Events Calendar 2017 and the rest of 2016

The Rest of 2016 Key West Calendar of Events

and…

(keep scrolling down)

 

Come to Key West The Island of Paradise!!

 

Key West Fishing Tournament 

April 9 to November 30

More than 40 species of fish are targeted during these months, with divisions for men, women, junior anglers (ages 10 to 14) and Pee Wees (under 10 years old). The Key West Fishing Tournament strongly encourages the release of game fish. All participating anglers receive certificates noting their catches and qualify for a variety of prizes.

WineDine KeyWest 

September 16 to October 16

Cuisine connoisseurs can enjoy multicourse prix fixe meals at as many as 30 Key West restaurants during WineDine KeyWest, billed as the island’s first restaurant month. Restaurants include casual waterfront spots, trendy bistros, eateries specializing in fresh Florida Keys seafood and award-winning gourmet emporiums. Diners can register free online to take part in the month-long moveable feast.

SoMo Marathon & Half Marathon 

October 6 to October 9

Presented by Pat Croce’s Rum Barrel, this event is one of a kind! Imagine running through the southernmost island in the United States while enjoying a break from the ordinary. The Southernmost Marathon & Half promises just that- 26.2 or 13.1 miles of ocean and gulf views, as well as iconic Key West landmarks. A full weekend of events include the race and a Sunday Paddle Board race for the Special Olympics of Monroe County.

Key West Theater Presents: Edwin McCain 

October 8

Edwin McCain’s voice is everywhere. At any given moment, a radio station is playing one of his songs. An American Idol hopeful is belting out “I’ll Be.” A newlywed couple is dancing to “I Could Not Ask for More.” McCain’s innate ability to write and perform songs that somehow every listener claims as their own has made him one of the most enduring and downright likable entertainers of our generation. Show starts at 8 p.m.

Key West Theater Presents: David Wilcox

October 9

David Wilcox is a brilliant song writer, a great singer, and one of the hottest guitar players in the world. With the release of David’s new CD, “Boy In The Boat” his music has come full circle. It’s a daring mix of diverse roots influences coupled with his remarkable style. The result? Something not only original but steeped in the raw funky tradition his fans have come to know and love. Tough but soulful; cool but passionate – the music keeps growing without losing its fiery edge.

Official 2016 Stone Crab Season Opening 

October 15

In mid-October, the most delicious local seafood becomes available, the stone crab. With a porcelain-like shell and briny meat, this crab is considered a sustainable resource in that only the claws are taken, then the crab is released back into the wild to grow new ones. Stone crab is only native to this region and is considered a delicacy. October 15 is a special day for locals who eagerly await the opening of the stone crab season in Key West.

Standup Paddle Invitational 

October 15 to October 16

Join a two mile paddle board and beach obstacle course at Higgs Beach to support the Special Olympics Florida – Monroe County. All ability levels are welcome.

Key West Halloween Half Marathon and 5K Run 

October 16

Competitors are encouraged to dress in their favorite costumes for this Halloween-themed running event. An awards party to follow at Schooner Wharf Bar.

Key West Theater presents: The Nighthawks 

October 19

When Mark Stutso, master of the deep groove, joined The Nighthawks at the beginning of 2010, the 21st-century version of the legendary American roots band was complete. With Paul Bell and Johnny Castle in the band for nearly a decade, and founding father Mark Wenner the remaining original, this team outshines all previous incarnations. Show starts 8 p.m

37th Annual Key West Fantasy Fest 

October 21 to October 30

This outrageous 10-day costuming and masking celebration 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. The 2016 festival theme is “Political Voodoo and Ballot-Box Barbarians.”

Goombay Festival 

October 21 to October 22

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.

The Smallest Parade In The Universe 

October 27

A dazzling event from 5-9 pm, at the corner of Caroline and William streets – at Key West Waterfront Brewery. Artists, craftsmen, model makers and creative types are encouraged to participate, making floats no larger than 18 inches! Proceeds benefit the MARC house. Up to $2,000 in prizes.

