://gaykeywestfl.com/womenfest/.

Key West Fantasy Celebration
2023-10-20 - 2023-10-29
Fantasy Celebration
Oct. 20-29 – details coming soon
Live Music, Cold Libations, Great Food, & Old and New Friends. Schooner Wharfstock ï¿½ Tune In, Turn On & Drop In!

The Harbor Walk of Lights 2023
2023-11-22 - 2023-12-31 | Harbor Walk of Lights – 16′ Nautical Christmas Tree at the foot of Williams St.
The “Harbor Walk of Lights” stretches along the seawall past Greene, William and Margaret Streets to the Key West Ferry Terminal. A nautical theme honors the maritime history of the Key West waterfront. The harbor walk area in the Historic Seaport glimmers with holiday displays throughout the season, all themed to celebrate the island city’s maritime heritage. Elements include tens of thousands of lights, dozens of lighted palm trees, a lobster trap holiday tree, a nautically decorated pine and a tree adorned with fishing buoys that resemble giant ornaments.

Lighting of the Bight: Key West Harbor Walk of Lights 2023
2023-11-22 18:00 - 23:00 | Harbor Walk plaza, Green and Elizabeth St, Key West, FL 33040
Gather on the Harbor Walk plaza at Greene and Elizabeth St. to best see the official lighting of the 2023 Key West “Harbor Walk of Lights” with lights and creative displays reflecting the “Maritime History of Key West.” The Key West “Harbor Walk of Lights” stays lit nightly through New Year’s Eve, stretching along the Key West Historic Seaport and Key West Bight Marina.

Wednesday, Nov. 22 – Free
The Lighting of the 2023 “Harbor Walk of Lights”
Lights come on at 6:00pm, holiday music starts at 5:00pm
This year featuring a SPECIAL Holiday display as a heartfelt salute to Jimmy Buffett!
LOCATION: The Harbor Walk plaza at Greene and Elizabeth St. for the best view. Enjoy creative holiday displays and thousands of lights honoring the “Maritime History of Key West”.
The Key West “Harbor Walk of Lights” traditional main features will light up that night, including the 20’ Fishing Buoy Tree, a 16’ Nautical Christmas Tree and the original Key West Lobster Trap Tree.
The official lighting is at 6pm, but at 5pm classic holiday music will start to fill the air. And for this SPECIAL year, Holiday music from Jimmy Buffett’s 2 Christmas albums will be mixed in with the traditional Christmas classics.
Stroll along the water’s edge for a merry infusion of colorful lights and nautical holiday displays. See light sculptures of ship’s anchors, tropical birds, tropical fish, a flock of pink flamingos, jolly pelicans, merry manatees, animated sea turtles and dancing dolphins, and even a festive moray eel, all under brightly lit holiday palm trees!
And with 3 blocks of sparkling holiday lights and displays around the Key West Bight Marina and Historic Seaport, the 2023 Key West “Harbor Walk of Lights” is destined to bring miles of holiday smiles to our One Human Family of visitors and locals alike.
