Every year, the City of Marathon adds to its collection of holiday light displays. Tight lines, Santa.
Every year, the City of Marathon adds to its collection of holiday light displays. Tight lines, Santa.

With an average year-round temperature that hovers near 80, Florida Keys residents have to invent ways to feel festive during the winter holiday season. Merrymakers who find themselves in South Florida in December can’t fall back on crispy air, crackling fireplace aromas, or fat wet snowflakes for atmosphere. We may wear sandals while the rest of the country is gripped by winter storms, but make no mistake — we work hard for our holiday cheer in this tropical climate. And we do just fine, thank you.


To accomplish peak Christmas, homes and businesses in the Middle Keys deck the halls – and some boat rigging – with plenty of lights. Here’s a rundown of the specifically “lit” events in the Middle Keys, plus some big ones that are “out of town,” and by that, we mean Key West or the Upper Keys.

Through Saturday, Dec. 7

  • The annual Zonta Festival of Trees is one of the best-loved events in the Middle Keys. Different groups and businesses decorate (creative!) trees and put them up for raffle. The trees are on display at the Florida Keys Country Club from 5 to 9 p.m. on Thursday and Friday, Dec. 5-6, and from noon to 4 p.m. on Saturday, Dec. 7. On Saturday night, it’s the big Zonta Gala (tickets are $70 each) and the tree winners will be revealed!

Friday, Dec. 6

  • In the mood to travel overseas? Head up to Islamorada’s15th annual Holiday Fest from 4 to 10 p.m. at Founders Park. It’s the event with the “snow” mountain and so much more.
  • The Marathon Lighted Bike Parade at 5 p.m. is a benefit for Wesley House Family Services. The event starts in front of Marathon airport terminal with cookies and Santa. The ride starts at 7 p.m. Parade-goers are encouraged to wear festive gear and be-deck the bikes with battery lights and more.
  • Indulge in some cupcakes and beer to benefit Florida Keys SPCA animal shelter from 5 to 7 p.m. at Shady Palm Art Gallery, Marathon.
  • Santa Claus visits Coldwell Banker Schmitt Real Estate starting at 5:30 p.m. Richard Smith is credited with the festive light design, and Mr. and Mrs. Claus will be on hand with welcoming laps and goodie bags for the children. Oh, and sample the free cookies!

Saturday, Dec. 7

  • The “Cookie Walk” is a choose-your-own bake sale from 9 a.m. to noon at the Marathon Moose Lodge.
  • Find some gifts and support the church’s good causes by visiting the Christmas Bazaar from 9 a.m. to 1 p.m. at St. Columba Church, Marathon.
  • The Key West Holiday Parade is a throw back to yesteryear — think cute kids in costumes and pretty floats. It starts at 7 p.m., and runs from Truman Avenue to Duval Street, Key West.
  • Take part in the 10th annual Light Up Key Largo from 5 to 9 p.m., with tree lighting at 8:30 p.m., at Murray Nelson Government Center, Key Largo.

Sunday, Dec. 8

  • This is another of the Middle Key’s best loved events: the Key Colony Beach Tucker DeGraw Memorial Boat Parade. It begins at dusk. The public is invited to view the spectacle from Sadowski Causeway as dozen(s) of lighted boats make more than one pass to awe the judges and win a cash prize.

Tuesday, Dec. 10

  • Lower Keys Community Choir and Keys Chamber Orchestra present “Shout the Good News” at 7:30 p.m. at Big Pine Methodist Church, Big Pine Key. The group will perform again on Wednesday, Dec. 11 at 7:30 p.m. at Venture Out on Cudjoe Key, and the final performance is set for Thursday, Dec. 12 at 7 p.m. at the San Pablo Catholic Church. The final performance will also include a reception, sponsored by the San Pablo Women’s Club.

Wednesday, Dec. 11

  • Expect a cuteness overload. The Florida Keys SPCA benefit offers pet photos with Santa in return for the community’s generous donations. Humans are invited to dress as well and pass through the offices of the Keys Animal Hospital from 4 to 7 p.m., collecting good karma and animal treats!