Parrot Heads Flock to Key West 25th Annual Meeting of the Minds 2016
November 2 to November 6
Parrothead convention and nirvana benefiting charity. Many events are members only. Live shows include members of Jimmy Buffett’s band. Highlights include the Margaritaville Street Fest on Friday from 1pm – 5:30pm on the 500 block of Duval Street (near Fleming Street) which is FREE and open to the public. As well as sharing an appreciation for Buffett’s music and the Caribbean atmosphere it promotes, Parrot Head club members focus on volunteerism and community service!

35th Annual Key West World Championship Races 

November 6 to November 13

Super Boat International returns with teams from all around the world who compete April through October in the National Series Points races and conclude in November for the famous Key West World Championships. High-speed offshore powerboats race in Key West Harbor and surrounding waters to continue Key West’s longstanding tradition in this annual challenge, known internationally as the Indianapolis 500 of powerboat racing. A portion of the 6.5-mile course runs through Key West Harbor, meaning smooth water where racers can achieve speeds above 140 mph and provide fans breathtaking displays of skill and power.

Key West Gallery presents: Salvador Dali, The Argillet Collection 

November 7 to November 12

This exhbition is a rare opportunity to meet Madame Christine Argillet, daughter of Dali’s legendary publisher and confidante Pierre Argillet. Rare titles from 1934 to the late 1960s include Etchings and Watercolors, in addition to works from Dali’s Suites such as Mythologie, Les Hippies, Goethe’s Faust, and Poemes Secrets d’Apollinaire.

Key West Film Festival 

November 16 to November 20

Showcasing films that exhibit excellence in storytelling, the festival’s lineup is to feature screenings and special events hosted at landmark venues throughout Key West, including the San Carlos Institute, Studios of Key West and Key West Theater. The four-day program is to include several films from multiple genres and categories as well as social events with filmmakers, actors and film lovers.

“What The World Needs Now: Burt Bacharach” 

November 18 to November 19

Presented by Waterfront Playhouse, the 77th season is to start with the timeless music of Burt Bacharach. The six-time Grammy Award winner and winner of three Academy Awards is a master of hit songs. A line-up of Key West’s best vocal talent will present another amazing concert. “Never be ashamed of writing a melody people remember” — Burt Bacharach

13th Annual Smart Ride

November 18 to November 19

Hundreds of bicyclists ride from Miami to Key West, a 165 mile course over two days, to raise money for the benefit of raising awareness for HIV/AIDS organizations in Florida. Cost is $95 per entrant.

International Sand Art Competition 

November 23 to November 27

Nontraditional artistry and beachside fun combine in a unique creative experience for participants and spectators. Visitors can watch leading U.S. and international sand sculptors construct and display large-scale creations over Thanksgiving weekend on the Atlantic Ocean beach at the Casa Marina Resort, 1500 Reynolds St.

Thanksgiving in Key West 2016

November 24

Traditional turkey is served in a tropical setting as residents and visitors celebrate the annual holiday. Many local restaurants have special Thanksgiving menus.

Key West Triathlon and Expo 

December 1 to December 3

The Key West Triathlon and Expo expects to host a maximum of 1,000 participants and some of the sport’s best known triathletes; TRIKW allows you to bask in the warm weather and the waters of the Atlantic Ocean while the rest of the country is experiencing winter. Olympic and Sprint distances.

Key West Lighted Bike Ride 

December 7

The Lighted Bike Ride helps to gather the needed toys for the struggling, working families of Key West for the holidays. At the Holiday Helpers Store, eligible parents walk through the store, empowered by the ability to pick free, new toys their children will want instead of just allocating non-specific toys to parents. The ride is a family event beginning with a registration at 5:30 p.m. with the Lighted Bike Ride beginning at 7:00 p.m. Families and individuals with lighted and decorated bikes ride through the streets for the community to see. Registration for the ride is one unwrapped toy for the Key West Holiday Store. Register online.

3rd Annual Parade of Paws & Holiday Bazaar

December 10

Pet parade to benefit the Florida Keys Society for the Prevention of Cruelty to Animals. Entrants gather donations and compete for bragging-rights titles, including King, Queen, Prince, Princess, Duke, and Dutchess. Blessing of the animals is at 9:45am.  Parade begins at 10am. After the parade there will be a Holiday Bazaar with food, entertainment and Santa photo opportunities. Higgs Beach Dog Park.

