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 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
  • Sixteenth Annual Open Air Art & Music Affair – Discover the best of Key West’s art and artists, plus live music by local and national acts at the famed Schooner Wharf Bar in Key West’s Historic Seaport. Colorful arts and crafts, exuberant musical entertainment and a day strolling Key West’s Historic Seaport are the main attractions at the annual Schooner Wharf Open Air Art & Music Affair. The event is centered around the Schooner Wharf Bar, 202 William St., and the adjacent harborwalk that stretches along the waterfront. From 9:30 AM to midnight. Contact: (305) 292-3302.

March 11

  • Ninth Annual Florida Keys SPCA Spring Social – Enjoy a paw-tastic experience to help raise funds to benefit a Keys-based animal shelter; event is open to the public, from 6:30-9:30 p.m. at the Key West Golf Course. Highlights include a VIP champagne reception prior to the main event, a first class dining experience with tables of food from restaurants all over Key West and parking provided at Florida Keys Community College with HTA Trolley service to and from the event. Also features a silent auction, live auction, raffles, complimentary beer & wine, music and more. VIP and General Admission tickets online at keystix.com.

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
  • Evening “Picnic Under The Stars” – Key West community organizations join forces for this family-friendly event and raise a toast to the environmental, education, arts and culture, and health care missions that each organization maintains while enjoying live music, food truck vendors, libations, and games and activities for kids. Bring a blanket to relax and enjoy gourmet picnic baskets from select restaurants available for pre-purchase, and raffle tickets featuring a cultural trip for two to Cuba, art bikes, and signed Guy Harvey prints will also be available. Staged at at Fort East Martello, starting at 5 p.m. Tickets for this joint fundraiser are $10 and can be purchased at the door or online. Contact: 305-295-6616 ext 111  / Email: cnottage@kwahs.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.
  • Easter at the Family-Friendly Sheriff’s Animal Farm! – Looking for a fun place to take the kids? The Sheriff’s Animal Farm is open 1 – 3 p.m. Bring the family and come visit the many animals at the farm; kids can visit and have their pictures taken with the Easter Bunny, hunt Easter eggs, participate in arts and crafts, visit the Home Depot workshop, listen to live music and much more. It is free of charge, but donations are welcomed because that is how the farm is sustained. The farm is located just off of College Road, on Stock Island, at the Sheriff’s Office Headquarters complex. Open the second and fourth Sundays of the month.
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

March 16

  • Music At Martello Series: Donovan Frankenreiter Concert – Enjoy pro surfer-turned musician Donavon Frankenreiter, back to send out his breezy, laid-back vibes and upbeat lyrics in an early evening performance offered by Key West Concerts at historic Fort East Martello, 3501 S. Roosevelt Blvd. The concert will kick off with local favorite Miguel Perez. Discounted tickets can be purchased in advance for $30 at www.KeyWestConcerts.com or at the 4:45 opening doors for $35. Children under 12 are free. Parking will be available for $5, bike parking is free.

March 17

  • Fascinating Facts About Our Cool History: “Florida’s Moving History, Planes, Trains & Automobiles” – Presented by Historic Markers , Inc. and the Florida Humanities Council, this speaker series are free to the public. Staged at the Eco Discovery Center, Truman Waterfront, 6 p.m. University of Florida’s Steve Noll transports you back to the steamboat era. Contact: 305-393-9777.

March 27

  • Visit the Family Friendly Sheriff’s Animal Farm – Looking for a fun place to take the kids? The Sheriff’s Animal Farm is open 1 – 3 p.m. Bring the family and come visit the animals at the farm, including miniature horses, a cow, pigs, goats, bunnies, alligators, tropical birds, Kinkajous, Sloths, a Lemur, Kramer the Emu, a family of Patagonian Cavys, a skunk, an opossum, tortoises and turtles, snakes and many more. It is free of charge, but donations are welcomed because that is how the farm is sustained. The farm is located just off of College Road, on Stock Island, at the Sheriff’s Office Headquarters complex. Open the second and fourth Sundays of the month.

March 31

  • Fascinating Facts About Our Cool History: “”Preserving Key West’s Unique Architecture” – Presented by Historic Markers , Inc. and the Florida Humanities Council, this speaker series are free to the public. Staged at the Eco Discovery Center, Truman Waterfront, 6 p.m. Architect Bert Bender shares the restoration of Custom House with a video, “Preserving Paradise,” and tells of the importance of Key West’s unique architecture. Contact: 305-393-9777. 

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 16

  • 19th Annual Earth Day 5k Run/Walk – Earth-friendly recyclable awards are to be given to the top overall male and female, top masters male and female and first- and second-place runners in each age group ranging from age 9 and under to 70-plus. Additional awards await top 5k walk finishers. Starts at 8 a.m., from McCoy Indigenous Park, located at Atlantic Boulevard and White Street.

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 22

  • 34th Annual Conch Republic Independence Celebration Kick-off Party at the Schooner Wharf Bar. – 202 William Street. Starts at 7:00PM. Tickets available at www.schoonerwharf.com. 

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.
  • Schooner Wharf Bar Wrecker’s Race Series Finale – This one-way race to the reef re-enacts the ancient wrecking tradition of the Keys. Viewing from harbor-front hotels and Mallory Square. More info at SchoonerWharf.com or 305 292-3302. Starts at 1:00PM. 

April 25

  • The Conch Republic Military Muster & Conchtail Party – At the Gardens Hotel on 526 Angela Street. Held from 6:00PM – 8:00PM. Admiral Finbar, First Sealord and the Conch Republic Military Brass honor our Republic’s Military Forces. The Conch Republic Military Needs You! Your chance to join and defend the Republic. Proceeds to benefit the Conch Republic Foster Children’s Program.

April 28

  • Conch Republic After Parade & Awards Ceremony – At the Schooner Wharf Bar, 202 William Street.  Starting at 9:00PM. Follow the parade Mardi Gras-style to the Official Headquarters of the Conch Republic Independence Celebration. Prizes awrded for the best “Creative Conchcepts” to entries and floats. For more info: 305 292-3302.

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.

April 29

  • The Victory Party – At the Schooner Wharf Bar, 202 William Street. Starts at 10:00PM. Come help us celebrate our victory over the evil forces of the “United States Border Patrol” . . . we always win! For more info: 305 292-3302. Tickets available at www.schoonerwharf.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. Call: 305-587-9392 or Email: info@mysterywriterskeywestfest.com. The MWKWF is sponsored by the Key West Citizen daily newspaper and the Florida Keys Council of the Arts.  Event registration is $175 (early-bird special of $150 for those who register by May 1) and includes all panels, presentations and four meals. 

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