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.

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.

March 2014

March 1 – March 26
  • Florida Keys Eco-Discovery Center presents: Art Exhibition - Tropical Botanic Artists are the creative force behind “Botanical Exploration in the Everglades: Braving One of North America’s Last Frontiers,” and the exhibit is to be displayed at the Florida Keys Eco-Discovery Center, 33 E. Quay Rd., Key West, during open hours Tues – Sat., 9 a.m. to 4 p.m. (closed Sunday & Monday). Admission to the exhibit is free and open to the public. The special exhibition features 28 original portraits of plants discovered in the Everglades by botanists in the 19th and 20th centuries, and given common and scientific names that reflect the identities of those intrepid plant explorers. The show includes graphite drawings of lichens that were discovered and named quite recently, and informational panels about botanical exploration, field collecting, how plants are named, and ways Everglades plants were and still are used by native peoples. Contact: 305-809-4750, Email:

March 1 – 31

  • Happy Birthday Tennessee Williams! - The Tennessee Williams Key West Exhibit (315 Truman Ave., off Duval St.), in cooperation with the Tropic Cinema, Key West Art and Historical Society, and Artist William Welch are celebrating the 103rd birthday of Tennessee Williams during the month of March. Events planned include a series of four classic movies adapted from Tennessee Williams’ award winning plays being shown at the Tropic, a Poetry Contest, an Artist Challenge, two receptions and an exhibit of original paintings by Tennessee Williams at the Custom House. Wednesday, March 26, a reception honoring the 103rd birthday of Tennessee Williams and his life in Key West is to be held at the Tennessee Williams Key West Exhibit from 6 p.m. to 8 p.m. Poetry Contest winners will be announced and read their poems; an exhibit of the paintings done during the Artists’ Challenge are to be displayed; and birthday cake, wine and other light refreshments. A suggested donation of $10 from attendees is appreciated. Contact: Dennis Beaver; Email:

March 1 – June 30

  • Key West Art & Historical Society presents: Marky Pierson, Night Visions in Technicolor - Emerging local artist and graphic designer Marky Pierson is to exhibit new paintings and designs focusing on three distinct categories: ‘Conch Night’ Series featuring the Hemingway House, Custom House and Curry Mansion; ‘Squishy Femme’ Series explores soft, squishy and everything womanly; ‘Graphic Design’ Series features graphic posters of iconic Key West images and large format paintings inspired by vintage tourism posters. Custom House Museum is located at 281 Front Street, and open daily 9:30 a.m. to 4:30 p.m. Contact: 305-295-6616.

March 1

  • 52nd 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; Email:
  • Fourth Annual Conchfest 2014 – A Celebration of Conch Heritage - At Bayview Park in Historic Old Town Key West from 11 a.m to 10 p.m., vendors are to be selling arts and crafts of every imaginable kind among other treasures. A host of activities are planned for native Conchs, Freshwater Conchs, Non-Conchs, and Conch Wanna-be’s. Sample foods for sale including conch fritters, conch salad, pork, and other more traditional fare. There will be childrens’ activities, entertainment and much more. Free admission.

March 2

  • Dance for Life! – 9AM – 2PM at the White Street Pier. There will be beats by DJ Primetime and moves by several dance instructors throughout the day! Join us at the front of White Street Pier and dance your morning away. There is no charge for this event but we are collecting donations for our Relay for Life team. Let’s get out there and have some fun! Come out and help fight back. Come. Dance. Donate.

