Christmas Season Key West, 2021

Christmas season is here and Key West knows how to celebrate! Starting just after Thanksgiving, expect to see decorations starting to pop. However, there is so much more than just lights to enjoy on our island! Specifically, check out the myriad of holiday entertainment and events below!

Tree Lightings, Menorah Lightings

Tree lightings often signal the beginning of the Christmas season. And while you may miss the actual lighting ceremonies, you can still enjoy the beauty of the lights throughout the entire month of December.

  • November 29, 2021 – The annual City of Key West tree lighting ceremony will be held from 6 to 8pm in Bayview Park.
  • December 3, 2021The Casa Marina Resort will be hosting a sand sculpture tree lighting at 6pm. Donations of unwrapped toys for the Boys and Girls Club will be accepted at the Casa Marina through December 2nd, and will be presented at the the lighting.
  • December 5, 2021Tree Trimming Party at the Schooner Wharf, 6pm.


Parades are something that Key West loves to put on! Moreover, for the holiday season you should expect parades on land and on sea. Surely, these events are sure to put a smile on any grinch’s face!

  • December 4, 2021 – The City of Key West’s annual Holiday Parade kicks off from Bayview Park at 7pm. What fun it is to watch a holiday parade, catching candy thrown from the floats, and sing holiday songs.
  • December 11, 2021 – Our annual lighted boat parade starts off from the Key West Bight. See holiday lights reflected off of the shimmering waters of Key West!


Shopping is a key activity when it comes to the holidays. Whether you want to pick up some island holiday decor to bring back home with you, or gifts to place under the tree, you can find it in Key West. For example, you can enjoy one of the special holiday bazaars. Or, you can visit one of the many local shops selling artisan wares with island vibes.

  • November 26, 2021 until everything is sold out – The MARC House Christmas tree sale is a great place to pick up decorations and support a great local cause!
  • December 10, 2021Custom House Holiday Concert & Bazaar will be held from 5pm until 9pm. Admission is free!
  • December 19, 2021The Key West Artisan Market will be held from 10 am to 2 pm at the Key West Wildlife Center and Higgs Beach. Keys-made items perfect for gift giving will stock the show. In addition, Santa is making an appearance! First, explore the curated outdoor market offering fine crafts, art and jewelry as well as a full bar and a variety of food choices. Then, buy and support the local artists. Plus, entry is free, as is parking. Please BYOB (bring your own bags).

Pet Events

Pet events are big in Key West. We love our furry family members. And, they are welcome at many businesses on the island. To that end, why not let them join in the family fun?

  • December 3, 2021Pet Pictures with Santa from 6 – 8pm. Of course, with dogs dressed up in their finery, this may be the cutest event of the year!
  • December 11, 2021Parade of Paws and Holiday Bazaar is fun for the entire family. From 10am until 2pm at the Higgs Beach Dog Park, enjoy shopping, pet parade, live music, smooch a pooch photo booth, and photos with Santa. And who does not love seeing dogs all dressed up and on parade!?
  • December 17, 2021 – And if happy hour is more your thing, bring your best buddy to the Gates Hotel from 5 to 8pm for the holiday Yappy Hour!

Family Events / Meet Santa

Family events like meeting Santa Claus really add to the holiday feel. Truly, no Christmas should go by without at least one sighting of Santa! Below, you can find out when and where to plan a special Santa visit!

  • December 1 – 24, 2021 – Drop off your letters to Santa in the mailbox in the lobby of the Reach Resort. In fact, they go directly to the North Pole!
  • December 3 & 4, 2021 – Meet Santa at the Key West Butterfly and Nature Conservatory.

Holiday Tours

Holiday Tours are a great way to see a few of the many sights the island of Key West has to offer. And, with things decorated for the holidays there is no better time to check things out! With that, find some great tour options below.

