Key West Historic Seaport

Schooner Wharf Bar 2025 Tree Trimming Party and Toy Drive
2025-12-07 18:00 - 21:00 (America/New_York)
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.

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!

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.

Bight Before Christmas Lighting of The Bight: Key West Harbor Walk of Lights 2025
2025-11-26 17:00 - 23:00 | 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.

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!

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 →

Just a Few Friends Key West 2025
2025-08-29 - 2025-09-01
Just a Few Friends Key West 2025
August 29 – September 1, 2025
A four-day island celebration honoring Jimmy Buffett’s legacy with live music, food, fun, and unforgettable experiences in Key West.

Come to Key West for Labor Day weekend to celebrate the 2nd Annual Just a Few Friends memorial, honoring our favorite son, the late Jimmy Buffett. Festivities kick off with an official pre-party meetup on Thursday, August 28. On Friday morning the City of Key West will proclaim “State of Florida Jimmy Buffett Day,” followed by activities on and off the water, foodie events, and great times. Saturday features a run/walk, the Margarita Bar Crawl, along with tours, lectures, rum tastings, and music events across town. Sunday’s highlight is the epic Second Line Parade starting at 5 p.m. culminating in a free music festival at Truman Waterfront Park with local and national entertainment, food trucks and vendors. The events concludes with a Come Monday celebration with a variety of activities and entertainment options to suit every interest.

Check out the full event schedule here: https://www.justafewfriendskeywest.com/schedule-at-a-glance

Taste of The Keys
2025-08-22
Taste the Keys is a month-long culinary celebration running October 1–31, showcasing delicious cuisine from some of the best restaurants in the Florida Keys. Enjoy special menus, unique flavors, and the chance to explore the Keys’ local spots!

Key West Pride 2025
2025-06-22 - 2025-06-29
KEY WEST PRIDE 2025! SPONSORED IN PART BY
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!

For more information:
Address: 808 Duval Street
Key West, FL 33040
Phone: 800-535-7797 | 305-294-4603

2025 Schooner Wharf Bar Minimal Regatta
2025-05-25 13:00 - 17:00
2025 Schooner Wharf Bar Minimal Regatta

Calling All Ship Wrights! Sunday, May 25, 2025
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 American Legion Post 28. Boats made of thin plywood and duct tape don’t sound very seaworthy, but they’re the only vessels allowed in the 33rd annual Schooner Wharf Minimal Regatta, expected to provide maximum merriment for spectators Sunday, May 26.
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
Register in person at Schooner Wharf Bar or online at https://schoonerwharf.com

Key West Songwriters Festival 2025
2025-04-30 - 2025-05-04
The Key West Songwriters Festival is the largest festival of its kind in the world, and known as a career starter for top country talent. The festival has kicked off the careers of household names such as Kacey Musgraves, Florida Georgia Line, Jake Owen, Michael Ray, Randy Houser and Maren Morris.
In its 29th year, KWSF has grown into a top destination for music lovers who flock to Key West for five days and nights of live music and storytelling from veteran songwriters and the next big hit-makers!

For more information, email marketing@ramsheadgroup.com or visit https://keywestsongwritersfestival.com!

43rd Annual Conch Republic Independence Celebration
2025-04-18 - 2025-04-27
43rd Annual Conch Republic Independence Celebration

Get your tickets here!

NAS Key West Southernmost Air Spectacular March 29 and 30, 2025
2025-03-29 - 2025-03-30
The Blue Angels & other military & civilian acts will fill the skies of the Florida Keys March 29-30th, at the NAS Key West Southernmost Air Spectacular air show at Boca Chica Field.
Buy tickets and learn more: https://air.show/key-west/

2025 40th Annual Schooner Wharf Bar Wrecker’s Cup Race Series
2025-02-23 13:00 - 17:00
The 2025 40th Annual Schooner Wharf Bar Wrecker’s Cup Race Series

