Christmas in Key West – 2013

Beautifully lit island B&B. Enjoy the Christmas Holiday in Key West!
Beautifully lit island B&B. Enjoy the Christmas Holiday in Key West!

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December is here and I for one can hardly believe it! For some, Christmas time is the most wonderful time of the whole year. And while Key West may not be your traditional idea of the picture of Christmas, we sure know how to get into the holiday spirit down here. Many events are set up specifically to celebrate the holiday. And you will find some great places to eat Christmas Dinner too. So, get your shopping done and get down to Key West to enjoy a Christmas laden with palm trees, warm weather, and lots of lights and holiday spirit!

Holiday Events

December 1 – 31

  • Key West “Bight’ Before Christmas” Holiday Celebration – Live holiday music, games for the kids, holiday cheer and a chance for photos with Santa highlight this event along the historic harbor walk linking colorful seaport restaurants, bars and businesses at the Key West Bight. Created as a gift to the community, the gala is produced by the Key West Bight Preservation Association and tenants of the Key West Bight.

December 1

  • “The Messiah” – As many as 90 singers from around the Florida Keys participate in the annual performance of George Frideric Handel’s holiday masterpiece. Directed by Dean Walters, the 31st consecutive production is to be staged at Key West United Methodist Church at the corner of Eaton and Simonton streets, and admission is free. Performance starts at 8 p.m. Contact: 305-296-2392.

December 2

  • Christmas Tree Lighting at Bay View Park –  6PM at  Bayview Park, Key West, FL 33040. 6:00 PM TO 7:00 PM. Phone: 305-294-2587.  Santa will be there to give out candy canes and hear what the wishes of the little ones are. Come out and hear the HOB Band and get in the spirit! Please contact Maria Ratcliff 809-3881 for additional information.

December 6 

  • Cymbalta withdrawal syndrome – 6:00 – 8:00pm; Click here for ticket info. 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. The tour features art, fine food from top local restaurants and holiday libations at each stop.
  • Keys Chorale 2013 Holiday Concert  – The Keys Chorale will present a holiday concert at the Key West United Methodist Church, corner of Eaton and Simonton streets at 8:00 PM. Tickets are $20 for general admission. Contact: 305-849-1474 or www.keystix.com.
  • Pet Photos with Santa and the Drag Queens – sponsored by the Xena Fund, from 5:30 pm to 7:30 pm at Grooming by John, 1014 Truman Ave. Santa, Deja and Desiray will pose for an only in Key West photo for your Christmas Cards. The $20 fee goes to Xena Fund. All pets must be leashed.

December 7

  • 2nd annual Cookies with Santa – At the Keys Federal Credit Union. From 2 – 5 PM. Call 305-294-6622 for more information.
  • Key West City Hometown Holiday Parade – FREE – Starts at 7:00pm on Truman Ave. at White St., then proceeding down Duval St. and ending at Eaton St.  This is the most charming hometown parade you’ll ever see in with creative floats, and tons of kids of all ages. Of course Santa will make a guest appearance.
  • Reserve your spot on the Conch Tour Train and be a part of the Parade! – You are all invited to be in the Christmas Parade on December 7th! The Waterfront Playhouse asks you to be a part of this holiday tradition! Go to www.waterfrontplayhouse.org to sign up for only $50 which goes to support the Waterfront Playhouse future building plans. Wear your Christmas colors and festive hats or costumes of any kind. Some Goodies and beads to throw to the eager children will be provided, but bring your own stash to distribute. Meet at Bayview Park at 6 pm.
  • Holiday Bar Crawl – This years meeting point is the Rum Barrel on the corner of Front and Simonton at 3pm. From there the event will make stops at Island Dogs, Shots and Giggles, The Bull and then Charlie Macks. The event will be hosted by comedian and radio personality Vinny K who will entertain the crowd along the way as well as give out over $5,000 in prizes as well as announce the winner of the 50/50 raffle. Tickets for the bar crawl are $25 and include a beer at every bar and can be purchased at KeysTix.com or by calling 305.748.7196. Donations of gift certificates and prizes are always needed.
  • Holiday Artisan Show and Book Sale – 9:00 AM at the Studios of Key West at 600 White Street.
  • Pet Photos with Santa and the Drag Queens – sponsored by the Xena Fund, from 1:00 – 4:00 pm pm at Grooming by John, 1014 Truman Ave. Santa, Deja and Desiray will pose for an only in Key West photo for your Christmas Cards. The $20 fee goes to Xena Fund. All pets must be leashed. Parking at Bare Assets available.