  • December 12 – 17, 20 – 23, 26, 2021Old Town Trolley Holiday Lights Tour offered at 6:30pm and 8pm. So, call 305-296-6688 for more information and reservations.
  • December 10 & 17, 2021Holiday Historic Inn Tour. Ever wondered what some of the historic old Inns looked like before deciding to stay there? Well, this is your prefect opportunity! 3 – 8pm. For tickets, call 305-296-4959.

Concerts / Musical Events

Concert and other musical events during the holidays can be so much fun and really bring out the spirit. Although you may not be coming to Key West specifically for a concert, why not check one out while you are here?

  • December 5, 12, 19, 24, 25, 26, 2021The Gardens Hotel located at 526 Angela Street is hosting Jazz in the Garden every Sunday from 5 to 7:30pm.
  • December 24, 2021 – January 1, 2022Sun Sun Concert Pier will be hosting live music every evening from 6pm until 9pm.

Plays / Theater

Plays and theater productions are very entertaining. Even though we don’t have the Rockets here in Key West, we might have something better! For instance, you can only find he truly wacky and weird where the weird go pro! Below are a couple of options. And if they do not appeal to you, surely a holiday themed drag show will!

  • December 14, 2021 A John Waters Christmas at the Key West Theater – 8pm.
  • December 15 – 17, 2021 Sugar Rum Cherry: A Burlesque Nutcracker at the Key West Theater – 8pm.

Athletic Events

Key West always seems to be having some sort of race, whether on bike, on foot, or on water. So, why would holiday times be any different? Afterwards, you can cool down with a drink from one of the many different watering holes here in Key West!

  • December 18, 202113th Annual 5K Rudolph Red Nose Run – for more information visit

Holiday Meals

For me, a foodie at heart, meals are an important part of the holidays. So, when I am going someplace new, I want to know where the best places to eat are. Below, find a listing of restaurants offering Christmas specials (list will be updated throughout the month). In addition, check out my restaurant reviews as most eateries stay open through the holidays. Restaurants do sell out for special nights like Christmas. Therefore, I highly recommend making reservations this time of year well in advance.


Four Marlins at the Reach Resort – Enjoy a Holiday themed brunch on December 19th and December 26th from 11:30am until 3pm. Reservations are recommended.

Christmas Eve

Four Marlins at the Reach Resort – Enjoy a special pre-Christmas dinner offered from 5:30 to 9:30pm. Reservations recommended.

Noche Buena at the Oldest House & Gardens – 5 – 8pm. Tickets necessary; therefore, please contact the Oldest House and Gardens for more details and reservations.

Sun Sun Beach Bar and Grill – Enjoy a special pre-Christmas dinner offered from 5:30 to 9:30pm. Reservations recommended.

Christmas Day

Casa Marina Resort – From 7am until 11am, enjoy a Christmas Day breakfast buffet or a la carte dining on the Flagler Patio, followed by a Christmas Day lunch and dinner buffet from Noon to 8pm. Afternoon buffet will include soup, salad, seafood, carving table, and holiday desserts all enjoyed to live music. Cost is $95 per adult and $29 per child.

Four Marlins at the Reach Resort – Enjoy a special Christmas dinner, served from 5:30 to 9:30pm. Reservations recommended.

Matt’s Stock Island Kitchen & Bar – Located at the Perry Hotel & Marina. Make reservations on RESY.

Sun Sun Beach Bar and Grill – From 4pm to 9pm, enjoy a signature toes in the sand experience and chef’s three course menu for $150 plus tax and tip per person. Reservations Required.

Yellowfin Bar at Ocean’s Edge Resort – Enjoy a three course meal for $99 per person. Of course, reservations are recommended.

More About Key West

Do you want to know more about our island? Visit all the different sections of this blog. Additionally, you can check out our sister site, for lots of information on other Key West activities, not Christmas related!

In closing, I hope you have a great Holiday!

Island Genn – Key West Concierge

About the author: Island Genn

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