You can get a special holiday collar for your best friend by clicking here.

Nutcracker Key West 

December 10 to December 18

Inspired by the unique and colorful environment of the Florida Keys, Clara and her young Prince encounter enchanted landscapes complete with snowy egrets on shimmering salt ponds, a wicked Rooster-King, an exquisite Sea-Star Fairy, and “underwater” sequences of almost unimaginable beauty. Local children, adults and community leaders are cast alongside a nationally-cast corps de ballet in this spectacularly crafted semi-annual production of a beloved classic. Shows held at the Tennessee Williams Theatre.

Hanukkah in Key West 2016

December 24, 2016 to January 1, 2017

Key West is home to one of Florida’s oldest Jewish communities – with Jews settling here when the City was incorporated in 1832. The first Key West Congregation, B’nai Zion was founded in 1887. Today, during Hanukkah, a large menorah is lit in from of the synagogue each night of the holiday, with Rabbi and congregants gathering for the “festival of lights”. A latke and salmon feast is held the first night. Stop by 750 United Street and celebrate.

Christmas in Key West 2016

December 25

Whatever gift you wish for, spending Christmas in Key West might be at the top of the list. While it never snows, and sometimes a palm tree is substitued for a traditional tree, there still is plenty of Christmas spirit in Key West. Look for historic homes that have added twinkle and magic with lights and displays. And to all a good night!

57th Annual Key West House & Garden Tours 

December 27 to December 28

Presented by the Old Island Restoration Foundation, the annual self-guided tours showcase festively dressed Key West homes and gardens. December tours are from 4-7 pm, both evenings. Transportation between homes is NOT included. Tickets are $30. Proceeds benefit the Old Island Restoration Foundation’s museums, collection and education, grant and scholarship programs.

New Year’s Eve Shoe Drop Celebration 

December 31

Celebrations include the lowering of the Conch Shell over Sloppy Joe’s on lower Duval Street, the lowering of famous Key West drag queen Sushi (riding a huge 6 foot high-heeled shoe) over the Bourbon Street Complex on upper Duval Street, and the lowering of the “pirate wench” from the mast of a schooner in the Historic Seaport.

 

Happy New Year 2017! And Come Down To Key West!

 

IT’S ONLY A PLAY! by Terrence McNally

December 13  to January 7, 2017

Presented by the Waterfront Playhouse. It’s opening night for a new Broadway play called, The Golden Egg, and all of New York show biz has gathered for the opening night party to anxiously await the reviews. It’s a celebration of theatre at its best…and theatre people behaving their not-so-best. It’s Only A Play was one of the biggest hits Broadway has seen in years. Variety called it “a mega-seller!” Performances at 8 p.m.

Red Barn Theatre presents: Picasso at the Lapin Agile

December 13 to January 14

In 1904, in The Lapin Agile — a bar in Paris — a 10-person cast of wonderful characters hold an imagined meeting of the young Alfred Einstein and Pablo Picasso, mixing the sublime and the ridiculous.

The Reverend Peyton’s Big Damn Band

January 6

The Reverend Peyton’s Big Damn Band promises to be a sandal-stomping, scorcher of a debut for these innovators of Americana. A lifelong student of American roots and blues music styles, and a self-proclaimed disciple of country-blues pioneers like Charley Patton and Mississippi Fred McDowell, The Reverend (Josh) Peyton has always been committed to authenticity. The charismatic multi-instrumentalist has innovated a way to plug in and play most anything you can lay hands on. At any time during a show he may produce an instrument built from a cigar box, or an axe handle, or a can of ham. Show time 8 p.m. at Key West Theater, 512 Eaton St.

35th Annual Key West Literary Seminar

January 7 to January 10

The 2017 topic is “Revealing Power: The Literature of Politics Stories.” A first-come, first-seated Sunday afternoon session is free and open to the public. The annual high-spirited gathering attracts literary aficionados from around the world for readings, discussions and lectures led by some of contemporary literature’s leading writers.

