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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.

January 2015

January 3

  • Key West Food and Wine Festival’s “Last Chef Standing” Cooking Competition - Last Chef Standing is a cooking competition that is all about skill, speed and ingenuity.  Each Saturday in January from 4:00 to 6:00 p.m., two local chefs will compete before a panel of expert judges and turn baskets of mystery ingredients into an extraordinary appetizer.  For the challenge, each chef has seconds to plan and minutes to make an amazing dish with the basket of mystery ingredients given to them moments before the clock starts ticking.  Hosted January 3rd by Grand Vin Wine Bar (1107 Duval) and Emceed by Amy Culver, this high energy, high pressure competition will have guests rooting for a winner and cheering for the losers.  Tickets can be purchased atwww.keywestfoodandwinefestival.com where you can also make an additional donation to VNA/Hospice.  For information, contact Kellee Bartley at 305-294-8812 x113 orkbartley@vnahospicekeys.org.

January 4

  • 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. (Green & Sustainability edition).

January 7

  • South Florida Symphony presents Tropical Beats II: Starry Night All in White – An elegant all in white dinner will be hosted at the luxurious Marriott Beachside Hotel in Key West. Guests will enjoy a sumptuous dinner where hosts are encouraged to create their own original centerpieces. This is a great opportunity to connect with others who love classical music and the symphony’s commitment to create high quality symphonic performances and music education programs. Experience elegance, artistic creations, inspired cuisine and great fun at the Marriott Beachside Ballroom at 6 p.m. Call for tickets. Contact: 954-522-8445.

January 8 

  • Distinguished Speaker Series: John Hemingway - Presented by the Key West Art & Historical Society, the Distinguished Speaker Series is held at the Custom House Museum, 281 Front Street, through April 2015. Scholars, historians and experts from a variety of disciplines will discuss different aspects of Key West’s rich history. John Hemingway is Ernest Hemingway’s grandson, and is to discuss the Hemingway legacy and his new book, “Strange Tribe, Three Generations of Hemingways in the Florida Straits.” Held on the second and fourth Thursdays of each month, the series runs from 6 – 7:30 p.m. unless otherwise noted. Lecture is to be held at 6 p.m. at the Tropic Cinema, admission $10, free for members.

January 8-11

  • 33rd Annual Key West Literary Seminar - Themed “How the Light Gets In, Literature of the Spirit,” the 33rd annual Seminar will explore literature’s relationship to the inexplicable — life’s essentials, what lasts and what is at the heart of us — through poetry, essay, fiction, and even silence. 888-293-9291. 

January 13 – February 17

  • Florida Keys National Marine Sanctuary Seminar Series - Register for the Florida Keys Community College’s “Sanctuary Seminar,” a six-week, non-credit lecture series hosted by Florida Keys National Marine Sanctuary. Lectures are Tuesday evenings 6:30 p.m. – 8 p.m., from January 13 – February 17, 2015 at Florida Keys Eco-Discovery Center in Key West. The tuition fee is $19 for all six lectures. Anyone interested in the marine life and maritime heritage of the Florida Keys National Marine Sanctuary can learn more in this series where experts share their knowledge of ecological and cultural resources of the sanctuary. To register call 305-809-3185.

January 16-17

  • 55th Annual Key West Historic House & Garden Tours - 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. Transportation between homes on the famous Conch Train is provided by Historic Tours of America. Tickets & times available online. Proceeds help benefit the Old Island Restoration Foundation. 
January 17 – 18
  • 10th Annual Seafood Festival – A family-friendly event with local fresh Keys seafood, drinks, marine-related crafts, youth activities, and live music. $5 admission; hours open from 11 a.m. – 8 p.m. on Saturday and Sunday from 11 a.m. to 5 p.m., at Bayview Park at Truman Avenue and Jose Marti Drive. Contact Vicki 305-872-9026 /  vicki@fkcfa.org

January 18

  • Key West Half Marathon & 5K – The perfect place to run in the middle of winter? Key West, during the Key West Half Marathon! Recognized by Runners World magazine as one of the 10 great half-marathons of the winter season, the run has attracted more than 1,000 annual participants and follows a 13.1-mile course through Old Town Key West past historic landmarks and the island’s scenic waterfront. Contact Barbara Wright 305-240-0727 / bwpromo3@bellsouth.net

January 18-23

  • Quantum Key West – The annual race week challenge features world-class competition and yachting teams from more than 12 countries and 24 American states. More than 100 racing yachts compete for class championships in this international regatta. To view the action, fans can book seats on spectator boats ranging from excursion catamarans to historic tall ships or from land at Key West’s Atlantic-front restaurants, resorts and beaches. 781-639-9545.  KWInfo@premiere-racing.com

January 24-25

  • 30th Annual Key West Craft Show – More than 100 juried artisans and crafters gather to display their talents at this popular outdoor festival on lower Whitehead Street in historic Old Town Key West. The show is free and will be held from 10 a.m. to 5 p.m. daily. Contact: 305-294-1241. 

