Key West Christmas Season, 2023

Key West is already starting to get into the holiday spirit, with Christmas decorations littering the stores and holiday lights going up around the town. The Christmas season offers so many celebrations to enjoy here in Key West. Parades, holiday markets, concerts, food, and more! While the weather is warm and you won’t find any snow here, there is certainly no shortage of festivities to make your holiday bright!

Tree Trimmings & Lightings

November 22, 2023

• The Lighting of the 2023 Harbor Walk of Lights – Lights come on at 6:00pm, holiday music starts at 5:00pm. This year featuring a SPECIAL Holiday display as a heartfelt salute to Jimmy Buffett! LOCATION: The Harbor Walk plaza at Greene and Elizabeth St. for the best view. Enjoy creative holiday displays and thousands of lights honoring the “Maritime History of Key West”. The Key West “Harbor Walk of Lights” traditional main features will light up that night, including the 20’ Fishing Buoy Tree, a 16’ Nautical Christmas Treeand the original Key West Lobster Trap Tree. The official lighting is at 6pm, but at 5pm classic holiday music will start to fill the air. And for this SPECIAL year, Holiday music from Jimmy Buffett’s 2 Christmas albums will be mixed in with the traditional Christmas classics. Stroll along the water’s edge for a merry infusion of colorful lights and nautical holiday displays. See light sculptures of ship’s anchors, tropical birds, tropical fish, a flock of pink flamingos, jolly pelicans, merry manatees, animated sea turtles and dancing dolphins, and even a festive moray eel, all under brightly lit holiday palm trees! And with 3 blocks of sparkling holiday lights and displays around the Key West Bight Marina and Historic Seaport, the 2023 Key West “Harbor Walk of Lights” is destined to bring miles of holiday smiles to our One Human Family of visitors and locals alike.

November 27, 2023

• Tree Lighting at Bayview Park – Join us at 6:00 PM for this joyous annual tradition and bring the family because Santa arrives when the tree is lit!

November 29, 2023

• Lighting of the Tree Celebration at 24 North Hotel – Join us for a magical evening at our Lighting of the Tree Celebration on Wednesday, November 29th, from 5-8 PM!  Admission is FREE, so bring your friends and family for a festive night out.  Capture the holiday spirit with photos with Santa and indulge in delicious food and drink specials. Shopping for the holiday? We’ll have local vendors on site for you to find that perfect gift! Be sure to visit the build your own hot chocolate bar benefitting MARC House! Let’s come together as a community and kick off the holiday season with joy and laughter. 

December 3, 2023

• Schooner Wharf Bar 2023 Tree Trimming Party and Toy Drive – Starting at 6:00PM. LOCATION: Schooner Wharf Bar and Galley On the Harbor Walk of Lights at William St. Maritime merry makers will deck the halls and make dreams come true at the popular waterfront winter wonderland. Great PRIZES for the Best Handmade Ornaments that are: Most Original, Most Nautical, Most Popular with the holiday crowd. All tree trimmers will be treated to a free holiday cocktail — egg nog, hot apple jack or Swedish Glogg. Then step into Santa’s southernmost workshop at Schooner Wharf. Share the holiday spirit, as local artists and authors sign and sell ORIGINAL WORKS for HOLIDAY GIFT GIVING. Bring a donation for the “Cheryl Cates Memorial Toy Drive” by Angles Just 4 Kids! Each of Santa’s helpers who donates an unwrapped gift will also receive a free holiday drink from Schooner Wharf Bar. Some of our favorite local musicians will be playing Holiday Tunes, Reggae, and Calypso with the island sound of Steel Drums to round out the festivities.
• Santa, Sweets, and Holiday Tree Lighting at the Key West Woman’s Club – Celebrate the season with the Key West Woman’s Club and Mayor Teri Johnston at the beautiful historic Hellings Curry Museum at 319 Duval St. Enjoy appetizers, desserts, Amsterdam eggnog, and holiday music performed by the Bahama Village Children’s Choir and the Key West Community Orchestra. Donations of unwrapped, new clothing items for students K-12 are appreciated. More info. at 305-294-2039. 4:30 – 6:30pm.