December 8

  • Story Slams: Holidaze – 8:00 PM at the Little Room Jazz Club located on 821 DUval Street. Call 305-540-6102 for more information.
  • Holiday Party, Open House and Book Signing – 5:00 PM at the Key West Art Center at 301 Front Street.

December 11

  • Drive in Movie at Ibis Bay – See ‘A CHRISTMAS TALE’ at 8 pm. Free movie & popcorn at Ibis Bay Resort at 3101 N. Roosevelt Blvd.

December 11 & 12

  • Key West High School Choir Winter Concert – 7 pm at The High School Auditorium on Flagler Ave.

December 13

  • Pet Pictures with Santa – FREE to attend. Hosted by The All Animal Clinic.  From 5:00 – 8:00pm – Photo sales benefit the Boys & Girls Club of Key West. Look for Santa at the Christmas tree at the foot of William St. on the Harbor Walk of Lights.
  • Cymbalta withdrawal syndrome – 6:00 – 8:00pm; Click here for ticket info. 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. The tour features art, fine food from top local restaurants and holiday libations at each stop.

December 13, 15, 16, 18, 19, 21, 22

  • Conch Tour Train – Sing along to Christmas Carols. Trains depart from Key West High School, 2100 Flagler Ave, at 6:00PM.  Call 305-294-5161 for tickets and information.

December 14 

  • 23nd Annual Schooner Wharf Bar Lighted Boat Parade – FREE. Children’s Steel Drum concert starts at 6:00pm – Parade starts at 8:00pm. Music and the reviewing stand is at the Schooner Wharf Bar on the Harbor Walk of Lights.
  • Sunset Watersports Lighted Boat Parade Dinner Cruise – 7pm to 9:30 pm. $69 plus tax per person. Call 305-292-7212 for reservations.
  • Danger Charter Lighted Boat Parade Sail – from 8 – 10 pm. Enjoy the parade from the water while feasting on hors d’oeuvers and fine wines. $85 plus tax per person. Call 305-292-7212 for reservations.
  • FKCC Ballet & Southernmost Dance Theatre Present: Holiday –  festive family friendly evening of dance and music. A delightful program showcasing the FKCC ballet students with the Southernmost Dance Theatre including everything from Sugarplum Fairies to Flamenco. Special guests include dancers from Dancetown Miami and from the Untouchables, finalist in America’s Got Talent TV competition. Musical guests are The Fabulous Spectrelle Review. 8:00 PM at the Tennessee Williams Theater. Tickets can be purchased at keystix.com.
  • Ruben Navarro Holiday Christmas Show – at Kelly’s Caribbean MUSE upstairs, 301 Whitehead St. Tickets are $12 in advance by calling 393-7802 or $15 at the door.
  • Montessori Holiday Bazaar – from 9am to 2pm.
  • Holiday Elf Art Reception – at the Tropic Cinema from noon to 1pm.
  • Castaways Christmas Party – at Pinchers Crabshack. From 2-5 PM. They will be collecting items for teens at the Wesley House. They will also do a gift exchange.
  • Santacon – at the Conch Republic Seafood Company. Wear your best Santa costume for this wacky event. 6:00 PM.

December 14, 15, 20 – 24

  • Holly Jolly Trolley – Enjoy caroling and tales with magical viewing glasses. Tours depart from Mallory Square. Call 305-296-6688 for information and tickets.

