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.

July 2014

July 4

  • 30th Annual Hospice of the Florida Keys & Visiting Nurse Association Picnic - Marking 30 years, Key West’s annual July 4 picnic is to benefit 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. The traditional buffet offers hamburgers, hot dogs and all the fixings for $25 per adult, $10 per child between 3 and 12 and free for children younger than three. General admission (no meal) tickets are $10 and include watermelon, popcorn and soft drink. For an elegant alternative, attendees can choose reserved beachfront seats with first-class service and a lavish buffet. Tickets for the “best seats on the beach” section are $125 per person. Live music, a silent auction and lots of children’s games round out the fun-filled family festivities. Contact: Casa Marina 305-294-8812

July 4-5

  • The Key Lime Festival - An All-American celebration of Florida’s official and one of the most tasty pies! Salute sweet Key Lime pie, and the tiny fruit that inspired it, with events ranging from a pie-eating contest to a wacky world record attempt for making the largest pie EVER.

July 10-13

  • Mel Fisher Days - This annual celebration brings together Mel Fisher fans and treasure-hunting enthusiasts in a celebration of the anniversary of Fisher’s discovery of the shipwrecked Spanish galleon Nuestra Senora de Atocha. Contact: 305-296-6534.

July 13-16

  • 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: loren@keywestdesign.com.

July 15-20

  • Hemingway Days - The 34th annual celebration of the legendary author’s work and lifestyle features literary readings, a theatrical premiere, short story competition, fishing tournament, Sloppy Joe’s Look-Alike Contest and a pre-birthday “party” commemorating Ernest’s July 21st birthday. Contact: (305) 296-2388 (Look-Alike); 294-0320 (literary)

July 16-19

  • Drambuie 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, 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: tim.greene@keywestmarlin.com.

July 17

  • Walk on White Monthly Art Stroll - This regular neighborhood gallery stroll is perhaps the best known among art lovers, held on the island city’s White Street from Southard to United streets and onto Truman Avenue the third Thursday of each month, from 6-9 p.m. The popular evening features exhibitions and receptions at galleries, shops and occasionally other venues. Highlight locations include Harrison Gallery; the quirky and inviting Stone Soup Gallery; and The Studios of Key West, offering regular exhibitions, performances, workshops and studio space in the style of America’s leading artist communities. Each month’s stroll highlights a different artistic genre.

July 19

  • 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! The Lazy Dog Paddle Board Race will take place before the 5K and kicks off at 6PM. The 4 mile paddle board challenge will start at the Beach by the Southernmost Beach Cafe. Visit website for more details. Contact: Barb Wright at 305-240-0727; Email: barb@keywestspecialevents.com.

August 2014

August 7-10

  • Key West Lobsterfest: A Crustacean Celebration! - Events include a Thursday night lobster boil, Friday night Duval Crawl, Saturday street fair with lobster-inspired culinary creations and a free concert, and a luscious lobster brunch Sunday. The festive feast celebrates the start of the Florida Keys lobster season. 
    Contact: 305-744-9804

August 14-17

  • Tropical Heat - Tropical Heat offers All Male-All Adult fever-pitch revelry on the island whose openness and respect for diversity have made it a world-renowned gay vacation destination. The festival includes more than a dozen intriguingly decadent events ranging from drag shows to themed pool parties and gatherings at island clubs. Contact: 305-294-4603; 800-535-7797; Email: guyaross@kwbgonline.org.

August 21

  • Walk on White Monthly Art Stroll - This regular neighborhood gallery stroll is perhaps the best known among art lovers, held on the island city’s White Street from Southard to United streets and onto Truman Avenue the third Thursday of each month, from 6-9 p.m. The popular evening features exhibitions and receptions at galleries, shops and occasionally other venues. Highlight locations include Harrison Gallery; the quirky and inviting Stone Soup Gallery; and The Studios of Key West, offering regular exhibitions, performances, workshops and studio space in the style of America’s leading artist communities. Each month’s stroll highlights a different artistic genre.

August 28 – September 1

  • Fifh Annual Key West Brewfest - More than 150 beers and micro-brews are on to be 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 great activities on tap. Contact: 800-354-4455; Email: info@keywestbrewfest.com.

September 2014

September 4-7

  • Womenfest Key West - Womenfest offers a wide range of activities guaranteed to appeal to a broad range of interests. Golfing with palm trees and iguanas, clothing-optional pool parties, a sizzling dance club scene, and women-only water excursions that range from jet skis to dolphin watching all promise to pique the interest of the more adventurous while film, live music, and special comedy shows offer the opportunity to enjoy paradise at a slower pace. All of this on a tropical island that is “close to perfect but far from normal.” Contact: 800-535-7797; 305-294-4603; Email: admin@kwbgonline.org.

September 5-7

  • 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: susan@redbone.org.
September 18-21
  • 42nd Annual Phil Peterson’s Key West Poker Run - It’s an All-American event as motorcycle enthusiasts from around the U.S. travel the Keys’ scenic Overseas Highway – designated Florida’s only All-American Road – from mainland Florida to Key West to raise money for charity. Winner takes all, and can win a new Harley-Davidson Motorcycle or cash. Stops are arranged throughout the Keys with a final celebration in Key West. Poker Run stops are to be open for riders starting Thursday through Sunday, Sept. 21; Keys-wide events planned for the entire week. Contact: Drew Peterson 305-235-4023; Email: drew@petersonsharley.com.

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: liz@somomarathon.com.

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: info@fantasyfest.net.

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: boboberle@hotmail.com.

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: beth@themeruns.com.

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: guyaross@kwbgonline.org

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: luckystreetgallery@gmail.com

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: dougtrikw@gmail.com 

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: boboberle@hotmail.com

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 www.gotothekeys.com.

Island Genn – Your Key West Concierge