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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 2016

January 1, 15

  • Key West Outdoor Movie – Enjoy free-admission outdoor movies at Bayview Park every first and third Friday through May 20th. Starts at dusk. Bring lawn chair, snack and refreshments. Check website for upcoming movie events. Contact: Jason 305-791-4375.

January 7-10

  • 34th Annual Key West Literary Seminar – The 2016 topic, “Shorts: Stories, Essays & Other Briefs,” will examine and celebrate literary short forms. A first-come, first-seated Sunday afternoon session is free and open to the public. The annual high-spirited gathering attracts literary aficionados from around the world for readings, discussions and lectures led by some of contemporary literature’s leading writers.  Contact: 888-293-9291.

January 8-10

  • Key West Wahoo Shootout – Join a bluewater spearfishing tournament, to be headquartered at The Waterfront Brewery. Species include Wahoo, King Mackerel, and Amberjack with up to $20,000 in prizes. Adult and Junior divisions as well as Captain’s prize. Contact: John Paul Castro: 305-896-4244 / Email: wahooshootout@gmail.com

January 10

  • Monthly Artisan Market: Green & Sustainable – 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 one Sunday each month, during season (thru April) outdoors at the Restaurant Store, 1111 Eaton. Free family & pet friendly event. Email: jill@dailyplan-it.net

January 15-30

  • Red Barn Theatre presents: Scott and Hem – In this fictional but probable meeting between F Scott Fitzgerald and Ernest Hemingway, the two legends literally and figuratively come to blows. Scott is holed up in a Hollywood hotel where he is hopefully writing more than he is drinking when Hem walks in for a visit. Contact: 305-296-9911.

January 15-16

  • 56th Annual Key West 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 each. March tours are offered 10 a.m. to 4 p.m. each day. Transportation between homes included. Tickets and times available online. Proceeds help benefit the Old Island Restoration Foundation.

January 16-17

  • 11th Annual Florida Keys Seafood Festival – A family-friendly event with local fresh Keys seafood, drinks, marine-related crafts, youth activities, and live music. $5 admission per person; hours open from 11 a.m. – 8 p.m. on Saturday; 11 a.m. to 5 p.m. on Sunday, at Bayview Park, Truman Avenue and Jose Marti Drive. Contact: Vicki 305-872-9026 / Email: vicki@fkcfa.org.

January 17

  • Key West Half Marathon & 5k Run – Recognized by Runners World magazine as one of the 10 great half-marathons of the winter season, the race follows a 13.1-mile course that includes Old Town Key West and the scenic waterfront. Contact: Barbara Wright 305-240-0727/ Email: bwpromo3@bellsouth.net

January 17-22

  • Quantum Key West Race Week 2016 – 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 typically 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.

January 19-20

  • Key West Theater presents: Winter Concert Series – Performance features the Indigo Girls (Emily Saliers and Amy Ray), known around the world for their signature harmonies. Key West Theater located at 512 Eaton Street. Tickets sold online.

January 22-24

  • Stock Island Marina Village 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/Email: lee@murraymarine.com.  

January 27-31

  • Key West Food & Wine Festival – Top chefs and restaurateurs display culinary creativity and the Keys’ indigenous cuisine in a tasty schedule of events for food lovers. Highlights include the lively “Duval Uncorked Deconstructed,” neighborhood wine strolls, food and wine pairings, intriguing seminars, an outdoor artisan wine market and a “Mile 0” grand tasting. Contact: 800-474-4319; 305-304-5218/Email: info@keywestfoodandwinefestival.com.
January 28
  • KWAHS Distinguished Speaker Series presents: John Hemingway – “Cuba at the Crossroads” is an evening presentation by John Hemingway, author and grandson of the iconic Ernest Hemingway. Hemingway, who grew up in Miami and has visited Cuba three times in the last year, is to share his perceptions of our neighboring island and the many contradictions that saturate it. From 6-7 p.m., at Tropic Cinema. Tickets are available at through the Tropic’s Box Office; $5 for members, $10 for nonmembers.  Contact: 305-295-6616 ext 115.
January 30
  • Miss Gay Southernmost USofA and Classic – The Miss Gay Southernmost USofA and Miss Gay USofA Classic are preliminary pageants to allow contestants to compete in the annual Miss Gay USofA pageant held in Dallas. A showcase of female impersonation, competition categories include evening gown, talent and interview performances. Contact: 305-747-8563.

