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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. 2015 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 2015

June 6

  • VFW Fishing Tournament – This family oriented tournament offers cash prizes for dolphin, wahoo, snapper and grouper, along with prizes for heaviest fish by a lady angler and heaviest fish by a juvenile angler. Heaviest Dolphin is worth $2,500. All proceeds benefit disabled and/or needy veterans in Monroe County. Hosted by VFW Post 3911 and Key West Harbor Yacht Club. Registration forms and rules are to be available at Key West Bait and Tackle; Murray Marine; Esky Rod Shop; Key West Harbor; VFW Post 3911; and Reef Light Tackle (Big Pine Key). Contact Pete Thomas 305-509-7244 /
  • 39th Annual Swim Around Key West – The Annual Swim Around Key West is a 12.5-mile endurance swim clockwise around the entire island of Key West. This is the 39th swimming of our event, started by founder Anna Fugina in 1977. The Annual Swim Around Key West is an independent and insured swim, permitted by the U.S. Coast Guard. We have three categories: solo swimmer, two-person relay team and three-person team. June 6, 2015 7:00 a.m. For more information, please contact: Bill Welzien at 305-394-5292.

June 10-14

  • Key West Pride – Key West shows its Pride every day, and this is your chance to be a part of the celebration! This five day celebration includes a film festival, dance parties, drag shows, bike tours, clothing-optional pool parties, water excursions, a street fair, Pride Pageants, and a ‘Pride in Our Community’ Parade down Duval Street. Contact: Guy Ross 305-294-4603 /

June 13

  • 10K Walk & Run Tutu Relay – A Tutu 10K Relay is based on the old relay idea we all remember from elementary school track meets, but with a twist… Throw down the baton and slip on a tutu! Any style or color you want, just make sure you can slip it off quickly so your teammate can put it on as fast as possible.Tutus must be worn, not carried. The tutu must be passed to a teammate at least twice during the race. Designated tutu passing locations will be marked around mile 2 and mile 4. The minimum number of team members is 2. There is no maximum number of teammates. Teams can run together, even if they are not the person wearing the tutu. IF YOU DON’T HAVE A TEAM, USE OUR CONTACT US FORM TO LET THEM KNOW AND THEY WILL COORDINATE A TEAM FOR YOU! Packet pickup and in-person registration at Salute! from 4pm – 6pm Friday night and Saturday morning from 6:30am-7:45am. Registration is $25 per person and increases to $30 per person on day of race. Beth A. Moyes: 305-747-8563.

June 18-21

  • 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. Email: for information. 

June 19-21

  • Key West Gator Club Dolphin Derby – A grand prize of $5,000 cash is to be awarded the boat team with the largest aggregate weight in dolphin during the derby’s two fishing days, with teams allowed to enter one qualifying fish each day. Second- and third-place teams will earn $2,500 and $1,000, respectively. Individual anglers can compete for trophies, prizes and cash totaling more than $15,000 in the tournament’s divisions for male, female and junior participants. Contact: Greg Oropeza 305-304-1348 /

June 20

  • 9th Annual Midsummer’s Night Dream & Spectacle – 5-11 p.m., at its historic and enchanting new venue, Fort East Martello in Key West. Hosted by the Key West Art & Historical Society and produced by Michael Shields’ Java Studios with proceeds to benefit The Society’s new children’s educational programs, everyone attending can be a participant in this playful and spontaneous celebration – a wonderland of costumed revelers, interactive art projects, feasting, dancing and multiple stages featuring poets, musicians, storytellers and theatrical antics celebrating the summer solstice and the power of dreams. Fort East Martello, 3501 S. Roosevelt Blvd., Key West. $10 advance tickets; $15 at the door; $10 for KWAHS members; children 12 and under admitted free. Artists contact: / 305-394-3804 / For information and tickets, visit

July 2015

July 3-5

  • The Key Lime Festival – A wacky Miss Key Lime Pageant, pie-eating and cooking contests and other tasty temptations await Key West visitors during the third annual Key Lime Festival. A Key Lime Martini and Margarita Sip and Stroll will kickoff the weekend-long event.
  • Superboat International Races – Super Boart International (SBI) is proud to announce the addition of Marathon, Florida to their schedule on Fourth of July weekend, 2015. July 3rd-5th, SBI and Conch Republic Offshore Powerboat Racing Association (CROPRA) will keep the tradition of racing on 4th of July and bring racing back to Marathon, Florida, where Superboats raced for years under and along the famous 7-Mile Bridge. For more information, please contact: John Carbonell at 305-296-6166.

July 4

  • Key West, Saturday, July 4, 2015 5:00 p.m. – 9:00 p.m. – Visiting Nurse Association & Hospice of the Florida Keys (VNA/Hospice) celebrates Independence Day as they host their largest fundraiser of the year, The 4th of July Picnic, at the Casa Marina – A Waldorf Astoria Resort (1500 Reynolds Street).  Now in its 31st year, the picnic is a Key West tradition for generations of locals and visitors alike. The party begins when doors open at 5 PM on Saturday, July 4th.  A meal grilled burgers, hot dogs and sides is included in the $25 (adults) and $10 (children ages 4-12) ticket prices.  Entry without a meal is $10.  Best Seats on the Beach admission ($150 per ticket) features reserved beachfront seats, exclusive dinner buffet with personal wait staff, two drink tickets, and a cash bar.  Free watermelon, popcorn and Pepsi products are offered with all admissions. Advance tickets can be purchased at or by calling 305-320-0676.  Tickets will also be available for purchase at the door on the day of the event.

