December is upon us, and while the stores have already been bombarding us with Christmas items for over a month now, this is the time we start to think about the holidays here in Key West. While the island stays warm, the holiday cheer will certainly have you in the Christmas spirit.
Tree Trimmings & Lightings
Signaling the beginning of the holiday season, these lighting ceremonies are beautiful, but so are the lights that we get to view with such please all season long!
11/23/22 – 12/31/22 – Key West Harbor Walk of Lights: check out the Historic Seaport lit up in all of its holiday glory!
11/25/22 – 12/24/22 – MARC Hour Annual Christmas Tree Lot: 1401 Seminary Street. Visit the Plant Store and pick up a Christmas tree, wreath, poinsettias, or ornaments to help decorate.
11/28/22 – City of Key West Tree Lighting: at 5:30pm at Bayview Park.
11/30/22 – Lighting of the Tree Celebration: Join Santa and us in celebrating our lighting of the tree together. There will be lots of yummy food, drinks and of course photos with Santa await. Save the date November 30, 2022 from 5PM to 8PM. Find us at Sunset Green Event Lawn at the Keys Collection on Roosevelt Blvd.
12/4/22 – Schooner Wharf Annual Tree Trimming Party: Schooner Wharf Bar Tree Trimming Party is Sunday, Dec. 4, 2022 starting at 6PM. We are looking forward to warm season’s greetings and plenty of holiday “spirits” at our annual Tree Trimming Party and Toy Drive. Ornaments will be entered in a contest and prizes will be awarded for the Most Original, Most Nautical and 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. We also host a Toy Drive on Tree Trimming Day, benefiting Angels Just for Kids to benefit Gerald Adams Elementary. Each of Santa’s helpers who donates an unwrapped gift to one (or all!) of these worthwhile causes will also receive a free holiday drink from Schooner Wharf Bar.Favorite local musicians, The Snow Globes with Ross Brown will be playing holiday tunes, reggae, classic and current favorites with the steel pan sound of the islands to round out the festivities.Come make our tree yours! Happy Holidays from the crew of Schooner Wharf Bar and Galley!
12/18/22 – Lighting of the Menorah: 5pm at Bayview Park.
We love our parades here in Key West! And here, we can enjoy them on both land and sea!
12/3/22 – Key West Holiday Parade: The amazing Key West Holiday Parade is Saturday December 3, 2022 at 7PM. This year has the most floats ever registered and last year there were over 60! The parade route starts at Bayview Park and then goes down Truman Ave. to Duval and then all the way down Duval Street to Greene. So festivi!!!
12/10/22 – Key West Lighted Boat Parade: This annual affair combines with the Harbor Walk of Lights to celebrate the Christmas Holiday. Each year a variety of boats decorate their sails, masts and hulls with Christmas lights. The official judge’s stand located at the Schooner Wharf Bar, judges this serious competition for the Best Nautical Holiday Decorations in Key West. 2022 will mark the 31st annual Key West Lighted Boat Parade. The lighted boat parade travels through the Key West Bight. Saturday, December 10, 2022 from 7:30 – 9:30 PM.
We all need to shop for the holidays. Whether it is big pr small, you can find an amazing gift at one of the local shops or bazaars. And, you’ll be sure to make someone very happy with a gift from Key West.
12/3/22 – Key West Church of God 3rd Annual Christmas Craft Fair: The craft fair will be held on December 3, 2022 from 9AM – 3PM. There will be Handmade Crafts, Local Artists, Homemade Jellies and Goodies, Silent Auction and more. There will be a $5 luncheon as well as a bake sale. SPECIAL GUEST, SANTA CLAUS! Save the date on your calendar and don’t miss the fun! All proceeds go to the Church Restoration Project. Located at 1419 White Street.