57th Annual Key West House & Garden Tours

January 13 to January 14

Tour a series of elegant and unique private homes of Key West, ranging from exquisite restorations to creative renovations, and the interior design that complements each. March tours are offered 10 a.m. to 4 p.m. each day. Transportation between homes is optional, via Conch Train. Tickets are $30. Proceeds help benefit the Old Island Restoration Foundation.

12th Annual Florida Keys Seafood Festival

January 14 to January 15

A family-friendly event with local fresh Keys seafood, drinks, marine-related crafts, youth activities, and live music. $5 admission per person; hours open from 11 a.m. – 8 p.m. on Saturday; 11 a.m. to 5 p.m. on Sunday, at Bayview Park, Truman Avenue and Jose Marti Drive.

30th Annual Quantum Key West Race Week 2017

January 15 to January 20

The annual race week challenge features world-class competition and yachting teams from more than 12 countries and 24 American states. More than 100 racing yachts typically compete for class championships in this international regatta. To view the action, fans can book seats on spectator boats ranging from excursion catamarans to historic tall ships or from land at Key West’s Atlantic-front restaurants, resorts and beaches.

Key West Half Marathon & 5k Run

January 15

Recognized by Runners World magazine as one of the 10 great half-marathons of the winter season, the race follows a 13.1-mile course that includes Old Town Key West and the scenic waterfront. Now in its 19th year, the race typically attracts American and international runners to compete in Key West’s balmy January climate. Named as one of the United States’ leading winter half marathons in Runner’s World, February, 2014; the same magazine included in its list of Best Destination Half Marathons; in April, 2015; Bucket List Best Half Marathons, and most recently in December, 2015 was ranked among 13 must-do U.S. half-marathons by Competitor.com.

Red Barn Theatre presents: Murder for Two

January 20 to February 12

Everyone. Is. Suspect…one actor investigates the crime and the other plays all the suspects and the BOTH play the piano. A highly theatrical duet loaded with killer laughs, it’s a perfect blend of music, mayhem, and murder in a witty, winking homage to old fashioned murder mysteries.

Conch Republic Cup, Key West Cuba Race Week

January 22 to February 3

The CRC is a historic race that started in 1997 with direct race to Varadero then expanded to Havana in 1999. The triangle race as it has been coined is a traditional race to Cuba that allows the racer to complete a triangle between KW and two Cuba cities – Varadero and Havana. The CRC is a non-profit organization with the mission to introduce as many of the US sailing community to Cuba as possible as well as revitalize racing in Cuba.

Kelly McGillis Classic International Flag Football Championship

January 23 to January 30

Women and girls from around the world are to meet on the playing field for hard-fought sporting action. Each year, more than 26 teams from across the United States, Mexico, Central America, Sweden and India participate.

6th Annual Key West Food & Wine Festival

January 25 to January 28

Sample wine, Key West cuisine, and fresh seafood on one of many “strolls”.

32nd Annual Key West Craft Show

January 28 to January 29

Open air art market and judged show offering an amazing variety of work, including sculpture, paintings, craft, and folk art. Whitehead Street and Caroline Streets, Key West.

THE TRIP TO BOUNTIFUL by Horton Foote

January 24 to February 11

Presented by the Waterfront Playhouse. The Trip to Bountiful is an American masterpiece about the universal pull that we all feel for “home.” Carrie Watts is an elderly widow, trapped in the tiny Houston apartment of her overprotective son and domineering daughter-in-law, who wants to return to her hometown of Bountiful – one last time before she dies. With pension check in hand, she breaks free. Her journey is filled with humor and tenderness that’s both touching and life-affirming. Performances at 8 p.m.

Key West Food & Wine Festival

January 25 to January 29

Top chefs and restaurateurs display culinary creativity and the Keys’ indigenous cuisine in a flavorful schedule of events for food lovers. Highlights include the lively “Duval Uncorked UnDone,” neighborhood wine strolls, food and wine pairings, intriguing seminars and a grand tasting.

