Key West Poker Run 2019 Dates

  1. Key West Poker Run 2019 Dates 2020
  2. Key West Poker Run 2019 Dates Date
  3. Key West Poker Run 2019 Dates 2021
  • Jones said the 2019 poker run season outpaced previous years, and credited the strong economy for the growth. “This year turned out to be really successful, in that we launched a lot of new events and we set records on some of our bigger events, like the Key West Poker Run,” he says.
  • This is footage of desert storm 2019 parade, through the channel at lake havasu before the poker run.

Known as Phil Peterson’s Poker Run, thousands of riders from all over the country enjoy this classic motorcycle ride. Starting in Miami and winding all the way down US 1 to Key West. During the ride, the motorcycle riders make 5 stops to draw a playing card. At the end of the ride, the person who drew the best hand wins!

Stu Jones, leader of the Florida Powerboat Club, says he is “picking up all the pieces” following his epic Key West Poker Run that took well over 200 teams from Miami to the USA’s Southernmost city for six days of fun, sun and Race World Offshore‘s Key West Offshore World Championships. Jones also revealed his group’s 2020 schedule, which will closely mirror this year’s itinerary. (See below for the complete schedule.)

Jones said the 2019 poker run season outpaced previous years, and credited the strong economy for the growth.

“This year turned out to be really successful, in that we launched a lot of new events and we set records on some of our bigger events, like the Key West Poker Run,” he says. “I think it reflects the state of the economy being at a very high level. The sport continues to grow, just because it’s a great sport and a great way to enjoy performance boating. We’re getting more people coming into this sector, and that’s why these events have become more successful. Seeing Key West go to record numbers, and going off without a hitch, was a real highlight.”

It’s been just about a decade since Jones operated his ubiquitous pace boat, 39′ Nor-Tech King of Clubs, which was a familiar fixture on FPC’s numerous runs through the years. This year, Jones could be seen driving his Project 1080 Cigarette (showcased in the May issue of Speedboat Magazine) during nearly every one of his group’s events, which was another red-banner moment.

“We put in 150 hours on the boat from January to November,” he reports. “That was a highlight for sure. The fact that I could start enjoying these poker runs in my own boat put a different slant on it for me and made them more enjoyable. Certainly one of the reasons it made my Key West run more fun is that I was able to drive my own boat all the way there and all the way back, and I haven’t been able to do that for a long time.”

The Cigarette project boat celebrates the club’s 25th anniversary and perfectly captures the whole spirit of what the poker runs are for Jones. “It was truly special for me,” he says, “and I think it was one of the reasons I really enjoyed the 2019 Key West run.”

Jones says that the international participation at his club’s events continues to expand, “not only from Canada, which has always been strong, but European boaters are making transatlantic crossings, putting their boats on freighters and bringing them over here for the season to enjoy,” he says. “We had about 10 teams this year from European nations—all of them had brought their boats over for this event.”

With more participants than ever, the onus was on FPC to give away a colossal amount of shirts and other goodies. “It all goes bye-bye at Key West—we finish it off there,” he grins. “There might’ve been a few things left over. Smalls and mediums.”


Key West 2019 Event Calendar


January 5 – Pole Vault in Paradise: Pole Vaulting Champions – Top national pole vaulters will perform their skills at the Truman Waterfront Park. FREE to attend. Begins 9am, Truman Waterfront Park (end of Southard Street).

January 10 – 13 – 37th Annual Key West Literary Seminar – This year’s topic is “Under the Influence.” Noteworthy and celebrated writers, including Margaret Atwood, Geraldine Brooks, Meg Cabot, Marlon James, Joyce Carol Oates and numerous others gather at readings, discussions, lectures, and parties. Registration is now sold out, but a waitlist is available.

January 17 – 20 – Key West Kingfish Mayhem – Bet you didn’t know that the richest tournament prizes in saltwater fishing is for kingfish! Part of the mackerel family, this sportfish is known for its incredible striking speed. First place prize is expected to be $15,000.