12/9/22 – Mingle & Jingle at the Shops at Mallory: Sip, shop, and stroll the stores, studios and galleries inside the historic Shops at Mallory (formerly Coast Guard Building/Clinton Square Market Mall, next to The Custom House). Shop the holidays and everyday from your neighbors — the small businesses of the Key West community appreciate you and welcome you to come mingle and get to know them. LOCATION: 291 Front Street, Key West. There are two entrances: off Front Street Custom House Holiday Bazaar and next to the Aquarium entrance (brick road where the trolley & trains pick up). Take a break from hustle & bustle outside, THE SHOPS AT MALLORY has benches for relaxing, air conditioning, public restrooms, shops, galleries, coffee, ice cream and more! Friday, December 9, 2022 from 4PM – 9PM.
12/11/22 – Holiday Sip & Shop at the Perry Hotel: Please join us for our annual Holiday Sip & Shop on Sunday, December 11, 2022 from NOON to 4PM. Wrap up your holiday shopping list with hand-crafted goods from local artists and vendors.
12/18/22 – ZEN Jewelry Pop-up at the Perry, Holiday Edition: learn a few tips & tricks from Karen for gifting and wearing jewelry with confidence and ease. Karen will have all her best selling jewelry on hand for your shopping pleasures! Bonus: all jewelry comes in a custom jewelry pouch with gem meanings, perfect for gifting. Additional holiday wrapping is available for all jewelry purchases! Sunday, December 18, 2022 from 10AM until 4PM.
12/18/22 – Key West Artisan Market Holiday Shop Local: December 18, 2022 from 10AM to 2PM at Indigenous Park/The Key West Wildlife Center located at Higgs Beach. The show will be stocked with keys-made items perfect for gift giving this holiday season. Enjoy bloody’s, mimosas along with a full bar from Great Events Catering, coffee, smoothies, natural juices and cut fruit, multiple food trucks and stalls offering eat-here or take-away for snacking or a delicious meal. Shop a curated outdoor market offering fine crafts, art and jewelry from talented Florida Keys makers. Stock your pantry and fridge with fresh produce, artisan cheeses, local seafood, honey, pickles and so much more. Listen to awesome local musicians doing your favorite Christmas standards, get an autographed novel from local talented writers and support our featured charity.AND…Santa Qlaus will be onsite starting at noon for free pictures with anyone who wants one!The market is conveniently located close to the Higgs Beach Dog Park, free West Martello Tower botanical gardens, White Street Pier and of course, the alluring Atlantic ocean across the street at Higgs Beach. Open 10 am to 2 pm every other Sunday in season, by locals, for locals. Free entry, free parking. Please BYOB (bring your own bags) #WhereTheLocalsMeet#SeeAndBeSeen#KWAM#ShopLocal
We all love our furry family members, and we know how to celebrate them here in Key West! So whether you are traveling with yours or you just miss them and want to get some doggie time in, here is your chance!
12/3/22 – Holiday Pet Pictures at Hank’s Saloon: Help raise funds for River’s wish senior dog sanctuary run by our beloved Jeanne Selander of Key West. Come say Hi to the fabulous and funny Q. Enjoy our silent auction, cocktails, mocktails and great food from Garbo’s Grill! first 40 attendees get a free doggie gift bag. All proceeds go to River’s wish nonprofit. Let’s help these sweet senior dogs while you get a festive picture with the grinch for your pet. Saturday, December 3, 2022 AT 11AM.
12/3/22 – Pet Pictures with the Grinch: 409 Caroline Street from 11am until 2pm.
12/4/22 – Pet Pictures with Santa: from 6 – 10pm at the foot of William Street at the Key West Bight.
12/10/22 – 9th Annual Parade of Paws: Join us for this family & dog friendly event. There will be a dog parade starting promptly at 10am where all in the community are welcome to parade their pups (costumes encouraged!) followed by a Holiday Bazaar where local vendors will showcase their businesses. This is the perfect place to get some last minute holiday shopping done! We will also be crowning our King, Queen & Royal Court for those that raised the most money over the next couple months leading up to this event! Santa will be there for pictures with the whole family, even our four legged friends! There will be live music, food and tons of fun! Interested in your animal being the next King, Queen, Prince, Princess, Duke or Duchess of Parade of Paws? Follow the link below, become a fundraiser by creating your pet’s own unique page and start raising funds to benefit the animals of the FKSPCA! You can promote your page on social media, email it out, or collect cash donations to bring in the day of the event. There will be amazing prizes for the top earners including a grand prize!Click this link to sign your pet up today! https://www.justgiving.com/campaign/paradeofpaws9 Interested in being a vendor or sponsor? We have 30 spots for local vendors to sell their goods to a crowd of 200 attendees and as a sponsor you would be supporting the homeless animals of the lower keys. For more information and applications please contact Tiffany at email@example.com or at (305) 294-4857 or go to https://fkspca.org/event/9th-annual-parade-of-paws/. Saturday, December 10, 2022 from 10AM until 2PM at the Higgs Beach Dog Park.
