Key West Christmas, 2019

Christmas time offers so many celebrations to enjoy here in Key West. Parades, holiday markets, concerts, and food!

Typically I am cooking for a big group, but there are some years where I just need to take it easy and let someone else handle the cooking. Luckily, there are a slew of restaurants in Key West that will be serving dinner for the holiday. Most eateries will offer their regular menu, but others will prepare holiday specials. Make your reservations now so that you can enjoy the great Key West weather while you are here without any worrying over the holiday cooking!

As for all of the other entertainment to get you into the holiday spirit, you can check all of those out below as well! Key West is where you can enjoy a ton of Christmas holiday festivities and fun while wearing just shorts and flip flops!!

Dream Catcher Charters offers visitors to Key West for Special Events Fishing Charters. Save Money and Have A Better Time Booking Direct.

Restaurants that will be open for Christmas and/or will be offering Christmas holiday specials: Check back as we will be updating this list with information as it comes in!

  • A&B Lobster House  – 700 Front St. – 305-294-5880
  • Antonia’s – 615 Duval St. – 305-294-6565
  • Azur 425 Grinnell St. – 305-292-2987
  • Bagatelle – 115 Duval St. – 305-296-6609
  • Banana Cafe – 1215 Duval St. – 305-294-7227
  • Benihana – 3591 S Roosevelt Blvd. – 305-294-6400
  • Bistro 245 at the Margaritaville Resort – 245 Front St. – 305-292-4320
  • Bliss – 411 Petronia St. – 305-240-1281
  • The Boat House – 700 Front St. – 305-294-9191
  • Cafe Marquesa – 600 Fleming St. – 305-292-1244
  • Cafe Sole – 1029 Southard St. – 305-294-1230
  • The Commodore – 700 Front St. – 305-294-9191
  • Duffy’s – 1007 Simonton St. – 305-296-4900
  • First Flight Island Restaurant and Brewery – 301 Whitehead Street – 305-293-8484
  • Four Marlins at the Reach Resort – 1435 Simonton St. – 305-296-5000
  • The Grand Cafe – 314 Duval St. – 305-292-4740
  • Hard Rock Cafe – 313 Duval St. – 305-293-0230
  • Hot Tin Roof  – 0 Duval St. – 305-296-7701 – CLICK HERE for special Christmas menu!
  • La Concha Hotel & Spa – 430 Duval St. – 305-296-2991 – To celebrate the holidays, La Concha Hotel & Spa in Key West, Fla., is inviting friends and families to spend Christmas Eve and Day at its dining outlets, 430-Duval and Wine-O Bar, for seasonal dinner specials. La Concha Hotel & Spa’s festive menu offerings will include oysters Rockefellerblue crab stuffed lobster tail topped with Hollandaise sauce and herb-crusted rack of lamb served with braised Brussel sprouts. A sweet potato maple cheesecake garnished with a drizzle of caramel brings a blissful end to a delicious meal. 
key west Christmas lights
Beautifully lit island B&B. Enjoy the Christmas holiday in Key West!
  • Latitudes — Sunset Key — 305-292-5394
  • La Te Da – 1125 Duval St. – 305-296-6706
  • La Trattoria Oceanside – 3591 S Roosevelt Blvd. – 305-295-6789
  • La Trattoria Old Town – 524 Duval St. – 305-296-1075
  • Little Pearl – 632 Olivia St. – 305-204-4762
  • Mangoes – 700 Duval St. – 305-294-8002
  • Martin’s – 917 Duval St. – 305-295-011
  • Matt’s Stock Island Kitchen – 7001 Shrimp Rd. – 305-294-3939
  • New York Pasta Garden – 1075 Duval St. – 305-292-1991
  • Nine One Five – 915 Duval St. – 305-296-0669
  • Ocean Grill – 1075 Duval St. – 305-296-4300
  • One Duval Street at the Pier House Resort – 1 Duval St. – 305-296-4600
  • Prime Steakhouse – 951 Caroline St. – 305-296-4000
  • Rooftop Cafe – 308 Front St. – 305-294-2042
  • The Saint Hotel – 417 Eaton St. – 305-294-3200
  • SHOR Seafood at the Hyatt Centric Resort – 601 Front St. – 305-809-4025
  • Southernmost Beach Cafe at the Southernmost Beach Resort – 1405 Duval St. – 305-295-6550
  • The Stoned Crab – 3101 N Roosevelt Blvd. – 305-433-9431
  • Sun Sun at the Casa Marina Resort – 1500 Reynolds St. – 305-296-3535
  • Tavern N Town at the Marriott Beachside – 3841 N Roosevelt Blvd. – 305-296-8100 – CLICK HERE for a special Christmas menu!
  • ViV Wine Bistro – 300 Petronia – 305-517-6799 – Enjoy Santa’s Dinner. GET TICKETS HERE!
  • Waterfront Brewery – 201 William St. – 305-440-2270
Key West Pets Santa
Santa and Indiana Bones at Pet Pictures with Santa at the Bight.

