Key West Historic Seaport

Hemingway 5K Sunset Run & Paddleboard Race
2018-07-21 | FL
As part of Hemingway Days, a six-day event that commemorates the life of Ernest Hemingway who lived and wrote in Key West during the 1930s, runners walkers and anyone who loves to paddle board will have the opportunity to test their skills.
Participants will have to paddle a 3-mile ocean course beginning at 5:30 p.m. The 5K run/walk will kick off at 7:30 p.m.
Competitors can enjoy a post-race awards party with food and raffles at the Southernmost Beach Café.
Paddleboard awards will be given to the first- through 10th-place male and female finishers. In the 5K, awards will be given to the top three male and female overall finishers, top three male and female masters, and top three male and female finishers in age categories ranging from 9 and under to 75 and over.
Register Online

Photo/Video Credit: keywesthalfmarathon.com/hemingway-event-details

25th Annual Battle of the Bars
2018-08-05 12:30 - 18:30 (America/New_York) | Schooner Wharf Bar, 202 William St, Key West, FL, 33040, United States
Some things you have to see to believe, and the 25th annual Battle of the Bars at Schooner Wharf Bar is one of those events.
This year’s showdown begins at 12:30 p.m. on Sunday, Aug. 5, when teams of seven from local bars and restaurants compete in a hilarious relay race that tests their mixing, serving and drinking skills. And in true Key West style, the judges can be bribed and “bought” with donations that benefit local charities. Teams can buy their way into the next round to advance in the standings.
The fastest team takes home the trophy and bragging rights, but prizes and awards are also given for the most generous teams with the Deepest Pockets and for the Most Outrageous Team Costume.
Battle of the Bars quickly becomes a spectator sport, as soon as the first team tests their skills on the obstacle course. The enthusiastic crowd immediately gets involved in the antics, cheers for their favorites and opens their wallets to help groups that help others. So come choose your team and support local charities.
See you at the Schooner Wharf Bar! To enter your team or for more information, call 305 292-3302 or visit

Photo Credit: Schooner Wharf Bar

22nd Annual Key West Lobsterfest
2018-08-09 - 2018-08-12 | FL
Calling all lobster lovers! The beginning of lobster season is approaching so celebrate at the biggest party of the summer.
Events include a lobster boil, street fair with arts, crafts, merchandise, and lots of lobster, a free concert, and a lobster brunch to conclude the festival.
Event Schedule

Lobster Boil
2018-08-09 17:00 - 20:00 | The Waterfront Brewery, 201 William St., Key West, 33040, United States
As part of Key West Lobsterfest, The Waterfront Brewery will be hosting the annual Lobster Boil on their rooftop! Enjoy over a pound of:

Lobster
Shrimp
Andouille Sausage
Crawfish

Sides include garlic bread and fresh tossed salad with choice of dressings. A variety of drink specials will be offered as well as live entertainment.
Space is limited so book early. Paid Parking is available on Caroline Street.
Book here
Adults(12+): $29.95 Children(11 & under): $15.95

9th Annual Key West Brewfest
2018-08-30 - 2018-09-03 | FL
The 9th Annual Key West Brewfest will be during Labor Day weekend. To kick off the event, there will be a party at The Waterfront Brewery located in the Historic Seaport on Thursday, August 30, 2018 at 6 p.m. Other events include pool parties, beer tasting, a pig roast and more!
Get your tickets here

Key West Brewfest – Opening Kick Off Party
2018-08-30 18:00 - 22:00 | The Waterfront Brewery, 201 William St., Key West, 33040, United States
The Waterfront Brewery is hosting a kick off party to Key West Brewfest! The Waterfront Brewery will be releasing new Waterfront Brewery brews during this event. Enjoy an evening of craft beers brewed in the same building as the party! Full menu and game room will be available.

Key West Womenfest
2018-09-05 - 2018-09-09 | FL
Thousands of singles, couples and groups of women flock to Key West each year for this renowned celebration for lesbians and their friends. Activities generally include dance parties, poolside gatherings, sailing and snorkeling, live music, comedy performances and more!
View event schedule here

Insider's Tour: Key West
2018-09-27 - 2018-09-29 | FL
Coming to Key West and the Historic Seaport is an exclusive Insider’s Tour from the Florida Trust for Historic Preservation. Historians, preservationists and Florida Trust members will make their way down to Key West for a historic weekend filled with tours of museums, private historic homes and more.

The Marker Waterfront Resort is the official hotel sponsor of the Insider’s Tour.