January 18 – 19 – 59th Annual Key West House & Garden Tour – Visit five Key West homes and tropical gardens. 4pm – 8pm. Tickets are $40, include Conch Train transportation, or $30 without the train pass.

January 19 – 20 – 14th Annual Florida Keys Seafood Festival – This festival celebrates Key West’s abundant fresh seafood with music & beverages served up by many of the Florida Keys commercial fisherman and families. Crab, lobster, ceviche, conch chowder, and other local cuisine is served up in a picnic setting. Entrance fee is $5 (children under 12 are FREE). 11 a.m. – 8 p.m on Saturday, 11 a.m. – 5 p.m on Sunday. Bayview Park at Truman Avenue and Eisenhower Drive, Key West.

January 20 – 21st Annual Key West Half Marathon – Over 1000 runners enjoy near perfect temperatures, flat terrain, and Key West scenery in one of the most popular running races of the year. Entry fee costs between $50 and $120.00, depending on when you register and which race you choose.

January 21 – Dr. Martin Luther King, Jr. Day – Celebrate the life, efforts, and accomplishments of one of the greatest champions of civil rights in the history of the United States. This family-friendly event will feature local food, speeches, and a parade in the historic Bahama Village neighborhood. FREE to attend. 12pm-4pm, Nelson English Park, 300 Catherine Street.

Key west poker run 2019 dates date

January 22 – Hot Tuna in Concert – Legendary 60’s/70’s band perform at the intimate Key West Theater. 21 and over show. Top national act performs two nights at the new Key West Amphitheater, overlooking the Key West harbor. 7:30, 21 Quay Road. Tickets cost $60-80. 8pm show, 512 Eatcon Street.

January 22 – 29 – 28th Annual Kelly McGillis Classic International Female Flag Football Championship & World Challenge – The world’s top female flag football players compete for championship titles. (Jan. 25 – 29 are game days; Jan 22 – 29 has full week of events including parties).

January 23 – 27 – 10th Annual Key West Food & Wine Festival – Sample wine, Key West cuisine, and fresh seafood on one of many “strolls”.Tickets for each event costs between $35 – $135.

January 25 – Air Supply in Concert – National pop-rock act Air Supply performs at the Sunset Green Event Lawn, part of the 24 North Hotel property. 6:30pm (show starts at 8pm). $65, general admission; $159 VIP.

January 26 – Key West Cemetery Stroll – Learn about Key West’s vast history through volunteer guides as they visit numerous graves and monuments within the Key West cemetery. Tours will be conducted at 9:30 am and 12 noon. Cost is $20 per person. Advanced reservations required.

January 26 – 27 – 34th Annual Key West Craft Show – Open air art market and judged show offering an amazing variety of work, including sculpture, paintings, craft, and folk art. Whitehead Street and Caroline Streets, Key West.

January 26 – Key West Cemetery Stroll – Learn about Key West’s vast history through volunteer guides as they visit numerous graves and monuments within the Key West cemetery. Tours will be conducted at 9:30 am and 12 noon. Cost is $20 per person.

January 27 – 25th Annual Master Chefs Classic – Benefiting the very worthwhile local charity ReMARCable Citizens (known locally as the MARC House), this event has many of Key West’s best local restaurants in competition for favorite dishes. Cost is $75 – $1400, depending on package selected. Usually sells out quickly. Tickets on sale November 1, 2108. 4 – 7pm. Margaritaville Resort & Marina, 245 Front Street.

January 29 – February 2 – 2nd Annual Mile 0 Fest – Four-day music festival featuring major acts from the “Red Dirt & Americana” genre. Concerts will be held throughout Old Town, including the new Truman Waterfront Park Ampitheatre, and bars and clubs on Duval Street. Cost is $349 for 4-day festival pass.