December 7, 2023

• Sand Sculpture Christmas Tree Lighting – On the beach at The Reach Resort, 1435 Simonton Street, Key West. Christmas Carole Sing Along and Holiday Cheer. Bring an unwrapped toy to donate to The Boys & Girls Club of the Keys.

December 10, 2023

• Lighting of the Menorah – Join in the jousts tradition at Bayview Park, 5:00PM.

Parades

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December 1, 2023

• 3rd annual Holiday Village & BeLighted Bike Ride! – Holiday Village is a fun-filled, festive evening for all ages and the best way to kick off the Holiday season! This year, Holiday Village will feature two rides as well as two large holiday themed inflatable obstacle courses for the kids! Who knows, it may even snow here in Key West. The BeLighted Bike Ride will begin at 8pm starting at the Truman Coffee Butler Amphitheater and follow the same route as the Fantasy Fest Parade followed by the “best bike” contest. *Get your tickets here https://onecau.se/belighted2023

December 2, 2023

• March of the Penguins – Join your fellow penguins as we once again March through the streets of Key West to spread joy for the holiday season. 6:00pm at Bayview Park.
• Key West City Hometown Holiday Parade – Starts at 7:00pm. LOCATION: Parade starts on Truman Ave. (at White St.) then proceeds to Duval St., then down Duval St. ending at Eaton St. The most charming hometown parade you’ll ever see with holiday floats, and tons of kids (of all ages). Of course Santa will make a guest appearance!

December 9, 2023

• 32nd Annual Schooner Wharf Bar & Galley/Absolut Vodka Lighted Boat Parade – Maritime merriment will fill the harbor for the holidays, as the 32nd Annual Schooner Wharf Bar & Galley/Absolut Vodka Lighted Boat Parade sails past and brightens up the bight. Vessels of all shapes and sizes will dazzle the crowd and judges with their Christmas creativity and will be decked out in their holiday best, featuring thousands of lights. There are boatloads of prizes, every entry will receive a prize package! ENTER YOUR BOAT NOW! SAVE THE DATE TO VIEW PARADE FOR A NIGHT OF HOLIDAY MAGIC! Come down to the Historic Seaport and the Harbor Walk of Lights throughout the holiday season. The Lighted Boat Parade Festivities start at 6:00 pm, Parade at 8:00 on Saturday, December 9th at 8 pm. For more information or to enter your boat, call 305-292-9520, visit SchoonerWharf.com or KeyWestChristmas.org.

December 11, 2023

• Local Holiday Parade – Fire Rescue will parade through the streets of Stock Island & Key Haven, spreading Holiday cheer to the locals.

Holiday Crafts

November 28, 2023

• Shell Ornament Painting Class – Join Painting the Keys for a fun night of painting ornaments! Arana is a great teacher who will walk you through the steps to create each design. They are pre sketched designs and there are accessories you can add on as well. The ornaments are real sea shells and you get to paint two different ones. Sacred Space from 3:30-5:30 pm. $55 per person. Limited to 12 students. All supplies included. No artistic ability or experience necessary.

December 3, 2023

• Christmas Workshop – Indulge in the festive spirit at Four Flamingos – Hyatt Centric, where The Key West Candle Company and Nautical Creations come together for a unique holiday experience. Join us for an enchanting afternoon from 12pm-2pm on December 3rd as you craft your own Christmas magic – blend personalized holiday fragrances into a Christmas Tree Dough Bowl candle and master the art of creating a stunning Macramé Christmas Wreath. In just under 2 hours, you’ll leave with two handcrafted treasures to adorn your home. While crafting, enjoy the delightful offerings from Four Flamingos with drinks and food available for purchase, making it a truly joyous and aromatic affair. This ticket is only good for 1 person. Each participant will need a ticket. Seats limited up to 16. Parking is available in the lot directly next door to Hyatt Centric – (0 Simonton street, Key West). Workshop will be held inside the Four Flamingos Dinning room located inside the Hyatt Centric Property (601 Front Street, Key West). This workshop is suitable for ages 12 and up. No refunds will be honored but an exchange may be permitted for a later date.