January 30-31

  • 31st Annual Key West Craft Show – Tens of thousands of attendees browse and buy among juried artisans and crafters who gather to display their talents at this popular outdoor festival on lower Whitehead Street in historic Old Town Key West. Contact: 305-294-1243/Email: kwartctr@earthlink.net.

January 31

  • 22nd Annual Key West Master Chefs Classic – Local restaurants vie for top honors in appetizer, entrée and dessert categories. Attendees sample the culinary treats while judges pick the winners. The show is held from 4-7 p.m. at the Westin Key West Resort & Marina pier. Event proceeds benefit the nonprofit Monroe Association for ReMARCable Citizens. Contact: 305-294-9526, ext 25.
  • Monthly Artisan Market: Culinary & Wine Show – 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. This is a special double feature for Nov. Market traditionally held one Sunday each month, during season (thru April) outdoors at the Restaurant Store, 1111 Eaton. Free family & pet friendly event. Email: jill@dailyplan-it.net.

February 2016

February 2

  • Mel Fisher Maritime Museum’s Free Lecture Series: The Silver Bars of the Treasure Galleon Atocha – The primary cargo of the shipwrecked 1622 galleon Nuestra Señora de Atocha was silver, most of which was found in one thousand large ingots. The examination of these silver treasure bars reveals much about the history and economy of the Spanish empire and the operation of the Atocha. A short video on the subject by PBS’ “History Detectives” will open this presentation, followed by further discussion and Q&A. Rumor has it you might even have a chance to lift a silver ingot – or at least try! Museum is located at 200 Greene Street, lecture is presented in the courtyard, and begins at 6:30 p.m. Chairs are provided on a first come first serve basis. Contact: 305-294-2633 ext 22. Email: cmalcom@mfmm.org

February 5, 19

  • Key West Outdoor Movie – Enjoy free-admission outdoor movies at Bayview Park every first and third Friday through May 20th. Starts at dusk. Bring lawn chair, snack and refreshments. Check website for upcoming movie events. Contact: Jason 305-791-4375.

February 4-6

  • Cuba 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. Contact: Justin or Loren Rea 305-744-0903 / Email: info@cudabowl.com

February 5-7

  • 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 9

  • Mel Fisher Maritime Museum’s Free Lecture Series: The Archaeology of a 16th Century Shipwreck – In 1991, the Mel Fisher Maritime Museum began research on an ancient, mystery shipwreck known only as the “St. Johns Wreck.” After many years of detective work, all evidence now indicates it is the site of the 1564 galleon Santa Clara. MFMHS archaeologist Corey Malcom will share details of the investigations – from the sea floor to the Spanish archives – that gave this shipwreck a name and allow its story to be told. Museum is located at 200 Greene Street, lecture is presented in the courtyard, and begins at 6:30 p.m. Chairs are provided on a first come first serve basis. Contact: 305-294-2633 ext 22 / Email: cmalcom@mfmm.org

February 12 & 13

  • 56th 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 / Email: tickets@oirf.org

February 13 & 14

  • GardenFest: The Green Market Place – Enjoy native plants, palms and orchids, Earth-based arts and crafts, green and healthy-living products and services and lunch and music in the “Beer Garden”. This year is to also feature a new ‘Kids Science Corner.’ Open from 10 a.m. to 4 p.m. each day. Key West Tropical Forest and Botanical Garden is located at 5210 College Road. Contact: 305-296-1504.