January 31 – Cuda Bowl – Cooler winter temperatures bring big barracuda up onto the saltwater flats, and catching them is a regular occurrence in this tournament. Last year 418 barracuda were caught and released. Tournament rules require artificial lures and flats boats only. Maximum 2 anglers per boat. Entry fee is $350 for two anglers. Hurricane Hole Marina on Stock Island.


January 29 – February 2 – 2nd Annual Mile 0 Fest – Four-day music festival featuring major acts from the “Red Dirt & Americana” genre. Concerts will be held throughout Old Town, including the new Truman Waterfront Park Ampitheatre, and bars and clubs on Duval Street. Cost is $349 for 4-day festival pass.

February 1 – 3 – Civil War Days Heritage Festival – During the Civil War Key West remained in Union hands. Learn about this interesting fact and much more about Key West’s rich history. Fort Zachary Taylor State Park, located at the end of Southard Street. Begins Friday at 8am, ends Sunday 5pm.

Key West Poker Run 2019 Dates 2020

February 2 – 12th Annual Rock & Roast – Get a taste of local cooking and music at this benefit for the Basilica School. Features pork roast dinner, silent auction, and music by Doerfels. 1010 Windsor Lane.

February 14 – Valentine’s Day in Key West – Everyone’s favorite island provides the perfect playground for lovers. Sunset sails, beach walks, and waterfront dining are popular with couples in Key West.

February 15 – 16 – 58th Annual Key West House & Garden Tour – Visit five Key West homes and tropical gardens. 10am – 4pm. Tickets are $30 in advance, $35 day of tour.

February 23 – Key West Cemetery Stroll – Learn about Key West’s vast history through volunteer guides as they visit numerous graves and monuments within the Key West cemetery. Tours will be conducted at 9:30 am and 12 noon. Cost is $20 per person.

February 23 – 24 – 54th Annual Old Island Days Art Festival – Open-air art show and market featuring oil paintings, watercolors, sculpture, photography and other works. 10am – 5pm on Whitehead Street & Caroline Street, Key West.


March 2 – 57th Annual Conch Shell Blowing Contest – Prizes are awarded for contestants ability to make sound and music from a conch shell by blowing into it like a trumpet. Registration is at 10am. Contest begins at 12 noon, Oldest House, 322 Duval Street. FREE to attend.

March 2 – 19th Annual Open Air Art & Music Affair – Arts and craft vendors display their creations at one of Key West’s favorite watering holes. Live music from local performers. Schooner Wharf Bar, Lazy Way Lane (end of William Street) 10am – midnight.

Key west poker run 2019 dates date

March 4 – 7 – Merkin Invitational Permit Tournament – Fly fishermen compete to catch Permit, one of the most challenging fish to catch on fly. Key West Yacht Harbor Marina (Stock Island).

March 7 – 10,000 Maniacs in Concert – Billboard-topping rock group from the 80’s plays at the intimate Key West Theatre. Although Natalie Merchant has moved as lead singer, this talented act is sure to have you tapping your toes to the numerous big hits they produced. 8pm show, 512 Eaton Street.Tickets cost $59.50 – $79.50

March 15 – 16 – 59th Annual Key West House & Garden Tour – Visit five Key West homes and tropical gardens. 10am – 4pm. Tickets are $30 in advance, $35 day of tour.

March 17 – Saint Patrick’s Day – Many people treat each day in Key West like St. Patrick’s Day. So when the holiday does actually come around, it is quite the party.

March 23 – Key West Cemetery Stroll – Learn about Key West’s vast history through volunteer guides as they visit numerous graves and monuments within the Key West cemetery. Tours will be conducted at 9:30 am and 12noon. Cost is $20 per person. Advanced reservations required.

Key west poker run 2019 dates 2019

March 30 – 2019 Key West Gala – Benefit and fundraiser for Equality Florida, the largest LGBTQ civilrights organization in Florida. FREE to attend. 5:30pm, Truman Little White House, 111 Front Street.

