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Key West Time
September 24th
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2017 Key West Events

Vacation Homes of Key West brings you an updated calendar of Key West Events to help you plan the trip you are dreaming about. Choosing a vacation rental property from Vacation Homes of Key West will provide you with a beautiful, and usually the most affordable place to stay for your favorite Key West events. If you are planning to come to the island for a more popular event, such as Fantasy Fest or New Years, we suggest you reserve your vacation rental well in advance so you don't miss out on your favorite place to stay.


January 2017

The Reverend Peyton's Big Damn Band

Jan 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.

57th Annual Key West House & Garden Tours

Jan 13 to Jan 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

Jan 14 to Jan 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.

Key West Half Marathon & 5k Run

Jan 15

Runners World magazine ranks Key West Half Marathon 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. International runners around the world come to Key West to compete in the beautiful January climate. Ranked by Competitor.com as the must-do U.S half- marathons.

30th Annual Quantum Key West Race Week 2017

Jan 15 to Jan 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.

Conch Republic Cup, Key West Cuba Race Week

Jan 22 to Feb 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

Jan 23 to Jan 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.

Key West Food & Wine Festival

Jan 25 to Jan 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.


February 2017

Cuda Bowl

Feb 2 to Feb 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.

Key West Garden Club Educational Lecture Series: Sponges, Past, Present and Future

Feb 2

Educational lectures are open to the public, from 1:30 - 3:30 p.m. Subjects pertain to gardening and environmental topics in the Florida Keys. Refreshments are served at the conclusion of each lecture. This month features Shelly Krueger, Florida Sea Grant Marine Agent with University of Florida.

Civil War Heritage Days Festival

Feb 3 to Feb 5

Colorful Civil War re-enactments, the roar of cannon fire and the sight of soldiers in Civil War uniforms are to greet visitors at Key West’s oceanfront historic Civil War-era Fort Zachary Taylor Historic State Park, as participants journey into the island’s past.

GardenFest: The Green Market Place

Feb 11 to Feb 12

A giant plant sale offers visitors the opportunity to peruse a wide array of native and exotic tropical plants, earth-based art and healthy living vendors. Enjoy a perfect day in the Garden where organic and healthy food vendors as well as a beer and wine bar will be available in the Courtyard along with the talents of local musicians. Open from 10 a.m. to 4 p.m. each day. Key West Tropical Forest and Botanical Garden is located at 5210 College Road.

34th Annual Wesley House Valentine’s Day Gala

Feb 14

This signature fundraiser features some of Key West’s most talented performing artists, the island’s largest silent auction, open bar, dancing, and an elegant and abundant dinner buffet. The Theme this year is Hat’s Off to Edith (Amsterdam) and Good Knight Edward. Located at Curry Mansion Inn, 511 Caroline Street 6:30-9:30 p.m. VIP tickets also available. Purchase tickets online.

57th Annual Key West House & Garden Tour

Feb 17 to Feb 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.

Presidential Families Series: In the Shadows of the White House

Feb 18

Presented by the Harry S. Truman Little White House., descendants of four former United States presidents are to share memories and insights about their forebears’ vacations and retreats during a presentation at Florida’s only presidential museum. Held on the grounds of the 111 Front St. residence where former President Truman spent 11 working vacations during his 1945-1953 administration.

Old Island Days Art Festival

Feb 25 to Feb 26

The 52nd annual outdoor fine art festival features oil paintings, watercolors, sculpture, photography and other offerings by more than 100 artists from around the United States and beyond. The event takes place on lower Whitehead Street in historic Old Town.


March 2017

Conch Shell Blowing Contest

Mar 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 a.m., contest starts at noon.

March Merkin Invitational Permit Tournament

Mar 13 to Mar 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.

57th Annual Key West House & Garden Tours

Mar 17 to Mar 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 a.m. to 4 p.m. each day. Transportation between homes NOT included. Tickets are $30. Proceeds help benefit the Old Island Restoration Foundation.


April 2017

Fourth Annual Cow Key Channel Bridge Run

Apr 2

Feel like running across a bridge in the Florida Keys without waking up early or breaking a sweat? Join zany-dressed participants for the world’s only Zero K across one of the shortest bridges in the Keys. The event is free to watch.