Red Barn Theatre presents: Murder for Two

January 20 to February 12

Everyone is suspect…one actor investigates the crime and the other plays all the suspects and the BOTH play the piano. A highly theatrical duet loaded with killer laughs, it’s a perfect blend of music, mayhem, and murder in a witty, winking homage to old fashioned murder mysteries.

Conch Republic Cup, Key West Cuba Race Week

January 22 to February 3

The CRC is a historic race that started in 1997 with direct race to Varadero then expanded to Havana in 1999. The triangle race as it has been coined is a traditional race to Cuba that allows the racer to complete a triangle between KW and two Cuba cities – Varadero and Havana. The CRC is a non-profit organization with the mission to introduce as many of the US sailing community to Cuba as possible as well as revitalize racing in Cuba.

THE TRIP TO BOUNTIFUL by Horton Foote

January 24 to February 11

Presented by the Waterfront Playhouse. The Trip to Bountiful is an American masterpiece about the universal pull that we all feel for “home.” Carrie Watts is an elderly widow, trapped in the tiny Houston apartment of her overprotective son and domineering daughter-in-law, who wants to return to her hometown of Bountiful – one last time before she dies. With pension check in hand, she breaks free. Her journey is filled with humor and tenderness that’s both touching and life-affirming. Performances at 8 p.m.

Cuda Bowl

February 2 to February 4

Shallow water flats anglers and guides are invited to hook-up and fight their barracuda rivals. Event is to be headquartered at Hurricane Hole Marina, Stock Island. Prizes and trophies are to be awarded for top angler and guide in light tackle spin and fly divisions.

Civil War Days Heritage Festival

February 3 to February 5

During the Civil War Key West remained in Union hands. Learn about this interesting fact and much more about Key West’s rich history. Fort Zachary Taylor State Park, located at the end of Southard Street. Begins Friday at 8am, ends Sunday 5pm.

Super Bowl LI (51st)

February 5

The NFL’s 51st-annual championship game is held and Key West bars offer a raucous and fun scene to watch the spectacle. Schooner Wharf Bar, at 202 William Street, has numerous large screen TV’s, food, and drink specials.

Valentine’s Day in Key West ♥

February 14

Everyone’s favorite island provides the perfect playground for lovers. Sunset sails, beach walks, and waterfront dining are popular with lovers in Key West.

Get your special one a Valentines present – just a little something here.

57th Annual Key West House & Garden Tour

February 17 to February 18

Tour a series of elegant and unique private homes of Key West, ranging from exquisite restorations to creative renovations, and the interior design that complements their architecture and adds a unique Key West flavor. The February tours are offered 10 a.m. to 4 p.m. each day. Transportation between homes NOT included. Tickets are $30. Proceeds help benefit the Old Island Restoration Foundation.

Red Barn Theatre presents: I Do! I Do!

February 21 to March 18

In this tuneful and heartwarming musical, we follow Agnes and Michael through 50 years of marital bliss, infidelity, children, incompatibility, old age, and simply joys. From the creators of “The Fantastics”, this endearing musical spans the years of 1895 to 1945, rolling out one catchy song after another in this bedroom comedy.

AVENUE Q

February 28 to March 25

Presented by the Waterfront Playhouse. Avenue Q is the winner of the Tony “Triple Crown” for Best Musical, Best Score and Best Book and one of the longest-running shows in Broadway history. Part flesh, part felt and all heart, Avenue Q tells the story of Princeton, a recent college grad. He and his friends struggle to find decent jobs, stable relationships and a purpose in life in a musical that is hilariously timeless – with hysterical songs such as “Everyone’s a Little Bit Racist,” “The Internet Is for Porn, ” and “It Sucks to Be Me.” Performances at 8 p.m.

Conch Shell Blowing Contest

March 4

An island tradition for over 50 years, this unique contest celebrates the historic importance of conch in the Keys and features contestants in several age categories attempting to make “music” with fluted conch shells. Contest located in the garden of the Oldest House, 322 Duval Street, free and open to all ages. Registration begins at 10 am, contest starts at noon.