December 15

  • Holiday Classic Car Show – Hosted by Lost Reef Adventures Dive Shop & SouthernMost Car Club from 12:00 – 4:00pm – FREE. Collecting unwrapped toys for the Domestic Abuse Shelter. Classic cars from every era on the plaza at Margaret St. near the decorated Lobster Trap Tree on the Harbor Walk of Lights. ALL BUSINESSES AROUND THE CAR SHOW AREA ARE OPEN FOR GREAT KEY WEST SHOPPING, FOOD AND BEVERAGES!
  • What happens if you overdose on doxycycline – From 1-3 p.m., kids and adults can visit the furry, fluffy and feathered residents of the Animal Farm and get a photo taken with Santa. The Monroe County Sheriff’s Office Animal Farm is situated at the county’s detention center just outside Key West at 5501 College Road. This event is free and open to the public. Contact: 305-293-7300.
  • Southernmost Christmas Tree Celebration – Holiday revelers enjoy free conch chowder and then board Conch Tour Trains to proceed to the continental United States’ Southernmost Point to set up the southernmost Christmas tree at sunset overlooking the Atlantic Ocean. The event is an annual community thank-you party presented by the Monroe Association for ReMARCable Citizens. The fun starts at 3 p.m., at 1401 Seminary St. Contact: 305-294-9526.
  • Nutcracker 5K & Fun Run – Pick up Saturday 14 from 5-7pm at Salute! Race day 7am day of registration, 8:30am 5K start; 9:30am half mile start. Face painting and awards for costumes from 7:30 – 9:30am. Register at www.raceroster.com.
  • Nutcracker Key West – Showing at the Tropic Cinema at 6pm.
  • The Music Room Presents Sounds of Joy – A musical celebration of the season. 4:00 at St. Paul’s Episcopal Church at 401 Duval Street. Call 305-294-7382 for more information.

December 17

  • Silver Key Lingerie Holiday Party – 6pm at the store located at 1108 White Street.

December 18 

  • Lighted Bike Parade – Arrive at Bayview Park between 5 and 6 pm for a 6:30 pm departure. Dress up and decorate your bike.
  • Christmas Chamber Music – 7pm. $40 per person, includes champagne and desserts. Call 305-517-6851 for more information and tickets.

December 19

  • Lighted Bike Parade – Meeting Point TBA –  between 5 and 6 pm for a 6:30 pm departure. Dress up and decorate your bike.
  • Conch Color’s 9th Annual Holiday Party – At Casa Antigua, 314 Simonton Street at 8pm. Enjoy hors d’oeurves, music by the Blessed Community Gospel Choir, and more!

December 20

  • Christmas by Coast Projects on Stock Island – 6404 Front Street will be hosting this event which will include a local holiday market, open fire, gift specials, open studios and workspace of the resident artists, holiday films screening outside, christmas music, caroling, and lights. Please call 305-395-9127 for more information.

December 21

  • “Violins in Motion” Holiday Concert  – by children from 6:00 – 8:00pm – FREE. An uplifting holiday musical performance on the plaza at Green & Elizabeth Streets, under the decorated Lobster Float Tree on the Harbor Walk of Lights.
  • Sail with Santa – From 5-7 pm. Sail aboard a Fury Catamaran and enjoy holiday music, treats, hot chocolate, beer ,wine, champagne, and soft drinks. $20.00 per person. Proceeds benefit Wesley House Family Services. Call 305-292-7212 for reservations.

December 22

  • Holiday Shopping at Monthly Artisan Market – Held from 10 a.m. to 2 p.m. at the Restaurant Store parking lot, this monthly event is to give residents and visitors alike a chance to shop fresh and local as the parking lot at 1111 Eaton St. is transformed into a showcase of art, photography and unique local handicrafts and gifts made exclusively in the Keys in one convenient location. Entertainment includes a singer and songwriter showcase, local authors, Key West Fringe theater performances, chef demonstrations, kid’s activities and live street art murals. Guests will be able to taste and buy local specialties, and enjoy concessions, beer and wine. Guests are encouraged to BYOB (bring your own bags). Contact: Sean Krikorian 573-619-2200 or Email: sean@dailyplan-it.net.
  • 30th Annual Christmas Concert – St Paul’s Episcopal Church at 401 Duval Street. Tickets are $20 and can be purchased at the Red barn Theater or at MacArthur’s Music.