Holiday Events in Key West:

Sunday, December 1, 2019 – Old Stone Concert Series – Christmas Community Chorus in the 35th annual performance. CLICK HERE for more information!

Tuesday, December 3, 2019 – Peter Mayer’s Stars & Promises 20th Anniversary Christmas Tour (Rams Head) – Key West Theater at 8:00PM. Peter Mayer, singer, songwriter and guitarist is set to embark on the 20th anniversary of his widely acclaimed Christmas tour “Stars and Promises”. Mayer has released 14 of his own albums, toured internationally with his own band, and has been lead guitarist for Jimmy Buffet’s Coral Reefer band for three decades. In 1999, Peter and his brother, Jim Mayer, began work on their first Christmas album, “Stars and Promises”. They recorded favorite traditional carols along with their own original Christmas songs that, over the years have become favorites of their audiences across the country. Since that first recording and tour in 1999, Mayer has released 3 additional Christmas albums and this year celebrates his 20th year on the road with his world-class 7 piece band. Stars and Promises is engaging in live performance, and made memorable with state of the art sound and production, Stars and Promises celebrates its 20th year, bringing its unique yuletide tradition to thousands of fans who have called this production, “A Christmas show like no other”.

Wednesday, December 4, 2019 – Wesley House Family Services Key West Lighted Bike Ride – 7pm. (Registration/Check-in: 6pm). It’s a festive, costumed peddling party toy drive which launches from Bayview Park. Registration is one unwrapped new toy. Register HERE!

Friday, December 6, 2019 – Pet Pictures with Santa. FREE to attend. 6:00 – 8:00pm – Photos by Rob O’Neal. LOCATION: Look for Santa at the Nautical Christmas Tree at the foot of William St. on the HarborWalk of Lights. Santa pics with the pets and kids, treats for all! Pics are $20 (cash only) to benefit the Boys & Girls Club. Get professional furry family photographs for that special holiday card this year!

Friday, December 6, 2019 – Key West Holiday Historic Inn Tour – 6pm – 8pm. Call (305) 296-4959. 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. Participating inns/venues this evening are: Hemingway Rum Co. Distillery, Amsterdam’s Curry Mansion Inn, The Weatherstation Inn, The Gardens Hotel, Island City House Hotel.

Friday, December 6, 2019 through Monday, December 23, 2019 – Old Town Trolley Holiday Lights & Sights Tours – Multiple nightly tours convey caroling passengers through streets and neighborhoods to revel in the magically illuminated city of Key West.

Friday, December 6, 2019 – First Friday Holiday Music with Karen Heins! – At the Green Pineapple from 5 – 7 pm. REGISTER HERE!

Friday, December 6, 2019 – Christmas Tree Lighting – 5:00pm at 24 North Hotel Key West, 3820 N Roosevelt Blvd, Key West, Florida 33040, Key West, United States. Please join us for a fun filled night of photos with Santa, Hot Cocoa and Cookies, Lighting of our 30 Foot Tree, and a Kid Zone for decorating ornaments for your tree! Free Community Event and Pet Friendly for well behaved leashed animals.

Saturday, December 7, 2019 – Key West City “Hometown Holiday Parade” – FREE! 7:00pm. LOCATION: Viewing starts on Truman Ave. (at White St.) then proceeds down 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!

