Key West Events Calendar

Dream Catcher Charters offers visitors to Key West for Special Events Fishing Charters. Save Money and Have A Better Time Booking Direct.

Dream Catcher Charters offers visitors to Key West for Special Events Fishing Charters. Save Money and Have A Better Time Booking Direct.

There is never a shortage of activity on Key West. A new year is here and the events keep on coming. One of the events that is near to my heart is the Key West Fishing Tournament, sponsored by Dream Catcher Charters, Inc; this tournament was founded in 1965 and has been going strong ever since. Anyone fishing in the Florida Keys can enter this seven month long tournament. Culinary delights start off the year here in the Keys; with events like the Seafood Festival and the Food and Wine Festival foodies are in heaven!  There are also many marathons and other physical events like flag football and SUP for those athletic types. And let’s not forget about the art scene; concerts, art openings, seminars and plays are abundant throughout the year, starting off with the 33rd Annual Literary Seminar in January. So no matter when you visit our island Paradise, you will find as much action and entertainment or relaxation as you are looking for.

November 2016

November 6-13

  • 35th Annual Key West World Championship Races – Super Boat International returns with teams from all around the world who compete April through October in the National Series Points races and conclude in November for the famous Key West World Championships. High-speed offshore powerboats race in Key West Harbor and surrounding waters to continue Key West’s longstanding tradition in this annual challenge, known internationally as the Indianapolis 500 of powerboat racing. A portion of the 6.5-mile course runs through Key West Harbor, meaning smooth water where racers can achieve speeds above 140 mph and provide fans breathtaking displays of skill and power. Contact: 305-296-6166 / Email: superboatracing@gmail.com.

November 2-6

  • 25th Annual Parrot Heads in Key West Meeting of the Minds – Several thousand fans of singer/songwriter/author Jimmy Buffett, known as Parrot Heads, make an annual pilgrimage to the subtropical island that inspired many of Buffett’s hits. Parrot Head club members focus on charitable, environmental, educational and humanitarian activities. Highlights include concerts by Buffett band members and friends, plus notable “trop” rockers. While most events are open only to registered Parrot Heads, the public is invited to the musical Margaritaville Street Fest on famed Duval Street.

November 3

  • Florida Straights Lighthouses – As part of the Distinguished Speaker Series, historian Eric Martin, president of the Florida Lighthouse Association, is to share details about these historic structures, built by the government up to 1590 years ago as important navigational aids. From 6-7 p.m., in the Helmerich Learning Center, at the Custom House.

November 3-6

  • Vincent – Leonard Nimoy’s Vincent dramatizes the life of Vincent van Gogh in this intimate one-man play adapted from the actual letters between the artist and his brother, Theo. Van Gogh’s story is so much more than that of the misunderstood genius who cut off his own ear. Contact the Waterfront Playhouse: 305-294-5015.

November 5-9

  • EYECONS – A master of impersonations, both visually and vocally, with impeccable comic timing. The show is all LIVE, no lip-sync. Thrill to his parodies of Marilyn Monroe, Carol Channing, Madonna, Joan Rivers, Reba McEntire, Bette Midler, Tina Turner, Julie Andrews, Barbra Streisand, Liza Minnelli, Judy Garland, Eartha Kitt, Cher, Bette Davis, Lucille Ball, even Lady GaGa. Show dates are 11/5, 11/8, 11/12, 11/17, 11/24, 11/26, 11/29. Show times 9 p.m., at La te da 1125 Duval St.

November 6-13

  • 36th Annual Key West World Championship Super Boat 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.

November 7-12

  • Salvador Dali – This exhbition is a rare opportunity to meet Madame Christine Argillet, daughter of Dali’s legendary publisher and confidante Pierre Argillet. Rare titles from 1934 to the late 1960s include Etchings and Watercolors, in addition to works from Dali’s Suites such as Mythologie, Les Hippies, Goethe’s Faust, and Poemes Secrets d’Apollinaire. At the Key West Gallery. For more information please email info@keywestgallery.com. 