The 2025 40th Annual Schooner Wharf Bar Wrecker’s Cup Race Series The much anticipated Schooner Wharf Bar Wrecker’s Cup Race Series is scheduled for the last Sunday of January, February March and April, 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. This all-in-fun race series recalls the tradition of the wreckers in the Key West of the 1800’s.
Vessels laden with rich cargoes from Gulf and Caribbean ports often became victims of storm and the unmarked reefs off Key West. The first wrecker to reach the site had the responsibility to save the passengers and crew—but they also won the right to salvage the cargoes. Some historians have
written that it was not unusual for 20 or 30 boats to race to a wreck. The Captains’ Meetings are held on the upper deck of Schooner Wharf at 7:00p.m. the Saturday before each race. Captains enjoy complimentary Pusser’s Rum punch and Schooner Wharf Galley hors d’oeuvres while reviewing race procedures.
The Awards Ceremony & Party is held at 7:00 p.m. on Sunday, race day. The popular Wreckers BBQ is served to captains & crew while they view film footage taken of the race by the official race committee boat and dance to some of the best live music offered on the island.
Trophies, Pusser’s Rum and Schooner Wharf bar tabs and Wrecker’s Race tee shirts are earned by the top 3 vessels in 6 classes –schooner, multi-hull, classic, monohull and under, monohull 30-39 feet and monohull 40 feet and over. At the race start Key West harbor is a magnificent sight, filled with colorful sails and spinnakers on vessels ranging from 16 feet to 120 feet. This original nautical event is another creation of Schooner Wharf Bar owners, Evalena and Paul Worthington, and is enjoyed by visiting yachters, local private boats and Key West charter vessels. You don’t need a boat of your own to participate, book passage and crew on one of the charter boats in the Wreckers’ fleet.
2025 Race Dates are Sunday, January 26 – February 23 – March 30 and April 27.
Come join the fun. Fair Winds and Full Holds — Wreck Ashore! For information please call 292-9520 or visit SchoonerWharf.com.

2025 40th Annual Schooner Wharf Bar Wrecker’s Cup Race Series
2025-01-26
2025 40th Annual Schooner Wharf Bar Wrecker’s Cup Race Series

The much anticipated Schooner Wharf Bar Wrecker’s Cup Race Series is scheduled for the last Sunday of January, February March and April, 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. This all-in-fun race series recalls the tradition of the wreckers in the Key West of the 1800’s. Vessels laden with rich cargoes from Gulf and Caribbean ports often became victims of storm and the unmarked reefs off Key West.
The first wrecker to reach the site had the responsibility to save the passengers and crew—but they also won the right to salvage the cargoes. Some historians have written that it was not unusual for 20 or 30 boats to race to a wreck. The Captains’ Meetings are held on the upper deck of Schooner Wharf at 7:00 p.m. the Saturday before each race. Captains enjoy complimentary Pusser’s Rum punch and Schooner Wharf Galley hors d’oeuvres while reviewing race procedures. The Awards Ceremony & Party is held at 7:00 p.m. on Sunday, race day. The popular Wreckers BBQ is served to captains & crew while they view film footage taken of the race by the official race committee boat and dance to some of the best live music offered on the island.
Trophies, Pussers Rum and Schooner Wharf bar tabs and Wrecker’s Race tee shirts are earned by the top 3 vessels in 6 classes –schooner, multi-hull, classic, monohull and under, monohull 30-39 feet and monohull 40 feet and over. At the race start Key West harbor is a magnificent sight, filled with colorful sails and spinnakers on vessels ranging from 16 feet to 120 feet. This original nautical event is another creation of Schooner Wharf Bar owners, Evalena and Paul Worthington, and is enjoyed by visiting yachters, local private boats and Key West charter vessels. You don’t need a boat of your own to participate, book passage and crew on one of the charter boats in the Wreckers’ fleet.
2025 Race Dates are Sunday, January 26 – February 23 – March 30 and April 27.
Come join the fun. Fair Winds and Full Holds — Wreck Ashore!
For information please call 292-9520. Visit SchoonerWharf.com. Photos of
previous races are available on the Schooner Wharf Facebook page.