December 5, 2023

• Watercolor Holiday Card Class – In this two hour class at Sacred Space, Arana from Painting the Keys will walk you through the steps to paint a set of four holiday cards. She is such a great teacher who will help anyone, at any skill level, have fun and create gorgeous cards to take home. You will leave the class with an original work of art made by you or we can have it shipped for an additional cost. Tuesday December 5th, 3-5 pm for $60 per person. Limited to 12 students. No artistic ability or experience necessary. All supplies included. *If you need to cancel, email us to do so 48 hours prior to the class for a full refund, less a $5 cancellation fee. As each class is limited to a small number of participants, cancellations within 48 hours are non-refundable. 

Shopping

December 2, 2023

• Church of God Christmas Craft Fair – Mark your calendars so you don’t miss our 4th annual Christmas Craft Fair. We will have local vendors with handmade crafts and delicious goodies. There will be a $5.00 Sloppy Joe or Hot Dog lunch as well as a silent auction. Also, Santa and Mrs. Claus will be there for photo opportunities for children of all ages. For more information, call 305-296-8844. 

December 8, 2023

• 7th Annual Holiday Concert & Bazaar at the Customs House – This festive free party features Key West’s finest artisans, musicians and choirs, food and libations, and a holiday light show designed by Key West High School’s Conch 5 Studios, which will be projected on the face of the Custom House.

December 10, 2023

• Key West Holiday Artisan Market – Shop for holiday treasures from local artisans while enjoying live music, tasty treats, fun drinks, activities for the kids – including a ‘snowman’ building contest and even a visit from old St. Nick. Southernmost Beach Resort, 1317 Duval St. 10am – 3pm.

December 15, 2023

• Holiday Open House – Join us for our first holiday season on Southard Street! With work by more than 30 local women, keep your holiday shopping in the community, celebrate the season with neighbors and enjoy after hours shopping. Come shop locally made art, gifts, jewelry, candles and more from 5-8 pm on Friday, December 15th. We have gifts in all price ranges, making it easy for your to shop for anyone on your list! Enjoy festive holiday snacks & drinks. Sacred Space Gallery is located at 529 Southard Street, across from Vignette, next to Sarabeth’s Restaurant.

December 16, 2023

• Deck the Halls with Art! – Finish Your Lists With An Extra Special Gift of ART. Enjoy Beautiful Artwork While Sipping Wine & Personally Meet The Artists of Guild Hall from 2 – 4pm! We Are All Passionate Local Artists That Love What We Do & Love Our Key West Community.

December 17, 2023

• Key West Holiday Artisan Market – Fine arts and crafts, jewelry, apparel, produce, delicious foods and more abound at this open-air bazaar. Higgs Beach / Wildlife Center, 1801 White Street. 10am – 2pm.

Pet Events

December 1, 2023

• 2023 Pet Pictures with Santa – Professional photos by Rob O’Neal. LOCATION: At the 16’ Nautical Christmas Tree on the Harbor Walk of Lights at William St. Santa pics with pets and kids big and small, treats for all! Pictures with Santa are $25 (cash only) to benefit our local Boys & Girls Club. Get professional furry family photos for that special holiday card this year, and also support the Kids in the lower Keys! 6 – 8pm.

December 9, 2023

• 10th Annual Parade of Paws – Our 10th annual Parade of Paws is here! Join us at Higgs Dog Park to celebrate all the dogs in our community! 10am until 2pm.
• Pet Pictures with the Grinch at the Hard Rock Cafe – Bring your critters for pet pictures with The Grinch. Proceeds benefit River’s Wish, Inc., a 501(c)(3) non-profit senior dog sanctuary. From Noon – 3pm.