March 30 – 31 – Naval Air Station Key West Southernmost Air Spectacular 2019 – The Blue Angels airsquadron will be performing their amazing acts of flight synchronicity. Air show will also feature parachute teams and otheraeronautical performers. Boca Chica Naval Air Field, mile marker 7. Gates open at 9am. Blue Angels perform at 2:30pm. FREE to attend.


April 4 – Beach Boys in Concert – The world-famous California band performs outdoors on the SunsetGreen Lawn, 3820 N Roosevelt Blvd, 6:00pm (show starts at 7:30pm). $99, general admission.

April 6 – The Revivalists in Concert – Popular major band performs at the new Key West Amphitheater,overlooking the Key West harbor. Doors open at 5pm, showtime is 6:30 at 21 Quay Road (Truman Waterfront Park, end ofSouthard Street). Tickets cost $45-75

April 6 – 38th Annual 7-Mile Bridge Run – The longest bridge in the Florida Keys, and an engineeringmarvel is home to one of the most anticipated and contested running races. Each year, approximately 1500 runnerstraverse the bridge while surrounded by stunning ocean scenery. Registration is online only in early February 2019. Only1500 entries are allowed and this event quickly sells out.

April 7 – 6th Annual Cow Key Channel Run – This 300-foot mock marathon over the tiny Cow KeyBridge features hilarious costumed runners, walkers, relay teams, and even pets. Prizes awarded for fastest, slowest, bestcostumed, best theatrical performance, and many more. This year’s theme is “Pirates of the Cowibbean.” FREE toparticipate. Check-in at 10-11:30am at Stock Island side of Cow Key Channel.

April 15 – 24th Annual Taste of Key West – For the benefit of AIDS Help, more than fifty Key Westrestaurants offer delicious tapas-sized portions at Mallory Square – each taste costing between $3 – $8. Always wellattended, this lively event will have you bouncing from cuisine to cuisine, all the while enjoying the generous selection offine wines available in a collectible wine glass. 6pm – 9pm, Mallory Square (400 Wall Street, Key West). Admission tothe event is FREE. Food tickets sold in $1 increments.

April 19 – 28 – 37th Annual Conch Republic Independence Celebration – Celebration of KeyWest’s brief secession from the United States. Event highlights include bed races on Duval Street, conch shell blowingcontest, arts & crafts show, Duval Street Parade, and the infamous bloody battle in Key West harbor where ConchRepublic vessels toss stale Cuban bread at Coast Guard vessels and each other in a mock secession. Kick-off party at theSchooner Wharf bar on Friday, April 19th, 7pm.

April 21 – Easter in Key West – Numerous local restaurants offer special Easter Brunch menus.

April 22 – Earth Day in Key West – Celebrate with one of earth’s most beautiful places, Key West! Visitthe coral reef, explore the mangrove islands in the backcountry, walk on the beach, and appreciate all that is unique aboutthe local eco-system. And while you are at it, please pick up any trash that you come across; the earth thanks you!


May 3 – 5 – 4th Annual Papio Kinetic Sculpture Parade – In recognition of Florida Keys artist Stanley Papio,known for his re-purposing of found objects into whimsical sculpture, this event showcases Key West’s creativity andwhimsy with a parade of human-powered artworks. Competition categories include art bikes and kinetic sculptures. The paradebegins Saturday, May 4 at noon in front of Customs House at 281 Front Street.

May 5 – 7 – 17th Annual Harry S. Truman Legacy Symposium – This year’s theme exploresPreservation & Protection of the White Houses, big and little, as well as Truman’s legacy enacting national fire laws.

May 8 – 12 – 24th Annual Key West Song Writers Festival – Features more than two-hundred topsongwriters performing at a variety of venues in Key West, including a concert on the Sunset Pier of the Ocean Key Houseat 1 Duval Street and a free concert on Duval Street.