Let’s be real. We all love the holidays, but none more than the kids. So, here are some family friendly events that the kids will love. They can even meet Santa! He is making his rounds here in Key West this month!
12/2/22 – Holiday Village and BeLighted Bike Ride: This premiere family-friendly event kicks off the Holiday Season in Key West. The fun begins at 4 pm on Friday, December 2, 2022 at the Coffee Butler Amphitheater in Truman Waterfront Park. The Holiday Village runs from 4 – 8 pm and the BeLighted Bike Ride leaves from the Amphitheater at 8 pm. The Holiday Village is the family-friendly pre-party to the bike ride, featuring over 20 community booths offering games, goodies, and crafts for the kids, bounce houses, DJ, food trucks, and photos with Santa! Enter the “best bike” contest at 7 and then cruise Duval St. at 8 pm on your ultra-lighted bike! Costumes are encouraged! Please reserve your tickets by clicking the link: www.wesleyhouse.org/belighted2022. You must acknowledge the waiver to purchase a ticket. Adults: $15, Kids, ages 4 – 17: $10, Ages 0 – 3: FREE, Bike Contest Entry with Ticket: $30.
12/3/22 – March of the Penguins: Grab your penguin onesie and join us and our festive flock as we waddle and frolic along the City of Key West Holiday Parade! All you need is a penguin costume of any type and candy for the kids along the route. Meet at Bayview Park by 6:15PM on December 3, 2022.
12/3/22 – Cookies with Santa: Keys Federal Credit Union and Publix invite you to have “Cookies with Santa” on Saturday, December 3, 2022 from 12:00pm to 2:00pm at the Key Plaza branch located at 3022 N. Roosevelt Blvd., Key West. Take a selfie with Santa, eat delicious Publix cookies, meet Plato the Publixaurus and take home fun goodies. For details call 305-294-6622 or go to KeysFCU.org.
12/3/22 – Meet Santa! – From 3PM – 8PM on Saturday, December 3, 2022 at the Key West Butterfly and Nature Conservancy. Free photos and goodies bags! Extended shopping hours!
12/4/22 – Eaton Street Christmas Stroll – Williams Hall is once again proud to join our neighbors as a stop on the 2022 Eaton Street Christmas Stroll! This free, family-friendly event begins on Sunday, December 4, 2022 at 4PM at St Paul’s Episcopal Church, where Keys Choral Arts presents a short program of music for the season. Continue strolling to Old Stone First United Methodist Church for Christmas music at 5:15PM, with voice, instruments, piano & organ. In between, make your way to: The Tropic Cinema for a classic Christmas short film and some fresh-popped popcorn, Studios of Key West, featuring the annual artists’ winter show, and a full bar plus the Mistletoe Holiday Berry Cocktail special at Hugh’s View on the roof. Williams Hall, for a tour of the renovated space, live music by Mateo Jampol & holiday snacks and drinks. Salt Gallery, to shop fine arts and crafts from local artists and artisans. Admission is free and we recommend grabbing tickets at the Tropic Cinema Box Office or online to guarantee seating. The Eaton Street Christmas Stroll is a gift to the community from your arts organizations in Key West—enjoy!
12/10/22 & 12/16/22 – Visit Santa at the North Pole: The Southernmost North Pole located upstairs at the historic Shops at Mallory Square. From NOON until 2PM.