July 9-12

  • Mel Fisher Days – Mel Fisher fans, past and present crewmembers, Fisher family members and treasure-hunting enthusiasts celebrate the anniversary of Fisher’s discovery of the shipwrecked Spanish galleon Nuestra Señora de Atocha. 305-296-6534

July 11-14

  • Del Brown Permit Invitational – 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.

July 21-26

  • Hemingway Days –  The 35th 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 22-25

  • 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. For anglers, the Key West Marlin Tournament provides a chance to emulate Ernest’s passion for deep-sea fishing. Contact: Tim Greene 305-304-0317 / Email:

July 23 – 25

  • Sloppy Joe’s 35th Annual Papa Hemingway Look-a-like Contest – The look-alike challenge takes place at Sloppy Joe’s Bar, 201 Duval St., frequented by Hemingway when he lived and wrote on the subtropical island throughout the 1930s. The contest’s preliminary rounds are set for 6:30 p.m. Thursday and Friday, July 23 and 24, and the newest ‘Papa’ is to be chosen during a final round beginning at 6:30 p.m. Saturday, July 25. Contact: 305-296-2388.

July 25

  • 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:
  • Hemingway Days Caribbean Street Fair – The annual Caribbean Street Fair will take place on Duval Street from 10:00am until 10:00pm on Saturday, July 25th. Local and regional vendors will show and sell everything from jewelry to local cuisine. The fair will benefit The Literacy Volunteers of America, a local not-for-profit providing free literacy tutoring for Monroe County adults and families.
  • Mattheesen’s REMARCABLE Ice Cream & Fresh Fruit Social – NOON – 4:00 PM at Higg’s Beach / West Martello Tower at 1100 Atlantic Blvd. Contact Person: Gordon Ross A summer after of amazing cold treats, make your own sundae both, warm mango cobbler with vanilla ice cream and more. The funds raised go to the Monroe Association of ReMARCable Citizens (MARC). Bring the family and bring your friends!

August 2015

August 2

  • 22nd Annual Battle of the Bars – 12:30PM – 6:30 PM at the Schooner Wharf Bar. 

August 6-9

  • Key West Lobsterfest – Every year Key West celebrates the opening of Lobster Season by throwing the biggest party of the summer. Thousands of lobster lovers descend on Key West for four glorious days and nights.

August 13-16

  • 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.

August 14-16

  • Second Annual Mystery Writers’ Key Wes Fest – Fans of mystery fiction can learn how their favorite authors craft tales of murder and mayhem. Presented in part by the Mystery Writers of America, 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.

September 2015

September 3-7

  • 6th Annual 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 /

September 10-13

  • 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 11-13

  • SLAM – 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 /

September 14-20

  • 43rd 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. Keys-wide events planned for the entire week. Contact: Drew Peterson 305-235-4023 / email:

September 25-26 

  • Conch Scramble on the Water Charity Golf Tournament – Join an on-the-water wacky charity golf tournament that brings together four-person teams to enjoy a game of nine holes by boat, to ‘drive’ biodegradable golf balls toward floating greens – without any sand traps. A live silent auction as well as a 50/50 cash raffle also are planned. A kick-off party and team registration is to be held Friday; teams tee off Saturday with shotgun start at 9 a.m. Proceeds benefit local Keys charities. Contact: Chris Trentine 305-481-5857 / Email:

October 2015

October 15-20

  • Key West Halloween Half Marathon and 5K Run – A Halloween-themed running event that encourages people to dress in their favorite costumes. The race day for the half marathon and 5K are scheduled for Sunday, Oct. 18. On the other event days, parties will be held at local restaurants and bars.

October 23-24

  • 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: Rodney Gullate 305-619-8989.

October 23 – November 1 

  • 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 /

October 26

  • 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. Contact: Beth Moyes 305-747-8563 / Email:

October 31

  • 2015 Fantasy Fest Parade – Each year, the Fantasy Fest Parade winds through the world famous Duval Street from the Gulf of Mexico to the Atlantic Ocean. Lavishly decorated floats and costumed revelers entertain tens of thousands of spectators in the premier Fantasy Fest event. With this year’s “All Hallows Intergalatic Freak Show” theme, expect the Fantasy Fest 2015 Parade to be the best yet! The parade kicks off at 7 PM on Saturday, October 31. For more information, please check out the websites: &

November 2015

November 4-8

  • 24th Annual Parrot Heads Meeting of the Minds – The annual event for those interested in the tropical lifestyle and music that Jimmy Buffett personifies. Visit for more information.For general information, please contact: Andrew Talbert at / Telephone: 305-292-1435.

November 8-15

  • Key West 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

November 11-15

  • Key West Film Fest – 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.

November 27-29

  • 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: Lee McMannis 305-619-9459

 December 2015

December 3-6
  • Hot Pink Holidays – Sponsored by the Key West Business Guild, this LGBT holiday event is full of of festive activities as well as special retail opportunities on the island. Events include “flash mob shopping sprees” for gifts galore, holiday lights tours, a hometown holiday parade experience and Christmas caroling.

December 3-20

  • Key West Holiday Fest – Each year a wide range of seasonal celebrations takes place throughout Key West. Events include the lighting of the Harbor Walk of Lights, tours of historic decorated inns, a holiday parade and much more.

December 5

  • 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. 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: 305-293-9600 / 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

Island Genn – Your Key West Concierge