Thank you to all of the event sponsors:

Read more about this event from the Florida Trust for Historic Preservation HERE
Read the KWHS blog with more details on the Insider’s Tour HERE

Southernmost Marathon
2018-10-06 | FL
Key West Running Festival | Full Marathon, Half Marathon & 5k
Be part of the Key West Running Festival by running a full marathon (26.2mi run), half marathon (13.1mi run) or 5K (3.1mi run) and enjoy the beautiful views all around.
Register here
Race Course

Bahama Village Goombay Festival
2018-10-19 | Bahama Village, FL, 33040, United States
Photo Credit: http://www.fantasyfest.com/photos
The Bahama Village Goombay Festival is a free family-friendly event! Held in Key West’s historic Bahama Village neighborhood, the lively Goombay is known for its island-style food, arts and crafts, nonstop live entertainment and dancing in the streets. Visitors can experience sights, sounds and flavors recalling Key West’s Bahamian heritage.

Fantasy Fest
2018-10-19 - 2018-10-28 | FL
The 39th Annual Key West Fantasy Fest is an outrageous costuming and masking celebration that features flamboyant masquerade competitions including one for pets, a headdress ball, exuberant promenades, street fairs and a grand parade that stars marching groups, island-style bands and lavish floats. Events take place at different locations in Key West and some in the Historic Seaport.
History of Fantasy Fest
On October 28, Schooner Wharf Bar will be hosting a groovy event that you won’t want to miss. There will be a body painting contest, live music and a contest for the sexiest Hippie Chick & Grooviest Dude. We’ll see you there!
*Images from www.fantasyfest.com

Schooner Wharf's Wharfstock
2018-10-24 | Schooner Wharf Bar, 202 William St, Key West, FL, 33040, United States
Photo Credit: Schooner Wharf Bar
Wharfstock is an event during Fantasy Fest taking place on October 24, 2018 at 7 p.m. Return to the days of peace, love, and music–Woodstock style! Come and get groovy with tie-dye, flower power, and psychedelic colors. There will be a body painting contest and live music. This is FREE event to enter and FREE to attend.
*Flyer Coming Soon*

38th Annual Key West World Championships
2018-11-04 - 2018-11-11 | Truman Waterfront, 202 Southard Street, Key West, 33040, United States
Logo/Photos: http://superboat.com – Header Image: Powerboat Hub
The Super Boat International Races was founded in 1989 and are the worlds biggest and fasted offshore racing series. This annual event has attracted many celebrity racers over the years, including don Johnson, Kurt Russell and Chick Norris.
The racecourse is rectangular and five miles in length. Race day #1 of the Key West series will be Wednesday, November 7, day #2 on Thursday, November 8 and day #3 on Friday, November 9. Check out the detailed race schedule here: Race Schedule.

Key West Film Festival
2018-11-14 - 2018-11-18 | FL
“The mission of the Key West Film Festival is to showcase films that capture Key West’s essence: Creativity, Diversity, Sustainability, and Beauty.”
This one-of-a-kind event will be showcase some of the best filmmakers in Florida as well as bring in visiting filmmakers in workshops. The four-day program will include films from different genres and categories and will be hosted a venues throughout Key West.
View schedule here
Purchase tickets here
Header Image from kwfilmfest.com

Lighting of the Key West "Harborwalk of Lights"
2018-11-21 | FL
Locals and visitors are invited to gather on the harborwalk at Greene and Elizabeth Street to watch the official lighting of the 2018 Key West “Harborwalk of Lights.” Watch as the fishing Buoy Christmas Tree, a real pine Nautical Christmas Tree and Lobster Trap Christmas Tree light up the night and honor the “Maritime History of Key West.”
With over 61,000 lights and 58 lighted palm trees, 2018 will be bigger than ever! Stroll down the harborwalk and enjoy the nautical displays, including ship’s anchors, tropical birds, tropical fish, manatees and aniamted sea turtles.
Start your holiday shopping at any of the unique shops at the Historic Seaport and grab a bite to eat at the waterfront.
The Harborwalk of Lights is lit every evening through New Year’s eve!