March 6

  • Mel Fisher Maritime Museum presents: Wreck of the Pirate-Slaver Guerrero  - A free lecture, presented by museum archaeologist Corey Malcom as he “reveals history” with a multi-media story about the Wreck of the Guerrero, the Cuban pirate-slaver which sank in 1827. Starts at 6:30 p.m., in the Mel Fisher Maritime Museum Courtyard, 200 Greene Street. Chairs provided. Public Welcome. Contact: Corey Malcom 305-294-2633 ext 20

March 13

  • Mel Fisher Maritime Museum presents: The Science of Shipwrecks - The Museum recently opened its new Science of Shipwrecks exhibit, featuring a behind-the-scenes look at the excavation and conservation of shipwrecks. Join museum archaeologist Corey Malcom as he “reveals history” with a multi-media look at the Spanish galleon, Santa Clara, which sank in 1564. This wreck is the focus of the museum’s ongoing research. Free lecture starts at 6:30 p.m., in the Mel Fisher Maritime Museum Courtyard, 200 Greene Street. Public welcome, chairs provided. Contact: Corey Malcom 305-294-2633 ext 20

March 14 – 15

  • 54th 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. Proceeds help benefit the Old Island Restoration Foundation. Contact: 305-294-9501; Email:

March 20

  • Mel Fisher Maritime Museum presents: Key West African & South Beach Cemeteries - MFMM has been active in revealing the story of the Key West African Cemetery at Higgs Beach since 2002, and it is home to an exhibit that tells its story. Join museum archaeologist Corey Malcom as he “reveals history” with a multi-media story of the Key West African Cemetery at Higgs Beach and the lesser known South Beach Cemeteries. Free lecture starts at 6:30 p.m., in the Mel Fisher Maritime Museum Courtyard, 200 Greene Street. Public welcome, chairs provided. Contact: Corey Malcom 305-294-2633 ext 20
  • Walk on White - This regular neighborhood gallery stroll is perhaps the best known among art lovers, held on the island city’s White Street from Southard to United streets and onto Truman Avenue the third Thursday of each month, from 5-8 p.m. The popular evening features exhibitions and receptions at galleries, shops and occasionally other venues. Highlight locations include Harrison Gallery; the quirky and inviting Stone Soup Gallery; and The Studios of Key West, offering regular exhibitions, performances, workshops and studio space in the style of America’s leading artist communities. This month’s showcase includes the fascinating art of Scott Gruppe, at the Debra Butler Design Studio. Meet Scott and experience his cutting edge work, best described as “poetry in motion.” Art lovers who turn off White onto Truman Avenue will find fine art and functional pottery at Honest Works Island Pottery and emerging talents, multimedia and renegade art at the dynamic Art Space Key West.

March 21

  • 7th annual Spring Social — dinner, music and auction to benefit Florida Keys SPCA from 6:30 to 9:30 PM at the Key West Golf Clubhouse, with life music, live and silent auctions, and your favorite restaurants preparing a great meal. All to benefit the shelter. Donation $80 VIP preferred dinner seating or $50 general admission.  Tickets available at FKSPCA and at the door. Contact:  (305) 294-4857 or

March 22

  • Keystock Music Fest - Crowds are expected to gather at the Truman Waterfront for the daylong event featuring several musical performances. Keystock is sponsored by Lazy Lakes RV Resort, Howard Livingston and the Key West Rotary Club. Festival hours are noon to 9:30 p.m., with gates set to open at 11 a.m. No coolers or chairs are allowed. Contact: Lazy Lakes 305-745-1079; 305-292-7729.

March 28 & 29

  • Fifth Annual Florida Keys Ocean Festival & Waterfront Craft Show - The unique marine environment of the Keys island chain, which includes the continental United States’ only living coral barrier reef, is to be celebrated at this festival. 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. The visitor center for the Florida Keys National Marine Sanctuary, the facility houses exhibits that showcase the region’s unique ecosystem including a living reef exhibit created by Mote Marine Laboratory. A fishing seminar is planned for kids ages 5-11 that features instruction and barge fishing. To participate, youngsters must register online. A Tuna Trot 5k run/walk is also to be a part of the festivities.