Key West Fishing Tournament Kickoff

Apr 7 to Apr 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.

35th Annual Conch Republic Independence Celebration

Apr 21 to Apr 30

With activities ranging from wacky bed race to a lighthearted sea battle featuring tall ships, the Conch Republic’s 10-day birthday party showcases the independent and eccentric spirit that characterizes the Florida Keys.

Harry S. Truman Legacy Symposium

Apr 21 to Apr 22

Key West’s political history is highlighted in panel discussions, a reception and tours of the Little White House where Truman spent many working vacations during his presidency. The 2017 theme is Harry S. Truman’s Legacy on Latin and South America. Located at 111 Front St.

The Final Sail

Apr 25 to Apr 30

This four-day challenge is the 'grand finale' of the 4-leg Quest for the Crest Sailfish Series. Team cash prizes include up to $50,000 for first place and $18,000 and $10,000 to second- and third-place anglers, plus trophies, respectively. Early entry fee is available.

Key West Paddle Classic

Apr 27 to Apr 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, paddle board clinics and races for kids.


May 2017

Papio Kinetic Sculpture Parade

May 5 to May 7

If one man’s junk is another man’s treasure, then the late Key Largo folk artist Stanley Papio was a treasure hunter extraordinaire. Fans of “outsider art” can celebrate the renegade metal sculptor’s legacy with a people-powered parade of mobile sculptures crafted in the spirit of his extraordinary creations. The Papio Kinetic Sculpture Parade features colorful sculptural floats, tricycles with exotically costumed riders, fantastically decorated bicycles and other moving works of art — all powered by human effort alone — and are to follow a route along the length of Key West’s Duval Street.

Key West Songwriters' Festival

May 10 to May 14

The 22nd annual showcase of musical magic features America’s foremost performing songwriters, with concerts staged in intimate, audience-friendly island settings

Key Lime Pie - Making Class : Make Your Own Mini-Pie!

May 19 to Aug 11

Go behind the scenes at Key West’s sweetest spot for key lime pie and learn to make Key Lime Pie Co.’s award-winning recipe of all-natural ingredients. In this class held each Friday, each participant will make his/her own mini key lime pie of graham cracker crust, key lime filling, and whipped topping—tasting encouraged! Experience pie making in our live kitchen—under the tutelage of one of our seasoned pie makers—where thousands of delicious key lime pies are made every week! After creating your mini pie masterpiece, you can pack it up for later or relax and savor right away. Class is approximately 1 hour in duration; $20 per person. Children under the age of 15 must be accompanied by a paid adult.


June 2017

Key West Pride

Jun 7 to Jun 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 Theater presents: Dave Mason

Jun 8

Fans can expect to hear such classics as “Feelin’ Alright,” “All Along the Watchtower,” “Dear Mr. Fantasy,” “We Just Disagree” and “Only You Know and I Know,” which appears on the Rock and Roll Hall of Famer’s Alone Together album. Starts at 8 p.m.

Key West Island Swim: FKCC Swim Around Key West

Jun 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.

Stoli Key West Cocktail Classic Finale

Jun 10

Regional winners from LGBT bars in 17 North American cities are to compete to create an original Key West cocktail that reflects the island’s sunny community spirit. The hotly contested final round starts at 7 p.m. on an open-air stage in the 700 block of Duval Street, with national and regional celebrity judges.

Fourth Annual Mystery Fest Key West

Jun 16 to Jun 18

Open to authors, aspiring authors and non-writing mystery-buffs alike—2017 headliners are John Hemingway, grandson of Ernest and author of 'Strange Tribe,' Keynote Speaker Clifford Irving, and Mystery Writers of America Florida Chapter past-President Randy Rawls. Lisa Black, James O. Born, Nancy J. Cohen and Heather Graham are the featured presenters among a criminally stellar hit-list of some two dozen high-profile and award winning mystery and crime fiction authors and true-crime experts.

Key West Africana Festival

Jun 22 to Jun 25

Three-day destination retreat, festival and academic conference focusing on Thought, Culture and Wellness within the African Diaspora. Thought: Workshops on topics of cultural, physical and spiritual wellness. Culture: Music, art and cultural tourism, exploring Afro-Caribbean culture in Key West.