May 12 – Mother’s Day in Key West – Celebrate your mom in style! Local restaurant have numerousbrunches available – dine indoor or outdoor, oceanfront or air-conditioned. Happy Mothers Day!

May 13 – 36th Annual Queen Mother Pageant – Drag queens compete for title of “Queen Mother,” judgedby their often hilarious, always talented performance in evening gown, talent, and interview skills. Benefits CompassionateCare Hospice and One Human Family Foundations. Cost is $25 for general admission, or tables from $200-$500 (thesesell out fast). Door open at 7pm, show starts at 8pm. LaTeDa, 1125 Duval Street.

May 14 to June 1 – Waterfront Playhouse presents: Red Speedo – Would you do anything to win an Olympic medal? What is the line in the high stakes world of modern sports? This is the dilemma posed in Red Speedo, a razor-sharp play about whether doping is acceptable in the pursuit of that elusive medal – and more importantly, when commercial endorsements are at stake. See website for show dates. Show times 8 p.m.

May 18 – 19 – 12th Annual Keys 100 Ultra – 100 and 50 mile ultra marathons starting near Key Largoand in Marathon FL, finishing in Key West. Cost: $150 to $275 for individuals (depending on race length and time ofregistration), and $720 to $840 for teams (depending on race length and time of registration).


June 1 – 43rd Annual Swim Around Key West – The Annual Swim Around Key West is a 12.5-mile endurance swim clockwise around the entire island of Key West, started by founder Anna Fugina in 1977. The Annual Swim Around Key West is an independent and insured swim, permitted by the U.S. Coast Guard. There are three categories: solo swimmer, two-person relay team and three-person relay team. Presented by Key West Athletics Association.

June 5 – 9 – 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 07 to June 09 – Big Pine – Original Big Pine & Lower Keys Dolphin Tournament – The Lower Keys Chamber of Commerce presents its 25th annual event, where anglers contend for more than $35,000 in cash prizes and awards. A special cash prize of $20,000 is awarded for the largest dolphin over 50 pounds. Additional prizes await winners in the open, ladies and youth divisions.

June 11 to June 13 – Islamorada – 42nd Annual Ladies Tarpon Fly Tournament – The Ladies Tarpon Fly is an all release, fly fishing challenge that has attracted many premier lady fly anglers and guides throughout its history. Whether your favorite species is tarpon or you are looking to put another feather in your cap, the tournament participants range from the expert to the novice who is trying to improve her fishing skills. Email Shandra Rummel to request your invitation!

June 15 – 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.


June 15 – 7th Annual VFW Fishing Tournament – Sponsored by the Southernmost VFW Post 3911, this family-oriented inshore and offshore 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, senior angler and active service member. The heaviest Dolphin: 1st-$3000.00; 2nd-$1000.00; and 3rd $500.00. Weigh-in at Murray Marine. All proceeds benefit VFW Relief Fund for Monroe County veterans and local charities

June 15 – Tropical Fruit Fiesta – Held on the grounds of the Truman Little White House, this event features a display Key West’s numerous tropical fruits, including mango, papaya, Key Lime, spanish lime, jackfruit, starfruit and others. Tastings, lectures, and opportunity to purchase locally grown produce. Growers compete for award of best fruits in each category. Fun event with genuine local color. 9am-1pm, Truman Little White House, 111 Front Street.

Jun 21 – Jun 23 – Key West International Guitar Festival: Bridges to Paradise – The festival features a fusion of master guitarists performing classical, jazz, Latin, blues, folk & contemporary music in historic venues throughout the island, in a series of world-class concerts. Food and wine events are to be paired with music throughout the island offering a culinary and cultural experience highlighted by a special event, “Virtuoso Chefs of Key West.” Featured artists include Mateo, Belle, Rolando Rojas and Larry Baeder.

