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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.

March 2015

March 1

  • The Key West Artisan Market is a vibrant, open air bazaar filled with artists, authors, chef-made cuisine, craftspeople, performers, fresh produce, baked goods, cheeses and flowers, craft beer & wine from residents representing the diversity of creativity, ingenuity and locally made products of the Keys & Key West.  Held the first Sunday of the month, in season (with a few bonus markets) outdoors @ the Restaurant Store 1111 Eaton. Free family & pet friendly event. (Free Wheelin’ edition & Custom Bicycle Show).

March 2-31

  • Happy Birthday Tennessee Williams! - Celebrate the 104th birthday of Tennessee Williams and his life in Key West during the month of March. Events planned include a series of classic movies adapted from Tennessee Williams’ award winning plays, a poetry contest, artist challenge and more. Contact: 305-842-1666.

March 6

  • Flash Mob America will be in Key West for a rehearsal dinner celebration!  We will be surprising the bride and groom  by “crashing” their  rehearsal and dancing for them the night before they say their I do’s and get married! If you would like to join us for this super fun event please register on our website here: event is 100% free to attend. Due to the secret nature of flash mobs I can not release the name of the venue but I can tell you it will be in the 33040 zip code.

March 7

  • 53rd Annual Conch Shell Blowing Contest - An Old Island Days tradition, this unique contest features novel sounds produced by contestants in several age categories as they attempt to make “music” on fluted conch shells. Contest located in the garden of the Oldest House, 322 Duval Street, free and open to all ages. Registration begins at 10:30 a.m. and contest begins at noon. Contact  305-294-9501 /

March 8

  • Howl at the Moon Member Drive and Party at the Key West Lighthouse Museum from 5:30 p.m. – 7:30 p.m. Entertainment by the Homemade Wine Band. Free for members of the Key West Art & Historical Society, or join as a member that night and you’ll receive a discount on the member rate or $10 for public. For more information, please contact Christine at 305-296-6616 ext. 111.

March 13-14

  • 55th Annual Key West House & Garden Tour – Tour a series of elegant and unique private homes of Key West, ranging from exquisite restorations to creative renovations, and the interior design that complements their architecture and adds a unique Key West flavor. The February tours are offered 10 a.m. to 4 p.m. each day. Transportation between homes NOT included. Tickets and times available online. Proceeds help benefit the Old Island Restoration Foundation. Contact: 305-294-9501. 

March 14

  • 37th Annual St. Patty’s Day Stroll. For more information please call 305-766-0239 or check out
  • Key West Open Tennis Tournament – from 9am – 2pm at Higgs Beach Courts, 900 Atlantic Blvd. Key West, FL 33040. Mixed Doubles, Double Elimination, Everyone is guaranteed two matches. Pro Set 8 games, No add scoring. $30.00 Fee. Entry Deadline is midnight on Thursday, March 12, 2015. Email: or call 305-922-2358.

March 15

  • Paradise Big Band - The 17 piece Paradise Big Band will feature local vocalists and guest musicians. This is an event you don’t want to miss! For more information, please contact: 305-295-7676 For tickets:

March 16 – 19

  • March Merkin Permit Invitational - A charity flats-and-fly-only tournament with a twist – in addition to catch and release, anglers earn extra points for tagging their caught fish. Held at the Key West Harbour Yacht Club on Stock Island. Contact 303-888-4546 /

March 21

  • Key West Historic Cemetery Stroll - Groups of visitors will be guided through the cemetery, stopping at a variety of graves whose stories will be told by volunteer interpreters. Some of the graves to be visited will be those of Wilhelmina Harvey, the Porter family, and Walter Maloney. For reservations and information, call Jane Newhagen at  305-340-1453 or email
  • 10th Anniversary Croquet Tourney - Join the merriment of Womankind’s 10th Anniversary Croquet Tournament on the oceanfront lawn of Edward B. Knight’s Thompson Island Estate, Saturday, March 21 and Sunday, March 22. The Croquet Tournament welcomes a lovely Saturday morn where players and spectators, all dressed in white, enjoy the sport of kings and a light brunch. A cash bar is available. The Croquet Championship culminates on Sunday evening as the trophy is awarded to the winner of the playoff round. Then, the merriment begins! Guest dressed in vintage garden party attire enjoy hors d’ oeuvres, dinner, and an open bar. There is dancing under the stars, the Imperial Silent Auction, and a sumptuous wine tasting by Vinos on Duval for all to enjoy. Tickets available at Details: Cali Roberts: 305-320-0608. 