Saturday, December 7, 2019 – Cookies with Santa – Come to Keys Federal Credit Union’s Key Plaza branch at 3022 N. Roosevelt Blvd. on Saturday, December 7th from 2:00pm to 4:00pm and have your photo taken with Santa, enjoy yummy Publix cookies, meet Plato the Publixsaurus and mail your letter to Santa in our magical North Pole delivery box. This event is free to the general public. Call 305-294-6622 for more information.

Sunday, December 8, 2019 – Eaton Street Christmas Stroll – KWT, The Studios, St. Paul’s Episcopal Church, Tropic Cinema, Keys Choral Arts & Key West United Methodist Church unite on December 8th! During this new holiday tradition on Eaton Street, each venue will host a short Christmas-themed performance with caroling as you walk from presentation to presentation. Key West Theater will be hosting Kristen McNamara and Paul Mandell for live performances in the Main Stage! The Eaton Street Christmas Stroll kicks off at 4:00 pm at St. Paul’s Episcopal Church. GET TICKETS HERE!

Monday December 9, 2019 through Friday, December 13, 2019 (Select nights) – The Nutcracker in Key West – Since 1892, there have been more than 11 million performances of The Nutcracker in countries all over the world. In 2005, Key West started to produce its version of the classic Christmas tale, and the play has blossomed into the largest stage performance in the Florida Keys. It’s such a grand spectacle that the performance is on a bi-annual schedule, so if you miss it this year, you’ll have to wait two years to see it again!

Monday, December 9, 2019 through Sunday, December 22, 2019 – Conch Tour Train Holiday Lights Tours – Multiple nightly tours begin with cider and cookies, and convey caroling passengers through streets and neighborhoods to revel in the magically illuminated city of Key West.

Tuesday, December 10, 2019 – Roman Holiday – Tuesday December 10th – Chef Martha Hubbard – Roman Holiday – $90.00 Time / Location: 6:00pm at 908 Fleming St. Menu: Winter salad greens with crispy prosciutto, goat cheese and lemon vinaigrette…

Tuesday, December 10, 2019 – Sunset Waterfront Shoppes Christmas Party – 5:30 – 7:30pm at 245 Front Street. Sunset Waterfront Shoppes and Margaritaville Resort & Marina invite you & the entire family to a FREE holiday celebration benefiting Kids Come First. Enjoy the 5:40 pm sunset & Christmas desserts as you sing along to your favorite holiday songs with the fabulous Christine Cordone. Take pictures with Santa, Mrs. Claus and Grandma Claus at the beautifully decorated grounds!! Win prizes provided by Little Switzerland, Island Cigar Factory, Sunset Trading & Gifts, Pearl Key West, Danger Chandlery, Key West Madhatter, Del Sol, Cariloha, Polar Bear Ice Cream, Saltwater Angler, Fury Water Adventures, Venter Surf & Sport & Gator Joes Coffee Shop. Please bring or purchase at the Sunset Waterfront Shoppes new clothing items, shoes, accessories, personal hygiene items, gift cards or toys for kids ages 0-21 which will be donated to Kids Come First.

Tuesday, December 10, 2019 – Keys Federal Credit Union ReMARCable Christmas Tree Auction — Keys FCU – Join us to raise funds for the MARC House at their annual Christmas Tree Auction. Beautiful trees, all laden with extra gifts, will be auctioned off by the hilarious Tom Luna. Doors open at 5pm and the auction begins at 7pm. At the Margaritaville Resort.

Wednesday, December 11, 2019 – A Peter White Christmas feat. Euge Groove, Vincent Ingala & Lindsey Webster at The Key West Theater – 8:00 PM at the Key west Theater. GET TICKETS HERE!

Wednesday, December 11, 2019 & Thursday, December 12, 2019 – Holiday Concert – Come out for an evening of joy and support the Key West High School Band and Choir for their annual combined Holiday Concerts on Wednesday, December 11th and Thursday the 12th at 7:00pm in the KWHS auditorium (same concert both nights). Admission is free; however, donations will gladly be accepted at the door. Both concerts are the same program and will feature the Jazz Band, Percussion Ensemble, Combined Concert Band, Wind Ensemble, Colorguard, Conchettes, Steel Pan Band, Freshmen Girls Choir, Mixed Choir, Chamber Choir, Women’s Choir, Mistys, VIPs, several soloists, and all 200+ musicians in a special combined piece. Please join us for a special night of musical joy to ring in the holiday season! Bring a friend and please share this!