Thursday, Dec. 12

A grand re-opening of Sombrero Beach. Details to follow.

Friday, Dec. 13

  • Cookies with Santa from 4 to 6 p.m. at Keys Federal Credit Union, Marathon.
  • This is another crowd pleaser — throwing the gigantic “switch” at 5:30 p.m. at the Florida Keys Electric Cooperative headquarters in Marathon to reveal one of the most impressive holiday light display (naturally!) in the Middle Keys.

Saturday, Dec. 14

  • What are the holidays without some season-inspired music? Marathon Community Theatre is putting on two shows in one day — 5 and 8 p.m. — to get everyone in the spirit. The show is directed by Kara Pascucci. Tickets are a bargain at $5 each.
  • Check out the Boot Key Harbor Lighted Boat Parade at 6 p.m., Middle Keys. Choose one of the restaurants or gathering places that ring the harbor for a chance to see the boats!

Sunday, Dec. 15

  • Crane Point Museum hosts Winter Wonderland (with “reindeer ponies!”) from 4 to 8 p.m. at Crane Point Museum, Marathon. Organizers promise a chocolate fountain, hot chocolate, young dancers, Santa stew and much more.

Tuesday, Dec. 24

Santa Claus will be making the Middle Keys rounds. Details to be announced.

The keys get lit - A group of people playing instruments and performing on a stage - Trombone
The Horace O’Bryant Middle School Band performs holiday tunes for the tree-lighting crowd Monday evening.


Friday, Nov. 29 

MARC Christmas Tree Sale

9 a.m. to 7:45p.m. daily until sold out

Saturday, Nov. 30

Holiday Artisan Market for Small Business Saturday from 9 a.m. to 2 p.m. at The Studios of Key West

Sunday, Dec. 1

I Love Stock Island Holiday Lighting Ceremony, 5:30 p.m. at Fishbusterz Seafood Market

Sunday, Dec. 1

Christmas Community Chorus concert of Handel’s “Messiah” at 7 p.m., Key West United Methodist Church. Free admission.

Monday, Dec. 2

City of Key West Tree Lighting at 6 p.m., Bayview Park, Key West.

Tuesday, Dec. 3

Giving Tuesday: Packing of Family Holiday Hunger Packs, 5:30 p.m. at SOS Callahan Community Kitchen, Key West. We are creating custom hunger packs for children and families in Key West. The hunger packs will be distributed before Holiday Break to children who might otherwise be hungry for the week without provided school lunches.

Tuesday, Dec. 3

Peter Mayer’s Stars & Promises 20th Anniversary Christmas Tour, 8 p.m. at Key West Theater.

Wednesday, Dec. 4

Key West Lighted Bike Parade, 5 p.m. at Bayview Park. Bring a new unwrapped toy.

Friday, Dec. 6

Pet pictures with Santa, 6 p.m. at the ”Nautical Christmas Tree” on William Street, Key West. $20 cash donation benefits Boys and Girls Club.

Friday, Dec. 6

Self-guided Holiday Historic Inn Tour includes five properties.

Friday, Dec. 6

The Holiday-themed “1st Friday on Fleming” at 6 p.m. in the 500 block of Fleming Street, Key West. It’s a buy-local block party hosted by more than a dozen locally owned galleries, shops, bars and eateries.

Saturday, Dec. 7

Key West Hometown Holiday Parade, 7 p.m. at Bayview Park, heads down Truman Avenue to Duval Street.

Sunday, Dec. 8

3rd Annual Eaton Street Christmas Stroll, 4 p.m. at St. Paul’s Church, Key West. Stroll among five venues and hear a performance at each location, including a Keys Choral Arts holiday performance.

Wednesday, Dec. 11

A Peter White Christmas feat. Huge Groove, Vincent Ingall & Lindsey Webster, 8 p.m. at Key West Theater

Friday, Dec.13

Stock Island Lighted Boat Parade, 4-10 p.m. at Stock Island Marina Village.

Friday, Dec. 13

Self-guided Holiday Historic Inn Tours. Visit keywestinns.com.

