Events & Festivals

January 2018

  • Dec. 14, 2017 – Jan. 6, 2018
    Waterfront Playhouse presents: Inspecting Carol
    Grab a large helping of holiday cheer with this hilarious, madcap comedy! It’s a cross between A Christmas Carol and Noises Off. Behind the scenes of a struggling theatre’s annual slapdash production of A Christmas Carol, rehearsals are at a standstill. Tim is no longer Tiny, Scrooge wants to do the play in Spanish (Feliz Navidad), and their funding is on hold pending an inspection. This laugh out loud spoof makes for a night at the theatre that is anything but show business as usual. “Inspecting Carol” is a delightful mix of “A Christmas Carol,” “Noises Off,” “Waiting for Guffman.”
  • Jan. 1, 2018 – Aug. 31, 2018
    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.
  • Jan. 11, 2018 – Jan. 14, 2018
    Key West Kingfish Mayhem
    Big fish, big money! Come fish for some of the largest kingfish in Florida Keys waters in this new tournament. Fishing headquartered at Stock Island Marina. First prize could earn $15,000 cash, based on a 50-boat field.
  • Jan. 11, 2018 – Jan. 14, 2018
    36th Annual Key West Literary Seminar
    The 2018 topic is “Writers of the Caribbean.” Literary aficionados from around the world are to gather for readings, discussions and lectures led by some of contemporary literature’s most acclaimed writers. The island nations of the Caribbean have produced some of the most powerful and exciting writers of our time. For the 36th annual Key West Literary Seminar, we look across the waves to the vital literature that has emerged from this region.
  • Jan. 12, 2018 – Jan. 13, 2018
    58th Annual Key West House & Garden Tours
    Tour elegant and unique private homes of Key West, ranging from exquisite restorations to creative renovations, and the interior design that complements each. January tours are offered 3 to 7 pm each day. Transportation between homes is available via Conch Train for $40 each, seating is limited. Tickets without transportation are $30 in advance and $35 on tour days. Proceeds benefit the foundation’s Oldest House Museum, grant and scholarship programs.
  • Jan. 13, 2018 – Jan. 14, 2018
    13th Annual Florida Keys Seafood Festival
    A family-friendly event with local fresh Keys seafood, drinks, marine-related crafts, youth activities, and live music. $5 admission per person; hours open from 11 a.m. – 8 p.m. on Saturday; 11 a.m. to 5 p.m. on Sunday, at Bayview Park, Truman Avenue and Jose Marti Drive.
  • Jan. 22, 2018 – Jan. 29, 2018
    Kelly McGillis Classic International Flag Football Championship
    Women and girls from around the world are to meet on the playing field for hard-fought sporting action. Each year, nearly 30 teams from across the United States, Mexico, Central America, Sweden and India participate.
  • Jan. 24, 2018 – Jan. 28, 2018
    Key West Food & Wine Festival
    Top chefs and restaurateurs display culinary creativity and the Keys’ indigenous cuisine in a flavorful schedule of events for food lovers. Highlights include the lively “Old Town Uncorked,” neighborhood wine strolls, food and wine pairings, intriguing seminars, winemaker dinner series and a grand tasting.
  • Jan. 26, 2018 – Jan. 27, 2018
    Key West Theater presents: Arlo Guthrie
    Arlo Guthrie has been known to generations as a prolific songwriter, social commentator, master storyteller, actor and activist. Born in Coney Island, New York in 1947, Arlo is the eldest son of Marjorie Mazia Guthrie, a professional dancer with the Martha Graham Company and founder of The Committee to Combat Huntington’s Disease, and America’s most beloved singer/writer/philosopher/artist Woody Guthrie. Arlo has become an iconic figure in folk music in his own right with a distinguished and varied career spanning over fifty years. Show starts 8 p.m. each night.
  • Jan. 28, 2018
    Key West Artisan Market presents: Culinary & Wine Show
    Culinary & Wine Show features local chef specialties, exotic cheeses, wine tasting and dozens of great vino by the bottle and case. Guests are encouraged to ride bikes or the bus which conveniently stops in front of the Restaurant Store. Parking is available in the Old Town Parking Garage at 300 Grinnell Street. Please bring your own bags.
  • Jan. 28, 2018
    24th Annual Key West Master Chefs Classic
    Local restaurants vie for top honors in appetizer, entrée and dessert categories. Attendees sample the culinary treats while judges pick the winners. The show is held from 4-7 p.m. at the Margaritaville Resort & Marina pier, 245 Front St. Event proceeds benefit the nonprofit Monroe Association for ReMARCable Citizens.