Thursday, December 12, 2019 – 7th Annual POSH (Paws Often Steal Hearts) – 6pm – 9pm. Benefiting Florida Keys SPCA! Benefit is located at the Audubon House & Tropical Garden. There will be live music, silent auction, Tapas-style appetizers, complementary specialty welcome drink and local priced cash bar! Tickets in advance $40 and $45 at the door, available at FKSPCA POSH Tickets.

Thursday, December 12, 2019 – Ornament Painting – Find out more by CLICKING HERE!

Friday, December 13, 2019 – Key West Holiday Historic Inn Tour – 6pm – 8pm. Call (305) 296-4959. 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. Participating inns/venues this evening are: Avalon Bed & Breakfast, Wicker Guesthouse, The Mermaid & The Alligator, Santa Maria Suites Resort, Key West Butterfly & Nature Conservatory.

Friday, December 13, 2019 – Stock Island Lighted Boat Parade – I Love Stock Island Festival is accepting entries for the 3rd annual Lighted Boat Parade at Stock Island Marina Village presented by Sunset Watersports. It’s just $25 recreational, $50 commercial to enter any boat, any size for a chance to win trophies, cash and prizes. Entries may reserve a slip for the night at SIMV at NO CHARGE and are welcome to embark passengers from our docks. Sign up online at hours before and after parade parties at the Salty Oyster and Matt’s Stock Island Kitchen & Bar at The Perry Hotel Key West, and Hogfish Bar & Grill at Safe Harbour Marina, LLC. FREE to attend, lots of places to watch (bring chairs if you want) – not crowded, FREE parking! Cold beer and full bar, food, snacks and great fun with your friends and neighbors. Tune in to the live radio broadcast on WEOW FM 92.7. Many boats will be accepting passengers to be IN the festivities.

Saturday, December 14, 2019 – Annual Parade of Paws & Holiday Bazaar – Higgs Beach / Higgs Dog Park from 10am – 2pm (9:00am check-in). Benefits the Florida Keys SPCA. Costumes encouraged!

Saturday, December 14, 2019 – Annual Gingerbread House Making Event – Won’t you and your family join us on December 14th at 11am for our annual Gingerbread House making event? Be sure to bring the family to the Oldest House and Gardens for one of the biggest children’s events in Key West. This event is free, no tickets necessary.

Saturday, December 14, 2019 – 12th Annual Rudolph Red Nose Run! 7 am – 10 am. Run for a good cause at the 12th Annual 5k Rudolph Red Nose Run to benefit for A Positive Step of Monroe County. Enjoy breathtaking views as you run or walk to the Southernmost Point of the United States. Huge Silent auction, raffle, and awards following the race. Location: Southernmost Beach Cafe, 1405 Duval Street | Key West, FL 33040. Sign up, register, and run with the locals and Rudolph to benefit this good cause!Learn more about this event.

Saturday, December 14, 2019 – Schooner Wharf 29th Annual Key West Lighted Boat Parade – FREE! Parade starts at 8:00pm. LOCATION: Viewing all along the Harbor Walk of Lights at the Historic Seaport. Reviewing stand is at the Schooner Wharf Bar and Galley. Come early for great shopping, live holiday music performance, dinner and drinks.

Saturday, December 14, 2019 – Sebago Lighted Boat Parade Party – From 7:30 – 9:30pm, enjoy this annual holiday spectacle from a front row seat on the water. Drinks and appetizers included! Call Island Genn at 1-888-362-3474 to make reservations!

Sunday, December 15, 2019 – Christmas on the Sheriff’s Animal Farm – 1pm – 3pm. FREE! The farm is open to the public from 1 to 3pm. Come visit the animals and have a photo with Santa. It’s free and donations are appreciated.*Due to the holidays, please note that the farm is only open for ONE Sunday during the month of December.