March 24

  • Shoe Burnin’ Festival at the Oldest House - Support the beams of the Oldest House Museum – our foundation is crumbling and needs YOUR support. Meet author Kurt Meyer. Learn about restoring old properties. Preserve the past for future generations. From 1:00 to 4:00 on Tuesday, March 24. Tickets $30 per person day of at the gate, $25 in advance online at Ticket includes signed copy of one of Meyer’s books, wine bar, and snacks. Come one, come all. Wear mismatched shoes and tell YOUR preservation story. Learn about efforts to restore and maintain the Oldest House in Key West. All proceeds go to the work of restoring our beams! We need you!! Join us for an entertaining afternoon! For more information call (305) 294-9501. 

March 28 

  • Miss Gay Southernmost USofA - The Miss Gay Southernmost USofA and Miss Gay USofA Classic are to be the first preliminary pageants to allow contestants to compete in the annual Miss Gay USofA pageant held annually in Dallas. This pageant of female impersonation starts on the Fury Water Sports Catamaran for a two-hour sunset cruise where all can meet contestants, judges, and sponsors. Miss Gay Southernmost USofA and Classic pageants will be Saturday night followed by performances on Sunday and Monday night at La Te Da. Contact: 305-731-6557.
  • Reggae Concert at Higgs Beach. 6 – 10 PM. Please call 305-296-9255 for more information. 

April 2015

April 4 – November 30

  • Key West Fishing Tournament sponsored by Dream Catcher Charters - More than 40 species of fish are targeted during these months, with divisions for men, women, junior anglers (ages 10 to 14) and Pee Wees (under 10 years old). The Key West Fishing Tournament strongly encourages the release of game fish. All participating anglers receive certificates noting their catches and qualify for a variety of prizes. Contact: Rob Harris 305-587-6718 or Doris 305-295-6601. 

April 4

  • Sixth Annual Florida Keys Ocean Festival and Craft Show - Presented by Florida-based Mote Marine Laboratory, the family-friendly free-admission Ocean Festival is set for 11 a.m. to 6 p.m. Scheduled attractions include live music, arts and crafts, kids’ activities including face painting, educational displays, food and beverages, a silent auction and more. The festivities take place at the Florida Keys Eco-Discovery Center, located on Key West’s Truman Waterfront past the end of Southard Street. Contact Jason Wolf 305-393-6022 /

April 5

  • The Key West Artisan Market is a vibrant, open air bazaar filled with artists, authors, chef-made cuisine, craftspeople, performers, fresh produce, baked goods, cheeses and flowers, craft beer & wine from residents representing the diversity of creativity, ingenuity and locally made products of the Keys & Key West.  Held the first Sunday of the month, in season (with a few bonus markets) outdoors @ the Restaurant Store 1111 Eaton. Free family & pet friendly event. (Mote Marine Ocean Festival edition).

April 8-11

  • 2nd Annual Viking Yacht Challenge - This fishing tournament is open to all Viking owners to join this family friendly, family fun tournament that features lots of trophy awards. Highlights include two fishing days, one lay day; anglers target primarily sailfish but there are also categories for tuna, dolphin, kingfish and wahoo. Boats can utilize four Key West Marinas for dockage: A&B Marina, Conch Harbor Marina, The Galleon Marina and Key West Bight Marina. Six anglers per boat are allowed. Contact: Mary Foust 609-296-6000 x 345 / Email:

April 13

  • Taste of Key West - Scores of area restaurants present mouthwatering samples of their cuisine to benefit AIDS Help Inc. The culinary celebration takes place at the Truman Waterfront overlooking Key West Harbor.  Contact: 305-296-6196.