March 29

  • Mote Marine presents: 2nd Annual Tuna Trot Race for the Reef 5K Run/Walk - A Key West Southernmost Runners sanctioned 5K race, the event starts at 8 a.m. from Eco-Discovery Center, 32 East Quay Road, Truman Waterfront Old Town. Race day registration is at 7 a.m., adults $30, age 13-18 years $20, 12 & under free with an adult. Awards are to be given to Male and Female Overall Winners, Masters (over 40) winners and more. Walker Awards will go to the first five male and female walkers. First 200 participants are to register receive a free t-shirt. Register online at Also, a Kids Fun Run follows after the race, along a half-mile course. Contact: Roberta 305-292-7963; Jason 305-393-6022; Email:
  • Mote Marine presents: 5th Annual Florida Keys Ocean Festival and Waterfront Craft Show - Located at the Eco-Discovery Center, 32 East Quay Road, Truman Waterfront Old Town, the festival is open from 11 a.m. to 6 p.m., for all ages and celebrates the Keys’ marine environment. It is a fundraiser for Mote Marine Laboratory’s Coral Reef Restoration Programs. Highlights include kids’ activities, a fishing seminar for kids — the first 100 kids under age 12 who are registered online receive a free rod — live entertainment all day, more than 70 arts, crafts, food vendors & exhibitors as well as a silent auction. Howard Livingston and the MM 24 Band are to headline the day of fun. Contact: Roberta 305-292-7963; Jason 305-393-6022; Email:

March 30

  • Monthly Artisan Market - The monthly artisan market is to be held from 10 a.m. to 2 p.m. at the Restaurant Store parking lot. The event is to give residents and visitors alike a chance to shop fresh and local as the parking lot at 1111 Eaton St. is transformed into a showcase of art, photography and unique local handicrafts and gifts made exclusively in the Keys in one convenient location. Entertainment includes a singer and songwriter showcase, local authors, Key West Fringe theater performances, chef demonstrations, kid’s activities and live street art murals. Guests are able to taste and buy local specialties, and enjoy concessions, beer and wine. Guests are encouraged to BYOB (bring your own bags). Contact: Sean Krikorian 573-619-2200; Email:
  • Impromptu Classical Concerts of Key West presents: Chamber Orchestra Kremlin - Chamber Orchestra Kremlin is renowned for violins, and their music will take you soaring. The New York Times states, ” . . . warm, full-blooded and virtuosic playing with colorfully shaped, gleaming phrases.” Performance is at 4 p.m., at Tennessee Williams Theater. Tickets $30 and $50, and are to be available online. Contact: Box office 305-295-7676; Email:

April 2014

April 1 – September 30

  • Key West Art & Historical Society presents: Key West or Bust, A History of Tourism - The Florida Keys have historically been an alluring travel destination for travelers around the world. With the onset of the Great Depression in the 1930s, tourism in Key West was the lynchpin in warding off bankruptcy. This exhibit explores the history of tourism in the Florida Keys from the 1920s until the 1980s while focusing specifically on transportation, accommodation, travel brochures and postcards. Custom House Museum is located at 281 Front Street, and open daily 9:30 a.m. to 4:30 p.m. Contact: 305-295-6616.

April 1-26

  • 18th Annual Sculpture Key West - This stunning annual art exhibit showcases the work of leading contemporary sculptors on the grounds of West Martello Tower, home of the Key West Garden Club, and the surrounding Higgs Beach. Contemporary sculptures in a wide variety of traditional and experimental media enhance the land and seascapes. Visit website for more information. Contact: 305-295-2800

April 3

  • Mel Fisher Maritime Museum Presents: Spanish Colonial Coins - MFMM recently opened its new Coins of the New World exhibit, the story behind the now infamous ‘pieces of eight.’ Join MFMM’s guest lecturer Carol Tedesco, author of “Treasure Coins of the Nuestra Senora de Atocha and the Santa Margarita,” as she shares her extensive knowledge about the coins found at the shipwrecks Atocha and Santa Margarita. Free lecture starts at 6:30 p.m., in the Museum Coin Gallery, 200 Greene Street. Public welcome, chairs provided. Contact: Corey Malcom 305-294-2633 ext 20

