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


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 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.


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.


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