It seems as though there is never a shortage of activity on Key West. 2014 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 32nd 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.
- 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: firstname.lastname@example.org.
- 35th Annual 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; Email: email@example.com.
October 17 & 18
- 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. Come for the run, stay for the fun!” ? Contact: Beth Moyes 305-747-8563; Email: firstname.lastname@example.org.
- Pop Up Museum: Stories of the Transatlantic Slave Trade: The Mel Fisher Maritime Museum’s newest traveling exhibit provides an overview of the Transatlantic Slave Trade. It also features the stories and archaeology associated with the Key West African Cemetery and the slave ship Henrietta Marie, which sank off the coast of the Florida Keys in 1700. The public is invited to view the exhibit October 20 – 31 during normal business hours at the Gato Building, located at 1100 Simonton, and at the Florida Keys Community College Library, located at 5901 College Road. There is no admission charge. email@example.com
- 32nd Annual Headdress Ball - This “over the top” contest includes an extravagant show with lots of Key West razzle dazzle, and is a competition “head and shoulders” above the rest with contestants judged from the shoulders up! Major cash prizes including a $1,500 grand prize. Tickets sell out quickly! Held at the Southernmost on the Beach, 508 South Street. Email: firstname.lastname@example.org
- Mangia Mangia, located at 900 Southard Street, will donate 25% of their total sales (food, alcohol and take-out orders) to Visiting Nurse Association & Hospice of the Florida Keys. VNA/Hospice is the only non-profit hospice and home health agency serving all of Monroe County, and community events like Mangia Mangia Nights help to increase awareness of VNA/Hospice’s mission to “enable individuals to remain in their home by providing compassionate, effective, life-enhancing health and supportive services.” For information, contact Kellee Bartley at 305-294-8812 x113 email@example.com.
October 29 – November 2
- Parrot Heads Meeting of the Minds Convention - This annual event is meant to assist with environmental concerns while showing members an amazing time in Paradise. The Parrot Head motto is to Party with a Purpose, so events for the Meeting of the Minds Parrot Head Convention include concerts, auctions and raffles all benefitting charity. To attend this Key West Parrot Head Convention you must be a member of a sanctioned Parrot Head Club. There are over 200 chapters in the North America, Australia, and Europe. For more information about the convention, visit the ‘Meeting of the Minds’ section of the Parrot Head Clubs’ official website www.phip.com.
- The BottleCap Lounge – Enjoy the 8th annual Virtual Parrothead “Meeting of the Minds” Happy Hour benefitting VNA/Hospice. This year’s special Halloween Happy Hour will feature live music by Texas’ Larry Joe Taylor, a Halloween costume contest with prizes, a raffle featuring a Margaritaville “Key West” Frozen Concoction Maker, a grab bag bottle pull, adult trick-or-treating sponsored by Three Olives Vodka, and celebrity bartenders earning their tips for VNA/Hospice. Fabulous food will be available from Bad Boy Burrito. For information, contact Kellee Bartley at 305-294-8812 x113 firstname.lastname@example.org.
- ABC Awareness 5K Walk/Run - Race begins at 8 a.m., at Salute Restaurant on Higgs Beach, with registration beginning at 7 a.m. The event raises money to cover mammograms, thin-prep pap tests, and other diagnostic and preventive measures in the Florida Keys. The 5K race, managed by the Southernmost Runners Club awards prizes for the best female and male runners and walkers, and many best-in-age categories. Teams of participants who raise funds with their own race sponsors, also receive awards. Live music adds to the festivities on race day. email@example.com
- Key West World Championship Race - High-speed offshore powerboats race in Key West Harbor and surrounding waters to continue Key West’s longstanding tradition in this 32nd 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.
- First Friday Upper Duval Art Stroll - A portion of Key West’s famed Duval Street known for its eclectic galleries comes alive with art exhibitions, receptions and culinary offerings during this monthly event. Participants can explore galleries, boutiques and food and wine emporiums during the event that usually takes place the first Friday of each month. Frangipani Gallery is to host an artists reception as part of their season opening group show, in tandem with the event, between 6-9 p.m., at 1102A Duval. Fran Decker 305-849-1581 / firstname.lastname@example.org
- Third Annual Key West International Latin Arts Festival - Experience “Vientos del Alma,” a celebration of traditional Latin American cultural arts featuring dance and percussion workshops, artists’ exhibits, poetry readings, wine tastings, culinary surprises and a spectacular theatrical concert. Vientos del Alma (Winds of the Soul) highlights include: InnerNacionalSound’s Christian Monzón and Valerie Carr, renowned Miami-based Tango Times dance luminaries Roxana Garber and Oscar Caballero and an outstanding international line-up of local and visiting musicians, folk dancers and thrilling performers. Visit website for details and tickets; events to be held at San Carlos Institute. Contact: 305-394-0808.
November 12 – 16
- Third Annual Key West Film Festival - 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. Contact: 941-527-9385; 305-295-9112.
- 3rd Annual Key West Chalk Fest - Artists from across Florida will take their craft to the streets of Key West. Each day from 10 a.m. to 6 p.m. both local and visiting artists are to use the promenade alongside the seawall at the Truman Waterfront as their canvas for intricate and colorful chalk art creations. A Key West Family and Pet Friendly Event! Free to the public.