March Merkin Permit Tournament

March 13 to March 16

A charity flats-and-fly-only tournament with a twist – in addition to catch and release, anglers earn extra points for tagging their caught fish. Held at the Key West Yacht Harbor Marina on Stock Island.

Saint Patrick’s Day ♣

March 17

Many people treat each day in Key West like St. Patrick’s Day. So when the holiday does actually come around, it is quite the party.

Get something green for St. Patrick’s Day here.

57th Annual Key West House & Garden Tours

March 17 to March 18

Tour a series of elegant and unique private homes of Key West, ranging from exquisite restorations to creative renovations, and the interior design that complements each. March tours are offered 10 am to 4 pm each day. Transportation between homes NOT included. Tickets are $30. Proceeds help benefit the Old Island Restoration Foundation.

Key West Theater presents: Get the Led Out

March 21

Led Zeppelin’s days of reunion touring may be over, but Get the Led Out’s Zeppelin tribute show hits all the right notes for fans looking to reminisce over the iconic band’s heyday. Handpicked by Jimmy Page himself to perform at one of his charity’s fundraising events, Get the Led Out have the band’s sound down to a tee. Event is age 21 and over.

Key West Theater presents: Buckwheat Zydeco

March 26

Over the course of Buckwheat Zydeco’s career, Buck has gigged with everyone from Eric Clapton (with whom Buckwheat also recorded) and U2 to The Boston Pops. The band performed at the closing ceremonies of the 1996 Summer Olympics to a worldwide audience of three billion people. Buckwheat Zydeco even performed at both of President Clinton’s Inaugurals. Showtime 8pm, for ages 21 and over.

Red Barn Theatre presents: Camping with Henry and Tom

March 28 to April 15

Bristling with humor, this delightful play is fictionally based on a 1921 camping trip taken by Henry Ford, Thomas Edison, and President Warren G. Harding. An easygoing satire of politics and history, it draws upon quotes and biographies to paint a realistic and far-from-sugar-coated picture of this trio, whose private personas often differed from the exemplary personalities known to the public.

36th Annual 7-Mile Bridge Run 

April 1

The longest bridge in the Florida Keys, and an engineering marvel, is home to one of the most anticipated and contested running races. Each year, approximately 1500 runners traverse the bridge while surrounded by stunning ocean scenery. Registration is online only in early February 2017. Only 1500 entries are allowed and this event quickly sells out.

4th Annual Cow Key Channel Run

April 2

This 300-feet long mock marathon over the short Cow Key Bridge features hilarious costumed runners, walkers, relay teams, and even pets. Prizes awarded for fastest, slowest, best costumed, best theatrical performance, and many more. FREE to participate. Check-in at 10-11:30am at Stock Island side of Cow Key Channel. Registration costs $5.

Key West Fishing Tournament Kickoff 

April 7 to April 9

Traditionally, 15 target species and $5,000 in cash prizes await anglers. Participants vie for cash awards for catching the heaviest dolphin, kingfish, cobia, blackfin tuna, mackerel, mutton snapper, wahoo, mangrove snapper and grunt. In addition, cash awaits boat teams that score the most releases of tarpon, permit, bonefish, barracuda, marlin and sailfish. Awards also are presented each year in the junior division for anglers under age 15.

GOOD PEOPLE by David Lindsay-Abaire

April 12 to April 29

Presented by Waterfront Playhouse. When Margie loses her job at the Dollar Store, she faces eviction and scrambles to make a break. She thinks an old fling, who’s made it out of South Boston to become a successful doctor, might be her ticket to a new start. An insightful dark comedy, this recent Broadway hit asks why some people manage to escape from the situations into which they are born – and some don’t. Funny and touching. Performances at 8 pm.

Easter in Key West 

April 16

Numerous restaurants have special Easter Brunch menus.

Earth Day in Key West

April 22

Celebrate with one of earth’s most beautiful places, Key West! Visit the coral reef, explore the mangrove islands in the backcountry, walk on the beach, and appreciate all that is unique about the local eco-system. And while you are at it, please pick up any trash that you come across; the earth thanks you!