Photo Credit: ROB O’NEAL

International Sand Art Competition
2018-11-21 - 2018-11-25 | FL
The International Sand Art Competition will be taking place Thanksgiving weekend in Key West! This unique event is where renowned sculptors compete against each other on the beach at the Case Marina Resort. Plan your trip to Key West to watch these talented artists work and cast your vote for People’s Choice.
List of 2018 Sculptors
Photo Credit: Johnny White, Rob O’Neal, Sand-Isle LLC

Schooner Wharf Bar's Tree Trimming Party
2018-12-02 | Schooner Wharf Bar, 202 William St, Key West, FL, 33040, United States
Rock around the Christmas tree at the Schooner Wharf Tree-Trimming and Toy Drive event! Bring an ornament for the Schooner Wharf tree and get a free holiday cocktail, eggnog, hot apple jack, or Swedish glogg. Prizes will be awarded for Most Original, Most Nautical, and Most Popular ornament.
More details coming soon!

Pet Pictures with Santa
2018-12-07 18:00 - 20:00 | FL
Santa is coming back to the Historic Seaport this year! The All Animal Clinic is hosting a Pet Pictures with Santa event and is free to attend. Look for Santa at the Nautical Christmas Tree at the end of William Street along the Harborwalk of Lights.
All photo sales benefit the Boys & Girls Club of The Keys Area, Inc.
Participating pets and kids will receive treats and goodies.

Photo Credit: Rob O’Neal

28th Annual Schooner Wharf Bar & Galley Lighted Boat Parade
2018-12-15 | Schooner Wharf Bar, 202 William St, Key West, FL, 33040, United States
The 28th Annual Schooner Wharf Bar & Galley Lighted Boat Parade will be on December 15, 2018 at 8:00 p.m.
For Key West and the Florida Keys, it’s a tropical tribute to the season and a big family affair. Parade participants and spectators on the docks watching the parade feel as if they are part of one big family. Vessels have ranged from a kayak with battery-powered lights, to fishing vessels, to classic schooners.
A starry night, a festive crowd and thousands of twinkling lights climbing heavenward from the sea—that’s Key West’s way of saying “Happy Holidays!” So join in spreading the spirit where mistletoe hangs from the mast and strings of lights adorn the riggings: at the 27th Annual Schooner Wharf Bar & Galley Lighted Boat Parade.
The captains’ meeting is on Thursday, December 13 at 8 p.m. at Schooner Wharf’s upper deck. For more information, please contact Schooner Wharf Bar at (305) 292-3302.

Holiday Classic Car Show
2018-12-16 11:00 - 16:00 | Conch Republic Seafood Company, 631 Greene St., Key West, FL, 33040, United States
Stop by the Holiday Classic Car Show to see classic cars from every era decorated for the holidays. Awards will be given to cars for Best Engine, Best Interior, Best Original & Custom, Best in Show and People’s Choice.
Please consider donating an unwrapped toy to donate to the Monroe County Domestic Abuse Shelter.

Left: Rob O’Neal
Middle & Right: KeyWestChristms.org

Schooner Wharf's Lowering of the Pirate Wench
2018-12-31 - 2019-01-01 | Schooner Wharf Bar, 202 William St, Key West, FL, 33040, United States
Join your friends and make new ones at the Schooner Wharf Bar’s New Year’s Eve Celebration.
The popular waterfront watering hole once again will present its nautical New Year’s Eve tradition with “Lowering of the Pirate Wench” from the towering mast of the tall ship America 2.0 docked in front of the bar in the Key West Bight.
Everyone’s favorite pirate wench and co-owner of Schooner Wharf Bar, Evalena Worthington, will descend dramatically against large, illuminated countdown numbers. The stroke of midnight will signal the start of 2019 with cannon fire and the jubilant sound of horns and noisemakers from the crowd against a backdrop of the ship’s crew dressed as pirates.
Schooner Wharf has complimentary hats, party favors and horns for everyone to feel festive while enjoying holiday drink specials and live music throughout the day and night. The bash was rated by AOL as the No. 2 New Year’s party in the nation – second only to the Times Square madness in New York City.
The Schooner Wharf event made the Huffington Post’s 13 Amazing New Year’s 2014 Photos From Around the World. Rob O’Neal’s photo of Evalena at Schooner Wharf in Key West was the only photo chosen from this continent.
Guaranteed to get you groovin’ and dancin’ into the New Year!
As the midnight hour approaches, hoist your drink – and your eyes – toward the top of the towering mast as the countdown begins and another year ends.
But the end of the year isn’t the end of the party – the Schooner New Year rocks until 4 a.m. All this and No Cover Charge.
Have a safe and exciting New Year, from your friends at Schooner Wharf Bar, “A last little piece of old Key West.”
For more information, please call Schooner Wharf at (305)-292-3302.