November 9

  • Delta Rae – Live is where Delta Rae truly flourish, having spent the last year and a half playing to sold out venues from coast to coast. Catch this hard working six piece rock band from Durham, NC. Show time 8 p.m. Contact: 305.985.0433 / Email: boxoffice@thekeywesttheater.com

November 10

  • Blues Traveler – The four original members of Blues Traveler, who have known each other since their early teens—John Popper, Chandler Kinchla, the late Bobby Sheehan and Brendan Hill —gathered over 25 years ago in the basement of their drummer’s parents’ Princeton, NJ, home; and the seeds were born for a band who have released a total of eleven studio albums, four of which have gone gold, three platinum and one six-­times platinum. Show time 8 p.m. Contact: 305.985.0433 / Email: boxoffice@thekeywesttheater.com

November 12

  • Womankind 15th Anniversary – From 6-9 p.m., come see the historic 1928 house of Joe Russell, the original owner of Sloppy Joe’s! At 920 Eisenhower Drive (next to Womankind). Tickets are $15, online at EventbriteContact: Kim Romano at 305.320.0607

November 13

  • Visit the Sheriff’s Animal Farm – Looking for a fun place to take the kids? The Sheriff’s Animal Farm is open 1 – 3 p.m. Bring the family and come visit the many animals at the farm. It is free of charge, but donations are welcomed because that is how the farm is sustained. The farm is located just off of College Road, on Stock Island, at the Sheriff’s Office Headquarters complex. Open house is held the second and fourth Sundays of the month. Contact: Farmer Jeanne Selander 305-293-7300.

November 14

  • WAR – With unforgettable hits such as “Lowrider”, “The Cisco Kids”, “The World Is A Ghetto”, “Why Can’t We Be Friends”, and countless others, WAR’s music is a timeless thread in the quilt of American pop culture. Show time 8 p.m. Contact: 305.985.0433
    / Email: boxoffice@thekeywesttheater.com

November 15

  • 2nd Annual Hungry Games – Enjoy a night of food and fun where you vote for your favorite team. A portion of the proceeds will go to the Key West High School Culinary Program. 6 – 8 PM at the Southernmost Beach Cafe. $40 per person. Cash bar available.  
  • South Florida Symphony Orchestra – The universal appeal of the great American Songbook combines the brilliant complex and lush timeless melodies with sophisticated intelligent and accessible lyrics. Music historians consider The Great American Songbook along with jazz to be the most important contributions made to American music in the 20th Century. Performance at the Key West Theater, 512 Eaton St.

November 16-20

  • 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 18-19

  • Burt Bachach – Presented by Waterfront Playhouse, the 77th season is to start with the timeless music of Burt Bacharach. The six-time Grammy Award winner and winner of three Academy Awards is a master of hit songs. A line-up of Key West’s best vocal talent will present another amazing concert. “Never be ashamed of writing a melody people remember” — Burt Bacharach. Contact: Box Office (305-294-5015) / Email: Box_Office@waterfrontplayhouse.org

November 19

  • Key West Recycles Day Fair and Art Contest – Staged at the Key West Tropical Forest and Botanical Gardens from 10 a.m. until 2 p.m. Come out and enjoy this free event and visit booths with local environmental groups, reused and recycled art displays, recycle booths and concessions. Items for reuse and recycling will also be collected, such as blankets, towels, canned goods, books, art supplies, travel toiletries, old medications, old flares and fireworks, and plastic bags. Contact: Dee Dee Green at 305-809-3776 / Email: dgreen@cityofkeywest-fl.gov

November 23

  • Lighting of the Key West Harbor Walk – The eagerly awaited pre-Thanksgiving event is to take place at 6 p.m. at Greene and Elizabeth streets, with the lighting of a holiday tree made from plastic foam trap floats, a fresh pine nautically decorated Christmas tree and a lobster trap tree along the Key West Historic Seaport’s Harbor Walk. The Harbor Walk is lit nightly through New Year’s Eve.

November 23-27

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

November 25-27

  • I Love Stock Island Festival – Featuring three great days of the very best Stock Island has to offer with concerts, foodie events, wine, beer & rum pairingshistory & art studio tours and the freshest, most delicious seafood in the Keys, straight off our boats! The event will host an island-wide clean-up the weekend of November 19. Festival Proceeds will stay in our community to help with local projects. Mark your calendars to join us for this inaugural event. www.ilovestockisland.com.