April 4-6

  • Key West Fishing Tournament Kick-Off - Fifteen target species and $5,000 in cash prizes highlight this open-to-the-public event, heralding the beginning of more than eight months of exciting Keys fishing. Cash awards await individual participants who catch the heaviest dolphin, kingfish, cobia, blackfin tuna, mackerel, mutton snapper, wahoo, mangrove snapper and grunt, and for boat teams that score the most releases of tarpon, permit, bonefish, barracuda, marlin and sailfish. Junior anglers under age 15 can also fish. Entries in the kickoff also are eligible for the Key West Fishing Tournament, which runs through Nov. 30, 2014. Contact: Rob Harris 305-587-6718; Email:

April 5

  • Migration Mania - The Great Egg Hunt and Wild Bird Show! From 10 a.m. to 3 p.m., this family-friendly educational event creates awareness and appreciation for the birds that visit the Garden. Enjoy educational activities, egg hunts, arts and crafts, games, live bird presentations and much more. Admission is $5 per person, Botanical Garden members are admitted free. Email:

April 6 – November 30

  • Key West Fishing Tournament - 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; Doris 305-295-6601; Email:

April 12

  • Public Book Launch and Signing - From 4-6 p.m., join Carol Tedesco, Roberta DePiero and Jane Newhagen who will present their new release, ‘After Life – Images from the Key West Cemetery’ at a public book launch and signing event at Salute on the Beach, 1000 Atlantic Blvd. With photography by Tedesco and DePiero and prose by Newhagen, ‘After Life’ captures the island’s unique final resting place in all its poignance, character and eccentricity. Email:

April 12 & 13

  • Key West Garden Club presents: Annual Garden Tours - Between 10 a.m. and 3 p.m. each day, the Key West Garden Club features five delightful gardens to explore. Tickets are $20 per person and can be purchased at any of the individual gardens or at the Garden Club at West Martello Tower. Visit website for more information. Contact: 305-294-3210.

April 14

  • 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 – July 31

  • 6th Annual Key West Art Garden - The cost of admission brings visitors an added value and wealth of beauty with 19 sculptures, each made of recycled materials, and some interactive, placed throughout the garden from local contemporary artists. Garden is open from 10 a.m. to 4 p.m. daily. Email:

April 18 – 27

  • 32nd 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 23 – 27

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

April 25 – 27

  • Key West Fringe Theater presents: Conch Republic (The Musical) - The story of those historic “mouse that roared” moments in April 1982 when Key West declared its independence from the United States. It’s a rollicking musical tale of the Conchs taking on the Feds in one of the greatest PR stunts ever. Show time 8 p.m., at The San Carlos Institute, 516 Duval Street. Visit website for tickets; three nights only! Contact: 305-295-7676.

May 2014

May 1-4
  • 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; Email:

May 3

  • Keystock Music Fest - Crowds are expected to gather at Truman Waterfront for a daylong event featuring several musical performances, including the Doobie Brothers and more. Keystock is sponsored by Lazy Lakes, Homes for Vets Inc., Southernmost Homes and Howard Livingston. Contact: Lazy Lakes 305-745-1079

May 7-11

  • Key West Songwriters’ Festival - The 19th-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 16-17

  • 12th 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. Contact: 305-294-9911

May 30 & 31

  • 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, fishing Saturday. Contact: John Stuempfig 305-304-7674 ; Email:

May 31

  • Third Annual Ladies Dolphin Tournament - Presented by Mercury, this tourney features more than $10,000 in cash and prizes for first- through fifth-place for the single biggest dolphin and first- and second-place prizes to the boat with the largest two fish aggregate. NEW this year is a prize for largest tuna. Proceeds and auction to benefit the JOSE WEJEBE MEMORIAL FOUNDATION.  Contact: Lee Murray 305-296-0364; Email:

June 2014

June 7

  • 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. The entry fee is $200 per boat and includes four tournament t-shirts, four tickets to the Captain’s meeting, four tickets to the awards barbeque and chances to win door prizes. 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 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:

June 11-15

  • 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; Email:

June 13-15

  • Fifth Annual Key West Bacchanalia - A food and wine event with a twist – enjoy a Grand Tasting Village, Celebrity Cook-off, Burger Wars, Bulldogs BBQ, seminars, dinner and mixology competitions and more! A spectacular three-day fiesta of food, spirits and wine. Enjoy celebrity chefs, Bravo TV Top Chef stars, world-renowned mixologists, and some of the best rums, spirits, wine, beer and food from local restaurants, in one of the Keys’ premier foodie events. Contact: Aga and James Hilferty 305-766-3356

June 14

  • Key West Island Swim: 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. A swim meet is held June 15. Contact: Lori Bosco 305-809-3562; Email:;

June 20-22

  • 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:

July 2014

July 10-13

  • Mel Fisher Days - This annual celebration brings together Mel Fisher fans and treasure-hunting enthusiasts in a celebration of the anniversary of Fisher’s discovery of the shipwrecked Spanish galleon Nuestra Senora de Atocha. Contact: 305-296-6534.

July 13-16

  • 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:

July 15-20

  • Hemingway Days - The 34th annual celebration of the legendary author’s work and lifestyle features literary readings, a theatrical premiere, short story competition, fishing tournament, Sloppy Joe’s Look-Alike Contest and a pre-birthday “party” commemorating Ernest’s July 21st birthday. Contact: (305) 296-2388 (Look-Alike); 294-0320 (literary)

July 16-19

  • Drambuie 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. Contact: Tim Greene 305-304-0317; Email:

July 19

  • 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! The Lazy Dog Paddle Board Race will take place before the 5K and kicks off at 6PM. The 4 mile paddle board challenge will start at the Beach by the Southernmost Beach Cafe. Visit website for more details. Contact: Barb Wright at 305-240-0727; Email:

August 2014

August 14-17

  • Tropical Heat - Tropical Heat offers All Male-All Adult fever-pitch revelry on the island whose openness and respect for diversity have made it a world-renowned gay vacation destination. The festival includes more than a dozen intriguingly decadent events ranging from drag shows to themed pool parties and gatherings at island clubs. Contact: 305-294-4603; 800-535-7797; Email:

August 28 – September 1

  • Fifh Annual Key West Brewfest - More than 150 beers and micro-brews are on to be 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 great activities on tap. Contact: 800-354-4455; Email:

September 2014

September 4-7

  • Womenfest Key West - Womenfest offers a wide range of activities guaranteed to appeal to a broad range of interests. Golfing with palm trees and iguanas, clothing-optional pool parties, a sizzling dance club scene, and women-only water excursions that range from jet skis to dolphin watching all promise to pique the interest of the more adventurous while film, live music, and special comedy shows offer the opportunity to enjoy paradise at a slower pace. All of this on a tropical island that is “close to perfect but far from normal.” Contact: 800-535-7797; 305-294-4603; Email:

September 5-7

  • 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:
September 15-21
  • 42nd Annual Phil Peterson’s Key West Poker Run - It’s an All-American event as motorcycle enthusiasts from around the U.S. travel the Keys’ scenic Overseas Highway – designated Florida’s only All-American Road – from mainland Florida to Key West to raise money for charity. Winner takes all, and can win a new Harley-Davidson Motorcycle or cash. Stops are arranged throughout the Keys with a final celebration in Key West. Poker Run stops are to be open for riders starting Thursday through Sunday, Sept. 21; Keys-wide events planned for the entire week. Contact: Drew Peterson 305-235-4023; Email:

October 2014

October 9-13

  • 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:

October 17-26

  • 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:

October 17 & 18

  • 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: Bob Oberle 305-304-2643; Email:

October 20

  • 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:

October 21

  • 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:

November 2014

November 2-9

  • 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.

November 7-10

  • 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.

November 28-30

  • 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:

December 2014

December 4-7

  • 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: 

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: Bob Oberle 305-304-2643; Email:

For more information about things to do and see in our island city, go to our Key West Web Site.

And for restaurant reviews check out our restaurant review section of this blog as well as our restaurant reviews at

Island Genn – Your Key West Concierge