April 15-19

  • Key West Sailfish Championship - This four-day challenge is to offer up to $50,000 for first place prize, $15,000 and $10,000 to second- and third-place anglers, respectively. Early entry angler fee per angler is available. Visit website for details. Contact: Mike Weinhofer 305-395-3474 /

April 17-26

  • 33rd Annual Conch Republic Celebration - With activities ranging from wacky bed race to a lighthearted sea battle featuring tall ships, the Conch Republic’s 10-day birthday party showcases the independent and eccentric spirit that characterizes the Florida Keys

April 18

  • Second Annual Cow Key Channel Bridge Run – Feel like running across a bridge in the Florida Keys without waking up early or breaking a sweat? Join zany-dressed participants for the world’s only Zero K across one of the shortest bridges in the Keys. The event is free to watch.

April 22

  • Tennessee Williams Theater Presents Kathy Griffin. Tickets available at

April 30 – May 3

  • Key West Paddleboard Classic - During this ocean paddleboard race, participants enjoy a challenging 12-mile course over crystal blue waters, circling Key West through scenic mangroves, passing by the Historic Seaport district and more. The race around Key West is open to paddlers on standup paddleboards, prone boards, outrigger canoes, dory boats, surf skis and kayaks. Other weekend beach and paddling activities are planned. Contact: Sue Cooper 305-304-4259 /

May 2015

May 2

  • Keystock Music Fest - Crowds are expected to gather at Truman Waterfront for an evening musical event. Keystock is sponsored by Lazy Lakes RV Resort and Howard Livingston and the Mile Marker 24 Band. Concert profits benefit Homes for Veterans Inc. VIP tickets, reserved seating, and general admission are to be available. No coolers or lawn chairs day of show. Musical acts to be announced. Contact: Joe Cleghorn 305-292-7729 /

May 3

  • The Key West Artisan Market is a vibrant, open air bazaar filled with artists, authors, chef-made cuisine, craftspeople, performers, fresh produce, baked goods, cheeses and flowers, craft beer & wine from residents representing the diversity of creativity, ingenuity and locally made products of the Keys & Key West.  Held the first Sunday of the month, in season (with a few bonus markets) outdoors @ the Restaurant Store 1111 Eaton. Free family & pet friendly event. (Conch Republic Days edition). 

May 6-10

  • Key West Songwriters’ Festival - The 20th-annual showcase of musical magic features America’s foremost performing songwriters, with concerts staged in intimate, audience-friendly island settings. Contact: Charlie Bauer 305-304-0814

May 14-17

  • Key West Land, Air, and Sea Poker Run - Presented by the Florida Powerboat Club, fans and aficionados can join a unique motorsports event as participants from around the United States can enjoy up to five days of motoring, boating and flying fun in tropical paradise. Featuring group rallies from Miami to Key West by air, land and by sea. See the cars, boats and motorbikes on display at the Poker Run Village, located at the Conch Republic Seafood Company, Friday 4 – 10 p.m., and Saturday 10 a.m. to 10 p.m. Admission is free to the public. Contact: 954-545-1414.

May 15-16 

  • 13th Annual Harry S. Truman Legacy Symposium - Key West’s political history is highlighted in panel discussions, a reception and tours of the Little White House where Truman spent many working vacations during his presidency. The 2015 topic is “America’s Greatest Humanitarian Effort – The Marshall Plan.”  305-294-9911 

May 22-23

  • Dolphin Masters Invitational - In this challenge headquartered at Conch Republic Seafood Company, more than $13,000 awaits the angler scoring the highest total combined weight of three dolphin catches. Many additional prizes await other top anglers, and there is no limit on the number of participating boats. Registration is Friday, at Conch Republic Seafood Co.,631 Greene St. Fishing Saturday from 7 a.m. to 3:30 p.m. Contact John Stuempfig 305-304-7674 /

May 28 – June 1

  • Sunset Celebration Welcomes Tall Ships - Historic sailing ships join the traditional sunset celebration at Mallory Square Dock for a 5-day festival of ship tours, sunset & day sails, artisans, performers, music, storytelling and more. Email: for more information. 

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 /

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

  • FKCC Swim Around Key West - Long distance solo swimmers and relay teams of two to six people, with or without fins, can compete in this United States Masters Swimming-sanctioned even, a 12.5-mile swim clockwise around the island of Key West. The clockwise route around the island takes swimmers through the waters of the Atlantic Ocean and Gulf of Mexico, ending where they began at Smathers Beach. Open for all age groups. Contact Lori Bosco 305-809-3562 /;

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 /

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.

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 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:

August 2015

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 /

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:

November 2015

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

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