The Southernmost Regatta - 2025
2025-01-20 - 2025-01-25
The Southernmost Regatta – 2025
Top sailing teams from around the world compete in the azure waters off Key West, showcasing colorful sails and avid sportsmanship during five consecutive days of racing. Competition is open to One Design and ORC Racing / Cruising Keelboats. Spectators can watch the races from various waterfront venues, mingle with sailors and view sailboats at the Galleon Resort’s marina, 617 Front Street, after each day’s races.
5 Days of Racing
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. Our plan is to provide a two races a day on two course, a One Design Course and an ORC Course. We will also offer one distance race a day for ORC cruisers.

Back to the Basics

The focus of The Southernmost Regatta is maximize your enjoyment on and off the water by getting back to the basics of what made racing in Key West great… the opportunity to race on blue water, experience the island culture and reconnect with our friends during the cold winter months.
Regatta Chair: Martin Kullman
Email: martin.kullman@thesailinginc.com
Phone: (727) 560-0164

Key West Art & Historical Society Historic Seaport Sail: Harry S. Truman in Key West
2025-01-10 10:00 - 12:00
Key West Art & Historical Society Historic Seaport Sail: Harry S. Truman in Key West
Two Hour Historic Harbor Tour with Truman Little White House Docent Rick Warmbold on the S/V Argo Navis talking about ‘Harry S Truman’s Eleven Key West Visits’
On Friday, January 10, Warmbold will lead an illuminating morning seafaring excursion presented by Key West Art & Historical Society aboard the luxury catamaran SV Argo Navis, departing from the dock at 0 Margaret Street at 10:00 a.m. and returning at 12:00 p.m.
Passengers will enjoy Bloody Marys, mimosas, or non-alcoholic beverages along with lite breakfast fare as Warmbold dives into Truman’s eleven working vacations and shares how Key West was not only a place for the President to recharge his batteries – he will tell you how things in Key West would shape the country and world. Truman’s staff said they got more done in Key West than in DC due to the peace and lack of distractions. The Presidents never truly had a day off – there are 175 days of his working holiday to explore.
This project is sponsored in part by S/V Argo Navis.

Date: January 10
Time: 10:00am – 12:00pm
Cost: $85.00 – $95.00
Location: S/V Argo Navis

Enjoy a 2-hour Historic Harbor Tour with Truman Little White House docent Rick Warmbold on the S/V Argo Navis, talking about “Harry S. Truman’s Eleven Key West Visits.” The trips departs from the Historic Seaport docks at 0 Margaret St. at 10 a.m. and returns at 12 p.m. Passengers will enjoy Bloody Marys, mimosas, or non-alcoholic beverages along with lite breakfast fare as Warmbold dives into Truman’s eleven working vacations, and shares how Key West was not only a place for the President to recharge his batteries – he will tell you how things in Key West would shape the country and world. Book reservations online in advance.

2024 Key West City “Hometown Holiday Parade”
2024-12-07 18:30 - 22:00
2024 Key West City “Hometown Holiday Parade”
SATURDAY, DECEMBER 7, 2024 – FREE!
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!

2024 Pet Pictures with Santa™ – Hosted by The All Animal Clinic
2024-12-05 18:00 - 20:00 | At the 16’ Nautical Christmas Tree on the Harbor Walk of Lights at William St.
Thursday, December 5 – FREE to attend
6:00pm – 8:00pm
2024 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 $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

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.

Schooner Wharf Bar 2024 Tree Trimming Party and Toy Drive
2024-12-01 18:00 - 22:00 | Schooner Wharf Bar, 202 William St, Key West, FL, 33040, United States
Sunday, December 1 – FREE to Attend
Schooner Wharf Bar 2024 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.

Bight Before Christmas Lighting of The Bight: Key West Harbor Walk of Lights 2024
2024-11-27 - 2025-01-01 | Harbor Walk of Lights – 16′ Nautical Christmas Tree at the foot of Williams St.
Bight Before Christmas Lighting of The Bight: Key West Harbor Walk of Lights 2024
Wednesday, Nov. 27 – Free

Main Harbor Walk Lighting at the 2024 “Fishing Buoy Christmas Tree”
Lights come on at 6:00pm – holiday music starts at 5:00pm – Greene and Elizabeth St. plaza.
Santa and Mrs. Claus will be making a NICE list and passing out treats!
SECOND lighting of the 2024 “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 2024 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!