Sunday, December 15, 2019 – Conch Republic Seafood “Holiday Classic Car Show” – FREE! 11:00 – 3:00pm. LOCATION: Conch Republic Seafood Company – Greene & Elizabeth St. Please bring an unwrapped toy for Monroe County Domestic Abuse Shelter.VOTE for the “Peoples Choice” award, awards for: BEST engine, interior, original & custom, Best in Show. See classic cars from every era decked out for the holidays! Florida Keys Southernmost Car Club. Non-member cars may enter same day FREE with an unwrapped toy!

Tuesday, December 17, 2019 – A Choral Christmas Feast – 7 – 9:30pm at St. Paul’s. Our first annual Christmas Concert, with soloists, pipe organ, flute, and violin. Music of Gjielo, Rutter, Vaughan Williams, and more. GET TICKETS HERE!

Wednesday, December 18, 2019 – Artisan Market, Key West – 10am – 2pm. FREE! A “shop local” holiday tradition, the open-air bazaar, this year at Higgs Beach, 100 Atlantic Blvd., is filled with Keys artists, authors, chef-made cuisine, craftspeople, performers, live music and adult beverages.

Wednesday, December 18, 2019 – 4th Annual Custom House Holiday Concert & Bazaar – Custom House Museum from 5pm – 9pm. FREE! This festive free party features Key West’s finest artisans, musicians and choirs, along with a spectacular holiday light show.

Thursday, December 19, 2019 – Christmas at St. Paul’s – Get in the spirit as our artists present an evening of seasonal music. The event will be held in St. Paul’s sanctuary which highlights the church’s acoustics and magnificent pipe organ. GET TICKETS HERE!

Saturday, December 21, 2019 – “Violins in Motion” Children’s Group Performance of Holiday Music!Collecting donations for JDRF
and Juvenile Diabetes Research. FREE! 6:30 – 8:00pm. LOCATION: On the Harbor Walk of Lights under the “Fishing Buoy Christmas Tree”, at Green and Elizabeth St. A holiday musical performance by budding musicians from 6 to 18 years old – for a sweet dose of Christmas spirit.

Sunday, December 22, 2019 – Lighting of the Menorah – At Bayview Park – 5:00PM.

December 22, 2019 – Christmas Rocks! – 8 – 11pm at the Key West Theater.  This won’t be your average Christmas concert!

Sunday, December 22, 2019 – Holiday Jazz in the Gardens – 5:30pm – 7:30 pm. FREE! Festive outdoor jazz performance at the Gardens Hotel. Cash bar & large wine selection.

Sunday, December 22, 2019 through Monday, December 23, 2019 – Holiday Tours at the Little White House – The pageantry and elegance of the holiday season is on full display in the former winter home of the 33rd President of the United States, Harry S. Truman. This is a rare opportunity to experience this special time of year through the lens of the not-to-distant past! Have a flute of bubbly at Truman’s original bar or warm up with a cup of hot chocolate. Take in all the vintage regalia belonging to the museum’s private collection as you enjoy an evening fit for a VIP.

Tuesday, December 24, 2019 – Christmas Eve Dinner at the Sunset Green Event Lawn at the Keys Collection – Join us under the stars with live music for our Annual Christmas Eve Dinner Buffet! $48 per person includes open bar with Roasted Pig, Honey Glazed Ham, Roasted Turkey, and so much more. 12 and under just $19. Seatings at 5 & 7pm. Purchase tickets HERE!

Tuesday, December 24, 2019 – Noche Buena ~ Christmas Eve Feast – Christmas is a huge deal to Latinos, but nothing is a bigger deal than Noche Buena. Noche Buena is what we call Christmas Eve, except, whereas most cultures celebrate the holiday on Christmas Day, we do the whole shebang on Christmas Eve and instead take it easy on Christmas Day. Noche Buena is a long celebrated tradition in latin communities and is proudly celebrated in Key West by local families. Wayne Garcia and his family will be enjoying “Noche Buena” in the Gardens at the Oldest House Museum this year and you are invited. Don’t go to a restaurant on one of the busiest nights in Key West, Join us in our private garden. Taste a traditional menu of Roast Pork…… a menu made with love & culturally delicious. Christians with Cuban and Puerto Rican heritage traditionally play dominos on Noche Buena, and cook entire pigs in a Caja China box atop burning coals. It is believed that the tradition dates back to the 15th century when Caribbean colonists hunted down pigs and roasted them with a powerful flame.
Full Menu in the works. Full open bar and entertainment provided. GET TICKETS HERE!