November 26 

  • Anonymous Angels Silent Auction – Kicking off the holidays and the annual season of giving, shoppers can give a gift that gives back. From 2-6 p.m., at St. Paul’s Episcopal Church. Items have been donated by Key West’s finest restaurants, shops and services. Auction proceeds benefit Anchors Aweigh Club, dedicated to twelve-step recovery programs for over 30 years. Contact: 305-619-9459.

November 27

  • Visit the Sheriff’s Animal Farm – Looking for a fun place to take the kids? The Sheriff’s Animal Farm is open 1 – 3 p.m. Bring the family and come visit the many animals at the farm. It is free of charge, but donations are welcomed because that is how the farm is sustained. The farm is located just off of College Road, on Stock Island, at the Sheriff’s Office Headquarters complex. Open house is held the second and fourth Sundays of the month. Contact: Farmer Jeanne Selander 305-293-7300

December 2016

December 1-3

  • Key West Triathlon and Expo – The Key West Triathlon and Expo expects to host a maximum of 1,000 participants and some of the sport’s best known triathletes; TRIKW allows you to bask in the warm weather and the waters of the Atlantic Ocean while the rest of the country is experiencing winter. Olympic and Sprint distances.

December 2-17

  • Hot Pink Holidays – Sponsored by the Key West Business Guild, these merry LGBT holiday weekends, sponsored by the Key West Business Guild, are full of festive activities as well as special retail opportunities on the island. Events include a Conch Train holiday lights tour and caroling. Holiday revelers also can celebrate with “Sandy Claws” at happy hours. Dates are Dec. 2-3, 9-10 & 16-17, 2016.

December 3

  • Marshall Tucker Band – These good ol’ boys from Spartanburg, South Carolina remain as a powerful force in the world of music, with its definitive blend of rock, rhythm & blues, jazz, country, and gospel. Show time 8 p.m. Contact: 305.985.0433 / Email: boxoffice@thekeywesttheater.com
  • Key West City Hometown Parade – The island city shows its holiday spirit with this annual hometown parade. Featuring marching groups and motorized and non-motorized floats, the festive procession traditionally draws entries from churches, civic organizations, businesses and neighborhood and school groups. Route includes Truman Avenue and White Street, proceeds down Truman to Duval, where it takes a right and continues on to Eaton Street.

December 3-31

  • 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.

December 4

  • Breakfast with Santa – Poolside at the Marker Waterfront Resort from 10am until 1pm. Get a photo with Santa or purchase two entrees and get one for free! 

December 5

  • Howard Jones – Along with ‘New Song’, a host of hits include ‘Things Can Only Get Better’, ‘What is Love?’, ‘Pearl In The Shell’, ‘Like to Get To know You Well’, ‘Hide And Seek’ (performed at Live Aid), ‘Look Mama’ and ‘No One Is To Blame’, which reached No.1 in the US. Highlights of his current high tech band features Jonathan Atkinson on electric drums and Robbie Bronnimann on sequencing and additional keyboards. Contact: 305.985.0433 / Email: boxoffice@thekeywesttheater.com
  • POSH – The Paws Often Steal Hearts, or POSH, party is to be held at the Audubon House & Tropical Gardens, 205 Whitehead St., to benefit the Florida Keys Society for the Prevention of Cruelty to Animals. Attendees are encouraged to wear island-style formal attire and “fascinator” hats. General admission tickets are $40 pre-purchased and $45 at the door, per person. Contact: 305-304-1232. 

December 7

  • Key West Lighted Bike Parade – 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 at 5:30 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. Contact: Claire Hiller at 305-809-5000 / Email: claire.hiller@wesleyhouse.org
  • POSH – From 6:30pm to 9:30pm, come to the Audubon House and Tropical Gardens located at 205 Whitehead Street for this 5th annual fundraiser for the Florida Keys SPCA. This is a gala style event. TICKETS!!
  • Key West Art & Historical Society Invites Members to Join Museum Store Shopping Parties, All Welcome to Holiday Concert & Bazaar – Shopping local goes a long way in Key West during the holiday season, especially when your purchase helps support a museum and its mission while giving you discounts.  On Wednesdays throughout the month of December, Key West Art & Historical Society gives back with private members-only shopping parties with refreshments and exclusive 30% discounts for members from 6:00PM-8:00PM at their three museum store locations: December 7 at Fort East Martello Museum, December 14 at Key West Lighthouse, and the final private shopping party on December 21 at the Custom House Museum, held in conjunction with the Society’s Holiday Concert & Bazaar  from 5PM to 9PM, open to the public and featuring Key West’s finest artisans, musicians and choirs, and a spectacular holiday light show.  Purchases made at all of their museum stores support Key West Art & Historical Society exhibitions and educational programming.  Show your membership card on any day to receive a 20% discount, and a 30% discount during the membership shopping parties.  For more information, Membership Coordinator at klivingston@kwahs.org or 305.295.6616 x106.