June 21 – 23 – Mystery Fest Key West – Renowned mystery writers, aspiring authors, true crime experts and fans meet in America’s southernmost city. The Fest features a who’s-who of award-winning and bestselling mystery/suspense authors and true crime experts, Mystery Fest Key West is a fun and fascinating meet-and-greet where writers can catch up with old friends and readers can meet leading authors, collect signed books and participate in workshops, panels, and presentations where the most devious of minds explain why—and how—they do it.

June 29 – Key West Mango Fest 2019 – Mango Fest of Key West features all things mango including mango tasting, mango trees, and mango daiquiris. The culinary competitions between local chefs and residents alike showcases the colorful abilities of what the mango, also known as the king of fruit, has to offer. The Vendor Village gives art collectors and foodies the experience of a festival atmosphere. Music is provided along with live radio broadcasts. From 10AM to 3PM, Bayview Park, 1400 Truman Ave.


July 4 – INDEPENDENCE DAY – Key West 4th of July Fireworks – Dazzling fireworks show is launched from the White Street pier on the south side of the island of Key West. Begins shortly after sunset. Popular tradition is to view the fireworks from the water aboard a boat. More information and reservations for boat options at Key West July 4th Fireworks Cruises

July 4 – 7 – Seventh Annual Key Lime Festival – A wacky talent show, pie-eating and cooking contests and other tasty temptations await Key West visitors during the annual Key Lime Festival. Four days of culinary events for every taste are planned, including favorites from past years like the Key Lime Cocktail Sip & Stroll, and new favorites for Key Lime lovers like The Key Lime Pie Hop.

July 5 – 7 – Inaugural Key West Mermaid Festival – A fin-tastic three-day weekend event designed to educate and raise awareness of the beautiful oceans is to be packed with many fun and ‘mervelous’ events. From Sunsets and Mojitos with Mermaids and a Salty Street Fair, to evenings of live performances along the Keys’ salty shores, attendees can enjoy mermaid meet-ups, book readings and signings, and more.

Key West Poker Run 2019 Dates Date

July 9 – The Happy Dog in Concert, Playing Dead Floyd – America’s best unknown jam band, The Happy Dog, makes their home in Key West, and the locals are ecstatic. Not content to copy the Grateful Dead, this stellar band is actually continuing the musical conversation that Jerry Garcia and the rest of the Dead developed. This is The Happy Dog’s first performance at the intimate Key West Theater, and will be professionally recorded. 7:00 showtime, Key West Theater, 512 Eaton Street.

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 513 permit on fly tackle off the Florida Keys in his lifetime. Begun in 2001, the tournament is based out of Hurricane Hole Marina. Each year the event makes a contribution to the Bonefish Tarpon Trust and the Jon Ain Memorial Fund to continue permit research.

July 16 – 21 – Hemingway Days – The 39th annual celebration of the legendary author’s work and lifestyle features literary readings, the Running of the Bulls, a short story competition, fishing tournament, 5k Run and Paddleboard Race, Sloppy Joe’s Look-Alike Contest and a birthday “party” commemorating Ernest’s July 21st birthday.

July 17 – 20 – Havana Club Key West Marlin Tournament – Anglers ply the waters once fished by writer 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.

July 24 – 25 – Lobster Mini-Sport Season – Two-day event draws hundreds of often frenzied recreational boaters in search of Florida lobster. Many rules apply, including: Bag limit: 6 per person per day for Monroe County. Possession limit – on the water: equal to the daily bag limit. Possession limit – off the water: equal to the daily bag limit on the first day, and double the daily bag limit on the second day. Possession limits are enforced on and off the water. Minimum size limit: must be larger than 3? carapace, measured in the water. A reminder that possession and use of a measuring device is required at all times, and night diving is prohibited in Monroe County (only during the sport season). Florida Salwater Fishing License plus lobster endorsement/stamp required. Please respect other boaters, stay away from shorelines, ecological reserves, no-take zones, and canals, use a dive flag, and do no harm to the sensitive coral and eco-system. Call Florida Fish & Wildlife (FWC) at 305-289-2320 for more information.