12/11/22 – Christmas on the Farm: Meet Santa and every child will receive a gift, craft table, live local musicians, and visit the animals. It’s FREE and donations are always appreciated! (Please note that this will be the ONLY open house for the month of December.) Sunday, December 11, 2022 from 1PM – 3PM.
12/17 & 12/24 – Winter Party on Blue Mojito Beach: 100% snow on the beach with a snow machine, Santa appearance, live DJ, food and dink specials, and a raffle benefitting Reef Relief.
12/18/22 – Holiday Classic Car Show: 11am to 3pm at the Conch Republic Seafood Company Parking Lot.
Tours are a great way to see the lights that the different residents and Inns put up to show their holiday spirit.
Various Dates 12/8/22 – 12/23/22 – Old Town Trolley Holiday Lights Tour: offered at 6:30pm and 8pm. So, call 305-296-6688 for more information and reservations.
Various Date 12/8/22 – 12/23/22 – Conch Tour Train: Holiday sights and festive nights tour. www.conchtourtrain.com/key-west-holidya-events.html.
12/9/22 & 12/16/22 – Holiday Historic Inn Tours: Explore different properties and enjoy food, beverages and entertainment as well on this fun holiday tour! Call 305-296-4959 for information and tickets.
12/12/22 – Reef Relief Holiday Lights Train Tour: Join us for a ride on the Conch Tour Train enjoying the holiday lights around town! Tickets are $30.00 per person, all proceeds benefit Reef Relief. You must pay to participate! Check in to receive your wristband will begin December 12, 2022 at 7:00 at Reef Relief. The train will leave promptly at 8:00 PM and will be around an hour long.Pick up and drop off will be at 631 Greene Street. TICKETS ARE NON REFUNDABLE but may be transferable if you let reef relief staff know.
12/22/22 – Tutu Bad Santa Trolley Tour: A Very Tutu Christmas just added your new favorite event! Bad Santa Trolley tour with Landon Bradbury – sponsored by Seedlip! Get your tickets now! There are only 30 spots! $50 includes trolley light tour, custom 22&Co Christmas Cup – with your name on it, holiday shot, and pictures with Bad Santa! (Must be ordered by December 1st) $25 includes trolley light tour, holiday shot, and pictures with Bad Santa! Meet at 22&Co at 7PM – trolley leaves at 8PM! December 22, 2022. Get tickets at www.eventbrite.com/e/tutu-christmas-trolley-tickets-456471046187
Concerts and Theater Productions
These concerts and plays can be entertaining and really bring out the holiday spirit.
11/27/22 – Messiah Concert: 7PM at the Key West United Methodist Church.
12/7/22 to 12/11/22 – Nutcracker Key West: Produced bi-annually, this is the largest community production brought to the stage in Key West. This year, 60 of our community’s children and adults and 15 professional dancers from around the world will join together again for to produce this outstanding historical recreation of Key West’s version of the Nutcracker, Nutcracker Key West.This special holiday tradition lives in the hearts and memories of all that participate, view, and give to this amazing show. Nutcracker Key West is dazzling and unique with her tiny chickens, humorous roosters, lively shrimp, and brilliant jewels of the Atocha. Shows December 7 – 11 at the Tennessee Williams Theater. Tickets are a must! www.etix.com/ticket/online/viewPerformanceGroup.jsp
12/8/22 – Scary Ghost Stories – A History of the Holiday’s Spooky Tradition with Aaron Sagers: Former Artist in Residence, Travel Channel/Discovery+ host, host of Netflix’s “28 Days Haunted,” and paranormal historian and journalist Aaron Sagers explores the spookier side of the season. Long before Ebenezer Scrooge changed his ways on the holiday in 1843 — and 143 years before Andy Williams first sang about the most wonderful time of the year — Christmas had already been established as the season for telling scary ghost stories. Even before it was “Christmas,” it was midwinter, solstice, Saturnalia, Sol Invictus, and Yule. It was the longest night of the year in the Northern Hemisphere. It represented death, and rebirth, and was a time when the veil between worlds was thin. And it is also a time of monsters, witches, goblins, and one horned Anti-Claus. Sorry Halloween, Christmas is THE season for spooky greetings.An award-winning media personality and travel expert, Aaron Sagers is a TV & on-camera host, producer, journalist, and author on a lifelong mission to make cross-cultural connections across the globe. Sagers is best known for his expertise as a Paranormal Journalist, Paranormal Pop Culture historian, and “nerd culture” expert. Helmerich Theater, $25, $20 mbrs. December 8, 2022 at 7PM at the Studios of Key West.