Final Sail in the Quest for the Crest Series

(Formerly known as the Key West Sailfish Championship)

April 25 to April 30

Three days of catch-an-release fishing by professional and amateur anglers with big cash prizes, including $50,000 for first place in the pro division and $18,000 and $10,000 to second and third place anglers, plus trophies. Early entry fee is available.

Red Barn Theatre presents: Short Attention Span Theatre

April 25 to May 13

What do you get when you take a company of actors, directors, and filmmakers and mix in fresh, fun, 10-minute plays? Short Attention Span Theatre, that’s what! This evening of shorts typically includes lots of laughs and incredible talent. A high-octane evening of fun for everyone!

Key West Paddle Classic 

April 27 to April 30

Presented by Lazy Dog Adventures, the challenge includes a 12-mile Elite Race around the island and a 4-mile open race. Other events include a kick-off registration party, paddleboard clinics and races for kids.

Second Annual Papio Kinetic Sculpture Parade

May 11 to May 13

The Key West Art & Historical Society presents this fun, family-friendly exhibition event that is also an art-inspired float parade powered by humans on bicycles. People of all ages can celebrate the creative, funky and wild designs on display.

Key West Pride

June 7 to June 11

Key West shows its Pride every day, and this is your chance to be a part of the celebration! The five-day schedule includes daytime pool and beach parties, late-night drag shows, on-the-water adventures ranging from snorkeling and kayaking to glass-bottom boat tours, a street fair, a 10k relay for tutu-wearing runners and walkers, and pageants to select Mr., Miss and Ms. Key West Pride.

Key West Island Swim: FKCC Swim Around Key West

June 10

The officially sanctioned event is a 12.5-mile swim clockwise around the island of Key West that is open to all age groups. Individual swimmers and relay teams can compete. The route takes swimmers through the waters of the Atlantic Ocean and Gulf of Mexico, ending where they began at Higgs Beach.

5th Annual VFW Fishing Tournament

June 10

Sponsored by the Southernmost VFW Post 3911, this family oriented tournament offers cash prizes for dolphin, wahoo, tuna, snapper and grouper, along with prizes for heaviest fish by a lady angler, heaviest fish by a juvenile angler, pee-wee and active service member. Heaviest Dolphin is worth $2,500. Entry fee $200 per boat By May 19, 2017; $250 per boat after May 19, 2017. All proceeds benefit disabled and veterans in need throughout Monroe County.

Fifth Annual Key Lime Festival

July 1 to July 4

A wacky talent show, pie-eating and cooking contests and other tasty temptations await Key West visitors during the fourth annual Key Lime Festival. A Key Lime martini Sip and Stroll, Key lime rum sampling and distillery tour as well as a new Key Lime Pie Hop are among events to kickoff the four-day tasty fest.

Here’s a Key Lime Cookbook to test out your own recipes.

Del Brown Permit Tournament

July 8 to July 11

Anglers fly-fish on the flats in a challenge that honors the late angling pioneer Del Brown, who caught and released more than 500 permit off the Keys. Professionals and guides are allowed to compete as well.

Bacardi Oakheart Key West Marlin Tournament

July 19 to July 22

Anglers ply the waters once fished by novelist Ernest Hemingway, vying for $50,000 in guaranteed cash prizes. Held in conjunction with Key West’s annual Hemingway Days festival, the event awards $25,000 to the first-place team. Teams can enter one fun fish (dolphin, tuna, wahoo or released sailfish) per day to add to their point total.

Hemingway 5K Sunset Run & Paddleboard Race

July 22

This is the original and oldest ongoing 5K Run in Key West and takes place as part of the the annual Hemingway Days Festival. The race course is a scenic flat course that runs past Key West’s most famous landmarks including the Ernest Hemingway Home, the iconic Southernmost Point and the famous Green Parrot Bar. Visit website for more details.

Tropical Heat
August 16 to August 20
The Key West Business Guild presents this all-male celebration that typically includes pool and dance parties, on-the-water adventures and a fashion show that raises money for a local non-profit organization.