July 20 – 27th Annual Hemingway 5K Sunset Run/Walk & Paddleboard Race – This is the original and oldest ongoing 5K Run in Key West and takes place as part of 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.


August 8 – 11 – 23rd Annual Key West Lobsterfest – Everyone will be partying on Duval Street, except the lobsters. Marking the official opening of lobster season, this crustacean-focused event features street fairs, live music, and arts & crafts. Street fair with free live concert on Saturday, noon-11pm, lower Duval Street.

August 14 – 18 – in Key West – 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.

Aug 29 – Sept 2 – 10th Annual Key West Brewfest – Nearly 200 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 (Aug. 31) are some of the offered activities.

Aug. 30 – Sep. 1 – Heroes Salute Tribute Weekend – Each fall, Hawks Cay Resort on Duck Key hosts an annual Heroes Salute program to honor military, fire and rescue, law enforcement and medical personnel; a special Labor Day Weekend event is planned to include an All-American barbecue, heroes tribute, live music concert, and fireworks show.


September 2 – Labor Day 2017 in Key West – Picnics, bar-b-que, beaches, and a day of leisure, all activities Key West is known for. Expect warm ocean temperatures, balmy nights, and a laid back crowd.

September 4 – 8Womenfest 2019 – Each year thousands of ladies come together over the Labor Day weekend and stay for a wide range of activities and events during four days of revelry and fun. Key West welcomes women from across the globe to an annual celebration that has become one of the largest gatherings of lesbians and friends in North America’s Womenfest.

September 6 – 8 – 4th Annual Florida Keys Poker Paddle – Please join Your Paddling Fools and Florida Keys Brewing Co. in Honoring and Supporting Our Courageous Service Men and Women and their Brave Families. Open to everyone to participate in a “poker” paddle race for kayaks and stand-up paddleboards in beautiful Islamorada. Essentially a “poker run” is an excuse to get together, have some fun and raise money and awareness for a great cause. The approximately 4-mile route will consist of five stops in mainly shallow water, including two sandbars. Packet Pick Up Party on Friday 9/6 as well as an Awards Ceremony Grand Finale Party on Sunday 9/8.

Sept 6 – 8 – Robert-James Sales S.L.A.M 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. A number of celebrities show their support by taking part in the tournament each year. Celebrity competitors have included Major League Baseball Hall of Famer Wade Boggs, former Denver Broncos football player Mark Cooper and former NASA space shuttle astronaut Bruce Melnick.

September 14 – Annual Swim for Alligator LighthouseSince 2013, swimmers participate in an 8-mile roundtrip race from Islamorada to the Alligator Lighthouse and back. Proceeds help provide scholarship opportunities to those students in need and who wish to pursue competitive swimming, as well as raise awareness of the need to preserve the treasured, historic offshore lighthouses along the Florida Keys.


October 11 – 12 – SoMo Marathon & Half Marathon – 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 including a 10k and 5k are planned.

October 15 – Official 2019 Stone Crab Season Opening – In mid-October, the most delicious local seafood becomes available, the stone crab. With a porcelain-like shell and briny meat, this crab is considered a sustainable resource in that only the claws are taken and the crab is released back into the wild to grow new ones. Stone crab is only native to this region and is considered a seafood delicacy. October 15 is a special day for locals who eagerly await the opening of the stone crab season in Key West.

October 18 – 27 – 40th 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.

Oct. 18 – 19 – Bahama Village Goombay Festival – Held in Key West’s historic Bahama Village neighborhood, the lively, family-friendly 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. FREE event, noon to midnight both days.

Oct. 17 – 20 – REEF Fest – Join Reef Environmental Education Foundation (REEF) in a celebration of marine conservation. Morning activities include ocean adventures of kayaking, snorkeling and diving, all alongside marine life experts. Afternoons feature free seminars from renowned experts in a variety of marine topics. Evenings boast food, drinks and fun with friends old and new. All events are open to the public.