Wednesday, December 25, 2019 – Sail with Santa on Fury Water Adventures – Festive trip to the reef including Holiday Music, Appetizers, Treats, Hot Chocolate, Beer, Wine, Champagne, Soda, Water & SANTA!!! Call Island Genn at 1-888-362-3474 for reservations!

Friday, December 27, 2019 through Saturday, December 28, 2019 – 60th Annual Key West House and Garden Tour – 3pm – 6pm. Presented by the Old Island Restoration Foundation, the annual self-guided tours from 3pm-6 pm each day showcase festively dressed Key West homes and gardens. Tickets are $30 in advance, $35 day-of-tour. Proceeds benefit the foundation’s museum and programs. Call 305-294-9501.

Friday, December 27, 2019 through Saturday, December 28, 2019 – Holiday Tours at the Little White House – The pageantry and elegance of the holiday season is on full display in the former winter home of the 33rd President of the United States, Harry S. Truman. This is a rare opportunity to experience this special time of year through the lens of the not-to-distant past! Have a flute of bubbly at Truman’s original bar or warm up with a cup of hot chocolate. Take in all the vintage regalia belonging to the museum’s private collection as you enjoy an evening fit for a VIP.

Saturday, December 28, 2019 – 60th Annual Home Tours “Holiday Style” -The annual Key West Home Tours™ are one of the oldest and longest running home tours in America, with the first tour in 1960. Old Island Restoration Foundation (OIRF) conducts the tours and they are funded in part by our generous supporters. Each tour features five lovely homes and gardens reflecting the varied tastes and originality of their owners. You will be enchanted by exquisite restorations, creative renovations and delightful interiors featuring art collections, antiques, and much more. All proceeds from the tours stay in our local community fulfilling OIRF’s mission of “Celebrating and sustaining Key West’s unique architecture, culture and history.” Grants are provided to local home owners and non-profits to fix up their buildings in the historic district, scholarships are provided to Key West High School students and funds are used to maintain Key West Oldest House Museum and Garden. NOTE: There is no transportation offered between homes during this event. GET TICKETS HERE!

Tuesday, December 31, 2019 – Annual Key West Dachshund Walk – 12:00 noon. Dachshund’s and Dachshund impersonators along with their human companions gather at Fleming and Whitehead Streets before parading through downtown streets lined with adoring fans.

Tuesday, December 31, 2019 – New Years Dinner at La Concha Hotel & Spa –To celebrate the holidays, La Concha Hotel & Spa in Key West, Fla., is inviting friends and families to spend the New Year at its dining outlets, 430-Duval and Wine-O Bar, for seasonal dinner specials. La Concha Hotel & Spa’s New Year menu boasts celebratory dishes, including a traditional lobster bisque served with fresh Cuban bread crostiniroasted prime rib with garlic mashed potatoes and grilled asparagus, as well as seared grouper served with jumbo lump crab meat and asparagus. 

Tuesday, December 31, 2019 – Key West New Year’s Eve Celebrations –

  • Rooftop Conch Shell Drop – at Sloppy Joe’s, 305-296-2388
  • Drag Queen Drop in a giant Red High Heal – at Bourbon St Pub, 305-293-9800
  • Pirate Wench down the Schooner mast – at Schooner Wharf Bar, 305-292-3302
  • Key Lime Wedge drop into giant Margarita – at the Ocean Key Resort, 305-296-7701-770
Key West inn Christmas tour
Santa taking a nap outside of the Mermaid and Alligator B&B on Truman Ave in Key West, Florida.

See what else is happening on the island during your visit by checking out our Key West Events Calendar, and for other things to do and see in our island city, go to our Key West Web Site.

Before making your reservations for Christmas dinner check out our restaurant reviews! Feel free to Email Me if you have any questions about Key West!!

Island Genn
Key West Concierge

About the author: Island Genn

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