December 22 – January 4

  • Surf and Turf Sunset Sail with Sebago – Enjoy a two hour sunset sail and a grilled surf and turf meal. Tours depart at 5pm and return at 7pm. Cost is $99 per person. Please call 305-292-7212 for reservations.

December 25

  • Get ready to set sail on one of Fury’s spacious catamarans for the Key West Christmas Ultimate Adventure. Check out all the activities that are included with your day trip that departs at 10:00 am and returns at 4:00 pm: Sailing the beautiful waters of Key West on Fury’s 65′ Catamaran, Special Holiday Menu, Snorkel the Reef, Parasailing, Jet Skiing, Water Slide, Kayaking. Cost is $140 plus tax per person. For reservations call 305-292-7212.

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

Restaurants Offering Christmas Dinner

  • Abbondanza at 1208 Simonton Street, will be open on Christmas Day offering their regular menu. Call 305-292-1199 for reservations.
  • Cafe Sole will be serving up a special Christmas dinner along with their regular menu from 4:00 to 10:30 pm. Please call 305-294-0230 for reservations.
  • The Commodore will be open on Christmas Day offering their regular menu. Located at 700 Front Street at the A&B Marina, you can enjoy a great view while dining. For reservations call 305-294-9191.
  • Doubletree Grand Key Resort dining room is having a Christmas Day Buffet for $32.95 per person and discounts for children. For reservations call 305-293-1818.
  • Duffy’s Steak & Lobster House on the corner of Truman Avenue and Simonton Street will be open on Christmas Day offering their regular menu. For reservation call 305-296-4900.
  • Grand Cafe will be serving a traditional Christmas dinner from noon until closing along with their regular menu. For reservations call 305-292-4740.
  • Hot Tin Roof located at the Ocean Key Resort at 0 Duval Street is serving a four-course Christmas dinner for $69 per person. For reservations please call 305-296-7701.
  • Kelly’s Caribbean Bar and Grill on Whitehead Street will be having a special menu for Christmas from 11AM to 10PM for only $32.95 per person. Call 305-293-8484 for reservations.
  • Little Palm Island Dining Room is offering a special Christmas Dinner this year. Little Palm is about a 30 minute drive from Key West followed by a 15 minute ferry ride to the island. This place screams Lifestyles of the Rich and the Famous! This very romantic spot that can only be gotten to by boat or seaplane has hosted many special and unforgettable dining experiences for me. For more information and reservations call 305-872-2524.
  • Pisces located at 1007 Simonton Street will be open on Christmas Day offering their regular menu. Call 305-294-7100 for reservations.
  • Rooftop Cafe will have regular hours of operation on Christmas Day, and will be offering their full menu in addition to holiday specials. Please call 305-294-2042 for reservations.
  • Pepto bismol and nexium is having a Christmas Day Celebration Buffet from Noon until 8:00 PM for only $49 plus tax and fees per person.
  • Tavern N Town at the Marriott Beachside will be having a celebratory Christmas Dinner on December 24th and 25th from  5:00 – 10:30 PM. They will also be having a Christmas Day Brunch from 11 AM to 2 PM. For more information or for reservations please call 305-296-3676.
  • Surf and Turf Sunset Sail with Sebago – Enjoy a two hour sunset sail and a grilled surf and turf meal. Tours depart at 5pm and return at 7pm. Cost is $99 per person. Please call 305-292-7212 for reservations.

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.

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Feel free to Email Me if you have any questions about Key West!!
Island Genn
Key West Concierge

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