Christmas to New Years in the Florida Keys


This week we look at the calendar of events which the Key West Travel Guide and has. They say that have the most complete guide which you can find.

Key West 2018/2019 Event Calendar

December 15, 2018 to January  2019


  • December 25, 2018 – HOLIDAYChristmas in Key West 2018 – Whatever gift you wish for, spending Christmas in Key West might be at the top of the list. While it never snows, and sometimes a palm tree is substituted for a traditional tree, there still is plenty of Christmas spirit in Key West. Look for historic homes that have added twinkle and magic with lights and displays. And to all a good night!

  • December 29, 2018 – MUSIC – JJ Grey and Mofro Concert – Outdoor concert by the Southern soul-rock band, at the new Sunset Green lawn venue, a part of The Gates Hotel property. 8pm, 3820 N Roosevelt Blvd.  Tickets cost $62.50 + tax & service fee.   For more information and tickets, visit
  • December 31, 2018 – CELEBRATIONKey West New Year’s Eve – Celebrations include the lowering of the Conch Shell over Sloppy Joe’s on lower Duval Street, the lowering of famous Key West drag queen Sushi (riding a huge high-heeled shoe) over the Bourbon Street Complex on upper Duval Street, the lowering of a Key Lime wedge on the Sunset Pier (0 Duval Street), and the lowering of the “pirate wench” from the mast of a schooner in the Historic Seaport.

Key West 2019 Event Calendar

January 2019 Key West Events

  • January 5, 2019 – SPORTSPole 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)
  • December 14 – January 6  Key West  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.”


  • January 1 – Nov 10  Key West 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. 5 – 7 Key Largo Key Largo Sailfish Challenge  Held at the height of the sailfish season, this event follows a boat-tournament format. Prizes and trophies await first, second and third place teams, and proceeds benefit the Coral Shores High School Band program. Up to six anglers can form a team to fish the challenge.


  • January 8 Key West Key West Theater presents: The Zombies Now in their 54th year and cited as being one of the most influential UK pop/rock bands of all time, a mid-’60s rock group who wrote gorgeous melodies. Dominated by Colin Blunstone’s breathy vocals, choral backup harmonies, and Rod Argent’s shining jazz- and classical-influenced organ and piano, the band sounded utterly unique for their era. To this day, they’re known primarily for their three big hit singles, “She’s Not There”, “Tell Her No”, and “Time of the Season”, however they have released multiple albums in recent years, both in the studio and live. Show starts 8 p.m.

  •  January 11 – 14  Key West  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. 12 – 14   Islamorada  Sixth Annual Baygrass Bluegrass Festival  Featuring several great Oldgrass, Newgrass and a blend of next generation Bluegrass as well as some tasteful variations of the genre.  Tickets to be available in advance online and at the gate. Monies raised help fund music, dance and art scholarships for local students.  Main event is located at the ICE Amphitheater, MM 87 bayside at Founders Park.  Other weekend musical activities are to be planned.   Attendees can bring blankets and lawn chairs, but coolers are not permitted.  Food and beverages available for purchase.


  • January 13 – 14 Key West 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


  • January 10 – 13, 2019 – LITERARY37th 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. More informationis available at or by calling 305-293-9291.



Stay With US

Whether you contemplate visiting the Keys for vacation or some of the many fishing and cultural activities going on all year around-Anytime  you are in the Keys: Winter, Spring, Summer or Fall……  STAY WITH    KeysCaribbean Luxury Resort Villas & Marinas IN OUR AMAZING PROPERTIES THROUGHOUT THE KEYS-

You will be glad you did…

In The Upper Keys:

In Key Largo and Islamorada, where KeysCaribbean Luxury Resort Villas and Marinas has the exclusive location -Mariners Resort Villas & Marinas

In The Middle Keys: 

In the Middle Keys, KeysCaribbean Luxury Resort Villas and Marinas has the Village at Hawks Cay Villas on Duck Key, Indigo Reef Resort Villas & Marina and the Coral Lagoon Resort Villas & Marina vacation rentals in Marathon

In The Lower Keys: 

In the Lower Keys, KeysCaribbean Luxury Resort Villas and Marinas has the Coral Hammock Resort Villas and Kings Point Marina & Condominiums vacation rentals

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