December 8

  • Bad Santa Movie & Picture Night – Poolside at eh Marker Waterfront Resort. Sit on Santa’s lap to let him know if you have been naughty or nice and watch the irreverently funny film, Bad Santa. 

December 9

  • Pet Pictures with Santa – Hosted by All Animal Clinic of Key West. Santa is to pose for photos with pets from 6-8 p.m. at the nautical Christmas tree at the foot of William Street on the Harbor Walk of Lights. Sales of photos, priced from $20, are to benefit the Boys & Girls Clubs of the Keys Area Inc. Contact: 305-294-5255 / Email: allanimalclinic@gmail.com
  • Holiday Historic Inn Tour – Enjoy an enchanted evening of five decorated inns and a sampling of holiday treats and cheer at each property. From 6-8 p.m., tours are self guided. Free trolley transportation is provided between inns but participants are welcome to bike or use their own transportation. Call the Lodging Association for tickets. Contact: 305-296-4959.
  • Painter Eric Anfinson’s 2017 Calendar Release Celebrated at Salt Island Provisions – With only a few weeks left of 2016, it’s time to consider how you’ll document and organize your upcoming year.  On Friday, December 9th, SALT Gallery invites the public to join them in celebrating artist Eric Anfinson and the release of his 7th annual calendar of paintings from 6pm – 8 pm at their location on 830 Fleming Street. A curated selection of the artist’s work from the year prior allow collectors and fans and a chance to live with one of his paintings every month of the year for the affordable cost of a calendar. The collectable, high-quality print calendar will be available for purchase for $24.99 at SALT Gallery or online at EricAnfinson.com, with special discounts available for multiple purchases. For more information, call 305.896.2980 or visit SaltIslandProvisions.com.

December 10 – 18

  • Nutcracker Key West – 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 Dec. 10-11 & Dec. 14-18 at the Tennessee Williams Theatre. Purchase tickets online.

December 10

  • 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. 
  • Parade of Paws and Holiday Bazaar – Bring your dogs, wear a t-shirt with a picture of your kitty with pride, or walk with a paddle displaying your pet’s photo! Holiday Bazaar inside the dog park features entertainment, food vendors, photos with Santa, gifts for that special person on your list and more! A unique opportunity to support the lifesaving mission caring for the Keys’ community’s homeless animals, the event supports the Florida Keys SPCA. Check in is 9 a.m. Event is from 10 a.m. to 2 p.m., Higgs Beach, at the Higgs Dog Park. Bring four-legged friends.

December 11

  • Devon Allmän – Devon Allman has toiled long and hard to establish his own musical identity, separate from his legendary dad, Gregg Allman. Royal Southern Brotherhood was formed during JazzFest in New Orleans. This unique quintet combines the vocal and musical talents of Devon, Mike Zito, and the legendary Cyril Neville with the veteran rhythm section of Charlie Wooton and Yonrico Scott. Their mixed sounds of funk, blues, rock and jazz proved to be a force to be reckoned with. Show starts 8 p.m. Contact: 305.985.0433 / Email: boxoffice@thekeywesttheater.com
  • Christmas on the Sheriff Animal Farm – 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. 
    Contact: 305-293-7300. 