Family Events

December 1, 2023

• Coke Florida Holiday Caravan 2023 – Bring your family out to enjoy festive activities and take photos with Santa! Wesley House Family Services Holiday Village at the Coffee Butler Amphitheater: 21 Quay Road, Key West, FL 33040. The Coke Florida Holiday Caravan Tour is a festive community engagement program activated annually in November and December at customer and partner locations across the state. The Holiday Caravan features the classic holiday-themed Coca-Cola truck on display, beverage sampling, and a special photo zone for families to take photos with Santa.

December 10, 2023

• Santa Claus Meet & Greet – Santa Claus is ditching the snow for sunshine and making his way down south! The Shops at Mallory Square is delighted to welcome the big man himself to our own backyard. Drop by with the entire family and have the little ones snap a picture with Jolly St. Nicholas. 
• Monroe Country Sheriff’s Christmas at the Farm – The Monroe County Sheriff’s Office invites everyone to come meet the animals during its annual Christmas on the Farm event. 5501 College Road, Stock Island. Donations welcomed! 1:00 – 3:00 pm.

December 15 – 30, 2023

• Winter Wonderland in Paradise! – This December, the Coffee Butler Amphitheater at the Truman Waterfront Park will transition into a Key West Winter Wonderland for an all ages, family friendly holiday experience. The transformation will include an ice skating rink, games, rides, attractions, music, light displays, and more. The amphitheater’s vendor village will offer a variety of food options and local artisans perfect for holiday shopping! The highlight of the event will be a custom ice skating rink, where both seasoned skaters and beginners can create lasting memories. Join us for themed skate nights, live music performances, and festive celebrations throughout the season. In addition to the ice rink, we will have thrilling rides like carousels, swings, and slides to keep the excitement going. Don’t miss out on the special holiday experiences, including photo opportunities and letters to Santa, crafts, and more. Rams Head Presents and We’ve Got The Keys are thrilled to bring this festive experience to our community and visitors, making the holiday season even more magical in the Keys. If you’re interested in becoming a sponsor or a vendor, please reach out to us at keywest@ramsheadgroup.com. Let’s create unforgettable memories together this holiday season!

December 16, 2023

• Come See Santa at Brady’s Pub – Jolly Old St. Nick will be meeting and greeting the kids and asking for their Christmas lists before heading back home to the North Pole to get ready for the big night! He will have toys for the kids too! Join Santa Claus from 2pm until 5pm! See you at Brady’s Pub located at 1900 Flagler Ave.

December 17, 2023

• Santa Claus Meet & Greet – Santa Claus is ditching the snow for sunshine and making his way down south! The Shops at Mallory Square is delighted to welcome the big man himself to our own backyard. Drop by with the entire family and have the little ones snap a picture with Jolly St. Nicholas. 
• Holiday Classic Car Show – from 11am – 3pm at the Conch Republic Seafood Company.

Holiday Tours

Select Nights from December 8 – 23, 2023

• Conch Tour Train Holiday Lights Tour – As one of Key West’s most long-standing and instantly recognizable attractions, this little-train-that-could has been delighting visitors to the Conch Republic since the 1950s! When the holidays come around, though, the holiday spirit becomes electric on the annual Holiday Lights Tour. Before boarding, indulge in some cookies and warm cider and don’t forget to study up on your caroling. Once the holiday cheer has been stoked, it’s time to light up the night as we cruise through Key West and marvel at the shimmering dance of color emanating from the thousands of lights adorning the light posts, businesses, and homes throughout the island. You’ll also receive a very special pair of glasses that enhances the light show to dazzling new levels!
• Old Town Trolley Holiday Lights Tour – Want to know the best way to see all the holiday lights across the island? It’s the Holiday Lights & Sights Tour presented by Old Town Trolley. Enjoy cookies, cider and a 60-minute Key West tour that is sure to put you in the holiday spirit. Check out the Sunset Celebration in Mallory Square, and then jump on the trolley at 6:00pm for the start of your tour.