July 2017

Fifth Annual Key Lime Festival

Jul 1 to Jul 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.

Annual 4th of July Fireworks

Jul 4

Fireworks blast from the end of White Street Pier at Higg’s Beach as the island takes on Independence Day Key West style. Bring your family to congregate with the locals at the end of White Street to get the best view from land of the southernmost fireworks show or book a cruise on one of many Key West charter vessels to watch from the water. This must see event is the perfect way to conclude the island celebration.

Del Brown Permit Tournament

Jul 8 to Jul 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.

Key West Mel Fisher Days

Jul 13 to Jul 15

Come commemorate the anniversary of Mel Fisher's famous 16-year search for the Spanish galleon Atocha and the discovery of the Atocha Mother Load . Annual Dock Party at Schooner Wharf Bar on Saturday, July 15th, with tours of salvaging vessels, raffle, silent and live auctions and live entertainment.

Hemingway Days

Jul 18 to Jul 23

The 37th annual celebration of the legendary author's work and lifestyle features literary readings, the Running of the Bulls, a short story competition, fishing tournament, 5k Run and Paddleboard Race, Sloppy Joe's Look-Alike Contest and a birthday "party" commemorating Ernest's July 21st birthday.

Hemingway 5K Sunset Run & Paddleboard Race

Jul 22 to Jul 23

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.


August 2017

Tropical Heat

Aug 16 to Aug 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

Aug 31 to Sep 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.


September 2017

Womenfest Key West

Sep 6 to Sep 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.

Lazy Dog Race the Reef

Sep 10

Attention paddle boarders! Register for Lazy Dog Key West’s ‘Race the Reef’ for a morning of fun in the beautiful keys sun. Riders will hop aboard a Sebago catamaran for a sunrise cruise out to the reef where they will toss in their paddle boards and stand-up paddle race 6 miles back to Higgs Beach in Key West. Upon arrival, breakfast on the beach will be provided by Salute restaurant and beer, wine, and cocktails will be available from a cash bar. Awards will shortly follow. Lazy Dog will provide transportation back to Sebago for those who left their car there in the morning.


October 2017

SoMo Marathon & Half Marathon

Oct 6 to Oct 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.

Sixth Annual Standup Paddle Invitational 2017

Oct 13 to Oct 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. Board rentals available through Lazy Dog.

38th Annual Key West Fantasy Fest

Oct 20 to Oct 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. The 2017 festival theme is "Time Travel Unravels."

The Smallest Parade In The Universe

Oct 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.


November 2017

36th Annual Key West World Championship Races

Nov 5 to Nov 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

Nov 15 to Nov 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.


December 2017

Key West Holiday Fest

Dec 1 to Dec 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.

Inaugural Key West Grand Prix of the Sea

Dec 8 to Dec 10

Experience non-stop racing action as Sea-Doo, Yamaha, and Kawasaki personal watercraft racers take to the water averaging 75 mph. This race is the final round in 2017 and serves as the overall championship for the PRO Enduro and International Amatuer Championship. Jetcross Jet Ski stand up races will also be a part of this family friendly event free to the public.

Key West Triathlon and Expo

Dec 9

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 Giant Shoe Drop of Drag Queen Sushi at the Bourbon St. Pub

Dec 31 to Jan 1

World famous drag queen, Sushi, is lowered in a giant red high heel shoe from the top of The Bourbon St. Pub, 724 Duval St., Key West. Huge crowd cheers below as this major Key West event is broadcast live on CNN. Live entertainment all night.

New Years Eve at Sloppy Joe's Bar - 24th Annual Dropping of the Giant Conch Shell

Dec 31 to Jan 1

World Famous Dropping of 'The Conch Shell' at Sloppy Joe's Bar at 201 Duval St. Watch the six foot Queen Conch Shell drop with synchronicity as the clock strikes mid-night with confetti, streamers, and lights filling the sky. Crowds start the party in the street at about 10:00 pm and wait til count down to midnight. No Reservations. No Tickets Sold.


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