 

 

February 2018

 

  •  Jan. 1, 2018 – Aug. 31, 2018 
    Key West Fishing Tournament
    Doris Harris 305-923-5934 
    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.
  • Jan. 23, 2018 – Feb. 17, 2018 
    Red Barn Theater presents: 20th Century Blues
    305-296-9911 
    This sharply funny and evocative exploration of time was the flat our hit of the 2016 Contemporary American Theatre Festival in the 25th season. The play centers on four women who bonded as protesters one night in jail in their youth. Through the vagaries of love, careers, children, and lost causes, the women reunite once a year for a photo shoot, chronicling their changing selves. But when these private photos have the potential to become part of a public exhibit, mutiny erupts and relationships are tested. Featuring Marjorie Paul-Shook, Annie Miners, Peggy Montgomery, Deborah Jacobson, Kathy Russ, and Justin Ahearn.show times and tickets online. Red Barn Theater is located at 319 Duval St.
  • Feb. 1, 2018 – Feb. 3, 2018 
    Cuda Bowl
    Loren Rea 305-360-6969
    Shallow water flats anglers and guides are invited to hook-up and fight their barracuda rivals. Event is to be headquartered at Hurricane Hole Marina, Stock Island. Prizes and trophies are to be awarded for top angler and guide in light tackle spin and fly divisions.
  • Feb. 2, 2018 – Feb. 4, 2018
    Civil War Heritage Days Festival
    305-292-6850
    Colorful Civil War re-enactments, the roar of cannon fire and the sight of soldiers in Civil War uniforms are to greet visitors at Key West’s oceanfront historic Civil War-era Fort Zachary Taylor Historic State Park, as participants journey into the island’s past.
  • Feb. 7, 2018 – Feb. 10, 2018 
    Inaugural Mile 0 Fest Key West
    Mile 0 Fest Key West is a brand-new music festival assured to be a “must see” in the burgeoning Red Dirt & Americana music scene. Take in the big shows at Truman Waterfront Park Amphitheatre, a brand new state-of-the-art facility located blocks off the hopping streets of Duval, OR get into a stripped down acoustic set with your favorite band leader at one of the theatres or bars off Duval. Throw your hat into the ring for one of the charity golf outings or a fishing derby! These are just a few of the many activities and memorable experiences that await you at the inaugural Mile 0 Fest.
  • Feb. 10, 2018 
    RESCHEDULED: Fourth Annual Parade of Paws and Shopping Bazaar
    305-294-4857 
    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! Shopping Bazaar inside the dog park features entertainment, food vendors, a Kissing Booth, gifts for that special Valentine 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.
  • Feb. 14, 2018
    35th Annual Wesley House Valentine’s Day Gala
    Jeremy Wilkerson 305-809-5000 
    This signature fundraiser features some of Key West’s most talented performing artists, the island’s largest silent auction, open bar, dancing, and an elegant and abundant dinner buffet. Feel the Love in the Air! Located at Curry Mansion Inn, 511 Caroline Street 6:30-9:30 p.m. VIP tickets also available. Purchase tickets online.
  • Feb. 14, 2018 
    Champagne & Aphrodisiacs Valentine’s Day Sail
    646-772-4880
    Celebrate this Valentine’s Day with your special someone on our Champagne and Aphrodisiacs Pairing Sunset Sail in Key West. As you sail along the beautiful turquoise green waters on the Schooner America 2.0, you and your loved one(s) will be able to take in all the romance that this Key West Valentine’s Day Sunset Sail has to offer while being treated to a delicious pairing menu that is sure to entice, consisting of hors d’ oeuvres expertly paired with champagnes and sparkling wines from around the world! Join Schooner America 2.0 on a Key West Valentine’s Day Sunset Sail that is sure to tickle your taste buds and create memories to last a lifetime.
  • Feb. 16, 2018 – Feb. 17, 2018 
    58th Annual Key West House & Garden Tour
    305-294-9501 
    Tour a series of elegant and unique private homes of Key West, ranging from exquisite restorations to creative renovations, and interior design that complements each. February and March tours are offered 10 am to 4 pm each day. Transportation between homes is not provided. Tickets are $30 in advance and $35 on tour days. Proceeds benefit the foundation’s Oldest House Museum, grant and scholarship programs.
  • Feb. 17, 2018 – Feb. 18, 2018
    GardenFest: The Green Market Place
    305-296-1504
    A giant plant sale offers visitors the opportunity to peruse a wide array of native and exotic tropical plants, earth-based art and healthy living vendors. Enjoy a perfect day in the Garden where organic and healthy food vendors as well as a beer and wine bar will be available in the Courtyard along with the talents of local musicians. Open from 10 a.m. to 4 p.m. each day. Key West Tropical Forest and Botanical Garden is located at 5210 College Road.
  • Feb. 24, 2018 – Feb. 25, 2018
    53rd Annual Old Island Days Art Festival
    304-294-1243 
    The 53rd annual juried outdoor fine art festival features oil paintings, watercolors, sculpture, photography and other offerings by more than 100 artists from around the United States and beyond. The event takes place on lower Whitehead Street in historic Old Town.
  • Feb. 28, 2018 – Apr. 9, 2018
    Tennessee Williams Birthday Celebration
    Shawn Cowles 305.295.6616 ext 1
    A kickoff party is to be staged at the home of the Tennessee Williams Key West Exhibit founders Dennis Beaver and Bert Whitt Feb. 28, and the festival, a 6-week commemoration of the literary icon who lived on the island for thirty-four years, is to continue into April and boasts a full roster of writing and painting contests, film and poetry forums, curator tours of the Tennessee Williams Museum at 513 Truman Avenue, a March 26th birthday party for the playwright, and 2 one-act theatre productions of the Pulitzer-Prize-winner’s work. Presented by the newly-merged Tennessee Williams Key West Exhibit and the Key West Art & Historical Society.
  • Feb. 28, 2018 
    Sunset Green Event Lawn presents: Michael McDonald
    Tickets 410.268.4545 
    With a career that encompasses five Grammys, numerous chart successes and personal and professional accolades, as well as collaborations with some of the world’s most prominent artists, Michael McDonald remains an enduring force in popular music. Hailing from St. Louis, McDonald arrived in Los Angeles in the early 1970s, honing his talents as a studio musician before becoming an integral part of Steely Dan. In the mid-‘70s McDonald was invited to join the Doobie Brothers as the band redefined their sound with McDonald serving as singer, keyboardist and songwriter on such Top 40 singles as “Takin’ It To The Streets,” “It Keeps You Runnin’,” “Minute By Minute” and “What A Fool Believes.” Sunset Green Event Lawn is a brand new multipurpose event space located at The 24 North Hotel in Key West.