January 25

  • 21st Annual Master Chefs Classic – Local restaurants vie for top honors in three categories; appetizers, entrees and desserts. Participants get to taste all the food made at this event while judges pick the winners. Held at Westin Key West Resort & Marina Pier at 245 Front Street, open from 4-7 p.m. Event proceeds benefit the nonprofit ReMARCable Citizens (MARC). Contact 305-294-9526, ext 25

January 28 – February 1

  • Key West Food and Wine Festival – Top chefs and restaurateurs showcase their culinary creativity and the Keys’ indigenous cuisine in a tasty schedule of events for food, wine and beer lovers alike. Attendees can participate in a slew of food-related adventurous events, brewing competitions and much more. Visit website for all festival happenings. Contact 800-474-4319; 305-304-5218 / info@keywestfoodandwinefestival.com

January 29-31

  • Cuda Bowl - Shallow water flats anglers and guides are invited to hook-up and fight their barracuda rivals. Event is to be headquartered at Hurricane Hole Marina, Stock Island. Prizes and trophies are to be awarded for top angler and guide in light tackle spin and fly divisions.

January 30 – February 1

  • King Mackerel Tournament - Big king mackerel migrate to the waters around Key West each winter, and a fittingly large prize awaits the winner of this challenge. The angler who weighs in the heaviest mackerel, also known as kingfish, is to go home with $10,000. Contact: Lee Murray 305-296-0364 / lee@murraymarine.com

February 2015

February 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. (Key West Food & Wine Festival Wine Market). 

February 6-8

  • Civil War Heritage Days Festival - Colorful Civil War re-enactments, the roar of cannon fire and the sight of soldiers in Civil War uniforms are to greet visitors at Key West’s oceanfront historic Civil War-era Fort Zachary Taylor Historic State Park, as participants journey into the island’s past. Contact: 305-292-6850.

February 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. 

February 21-22

  • 50th Annual Old Island Days Art Festival - The annual juried fine art show is set on lower Whitehead Street and Caroline Street in historic Old Town. The highly acclaimed show, from 10 a.m. to 5 p.m. daily, features oil paintings, watercolors, sculpture, photography and other offerings by artists from around the United States. Contact: Lois Songer 305-294-1243 / Email: kwartctr@earthlink.net

February 28

  • World Sword Swallower’s Day at Ripley’s Believe It or Not! – Sword swallowers will risk their lives when they “drop swords” at Ripley’s Believe It or Not! Odditoriums around the world on February 28. Watch as solid steel will go down the hatch – hopefully without a scratch — as individuals demonstrate sword swallowing skills at a free performance at Ripley’s Key West Odditorium, located at 108 Duval Street. The show will start at 2 p.m. with an official worldwide “swallow” at 2:28 p.m. to coincide with the 2/28/15 date. Sword swallowing shows outside the museum are FREE. Regular admission is required for people wanting to tour the Odditorium. Contact: 305-293-9939

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 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 / oldisland@comcast.net

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 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 / DHorn18669@aol.com

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

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 / jwolf@mote.org

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: marketing@vikingyachts.com

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 / fishnkw@aol.com

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 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 / sue@lazydog.com

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 / jcleghorn@bellsouth.net

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 / wave.whacker@hotmail.com

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: TallShipsKeyWest@gmail.com 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 / psty2k@yahoo.com

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 / guyaross@kwbgonline.org

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 / aqualb@aol.com; lori.bosco@fkcc.edu

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: cnorwood@keywestafricanafestival.com 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 / greg@smithoropeza.com

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: tim.greene@keywestmarlin.com

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: barb@keywestspecialevents.com

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. michaelhaskins@bellsouth.net.

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 / info@keywestbrewfest.com

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 / susan@redbone.org

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 / info@fantasyfest.net

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: beth@themeruns.com

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: 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: 305-293-9600 / Email: schroedkw@aol.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