February 14

  • 33rd Annual Wesley House Valentine’s Day Gala – This signature fundraiser features some of Key West’s most talented performing artists, the island’s largest silent auction, open bar, dancing, and an elegant and abundant dinner buffet. The Theme this year is New Orleans Masquerade. Come with your best mask ready for some delicious food. Located at Curry Mansion Inn, 511 Caroline Street 6:30-9:30 p.m. VIP tickets also available. Purchase tickets online. Contact: 305-809-5000.
  • Key West Impromptu Classical Concerts presents: Eroica Trio – The most sought-after trio in the world, the Grammy®-nominated Eroica Trio thrills audiences with flawless technical virtuosity, irresistible enthusiasm and sensual elegance. Whether playing the great standards of the piano trio repertoire or daring contemporary works, the three young women who make up this celebrated ensemble electrify the concert stage with their passionate performances. Show starts 4 p.m., at St. Paul’s Episcopal Church, 401 Duval St.

February 16

  • Mel Fisher Maritime Museum’s Free Lecture Series: The Search for the Spanish Pirate-Slaver Guerrero – On December 19, 1827, while attempting to sail to Cuba with 561 African captives, the Havana-based pirate slave ship Guerrero became engaged in battle with a British Royal Navy schooner; in the confusion both ships wrecked on a Florida Keys reef. In a bold, audacious move, many of the pirates escaped, but Guerrero was a total loss and never sailed again. Enjoy an overview of the ship’s fascinating history and outline today’s efforts to locate and document its remains on the sea floor. Museum is located at 200 Greene Street, lecture is presented in the courtyard, and begins at 6:30 p.m. Chairs are provided on a first come first serve basis. Contact: 305-294-2633 ext 22 / Email: cmalcom@mfmm.org

February 21

  • Monthly Artisan Market: Recycle-Upcycle – 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 one Sunday each month, during season (thru April) outdoors at the Restaurant Store, 1111 Eaton. Free family & pet friendly event.

February 23

  • Mel Fisher Maritime Museum’s Free Lecture Series: History, Archaeology of Key West Turtling Industry – The long-running Key West turtling industry helped to shape the island’s identity and economy for over 150 years, but it was done at an unsustainable cost to Keys and Caribbean Green Sea Turtles. The story of this unique business is examined through historical research, oral history, and the archaeological excavation of the Key West Turtle Kraals. Museum is located at 200 Greene Street, lecture is presented in the courtyard, and begins at 6:30 p.m. Chairs are provided on a first come first serve basis. Contact: 305-294-2633 ext 22 / Email: cmalcom@mfmm.org.

February 27

  • 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 27. 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 2:27 p.m. to coincide with the 2/27/16 date. Sword swallowing shows outside the museum are FREE. Regular admission is required for people wanting to tour the Odditorium.
February 27 & 28
  • Old Island Days Art Festival – The 51st annual juried outdoor fine art festival features oil paintings, watercolors, sculpture, photography and other offerings by more than 100 artists from around the United States and beyond. The event takes place on lower Whitehead Street in historic Old Town. Contact: 304-294-1243.

March 2016

March 1-31

  • Happy Birthday Tennessee Williams! – Celebrate the 105th birthday of Tennessee Williams and his life in Key West during the month of March. Highlights include a series of classic movies adapted from Williams’ award winning plays, a poetry contest, artist challenge, staged readings from his plays, letters & journals, a film forum, and much more. Visitors are invited to tour the educational and historic Tennessee Williams Key West Exhibit, at 513 Truman Avenue, near Duval St. For month-long events, tickets and venues, visit twkw.org.

March 5

  • Conch Shell Blowing Contest – An island tradition for over 50 years, this unique contest celebrates the historic importance of conch in the Keys and features contestants in several age categories attempting to make “music” with fluted conch shells. Contest located in the garden of the Oldest House, 322 Duval Street, free and open to all ages. Contact: 305-294-9501 / Email: oldisland@comcast.net

March 11 & 12

  • 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 2016 topic is “Harry’s War … the Legacy of the Korean War.” Located at 111 Front St. Contact: 305-294-9911.
  • 56th Annual Key West 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 each. March 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 / Email: tickets@oirf.org