Friday, Dec. 13

Bad Santa Photos, 8-11 p.m. at 22 & Co., Key West. Nice holiday pictures are taken at the mall, but the closest mall is 126 miles away. Why not be naughty this year and take your Bad Santa picture at 22&Co., courtesy of photographers Tom Flip Photo, Landon Bradbary and Theo Alexander? This is going to be fun. Adults only.

Saturday, Dec. 14

Parade of Paws & Holiday Bazaar, 10 a.m. to 2 p.m. at Higgs Beach, Key West.

Dog parade starts promptly at 10 a.m. (costumes encouraged0, followed by a Holiday Bazaar of local vendors.

Saturday, Dec. 14

Krampus Walk, 7:30 p.m. at 22 & Co., Key West.

Feeling more naughty than nice? Do you think that you deserve your proper punishment? Join a few Krampus as we make our way from 22&Co. down to Mary Ellen’s, finishing at the 2¢ Back Bar at General Horseplay.

Saturday, Dec. 14

29th Annual Schooner Wharf Lighted Boat Parade, 8 p.m at The Historic Seaport, Key West.

Saturday, Dec. 14

12th Annual Rudolph Red Nose Run 5k at 7 a.m., Southernmost Beach Café.

Sunday, Dec. 15

Key West Artisan Market: Holiday Shop Local, 10 a.m. at Higgs Beach, Key West.

Sunday, Dec. 15

Christmas on the Farm, 1-3 p.m. at Monroe County Sheriff’s Office Animal Farm & Petting Zoo, Collewge Road, Stock Island.

Tuesday, Dec. 17

Keys Choral Arts Concert, 7 p.m. at St. Paul’s Episcopal Church, Key West.

Wednesday, Dec. 18

Artisan Market, 10 a.m. to 2 p.m. at Higgs Beach, Key West.

Wednesday, Dec 18

KWAHS Holiday Concert & Bazaar, 5-9 p.m. at Custom House, Key West.

The popular celebration features local artisans, musicians and choirs, food and drinks, free admission to the museum and a holiday light show of magical vector projections on the face of the Custom House.

Thursday, Dec. 19

Christmas Concert, 7 p.m. at St. Paul’s Episcopal Church, Key West.

Dec. 19- 21

Sugar Rum Cherry: A Burlesque Nutcracker, 8 p.m. at Key West Theater.

A naughty and spirited two-act reverie, inspired by the famed Tchaikovsky holiday classical “The Nutcracker” ballet, is sure to bring laughter to Key West’s holiday festivities. Clara, a young ingénue, celebrates the season with one too many sugar rum cherry cocktails. That night she dreams of sword fights and sailors and a world unlike any other in the “Land of Libations.” The show stars Tatah DuJour, Moana Amour, Jenna Beth and Auroura Natrix.

 Sunday, Dec. 22

Lighting of the Menorah, 5 p.m. at Bayview Park, Key West. Join Rabbi Jacob Zucker and Hebrew School students from Chabad Key West for the lighting opf the menorah on the first night of Chanukah.

Sunday, Dec. 22

Christmas Rocks! 8 p.m. at Key West Theater. All ages welcome to this unique Christmas concert of classics and unexpected surprises. The Christmas Rocks! band is lead by Joe Tripp & Destiny Montgomery and includes your favorite local musicians.

Dec. 27 & 28

Old Island Restoration Foundation’s 60th Annual Key West Home Tours “Holiday Style,” 3-7 p.m.

Each tour features five lovely homes and gardens reflecting the varied tastes and originality of their owners.

The keys get lit - A group of people posing for the camera - Nativity scene


Friday, Dec. 6

With a mountain of snow, a holiday bazaar and a nighttime parade, the 15th annual Islamorada of Chamber of Commerce Holiday Festival is set to excite on Friday, Dec. 6, from 4 to 10 p.m. at Founders Park. Oh, and how can we forget the 35-foot high tree blowing magical snow through its branches.

