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.

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 1

  • The Marker Waterfront Resort located in the southernmost city of Key West will be hosting its first ever pin-up girl contest, in partnership with M.I.A. Beer Company and Southernmost Tattoo. Guests and locals can enter to strut their best 1950’s-inspired looks on Saturday, October 1 at the Old Town Key West property. Judges for the contest will be picked at random from a $5 raffle. First, second and third place pin-up girls will receive a prize pack including gift certificates to Southernmost Tattoo, local Key West vintage clothing stores and other prizes to make their pin-up girl dreams come to life. The contest will take place at the Marker Resort’s poolside area starting at 5 p.m. M.I.A. Beer Company will host a tap takeover for the event featuring some of their fan favorite brews including Miami Weiss, Tourist Trappe, Snowbird and Moo over Miami. As an ode to Miami’s Cuban culture, the Marker will also be hosting a pig roast during the contest, complete with mojo-style roast pork with rice and beans for $15 per plate. To compliment the dishes, specialty cocktails featuring the M.I.A. brews will be available for $10. The Marker will donate a portion of its event sales to the family fund for Piero Rodriguez – the late founder of M.I.A. Beer Company. Additionally, proceeds from the raffle will go to Sister Season, a Key West non for profit that provides help to those tourism-related industries who experience economic hardships. Entry to both the event and pin-up contest is free. Guests and locals looking to participate in the contest can contact Shawna Allen at

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