March 12

  • Key West Botanical Garden Celebrates 80 Years – In 2016 the Key West Botanical Garden Society is to celebrate 80 years in the making. Follow along with them as they share 80 years of history and celebrate all the people and supporters, who got them there. It all leads up to a big 80th anniversary jubilee on March 12th, 2016. From 1936 to 2016, the Garden will present a Five-Part Series with historic information to share. Contact: 305-296-1504 / Email: events@kwbgs.org

March 13

  • Monthly Artisan Market: Free Wheelin’ Custom Bicycle Show – 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 one Sunday each month, during season (thru April) outdoors at the Restaurant Store, 1111 Eaton. Free family & pet friendly event.
March 14-17
  • March Merkin Permit Tournament – 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 / Email: DHorn18669@aol.com

April 2016

April 2 

  • Seventh Annual Florida Keys Ocean Festival & Waterfront Craft Show – Presented by Florida-based Mote Marine Laboratory, the annual event features a kids’ fishing seminar, touch tanks and live animals, educational activities, a planned art auction, marine-themed games, refreshments, food and local vendors. The show is set to take place at the Florida Keys Eco-Discovery Center on the Truman Waterfront, and celebrates the treasured Keys waters and environment. Contact: Jason Wolf 305-393-6022 / Email: jwolf@mote.org
  • Keystock Music Festival – Crowds are expected to gather at Truman Waterfront for an evening musical event that in the past has hosted Grand Funk Railroad, Doobie Brothers and Three Dog Night. No coolers or lawn chairs day of show. VIP tickets can be purchased through Lazy Lakes by calling 305-745-1079.  

April 2 & 3

  • Naval Air Station Key West 2016 Southernmost Air Spectacular – The U.S. Navy flight demonstration team Blue Angels and other military and civilian aerial performances will fill the skies at this free-admission, family friendly event. In addition to the Blue Angels, aerial demonstrations by military and civilian performers, and static military and vintage aircraft are planned. Contact: (305) 293-2673 / Email: timothy.w.campbell@navy.mil

April 3

  • Monthly Artisan Market: Ocean Awareness – 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 one Sunday each month, during season (thru April) outdoors at the Restaurant Store, 1111 Eaton. Free family & pet friendly event.

April 10

  • Third 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 12-17

  • The Final Sail – This four-day challenge is the ‘grand finale’ of the 4-leg Quest for the Crest Sailfish Series. Team cash prizes include up to $50,000 for first place and $18,000 and $10,000 to second- and third-place anglers, plus trophies, respectively. Early entry fee is available.

April 21-24

  • Fringe Theater of Key West presents: Conch Republic, The Musical! – The smash hit returns for its riotous fourth year. The rollicking musical tells the tale of the Conchs taking on the Feds, succeeding from the U.S. to keep the town open to tourism. A tale so wacky it has to be true! Show dates, times and tickets online. Performances at Key West Theater (Formerly Eaton Street Theater), 512 Eaton Street. Contact: 305-707-4053.

April 22 – May 1

  • 34th Annual Conch Republic Independence 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. Contact: 305-296-0213. 

April 24

  • Monthly Artisan Market: Conch Republic “Brew” Days – 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 one Sunday each month, during season (thru April) outdoors at the Restaurant Store, 1111 Eaton. Free family & pet friendly event.

April 28 – May 1

  • Key West Paddle Classic – Presented by Lazy Dog Adventures, the challenge includes a 12-mile Elite Race around the island and a 4-mile open race. Other events include a kick-off registration party, paddleboard clinics and races for kids. Contact: Sue Cooper 305-304-4259 / Email: sue@lazydog.com.

May 2016

May 4-8

  • The 21st 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 / Email: kwswf@aol.com

May 11-15

  • Kamp Key West – This annual event is designed for LGBTA outdoor enthusiasts and adventurists who recall the fun and games of summer camp. Attractions include on-the-water subtropical island activities and games for adults.