Saturday, Dec. 7

 Culminating with the lighting of the 35-foot tree, the 10th annual Light Up Key Largo is set for Saturday, Dec. 7 at the Murray Nelson Government & Cultural Center. From 5 to 9 p.m., families and children will be immersed in scenes of the holidays. Kids can enjoy an ice skating rink, story time and crafts while parents shop at vendor tents. New this year is the wreath-decorating contest and trolley rides from Rowell’s Waterfront Park, where festival goers can park, to the Murray Nelson.

Sunday, Dec. 8 

For the seventh year, Bluewater in the Keys, MM 86.4, bayside, hosts “Rock n’ Roll Christmas & Live Nativity,” on Sunday, Dec. 8, from 5 to 6:30 p.m. It’s a night of family fun, live animals, craft making, photos with Santa, cookie decorating, music and re-enactment of the birth of Christ.

Friday, Dec. 13

Bikes decorated in lights will parade on Dec. 13 as part of the annual Cindy Claus Lighted Bike Parade. Held at The Catch, the route is longer this year as bikes will ride north from down U.S. 1 to Snapper Avenue, make a right to Blue Runner Street, another right onto Transylvania and back south to The Catch. Nineteen years ago, local Realtor Jane Wasmund contacted Cindy Smith, a postal worker, via the Key Largo Post Office and asked a question: “Who answers the Santa Mail?

The postmaster gave permission and these two ladies sought to answer local children’s Santa letters. For 20 years now, they have been granting actual wishes and helping families in need in the Upper Keys. With their contacts at day cares, schools, churches and other organizations, they have made holiday wishes come true for countless families.

Dec. 14-15

Bring your pup to Keys Kritters Pet Store, MM 100.5, on Saturday and Sunday, Dec. 14 and Dec. 15 from 11 a.m. to 4:30 p.m. for a picture with Santa during the annual Pets and Pina Coladas event. A $5 donation gets you a Keys style picture with Saint Nick, a goodies bag for your pet and a refreshing pina colada for you. The event benefits Coral Shores High School Marine Lab.

Saturday, Dec. 14

The annual U. S. Marine Corps Reserve Toys for Tots-sanctioned event, “Run for Fun,” a motorcycle poker run, is set for Dec. 14. The U.S. Marine Corp and sheriff’s-escorted parade leaves Gilbert’s Resort at 11 a.m. and will parade down U.S. 1 to Founders Park in Islamorada. A 5-ton USMC truck will be decorated with banners announcing and thanking supporters and acknowledging sponsors and displaying their logos. There will be additional antique military vehicles leading the parade of motorcycles and vintage cars.

At Founders Park, live music will feature Allan Truesdell’s Usual Suspects with a special appearance by Jimmy Hawkins, and the Taylor King Band. Participants in the poker run will draw their final cards. There will also be entertainment and activities for families and children, as well as food and beverage vendors. The winning hand will be determined at 3 p.m. There will be a cash prize for the winning hand. The event culminates with Pops in the Park by the Keys Community Concert Band from 4 to 5 p.m.

Sunday, Dec. 15 

Santa Claus and the carolers are coming to town again on Sunday, Dec. 15 thanks to the Islamorada Firefighters Benevolent Association and Islamorada Fire Rescue. The man with the big red bag, and singers, will begin the journey at 5:30 p.m. at the Islamorada Mobil in Lower Matecumbe, heading northward and making 20-plus stops that include Robbies, Moose Lodge, Southwinds Park, Venetian Shores , Founders Park, Plantation Yacht Harbor, Key Heights Drive, Indian Mound and Plantation Key Colony, among others.

Saturday, Dec. 21

Boats will shine yet again under the nighttime sky for the 2019 Key Largo Boat Parade on Saturday, Dec. 21 at 7:30 p.m. Sailboats to paddleboards will traverse the waters of Blackwater Sound to kick off the holidays. Boats will line up at Dusenbury Creek Green Marker 41 at 6:30 p.m., then head north along the shoreline to Stillwright Point at 7:30 p.m. The best public viewing locations for the parade are the Marriott Resort, Jimmy Johnson’s Big Chill, The Caribbean Club and Sundowners Restaurant.

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