City of Key West Lighting of the Menorah Ceremony 2023
2023-12-10 17:30 - 19:30 (America/New_York) | Bayview Park, 1400 Truman Avenue, Key West, 33040
City of Key West Lighting of the Menorah Ceremony 2023
Dec 10, 2023 | 5:30 PM – 7:30 PM | Join the City of Key West for its Annual Lighting of the City Menorah Ceremony at Bayview Park!

Conch Republic Seafood Company's 2023 Holiday Classic Car Show
2023-12-17 11:00 - 15:00 | Conch Republic Seafood Company parking lot – Greene & Elizabeth St., 631 Greene Street, Key West, FL, 33040, United States
Sunday, December 17 – FREE
The Florida Keys Southernmost Car Club presents
cele
FREE • 11:00am – 3:00pm
LOCATION: Conch Republic Seafood Company – on the Harbor Walk of Lights at Greene St.
TOY DRIVE: Please bring an unwrapped toy for Monroe County Domestic Abuse Shelter.
VOTE for the “Peoples Choice” award for: BEST sports car, pick up, engine, interior, original & custom, pre & post 1950, Best in Show.
See classic cars from every era decked out for the holidays!
Run by the Florida Keys Southernmost Car Club.
Non-member cars may enter same day FREE with an unwrapped toy!

18th Annual Florida Keys Seafood Festival
2024-01-13 - 2024-01-14
Bring the whole family for the freshest seafood caught, cleaned, prepared and served by local fishermen, along with live music both days, plus a kids eco-discovery zone and great shopping and art. Hours on Saturday are 11 a.m. to 7 p.m., and Sunday 11 a.m. to 5 p.m. $10 admission is good for both days and includes entry in a raffle for $250 worth of seafood. The festival takes place at Bayview Park, 1320 Truman Ave!

ASSOCIATION: 305-743-0294 | FESTIVAL DIRECTOR: 305-619-0039

Email: flkeysseafoodfestival@gmail.com

PO Box 501404 | Marathon, FL 33050-1404

26th Annual Key West Marathon and Runfest
2024-01-14 06:30 - 11:00
26th Annual Key West Marathon and Runfest
January 14th – Half Marathon starts at 6:30am and the 5K starts at 7:00am.
Key West Half Marathon voted one of the 10 best half-marathons across the nation for 2023 in USA Today!!!
Runner’s World has officially named the Hemingway 5k Sunset Run as one of the best 5Ks to run this summer
RUNNER’S WORLD MAGAZINE RANKS KEY WEST HALF MARATHON NUMBER 1 OF 14 IN U.S. FOR BEST DESTINATION RACES
Competitor Magazine calls “ One of the 20 Must Do Races”
Register at https://www.keywesthalfmarathon.com

Schooner Wharf Knot & Shot Competition
2024-01-16 - 2024-01-18 | Schooner Wharf Bar, 202 William St, Key West, FL, 33040, United States
2024 Schooner Wharf Knot & Shot Competition
Key West wouldn’t be Key West without sailors and Schooner Wharf Bar, and sailors wouldn’t be sailors without rum and ropes!
Watch what happens when all four of them combine on the docks at Schooner Wharf Bar, your After Sail Headquarters! Sailors and any interested challengers will frustrate themselves and entertain the crowd as they race to tie a bowline and lasso a piling. But add a shot of Mt. Gay Rum and an icy cold beer to the contest and a good time is inevitable. Entrants stand in front of an ice luge and swallow an icy shot of Mt. Gay that is poured from the top. They then have to tie a bowline and use it to lasso a piling that is on wheels, several feet away. The sailor then pulls the piling to him or her and picks up a cold beer, that is sitting on the base of the piling. They then drink the beer and turn the supposedly empty bottle upside down on their head.
Our Knot & Shot Competition is a fun and good natured race against the clock and other sailors.
Prizes will be given for the best times, and winners can receive great prizes from Harken yacht equipment, Sailing Services, Schooner Wharf Bar gift certificates and plenty of Mt. Gay Rum and Mount Gay XO. Spectators can enjoy the laughs and drinks while they share sailing stories with local sailors.
2024 Knot & Shot Crucial Information flyer – coming soon!

