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.

It seems as though there is never a shortage of activity on Key West. 2014 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 32nd 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.

October 2014

October 9-13

  • 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 17-26

  • 35th Annual Fantasy Fest - This outrageous 10-day costuming and masking celebration features flamboyant costume competitions including one for pets, promenades, street fairs and a grand parade that stars marching groups, island bands and lavish floats. More than 40 masquerade contests, themed parties, parades and other spectacles are to challenge the creativity of mask and costume designers. Contact: 305-296-1817; Email:

October 17 & 18

  • 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. Contact: Bob Oberle 305-304-2643; Email:

October 20

  • Heroes and Villains 5k Run/Walk - Be super, be evil, be AWESOME and get your run on! Dress up as your favorite Superhero or Super Villain and run, walk or fly to the finish line. Prizes are awarded for most creative, best group, scariest and funniest characters. Winner medals and awards are to given for overall male and female winners, masters (40+) male and female winners. Register online. Race starts at 6 p.m. The race begins and ends at The Reach, A Waldorf Astoria Resort and ends with a luau. Come for the run, stay for the fun!” ? Contact: Beth Moyes 305-747-8563; Email:

October 21

  • 32nd Annual Headdress Ball - This “over the top” contest includes an extravagant show with lots of Key West razzle dazzle, and is a competition “head and shoulders” above the rest with contestants judged from the shoulders up! Major cash prizes including a $1,500 grand prize. Tickets sell out quickly! Held at the Southernmost on the Beach, 508 South Street. Email:

October 27

  • Mangia Mangia, located at 900 Southard Street, will donate 25% of their total sales (food, alcohol and take-out orders) to Visiting Nurse Association & Hospice of the Florida Keys.  VNA/Hospice is the only non-profit hospice and home health agency serving all of Monroe County, and community events like Mangia Mangia Nights help to increase awareness of VNA/Hospice’s mission to “enable individuals to remain in their home by providing compassionate, effective, life-enhancing health and supportive services.” For information, contact Kellee Bartley at 305-294-8812 x113

October 29 – November 2

  • Parrot Heads Meeting of the Minds Convention - This annual event is meant to assist with environmental concerns while showing members an amazing time in Paradise. The Parrot Head motto is to Party with a Purpose, so events for the Meeting of the Minds Parrot Head Convention include concerts, auctions and raffles all benefitting charity.  To attend this Key West Parrot Head Convention you must be a member of a sanctioned Parrot Head Club. There are over 200 chapters in the North America, Australia, and Europe.  For more information about the convention, visit the ‘Meeting of the Minds’ section of the Parrot Head Clubs’ official website

October 31

  • The BottleCap Lounge – Enjoy the 8th annual Virtual Parrothead “Meeting of the Minds” Happy Hour benefitting VNA/Hospice.  This year’s special Halloween Happy Hour will feature live music by Texas’ Larry Joe Taylor, a Halloween costume contest with prizes, a raffle featuring a Margaritaville “Key West” Frozen Concoction Maker, a grab bag bottle pull, adult trick-or-treating sponsored by Three Olives Vodka, and celebrity bartenders earning their tips for VNA/Hospice.  Fabulous food will be available from Bad Boy Burrito. For information, contact Kellee Bartley at 305-294-8812 x113

November 2014

November 2-9

  • Key West World Championship Race - High-speed offshore powerboats race in Key West Harbor and surrounding waters to continue Key West’s longstanding tradition in this 32nd 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.

November 7-10

  • Third Annual Key West International Latin Arts Festival - Experience “Vientos del Alma,” a celebration of traditional Latin American cultural arts featuring dance and percussion workshops, artists’ exhibits, poetry readings, wine tastings, culinary surprises and a spectacular theatrical concert. Vientos del Alma (Winds of the Soul) highlights include: InnerNacionalSound’s Christian Monzón and Valerie Carr, renowned Miami-based Tango Times dance luminaries Roxana Garber and Oscar Caballero and an outstanding international line-up of local and visiting musicians, folk dancers and thrilling performers. Visit website for details and tickets; events to be held at San Carlos Institute. Contact: 305-394-0808.

November 12 – 16

  • Third Annual Key West Film Festival - 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 Tropic Cinema and San Carlos Institute. 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. Contact: 941-527-9385; 305-295-9112.

November 28-30

  • ART!KEY WEST! - This annual event comprises three days of artistry throughout historic Old Town, with spotlight events rotating among the island’s multiple cultural districts. Highlights include live mural painting, gallery openings and showcases, performance art, theater and musical performances. Contact: Marky Pierson 305-619-2275; Email:

December 2014

December 4-7

  • TRIKW Swim-Bike-Run in Paradise - 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. Contact: Doug Bradshaw 305-797-8361; Email: 

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. Contact: Bob Oberle 305-304-2643; Email:

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

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