Key West Events Calendar

Dream Catcher Charters offers visitors to Key West for Special Events Fishing Charters. Save Money and Have A Better Time Booking Direct.

Dream Catcher Charters offers visitors to Key West for Special Events Fishing Charters. Save Money and Have A Better Time Booking Direct.

There is never a shortage of activity on Key West. A new year is here and the events keep on coming. One of the events that is near to my heart is the Key West Fishing Tournament, sponsored by Dream Catcher Charters, Inc; this tournament was founded in 1965 and has been going strong ever since. Anyone fishing in the Florida Keys can enter this seven month long tournament. Culinary delights start off the year here in the Keys; with events like the Seafood Festival and the Food and Wine Festival foodies are in heaven!  There are also many marathons and other physical events like flag football and SUP for those athletic types. And let’s not forget about the art scene; concerts, art openings, seminars and plays are abundant throughout the year, starting off with the 33rd Annual Literary Seminar in January. So no matter when you visit our island Paradise, you will find as much action and entertainment or relaxation as you are looking for.

 June 2016

June 8-12

  • Key West Pride – 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.

June 10-12

  • Third Annual Mystery Writers’ Key West Fest – Fans of mystery fiction can learn how their favorite authors craft tales of murder and mayhem. The festival features acclaimed authors sharing insights on intrigue with readers and offers aspiring writers a chance to pitch their plots to editors and e-book publishers. Call: 305-587-9392 or Email: The MWKWF is sponsored by the Key West Citizen daily newspaper and the Florida Keys Council of the Arts.  Event registration is $175 (early-bird special of $150 for those who register by May 1) and includes all panels, presentations and four meals. 

June 11

  • VFW Fishing Tournament – 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. All proceeds benefit disabled and/or needy veterans in Monroe County. Contact: Pete Thomas 305-509-7244 / Email:

June 16 – 19

  • Key West West Africana Festival – Explore music, art, and Key West’s Afro-Caribbean culture during a three-day destination retreat focusing on thought, culture and wellness. The festival is to integrate music, art and cultural tourism, exploring Afro-Caribbean culture in Key West. Join scholars as they discuss their research and wellness experts present their practice areas. Contact: Chris Norwood at

June 17-29

  • Michael Charles in Concert at Chicagos Key West – Blues Hall of Famer Australian artist Michael Charles embarks on his ninth consecutive tour in 2016, the Coming Back Home Tour, which will once again take him to the far corners of the USA, Canada, and Australia. Charles has graced countless stages all over the world. Shows are set for 8:30 p.m. at Chicagos, 610 Greene St. Contact: 305-741-7891.

June 18

  • Key West Island Swim: FKCC Swim Around Key West – 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. Contact: Lori Bosco 305-809-3562 / Email:;

June 29

  • The Marker Resort’s monthly Art Night, in collaboration with the Studios of Key West. This month’s featured artist, Aliana Plowdrey, specializes in painting with a focus on the feminine figure and form. Participation in the class is $30 for resort guests and Studio members, and $40 for locals. The event takes place from 5 – 7 p.m. and food and drink options will also be available for purchase at Cero Bodega.

June 30

  • In celebration of the upcoming release of the all-female remake of the comedy classic Ghostbusters, the resort will be hosting a special Marker Movie Night, featuring the original 1980’s film on Thursday, June 30 at 8:30 p.m. Complimentary for all, guests and locals alike can relax by the pool and share some laughs under the stars. The Marker’s poolside restaurant, Cero Bodega will also offer special Ghostbusters-themed cocktails including the Marshmallow Mai Tai, made of vodka, Licor 43, fresh pineapple juice, lime and toasted marshmallow and cherry garnish. Also available is the Gatekeeper, made with Riazul tequila, fresh squeezed orange juice and grenadine. Both refreshing summer cocktails are available for purchase throughout the month of July for $8.

July 2016

July 1

  • The Marker’s Poolside Pop-Up’s features some of the island’s favorite local vendors including artisan jeweler The Gilded Peach and family-style boutique Tucker Provisions, guests and locals will be able to browse various locally-made products while relaxing poolside. From 2 – 5 p.m., guests and locals can escape to this tropical oasis and sample themed lite bites and cocktails while enjoying a variety of entertainment under the sun and beyond sunset.

July 2-4

  • Fourth Annual Key Lime Festival – 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, and Key lime rum sampling and distillery tour are among events to kickoff the weekend-long event.

July 4

  • 32nd Annual Hospice of the Florida Keys & Visiting Nurse Association Picnic – Benefits Hospice of the Florida Keys and the Visiting Nurse Association takes place at the luxurious Casa Marina Resort & Beach Club, A Waldorf Astoria Collection, located at 1500 Reynolds St. overlooking the Atlantic Ocean. The celebration is scheduled to start at 5 p.m. with fireworks starting at 9 p.m., courtesy of the Key West Rotary Club. Live music, a silent auction and lots of children’s games round out the fun-filled family festivities. Contact: Casa Marina at 305-294-8812.

July 11-14

  • Del Brown Permit Tournament – 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. Contact: Loren Rea 305-360-6969 / Email:

July 15 – 16

  • Mel Fisher Days – 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. Kick-off party will be Friday, 4:30pm-9pm, at the Schooner Wharf Bar with salvage boat tours, raffles, drink specials and live entertainment. ”Party like a Local” Block party is Saturday, 6pm – 10pm, at Custom House on Front Street, and features $2,500 T-Shirt lottery, food and drink vendors, free concert and a silent auction. 100% of all net proceeds from these events will benefit Wesley House Family Services, Inc. For More information, visit or call 305-296-6533.

July 19-24

  • Hemingway Days – The 36th annual celebration of the legendary author’s work and lifestyle features literary readings, Running of the Bulls, short story competition, fishing tournament, Sloppy Joe’s Look-Alike Contest and a birthday “party” commemorating Ernest’s July 21st birthday. Contact: (305) 296-2388 (Look-Alike); 797-0579 (literary).

July 20-23

  • Bacardi Oakheart Key West Marlin Tournament – 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. Contact: Tim Greene 305-304-0317 / Email:

July 23

  • Hemingway 5K Sunset Run & Paddleboard Race – 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. Contact: Barb Wright at 305-240-0727 / Email:

August 2016

August 11 – 14

  • Tropical Heat – 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. Contact: 305-294-4603.

September 2016

September 1-5

  • Seventh Annual Key West Brewfest – 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. Contact: 800-354-4455 / Email:

September 8-11

  • Womenfest Key West – 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. Contact: 305-294-4603.

September 9-11

  • Robert James Sales S.L.A.M. Celebrity Tournament – 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. Contact: Susan Ellis 305-664-2002 / Email:

October 2016

October 6 – 9

  • SoMo Marathon & Half Marathon – 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. Contact: 305-766-5284 / Email:

October 21-22

  • Goombay Festival – 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.

October 21-30

  • 37th Annual Key West Fantasy Fest – 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.” Contact: 305-296-1817 / Email:

October 23

  • Key West Halloween Half Marathon and 5K Run – Competitors are encouraged to dress in their favorite costumes for this Halloween-themed running event. Email:

November 2016

November 6-13

  • 35th Annual Key West World Championship Races – 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. Contact: 305-296-6166 / Email:

November 23-27

  • International Sand Art Competition – 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.

December 2016

December 1-3

  • Key West Triathlon and Expo – 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.

December 31

  • New Year’s Eve Shoe Drop Celebration – 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.


For more information about things to do and see in our island city, go to our Key West Web Site.

And for restaurant reviews check out our restaurant review section of this blog as well as our restaurant reviews at

Island Genn – Your Key West Concierge