December 8, 2023

• Holiday Inn Tour – Key West is known for its beautiful historic inns, and the Holiday Historic Inn Tour is the perfect way to visit these magnificent properties decorated for the season, featuring art, fine food from top local restaurants and holiday libations at each stop. Stops on the 2023 Holiday Historic Inn Tour: Night #1 – December 8: Key West Butterfly Conservatory, Wicker Guesthouse, The Mermaid & The Alligator, The Marquesa Hotel. Tickets can be purchased by calling 305-296-4959 or online https://www.etix.com/ticket/online/viewPerformanceGroup.jsp?group_id=1527 any day prior to the date of the tour.”

December 15, 2023

• Holiday Inn Tour – Key West is known for its beautiful historic inns, and the Holiday Historic Inn Tour is the perfect way to visit these magnificent properties decorated for the season, featuring art, fine food from top local restaurants and holiday libations at each stop. Stops on the 2023 Holiday Historic Inn Tour: Night #2 – December 15: Papa’s Pilar Distillery, Island City House, The Conch House Heritage Inn, The Lighthouse Inn. Tickets can be purchased by calling 305-296-4959 or online https://www.etix.com/ticket/online/viewPerformanceGroup.jsp?group_id=1527 any day prior to the date of the tour.”

Concerts & Theater Productions

December 3, 2023

• Messiah Concert at Key West Methodist Church – Join us for the Messiah concert at Key West Methodist church from 7 – 9pm. More info at: https://keywestumchurch.org/

December 20, 2023

• Peter Mayer: Stars & Promises Christmas Tour – at 8:00P. Questions? Please email boxoffice@thekeywesttheater.com – Peter Mayer is a guitarist, vocalist, songwriter, touring musician and recording artist in Nashville, Tennessee. With his unique writing style, distinctive voice and virtuoso musicianship, Mayer creates compelling and soulful music for an electrifying live performance. Mayer has released 25 albums to date and tours year round with the Peter Mayer Group. He is the lead guitarist in Jimmy Buffett’s Coral Reefer Band and has shared the stage with a regalia of bright lights in the music industry including: James Taylor, Paul McCartney, Ringo Starr, Don Henley, Dave Matthews, Joe Walsh, and many others.

December 23, 2023

• Holiday Rockabilly Christmas Concert with Jericho – Get into the holiday spirit at The Perry’s festive live on the lawn concert featuring Jericho! Join us for an enchanting evening filled with live music, seasonal tunes, and joyful celebrations. Bring your family and friends, grab your blankets or chairs, and immerse yourself in the magical ambiance of the season. Don’t miss out on this memorable holiday concert under the stars at The Perry!

December 24, 2023

• Holiday Jazz in the Garden – The Gardens Hotel at 526 Angela street welcomes holiday sprit seekers to enjoy festive outdoor jazz in its famous garden, with a full cash bar on site and a 20% Christmas discount on bottled wine and bubbly. More info at: https://www.gardenshotel.com/

Parties & Fundraisers

November 28, 2023

• The ReMARCable Christmas Tree & Wreath Auction – Join us on Giving Tuesday at the Opal Key Resort & Marina for a live auction of amazingly decorated Christmas Trees and Wreaths. Each Tree is more spectacular than the next! Our auctioneer is Local Celebrity DJ Sanaris Peacock. Support MARC and take the guesswork out of decorating your Christmas Tree! Tree Preview begins at 5:30PM. Live auction begins at 7PM. $20 suggested donation for bidding paddles. Light appetizers and Cash bar.

December 2, 2023

• Christmas Parade Party – Elevate your Key West Christmas Parade experience with our exclusive VIP balcony view at RockHouseLive! Enjoy the festivities from the best seat in the house while sipping on holiday cheer! Limited spots available—grab your VIP pass now! And don’t forget about our Terrace Party for an unforgettable holiday celebration From 6pm until 4am!