Eighth Annual Key West Brewfest

August 31 to September 4

More than 150 beers and micro-brews are on tap at this “tasty” annual event that benefits the charitable efforts of the Key West Sunrise Rotary Club of the Conch Republic. Events from beer dinners, beer brunches, happy hour parties, pool parties, late-night parties, seminars and the Signature Tasting Festival Event are some of the offered activities.

Womenfest Key West
September 6 to September 10
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.
Robert James Sales S.L.A.M. Celebrity Tournament
September 8 to September 10
In the first of three tournaments in the annual Redbone Celebrity Tournament Series, also called The Trilogy, anglers target tarpon, permit and bonefish to achieve the coveted “flats grand slam.” The event raises funds for the fight against cystic fibrosis.
WineDine KeyWest
September 15 to October 15
Relax, dine and play during this month-long moveable feast. Cuisine connoisseurs can enjoy multicourse prix fixe meals at several Key West restaurants during WineDine KeyWest. Restaurants include casual waterfront spots, trendy bistros, eateries specializing in fresh Florida Keys seafood and award-winning gourmet emporiums.
SoMo Marathon & Half Marathon
October 6 to October 8
This event is one of a kind! Imagine running through the southernmost island in the United States while enjoying a break from the ordinary. The Southernmost Marathon & Half promises just that- 26.2 or 13.1 miles of ocean and gulf views, as well as iconic Key West landmarks. A full weekend of events include the race and a Sunday Paddle Board race for the Special Olympics of Monroe County.
Sixth Annual Standup Paddle Invitational 2017
October 13 to October 16
Join a 2-mile paddle board and beach obstacle course to support Special Olympics Florida Monroe County. This all-levels event is fun for beginners and experienced paddlers alike. Race is to be a loop style course offering a great view for our spectators. Registration fee $35.

38th Annual Key West Fantasy Fest

October 20 to October 29

This outrageous 10-day costuming and masking celebration 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.

Looking for something to add to your costume? Click here.

The Smallest Parade In The Universe

October 27

A dazzling event from 5-9 p.m., at the corner of Caroline and William streets, at Key West Waterfront Brewery. Artists, craftsmen, model makers and creative types are encouraged to participate, making floats no larger than 18 inches! Proceeds benefit the MARC house. Up to $2,000 in prizes.

36th Annual Key West World Championship Races

November 5 to November 12

Super Boat International returns with teams from all around the world who compete April through October in the National Series Points races and conclude in November for the famous Key West World Championships. High-speed offshore powerboats race in Key West Harbor and surrounding waters to continue Key West’s longstanding tradition in this annual challenge, known internationally as the Indianapolis 500 of powerboat racing. A portion of the 6.5-mile course runs through Key West Harbor, meaning smooth water where racers can achieve speeds above 140 mph and provide fans breathtaking displays of skill and power.

Key West Film Festival

November 15 to November 19

Showcasing films that exhibit excellence in storytelling, the festival’s lineup is to feature screenings and special events hosted at landmark venues throughout Key West, including the San Carlos Institute, Studios of Key West and Key West Theater. The four-day program is to include several films from multiple genres and categories as well as social events with filmmakers, actors and film lovers.

Key West Holiday Fest

December 1 to December 31
Each year a wide range of seasonal celebrations takes place throughout Key West during the month of December. Events include the lighting of the Harbor Walk of Lights, tours of historic decorated inns, a holiday parade and much more.

The Key West Triathlon and Expo

December 1 to December 2

The Key West Triathlon and Expo expects to host a maximum of 1,000 participants and some of the sport’s best known triathletes; TRIKW allows you to bask in the warm weather and the waters of the Atlantic Ocean while the rest of the country is experiencing winter. Olympic and Sprint distances.

New Year’s Eve Shoe Drop Celebration

December 31

The Southernmost City celebrates with a descending 6-foot red high heel shoe carrying drag queen Sushi at the Bourbon Street Pub/New Orleans House complex, 724 Duval St. Seconds before midnight, the high heel bearing a lavishly gowned and coiffed Sushi is to be lowered from the second-story balcony of the complex toward the cheering crowds below. As midnight strikes and the New Year officially begins, she will land and gleefully pop the cork on a ceremonial bottle of champagne.

Check back as we update as events develop!