October 24 – Headress Ball – Costume contest featuring dazzling headdresses created over many months and worn and displayed in this awe inspiring event. HUGE works of art, each more inventive and imaginative then the previous. Grand prize is $1500. Truman Waterfront Amphiteater, end of Southard Street.

October 30 – November 3 – 28h Annual Meeting of the Minds 2019 – Parrothead convention and nirvana benefiting charity. Many events are members only. Live shows include members of Jimmy Buffett’s band. Highlights include the Margaritaville Street Fest on Friday from 1pm – 5:30pm on the 500 block of Duval Street (near Fleming Street) which is FREE and open to the public.


Nov 2 – 27th Annual ABC 5K Walk/Run – Sponsored by Zonta, this running race benefits women’s health screenings and breast cancer awareness in the Lower Florida Keys. Race begins and ends at Salute on Higgs Beach.

Nov 3 – 10 – 38th 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.

Key West Poker Run 2019 Dates 2021

Nov 20 – 24 – 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 San Carlos Institute, Studios of Key West and Key West Theater. The four-day program is to include several films from multiple genres and categories as well as social events with filmmakers, actors and film lovers.

November 28 – Thanksgiving in Key West 2019 – Traditional turkey is served in a tropical setting as residents and visitors celebrate the annual holiday. Many local restaurants have special Thanksgiving menus.


Dec 1 – 31- Key West Holiday Fest – Each year a wide range of seasonal celebrations takes place throughout Key West during the month of December. Events include the lighting of the Harbor Walk of Lights, tours of historic decorated inns, a holiday parade and much more.

Dec 4, 2019 – Key West Lighted Bike Ride – The Lighted Bike Ride helps to gather the needed toys for the struggling, working families of Key West for the holidays. At the Holiday Helpers Store, eligible parents walk through the store, empowered by the ability to pick free, new toys their children will want instead of just allocating non-specific toys to parents. The ride is a family event beginning with a registration/checkin at 6 p.m. with the Lighted Bike Ride beginning at 7:00 p.m. Families and individuals with lighted and decorated bikes ride through the streets for the community to see. Registration for the ride is one unwrapped toy for the Key West Holiday Store. Register online.

Dec 7 – TRIKW Sprint & Olympic Triathlon – The Key West Triathlon expects up to 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. Event highlights feature an Aquabike competition this year, along with a .76 km Atlantic Ocean swim from Higgs Beach, a 20km U.S. 1 cycling ride along South Roosevelt Boulevard and a 5km run along Smathers Beach.

Dec 13 – 15 – Third Annual I Love Stock Island Festival -Celebrate Stock Island’s culture and heritage with culinary offerings featuring fresh-off-the-boat seafood, wine and beer tastings, history and art studio tours, live music and other elements that showcase the eclectic island and its working waterfront. Highlights include a lighted boat parade from Stock Island Marina Village; kid’s activities & Little Mr. & Miss contest, and more.

Dec 27 – 28 – 60th Annual Key West Home Tours – Presented by the Old Island Restoration Foundation, the annual self-guided tours from 3-6 p.m. each day showcase festively dressed Key West homes and gardens. You will be enchanted by exquisite restorations, creative renovations and delightful interiors featuring art collections, antiques, and much more. All proceeds from the tours stay in the Key West local community fulfilling OIRF’s mission of “Celebrating and sustaining Key West’s unique architecture, culture and history.”

Dec 31 – New Year’s Eve with your choice of 4 celebrations to bring in the New Year 2020. You can:

  1. Go to Sloppy Joe’s Bar to see a huge conch shell lowered. Always a crowded and fun time.
  2. Watch as a pirate wench is lowered from the mast of a schooner.
  3. There’s a free concert on the Sunset Pier @ Ocean Key House on 1 Duval St. They’ll lower a key lime wedge.
  4. And you can see Sushi who is a drag queen celebrity in Key West lowered from a balcony in a huge high-heeled show.