May 13-15

  • Papio Kinetic Sculpture Parade – The Key West Art & Historical Society presents this inaugural, family-friendly exhibition event that is also an art-inspired float parade powered by humans on bicycles. People of all ages can celebrate the creative, funky and wild designs on display.

June 2016

June 8-12

  • Key West Pride – Key West shows its Pride every day, and this is your chance to be a part of the celebration! The five-day schedule includes daytime pool and beach parties, late-night drag shows, on-the-water adventures ranging from snorkeling and kayaking to glass-bottom boat tours, a street fair, a 10k relay for tutu-wearing runners and walkers, and pageants to select Mr., Miss and Ms. Key West Pride.

June 10-12

  • Third Annual Mystery Writers’ Key West Fest – Fans of mystery fiction can learn how their favorite authors craft tales of murder and mayhem. 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. Email: info@mysterywriterskeywestfest.com

June 11

  • VFW Fishing Tournament – This family oriented tournament offers cash prizes for dolphin, wahoo, tuna, snapper and grouper, along with prizes for heaviest fish by a lady angler, heaviest fish by a juvenile angler, pee-wee and active service member. Heaviest Dolphin is worth $2,500. All proceeds benefit disabled and/or needy veterans in Monroe County. Contact: Pete Thomas 305-509-7244 / Email: psty2k@yahoo.com.

June 16 – 19

  • 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. Contact: Chris Norwood at cnorwood@keywestafricanafestival.com

June 18

  • Key West Island Swim: FKCC Swim Around Key West – The officially sanctioned event is a 12.5-mile swim clockwise around the island of Key West that is open to all age groups. Individual swimmers and relay teams can compete. The route takes swimmers through the waters of the Atlantic Ocean and Gulf of Mexico, ending where they began at Higgs Beach. Contact: Lori Bosco 305-809-3562 / Email: aqualb@aol.com; lori.bosco@fkcc.edu

July 2016

July 2-4

  • Fourth Annual Key Lime Festival – A wacky talent show, pie-eating and cooking contests and other tasty temptations await Key West visitors during the fourth annual Key Lime Festival. A Key Lime martini Sip and Stroll, and Key lime rum sampling and distillery tour are among events to kickoff the weekend-long event.

July 4

  • 32nd Annual Hospice of the Florida Keys & Visiting Nurse Association Picnic – Benefits 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. Live music, a silent auction and lots of children’s games round out the fun-filled family festivities. Contact: Casa Marina at 305-294-8812.

July 11-14

  • 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 20-25

  • Hemingway Days – The 36th 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 20-23

  • Bacardi Oakheart 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 festival, 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 23

  • 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 2016

August 11 – 14

  • 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.

September 2016

September 1-5

  • Seventh Annual Key West Briefest – 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 / Email: info@keywestbrewfest.com.

September 8-11

  • 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 9-11

  • 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

October 2016

October 6 – 9

  • 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 21-22

  • 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. Visitors can experience sights, sounds and flavors recalling Key West’s Bahamian heritage.

October 21-30

  • 37th Annual Key West Fantasy Fest – This outrageous 10-day costuming and masking celebration features flamboyant masquerade competitions including one for pets, a headdress ball, exuberant promenades, street fairs and a grand parade that stars marching groups, island-style bands and lavish floats. The 2016 festival theme is “Political Voodoo and Ballot-Box Barbarians.” Contact: 305-296-1817 / Email: info@fantasyfest.net.

October 23

  • Key West Halloween Half Marathon and 5K Run – Competitors are encouraged to dress in their favorite costumes for this Halloween-themed running event. Email: halloweenhalf@exclusivesports.com.

November 2016

November 6-13

  • 35th Annual Key West World 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 / Email: superboatracing@gmail.com.

November 23-27

  • International Sand Art Competition – Nontraditional artistry and beachside fun combine in a unique creative experience for participants and spectators. Visitors can watch leading U.S. and international sand sculptors construct and display large-scale creations over Thanksgiving weekend on the Atlantic Ocean beach at the Casa Marina Resort, 1500 Reynolds St.

December 2016

December 1-3

  • 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.

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.

 

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