Photos by Carol Tedesco & Rob O’Neal

For more information and to check out an updated schedule of events, visit https://keywestchristmas.org/

Key West Fantasy Fest 2024
2024-10-18 - 2024-10-27 | Fantasy Fest, 602 Greene Street, Key West, FL, 33040, United States
Key West Fantasy Fest 2024!
Key West Fantasy Fest 2024 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!
For more information and to view the schedule of events, visit https://www.fantasyfest.com/

1st Annual Just a Few Friends Key West Favorite Son Celebration in Honor of Jimmy Buffett
2024-08-30 - 2024-09-02
Come celebrate the life of Jimmy Buffett at the 1st Annual Just a Few Friends Key West Favorite Son Celebration August 30-September 2, 2024!

“Join us in Key West over Labor Day weekend for a thrilling lineup of events and activities. The festivities kick off on Friday, August 30, with brunch followed by a proclamation for Jimmy Buffett Day declared by the Florida State Legislature, an author’s talk by Ryan White, and a Cheeseburger Contest and tribute band welcome party on the beach.
Saturday, August 31, features a5K run/walk, our epic Margarita bar crawl, sunset cruise, and a variety of evening entertainment. Sunday, September 1st begins with a luxury catamaran bubbles brunch, pre-parties at various locations, and the don’t-miss Second Line memorial walking parade. The day culminates with a free outdoor “Party in the Park” featuring live music on the Friends of Bubba stage overlooking the ocean at the picturesque Truman Waterfront Park, where Will Kimbrough, co-writer of “Bubbles Up,” will be one of the performers!
Finally, Monday, September 2, offers a sailing adventure on a schooner, a mustache contest, pool party and a farewell but not forgotten concert with The Nautical Wheelers: A Tribute to Jimmy Buffett featuring Roger Bartlett. Each day brings dozens of diversions, including live music, walking & bicycle tours, rum tastings, meetups, club events, and much more.
Don’t miss a moment of the fun—sign up to receive regular updates and order your souvenir parade pass to participate in Key West or virtually from home. Either way, join Just a Few Friends for a fabulous celebration of life and a toast for our Favorite Son.”

MORE INFORMATION: https://www.justafewfriendskeywest.com/

Key West Brewfest 2024
2024-08-29 - 2024-09-02 | Southernmost Beach Resort, 1319 Duval Street, Key West, FL, 33040, United States
Brewfest is a multi-day festival hosted by Southernmost Beach Resort! It includes beer pairing dinners, pool parties, tap takeovers, and culminates with a signature tasting event with over 150 beers available for tasting. Events take place at many restaurants, hotels, and bars around town making Brewfest a great way to experience Key West!
Why Brewfest?
At its heart Brewfest is a fundraising event put on by the Rotary Club of Key West Sunrise in the Conch Republic, a non-profit organization dedicated to serving the community and worldwide needs. Proceeds from the event benefit local scholarships and the Take Stock in Children program.
Location: Southernmost Beach Resort
1319 Duval Street, Key West, FL 33040
SCHEDULE OF EVENTS:

Inaugural Key West Rumfest
2024-08-14 - 2024-08-18
Presenting the 2024 Rum Fest

Welcome to America’s Southernmost continental Caribbean Island, What better place is there to celebrate RUM.
August 16th is National Rum Day. Events Aug 14-18 2024
“Celebrating our Inaugural year, bringing the world of rum to the Southernmost city in the USA.”
The Key West Rum Festival is soon to be the renowned event that brings together rum enthusiasts, experts, and professionals around the world.

info@rumfestkeywest.com/
Questions? Call 910-599-6430 or email info@rumfestkeywest.com/
Restaurant partners include our very own Conch Republic Seafood Co!