37th Annual Key West Literary Seminar
2019-01-10 - 2019-01-13 | FL
The 2019 Key West Literary Seminar topic is “Under the Influence.” The Keynote Speaker is an author of more than 50 books with a combination of poetry, fiction and critical essays, Margaret Atwood.
View program overview HERE

Header Image/Logo Photo Credit: www.kwls.org/seminar

Key West Food & Wine Festival
2019-01-23 - 2019-01-27 | FL
The 2019 Key West Food & Wine Festival will feature over 20 wine and food themed events. Events include waterfront tastings, winemaker/chef collaborations and other unique events! This annual event attracts thousands of people from around the world who come to enjoy a diverse range of wines cuisines on the beautiful island of Key West.
View the event schedule HERE
Get tickets HERE

Mile 0 Fest Key West
2019-01-29 - 2019-02-02 | FL
This four-day musical event is a combination of rock and roll, country, folk and blues. Mile 0 Fest will feature powerhouse performers and new artists are continuously being added to the line-up.
2019 Line-Up

View full 2019 line-up here

54th Annual Old Island Days Art Festival
2019-02-22 - 2019-02-24 | Old Town
Artists from around the country are attracted to this nationally recognized fine arts event every year in Key West. This outdoor festival takes place on two blocks of Whitehead Street and another block of Caroline Street. Exhibitors include painters, sculptors, photographers, collage artists and other non-functional fine art.
Exhibitors will set up along Whitehead Street from Greene Street to Eaton and on Caroline Street through the famous Presidential Gates into the beautiful Truman Annex.

34th Annual Schooner Wharf Bar Wrecker’s Cup Race Series
2019-02-24 | Schooner Wharf Bar, 202 William St, Key West, FL, 33040, United States
This is the second race of the Schooner Wharf Bar Wrecker’s Cup Race. 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. On Saturday before each race, Captains Meetings commence on the upper deck of Schooner Wharf at 7pm. Each captain will be served a complimentary Pusser’s Rum Punch and hors d’oeuvres.
The Awards Ceremony & Party is held at 7pm. on Sunday each race day!

Schooner Wharf Open Air Art & Music Affair
2019-03-02 10:00 - 23:30 | Schooner Wharf Bar, 202 William St, Key West, FL, 33040, United States
Come on down to the 19th Annual Schooner Wharf Open Air & Music Affair! Enjoy a colorful waterfront setting, arts and crafts by skilled Florida Keys artisans and tunes by talented local and visiting musicians. This event is unique because the show features award winning local and national artists and crafters whose work isn’t shown anywhere else.
This event is a wonderful opportunity to meet renowned artists and purchase an authentic piece of art. Enjoy cocktails, great food and have a one-of-a-kind experience!
Location: Schooner Wharf Bar, Lazy Way Lane (end of William Street)

Left: Isiah Meondoza with his original paintings and hand crafted woodwork
Right: Dwight Kalb exhibiting his vibrant oil canvases

Naval Air Station Key West Southernmost Air Spectacular
2019-03-30 09:00 - 2019-03-31 14:30 | Naval Air Station Key West, Boca Chica Field, Key West, 33040, United States
Watch the The Blue Angels air squadron perform their amazing acts of flight synchronicity. This air show will also feature parachute teams and other aeronautical performers.
Location: Boca Chica Naval Air Field, mile marker 7. Gates open at 9am. Blue Angels perform at 2:30pm.
https://www.facebook.com/southernmostairspectacular/videos/321213065174013/

Annual 7-Mile Bridge Run 2019
2019-04-06 06:30 - 21:30 | 7-Mile Bridge
The 7-Mile Bridge Run is put together by the Marathon Runners Club and is the only known run that is completely surrounded by water from start to finish. Next year will be the 38th year of the race on the longest bridge in the Florida Keys.
This annual event is organized by the Marathon Runner’s Club to celebrate the opening of the bridge in 1982. The race is capped at 1,500 runners each year. All proceeds go to children’s organizations.
https://www.facebook.com/7mbrun/

Annual Cow Key Channel Run
2019-04-07 10:00 - 15:00 | Cow Key Channel Bridge, Cow Key Channel Bridge, Key West, FL, 33040, United States
Do you feel like running across a bridge in the Florida Keys without waking up early or breaking a sweat? This 300-foot mock marathon over the tiny Cow Key Bridge features funny costumed runners, walkers, relay teams, and even pets.
Prizes awarded for fastest, slowest, best costumed, best theatrical performance, and many more!

Cow Key 2018 Highlights – Discow Inferno! from Wonder Studios on Vimeo.