12/9/22 – Custom House Holiday Concert & Bazaar: This is the sixth annual Holiday Concert and & Bazaar on Friday, December 9, 2022, from 5 pm to 9 pm, located on the sweeping historic porch and street in front of the Key West Museum of Art & History. The immensely popular celebration will feature some of the 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 is projected on the face of the Custom House. There will be plenty of food and festive libations at this event that is free and open to the public.
12/16/22 to 12/17/22 – The 12 Days of Christmas: Holiday Show Spectacular: This is a lighthearted, enchanting gift of cheer for the holidays. A Victorian style extravaganza, based on the classic Christmas song, combines the talents of world class performers, circus style entertainers, and exquisite singers. The star studded cast, lead by Julliard school of music graduate, Shelly Watson, is sure to dazzle and delight every audience member on December 16th and 17th, 2022 at the Key West Theater, 512 Eaton Street. Tickets available at thekeywesttheater.com
12/18/22 – Children’s Winter Concert at the Key West Botanical Garden: December 18, 2022 from 1PM – 3PM. The Key West Tropical Forest & Botanical Garden is proud to host our children’s winter concert again featuring local musician, MATEO JAMPOL! Join us for a Snowy (snow cone filled) Sunday concert celebration, followed by holiday activities! Tickets sold at the door: $5/child, max $10/family, KWBGS members/FREEBeverages, snow cones, and treats will be sold while supplies last.
12/18/22 – Christmas Rising at the Key West Theater: Featuring Destiny Montgomery, Joe Tripp, Larry Smith, Christine Cordone, Al Romano, Kaira Jayde, Erin McKenna, Bria Ansara and more! December 18, 2022. Doors open at 7:00PM, show starts at 8:00PM. Questions? Please email firstname.lastname@example.orgYour favorite Christmas show is back, with a new twist! After two years, Christmas rises from the ashes of lockdown! Destiny Montgomery and Joe Tripp resurrect their production with music genius Larry Smith and many wonderful performers, including Christine Cordone, Al Romano, Kaira Jayde, Erin McKenna, Bria Ansara and more. Family friendly, this is a show you won’t want to miss! www.axs.com/events/456989/christmas-rising-tickets
12/25/22 – Holiday Jazz in the Garden: 5 – 7pm at the Gardens Hotel located at 526 Angela Street.
Key West has hosted some pretty incredible parties through the years. And ringing in a new year island style is the best time of year to party!
12/31/22 – New Year’s Eve: celebrations include the Conch Shell Drop at Sloppy Joe’s Bar on Duval Street, The Red High Heel Drop with Drag Queen Sushi at the Bourbon Street Pub, the Pirate Wench Drop at eta Historic Seaport, and the Key Lime Wedge in a Margarita Glass drop with live music from Beatles tribute band with Tony Baltimore at the Ocean Key Resort.
We alas have a race or some sort of athletic event happening in Key West. Do, why should hte Christmas season be any different?
12/17/22 – 14th Annual Rudolph Red Nose 5K: Don your festive holiday jammies and join in the 14th A Positive Step 5K, taking place Saturday morning, December 17, 2022 starting and ending at the Southernmost Beach Café,1405 Duval Street, Key West. Race day check-in starts at 7AM with 8AM start time. After the race, enjoy refreshments, prizes and a fabulous silent auction. Pre-race packet pickup is Friday, Dec. 16, 2022 from 5PM-7PM 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.Proceeds benefit A Positive Step of Monroe County, Please visit www.apsmc.org
Meals are an important part of the holidays for me. 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.
Hard Rock Cafe
Rams Head Southernmost
Sun Sun at the Casa Marina Resort
Tavern N Town at the Marriott Beachside Resort
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