39th Annual Schooner Wharf Wreckers Cup Race 2024
2024-01-28 13:00 - 17:00 | Schooner Wharf Bar, 202 William St, Key West, FL, 33040, United States
39th Annual Schooner Wharf Bar Wreckers Cup Race Series 2024
No protests, no pageantry, just race with us – or against us!
Wrecker’s Race 2024 Release Form and Entry Form – coming soon or register online: ONLINE ENTRY FORM
The much anticipated first race of the Schooner Wharf Bar Wrecker’s Cup Race Series is scheduled for Sunday, January 28 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 in the Sail Loft at Schooner Wharf at 7:00 p.m. the Saturday before each race. Captains enjoy complimentary Pusser’s Rum punch while reviewing race procedures.
The Awards Ceremony & Party is held at 7:00 p.m. on Sunday, race day. Captains & crew can see themselves under sail while viewing film footage taken of the race by the official race committee boat. Gabriel Wright will be entertaining with current and classic favorites.
Trophies and prizes are earned by the top 3 vessels in 6 to 7 different classes—schooner, multi-hull, classic, monohull 29′ and under, monohull 30-39 feet, monohull 40 feet and possibly a Hobie Cat class!
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.

2024 Annual Schooner Wharf Wreckers Cup Race - Second Race
2024-02-25 13:00 - 17:00 | Schooner Wharf Bar, 202 William St, Key West, FL, 33040, United States
Annual Schooner Wharf Bar Wrecker’s Cup Race Series 2024
February 25
No protests, no pageantry, just race with us – or against us!
Wrecker’s Race 2024 Release Form and Entry Form
or register online: ONLINE ENTRY FORM
2024 Wreckers Race Results
Ahoy Mates! It’s time to clean the bottom and pile on the sails.
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 in the Sail Loft at Schooner Wharf at 7:00 p.m. the Saturday before each race. Captains enjoy complimentary Pusser’s Rum punch while reviewing race procedures..
The Awards Ceremony & Party is held at 7:00 p.m. on Sunday, race day. Captains & crew can see themselves under sail while viewing film footage taken of the race by the official race committee boat. The popular Big Daddy Rich will be playing Rock, Soul, Blues, Country, Rare 1 Hit Wonders and AM Gold from the 60s and 70s all with fun and energy.
Trophies and prizes are earned by the top 3 vessels in 6 to 7 different classes –schooner, multi-hull, classic, monohull 29′ and under, monohull 30-39 feet, monohull 40 feet and possibly a Hobie Cat class!
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.
SUNDAY, January 28, 1:00 PM • Captains’ Meeting Saturday, January 27, 7:00 PM
SUNDAY, February 25, 1:00 PM • Captains’ Meeting Saturday, February 24, 7:00 PM
SUNDAY, March 31, 1:00 PM • Captains’ Meeting Saturday, March 30, 7:00 PM
SUNDAY, April 28, 1:00 PM • Captains’ Meeting Saturday, April 27, 7:00 PM

The Race Course is 7 miles from Key West Harbor to Sand Key. Race starts are: 1:00 PM and 1:05 PM for up to seven different classes. Wrecks rarely occurred in good weather, but the Schooner Wharf Wrecker’s Cup Races are conducted SAFETY FIRST. Stand by on #68 if severe weather is forecast. The Captains’ Meetings are held in the Sail Loft at Schooner Wharf Bar at 7:00 PM the evening before the race. The Award Party & Ceremony is held at 7:00 PM on Race Day. Awards in each race will include Original Trophies, Pusser Rum & Goodies, Schooner Wharf Bar Tabs and Wrecker’s Race Tee Shirts. Co-Sponsored by PUSSER’S RUM and presented by SCHOONER WHARF BAR.

24th Annual Schooner Wharf Open Air Art & Music Affair
2024-03-02 21:30 - 2024-03-03 00:00 | Schooner Wharf Bar, 202 William St, Key West, FL, 33040, United States
Call To Artists! The 24th Annual Schooner Wharf Open Air Art & Music Affair is scheduled for Saturday, March 2nd, 2024.
Open to artists of all mediums, including but not limited to painting, printmaking, sculpture, drawing, carving, photography and mixed media. All original artists are encouraged to apply. Space is limited. For more
information go to schoonerwharf.com/24artaffair.htm. For applications or questions, send e-mail to swartaffair@yahoo.com or call Capt. Carl at (305) 304-2275.
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 2nd, in Key West Historic Seaport.
Not only is the festival a rollicking good time, it is a fantastic opportunity to meet renowned artists in a casual atmosphere, purchase a distinctive piece of art, and have a cocktail while supporting a worthwhile cause.
Come celebrate the distinctive and unique flavor of the island, with great music, food, and cocktails in a casual atmosphere where you can mingle with the artists, and watch them work. Enjoy the playful off beat spirit of Key West with great food, cocktails, unique art, and top notch music, March 5th, Saturday from 9:30 into the night with us here at Schooner Wharf!

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

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

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!

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.

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/.

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!

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:

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 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/

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/

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.

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.

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!

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.

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

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.

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.

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/

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

Get your tickets here!

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!

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 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