December 15, 2023

• Christmas Trivia @ Winslow’s Bungalows – Join us for a jolly evening of Christmas trivia at Winslow’s Bungalows! Test your knowledge of all things festive and have a holly jolly time with friends and family. Get into the holiday spirit as we challenge you with questions about Santa, carols, and holiday traditions. Located at the Kimpton Winslow’s Bungalows, this in-person event promises laughter, friendly competition, and a chance to win fabulous prizes. So put on your Santa hat and join us for a merry night of Christmas trivia! Ho ho ho!

December 17, 2023

• Gingerbread House Making Party + Fundraiser – Doors: 6:00pm; Event: 6:30pm-8:30pm; Award Ceremony: 8:30pm-9:00pm. Get Creative this Christmas & make a Gingerbread House (Estate, Bungalow, Shack, or Condo) for a great cause! Hosted by Amanda Anderson, Comedy Key West + One Love Food Truck. Your ticket includes ALL the materials for making a gingerbread house light tapas provided by One Love Food Truck. Beer/ Wine / CBD / Kava / Kratom / Sodas available for purchase. Christmas Costumes + Attire Encouraged!!! Dress up + Enter for a chance to WIN Best Costume Prize. Enter Your Completed Gingerbread House for the chance to win PRIZES! A portion of the proceeds will support charity. Your host + party coordinator Amanda Anderson will be facilitating the fun + creativity of building your dream gingerbread home. There is a 50 guest maximum. Please reserve your seats today! THIS EVENT WILL SELL OUT! Tickets purchased in advance will ensure that groups can sit together. Please let us know in advance if you will be joining another party. It’s a bar like environment + Tom Dustin will be telling jokes 18+. Tickets: $50 Per Person. https://www.comedykeywest.com/shows/241559

December 24, 2023

• Christmas Eve Party – Save the date! December 24th, the biggest Christmas Eve Party is happening at RockHouseLive Key West with DJ Louie M! Get ready for a night filled with incredible beats, holiday spirit, and non-stop fun!  Let’s make this holiday eve one to remember! See you there! Tickets are $10 at www.eventbrite.com.

Athletic Events

December 16, 2023

• 15th Annual Rudolph 5K – Don your festive holiday jammies and join in the 15th annual A Positive Step 5K, taking place Saturday morning, December 16, starting and ending at the Southernmost Beach Café,1405 Duval Street, Key West. Race day check-in starts at 7:00am with 8:00am start time. After the race, enjoy refreshments, prizes, and a fabulous silent auction. Pre-race packet pickup is Friday, Dec. 15 from 5:00-7:00pm at the Southernmost Beach Café. Runners and walkers of all ages and abilities are welcome to participate; registrants receive a free t-shirt. Presented by A Positive Step of Monroe County, a 501(c)(3) non-profit organization serving Monroe County’s highest risk kids and their families since 1999 and the Key West Southernmost Runners Club. Donations are tax deductible; proceeds benefit APSMC. Covid-19 safety protocols will be observed; prizes for most festive and unusual PJ’s. Race begins at Southernmost Beach Café, right on South Street, to Casa Marina, past Higgs Beach and White Street Pier to a turnaround point and back. All Miles will be marked.

Holiday Eats

December 10, 2023

• The Side Bar Cookie Swap – Bring 2 dozen cookies of any style cookie you would like. Print out the recipe “ IF YOU WISH” to share if not- ( AT LEAST THE INGREDIENTS) Know the name of your cookie. What you bring your can take home- two tupperwares- one to display “your baked/bought” cookies and one to put your “take home” cookies into. We will have specialty Christmas cocktails, Christmas movies on the screen and onsies/ Christmas pajamas on for comfort. Come and join in the fun. Invite your friends, the venue is always cold so we will have our winter!

December 24, 2023

• 4th Annual Cookie Throw Down! – Break out your best cookie recipe and submit your creation to the 4th annual Holiday Cookie Throw-down at the Marker Resort!! December 24th at 12pm. Resort guests will be your judges! Prizes will be awarded! You must RSVP by Dec 20th to: Amy Andrade aandrade2010@live.com

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, www.gotothekeys.com 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