- Parade of Paws - The Florida Keys SPCA is to unleash a new event this fall at Higgs Beach Dog Park: The Parade of Paws, to benefit the nonprofit’s animal-care fund. The event debuts from 9 a.m. to 1 p.m. at the dog park off Atlantic Boulevard at Higgs Beach. Registration starts at 8 a.m. and the “blessing of the animals” is set for 8:45 a.m., while the fair-like event opens at 9 a.m. with entertainment, contests, food, photos with Santa and other activities. People are asked to collect donation pledges before and then come to parade their pets. Contact 305-294-4857 or email@example.com
- International Sand Art Competition - The oceanfront Casa Marina Resort, located at 1500 Reynolds St., opens its gates to the public during Thanksgiving weekend to host the first International Sand Sculpting Competition held in Key West. Spectators can watch and marvel as six world-renowned sand sculptors compete against each other, creating intricate sculptures using their own unique designs and skill sets. firstname.lastname@example.org
- 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: Marky Pierson 305-619-2275; Email: email@example.com
- TRIKW Swim-Bike-Run in Paradise - 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: firstname.lastname@example.org
- Fort Taylor Pirate Invasion - Experience three days of piracy as Fort Zachary Taylor Historic State Park transforms into a British stronghold defending her shores against an invasion of pirates. Step back in time to encounter piracy from 1675 through 1825 with pirate encampments, living history demonstrations, live battles, activities for the kids, and more, from 10 am. to 5 p.m. daily. Visit website for details and activities schedule. Jai Somers 305-797-1659 / email@example.com
- Key West Holiday Parade - The island city shows its holiday spirit with this annual hometown parade. Featuring marching groups and motorized and nonmotorized floats, the festive procession traditionally draws entries from churches, civic organizations, businesses and neighborhood and school groups. Starting at Truman Avenue and White Street, it proceeds down Truman to Duval, where it takes a right and continues on to Eaton Street. Contact: 305-809-3881
- 24th Annual Lighted Boat Parade - Lighted and decorated vessels from rowboats to tall ships proceed around Key West’s Historic Seaport and harbor areas. Parade is scheduled to begin at 8 p.m. Holiday revelers can watch and applaud from bars, restaurants and resorts in and around the Historic Seaport. Contact: 305-292-3302
- Inspired by the unique and colorful environment of the Florida Keys, Clara and her young Prince encounter enchanted landscapes complete with snowy egrets on shimmering salt ponds, a wicked Rooster-King, an exquisite Sea-Star Fairy, and “underwater” sequences of almost unimaginable beauty. Local children, adults and community leaders are cast alongside a nationally-cast corps de ballet in this spectacularly crafted semi-annual production of a beloved classic. Shows held at the Tennessee Williams Theatre. Box office 305-295-7676
- From 1-3 p.m., kids and adults can visit the furry, fluffy and feathered residents of the Animal Farm and petting zoo and get a photo taken with Santa. The Monroe County Sheriff’s Office Animal Farm is situated at the county’s detention center just outside Key West at 5501 College Road. This event is free and open to the public. The Sheriff’s Animal Farm is open the second and fourth Sundays of the month. 305-293-7300
- Key West Dachshund Walk - Frost-free Key West becomes a “wiener wonderland” when about 200 dachshunds and their owners take a noontime New Year’s Eve stroll through the island’s picturesque downtown. Spectators can watch the fun and meet the canine participants on Fleming Street between Whitehead and Duval streets. firstname.lastname@example.org
- 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: Bob Oberle 305-304-2643; Email: email@example.com
- New Year’s Eve Conch Drop at Sloppy Joe’s - The arrival of 2015 is to be heralded on the island’s Duval Street with the “drop” of a gigantic manmade conch shell, the symbol of the Florida Keys, to the flat roof of Sloppy Joe’s Bar, 201 Duval. Thousands of spectators gather on Duval for the annual gala, emceed by a rooftop host starting at 10 p.m. and featuring dancing in the street and a countdown to midnight recorded on a huge clock.
- New Year’s Eve Pirate Wench Drop at Schooner Wharf - For piratical partiers, a New Year’s Eve salute to Key West’s rowdy seafaring roots is scheduled at the island’s Historic Seaport. At midnight, a winsome pirate wench is to descend from the top of the mast of the tall ship America 2.0 as cannon blasts welcome 2015. Scallywags in attendance can expect live music, dancing and festivities at the Schooner Wharf Bar, 202 William St.
- New Year’s Eve Key Lime Wedge Drop at the Ocean Key Resort, ZERO DUVAL STREET - At the Ocean Key Resort & Spa, 0 Duval St. on Key West Harbor, a huge replica of a Key lime wedge splashes down into a larger-than-life margarita glass as crowds welcome the new year on the property’s Sunset Pier. 305-295-7005
- 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
- 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 / firstname.lastname@example.org
- 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 / email@example.com
- 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
- 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 / firstname.lastname@example.org
- 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 / email@example.com
- 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 / firstname.lastname@example.org
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
- 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 / email@example.com
- 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 345Email: firstname.lastname@example.org
- 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 / email@example.com
- 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 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 / firstname.lastname@example.org
- 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 / email@example.com
- 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
- 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
- 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 / firstname.lastname@example.org
- 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 / email@example.com
- 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 / firstname.lastname@example.org
- 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 / email@example.com; firstname.lastname@example.org
- 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 / email@example.com
- 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.
- 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)
- 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. firstname.lastname@example.org.
- 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 / email@example.com
- 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 / firstname.lastname@example.org
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 / email@example.com
- 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
- 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.
For more information about things to do and see in our island city, go to our Key West Web Site.
Island Genn – Your Key West Concierge