December 14

  • Key West Art & Historical Society Invites Members to Join Museum Store Shopping Parties, All Welcome to Holiday Concert & Bazaar – Shopping local goes a long way in Key West during the holiday season, especially when your purchase helps support a museum and its mission while giving you discounts.  On Wednesdays throughout the month of December, Key West Art & Historical Society gives back with private members-only shopping parties with refreshments and exclusive 30% discounts for members from 6:00PM-8:00PM at their three museum store locations: December 7 at Fort East Martello Museum, December 14 at Key West Lighthouse, and the final private shopping party on December 21 at the Custom House Museum, held in conjunction with the Society’s Holiday Concert & Bazaar  from 5PM to 9PM, open to the public and featuring Key West’s finest artisans, musicians and choirs, and a spectacular holiday light show.  Purchases made at all of their museum stores support Key West Art & Historical Society exhibitions and educational programming.  Show your membership card on any day to receive a 20% discount, and a 30% discount during the membership shopping parties.  For more information, Membership Coordinator at klivingston@kwahs.org or 305.295.6616 x106.

December 15

  • Poet Elizabeth Bishop Featured in KWAHS Distinguished Speaker Series presented by Author Thomas Travisano:  On Thursday, December 15, from 6:00-7:00 pm, Key West Art & Historical Society welcomes the public to the Helmerich Research & Learning Center on the third floor of the Custom House Museum for “Elizabeth Bishop: All the Untidy Activity Continues,” a presentation by Distinguished Speaker Series guest Thomas Travisano, founding president of the Elizabeth Bishop Society and author of numerous books and articles about the Pulitzer Prize winning poet who once owned and lived in the house at 624 White Street in Key West.  Tickets are available at through KWAHS.ORG/LEARN; $8 for members, $15 for nonmembers.  For more information contact Adele Williams, Director of Education, at 305-295-6616, x115. Sponsored by the Helmerich Trust.  

December 16

  • Holiday Historic Inn Tour – Enjoy an enchanted evening of five decorated inns and a sampling of holiday treats and cheer at each property. From 6-8 p.m., tours are self guided. Free trolley transportation is provided between inns but participants are welcome to bike or use their own transportation. Call the Lodging Association for tickets. Contact: 305-296-4959.

December 17

  • Gingerbread House Event – From 11am until 3pm, you are invited to the Oldest House and Gardens at 322 Duval Street to build an edible house! Each person attending is encouraged to bring edible items for house (or car or boat or entire town) building and decorations, like gumdrops, candy canes or cookies to share. There will be tables full of house building and decorating supplies to create any gingerbread “house” you can imagine. Everyone attending will take their gingerbread creations home for a festive addition to holiday celebrations.For more information call: 305-294-9501.

December 21

  • Inaugural Holiday Concert and Bazaar at the Custom House Museum – The event, from 5-9 p.m., will feature Key West’s finest artisans, musicians and choirs, along with a spectacular holiday light show. Browse hundreds of unique gift options while enjoying the music, food and libations on and around the island’s architectural crown jewel, with eggnog to lift the frazzled ‘final shopping days’ spirits and Santa on hand for last minute requests and ‘selfie’ photos. Open and free to the public.

December 22

  • Holiday Concert & Pop-up Shops – Poolside at the Marker Waterfront Resort, listen to Rusty Lemmon and friends sing holiday favorites while you get some last minute shopping in. 

December 23-24

  • The City of Key West is offering free transportation via bus during these days to help you get your last minute holiday preparations met!

December 23-25

  • The City of Key West is offering free metered parking in Old Town for these days! 

December 27-28

  • 57th Annual House & Garden Tour – Presented by the Old Island Restoration Foundation, the annual self-guided tours showcase festively dressed Key West homes and gardens. December tours are from 4-7 p.m., both evenings. Transportation between homes is NOT included. Tickets are $30. Proceeds benefit the Old Island Restoration Foundation’s museums, collection and education, grant and scholarship programs. Contact: 305-294-9501.

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.
  • New Year’s Eve Conch Shell Drop at Sloppy Joe’s – The arrival of 2017 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 Even Pirate Wench Drop at the Schooner Wharf Bar – 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 2017. Scallywags in attendance can expect live music all day, dancing and festivities at the Schooner Wharf Bar, 202 William St. 
  • Key West Dachschund 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. Email: keywestdachshundwalk@gmail.com

 

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

And for restaurant reviews check out our restaurant review section of this blog as well as our restaurant reviews at www.gotothekeys.com.

Island Genn – Your Key West Concierge