March 2018

  • Mar. 3, 2018 
    Conch Shell Blowing Contest
    305-294-9501
    An island tradition for over 50 years, this unique contest celebrates the historic importance of conch in the Keys and features contestants in several age categories attempting to make “music” with fluted conch shells. Contest located in the garden of the Oldest House, 322 Duval Street, free and open to all ages. Registration begins at 10 a.m., contest starts at noon.

  • Mar. 12, 2018 – Mar. 15, 2018 
    March Merkin Invitational Permit Tournament
    A charity flats-and-fly-only tournament with a twist – in addition to catch and release, anglers earn extra points for tagging their caught fish. Held at the Key West Yacht Harbor Marina on Stock Island.

  • Mar. 14, 2018
    Key West Theater presents: Mike Love
    305-985-0433 
    Meet Mike Love. No, not one of the Beach Boys! One of reggae music’s rising stars. Born and raised in Oahu, Hawaii to a musical family that spans generations, Mike Love brings a multitude of influences to the table, all tied together by the common goal of making the world a better place. Doors open 7 p.m., show starts 8 p.m.

  • Mar. 16, 2018 – Mar. 17, 2018 
    58th Annual Key West House & Garden Tours
    305-294-9501
    Tour a series of elegant and unique private homes of Key West, ranging from exquisite restorations to creative renovations, and interior design that complements each. February and March tours are offered 10 am to 4 pm each day. Transportation between homes is not provided. Tickets are $30 in advance and $35 on tour days. Proceeds benefit the foundation’s Oldest House Museum, grant and scholarship programs.

  • Mar. 28, 2018 
    Tennessee Williams Theater presents: Little River Band
    Bringing their vocal and musical energy along with some cool arrangements to their timeless classic hits, each show creates new memories for the audience. Through the ’70’s and ’80’s, LRB enjoyed huge chart success with multi-platinum albums and chart topping hits like: “Reminiscing,” “Cool Change,” “Lonesome Loser,” “The Night Owls,” “Take It Easy On Me,” “Help Is on Its Way,” “Happy Anniversary,” “We Two,” “Man On Your Mind,” “The Other Guy,” and “It’s A Long Way There.” Show starts 8 p.m., Tennessee Williams Theater located at 5901 College Road.