27th Annual Key West Lobsterfest
2024-08-08 - 2024-08-11
A Celebration of our favorite Crustacean: August 8-11, 2024!

Lobsterfest Schedule of Events August 8 – 11, 2024

Thurs Aug 8

Original Lobster Boil

Feast on a traditional Lobster Boil at an historic Key West location! Space is very limited – Tickets Required
EVENT DETAILS & Tickets

6pm-9pm

The Porter Mansion courtyard at Caroline’s Cafe

Fri Aug 9

Pool Party at the Marker Resort

Party poolside at the Marker Key West Harbor Resort – Free Admission
EVENT DETAILS

3pm-6pm

Marker Resort

Fri Aug 9

Lobsterfest Duval Pub Crawl

Includes Official T-Shirt. Only $25 in Advance, Best Deal on the Island!
EVENT DETAILS & Tickets

8pm-12am

Duval Street Bars

Sat Aug 10

Street Fair & Free Concert

Enjoy a wide variety of lobster from booths set up along Duval Street. Free Admission
EVENT DETAILS

12pm-11pm

100 – 500 Blocks of Duval Street

Sun Aug 11

Lobster Brunch

Last chance of the weekend for fresh Florida Lobster. All you care to eat and drink. – Tickets Required.
EVENT DETAILS & Tickets

10am-2:30pm

First Flight Island Restaurant & Brewery

For more information and to purchase tickets, visit https://keywestlobsterfest.com/.

Hemingway 5K Sunset Run & Paddleboard Race
2024-07-20
Runners, walkvers and paddleboard enthusiasts can test their skills and celebrate Ernest Hemingway’s sporting lifestyle Saturday, July 20th during the Hemingway 5k Sunset Run and Paddleboard Race. The athletic challenges are part of Hemingway Days!

SATURDAY, JULY 20, 2024 – RACE DAY!
3:00 pm – 7 pm: Race Registration Booth

Location: Outside Southernmost Beach Cafe, 1405 Duval Street

5:30 pm: Start of Paddleboard Race

Location: Outside Southernmost Beach Cafe, 1405 Duval Street

7:30 pm: Start of 5K Run/Walk

Location: Southernmost Point

8:00 pm – 10 pm The Awards/Beach Party featuring Tastings of Papa’s Pilar Rum, Islamorada Beer and Snacks, raffles and entertainment by Island Steel Drum Player Ivan Bertie!!

Location: Outside Southernmost Beach Cafe, 1405 Duval Street
Inside will be Happy Hour Prices on Food and Drinks all evening on the 20th.

Results will be posted race evening www.keywesthalfmarathon.com and our Facebook page.

Key West Pride 2024
2024-06-05 - 2024-06-09
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!
Visit https://gaykeywestfl.com/pride/?utm_source=Fla-Keys.com&utm_medium=Event+Listing&utm_campaign=General&utm_id=Sponsored+Event for more details and to see a schedule of events!

Schooner Wharf Bar Minimal Regatta - May 26, 2024
2024-05-26 12:00 - 17:00
Watch sailors make a splash in homemade vessels made from plywood and duct tape in the craziest regatta you’ll ever see on the waters of Key West Bight. Watch from the Historic Seaport walkways near Schooner Wharf. 12 noon at 202 William St.
More info: https://www.schoonerwharf.com/special.htm#current

42nd Annual Conch Republic Independence Celebration
2024-04-19 - 2024-04-28
42nd Annual Conch Republic Independence Celebration – April 19-28, 2024

Conch Republic Days is an annual 10 day festival held in April where we celebrate our independence! 2024 event dates are April 19-28. Visit www.conchrepublic.com for more information and events.
“We Seceded Where Others Failed! Party with Pirates, Admirals, Generals, Ambassadors & Island Royalty. 10 Days of FUN-Filled festivities for all ages! 20+ events at historic and unique venues in Key West. We Seceded… Where Others Failed!”
Email: Office.of.the.Conch.Republic@gmail.com
Phone: (305) 304-2400
