Key West Christmas – 13 Fun Things To Do During The Holidays

Key West Christmas – 13 Fun Things To Do During The Holidays

Key West Christmas

Why visit Key West in December? It’s simple. The weather is warm and sunny, with average temperatures of 77 degrees and the water temperature is excellent for water sports.

As you can imagine, December attracts plenty of people who want to escape the cold back home and experience Key West instead. You won’t have a white Christmas in Key West, but you can still have a great holiday. Let’s take a look at the top 13 fun things to do during the holidays in Key West.

Key West Christmas - Santa On The Chimney

1) Key West Holiday Historic Inn Tour

For two nights in mid-December, visitors can take a self-guided tour of four of Key West’s most charming inns. The inns are lit with beautiful decorations to celebrate the holiday season. Visitors can tour four different historic properties on each night.

Historic inns that have been available for previous tours include:

  • The Mermaid & The Alligator Guest House
  • Winslow’s Bungalows
  • Wicker Guesthouse
  • Weatherstation Inn
  • The Key West Butterfly & Nature Conservatory
  • The Gardens Hotel
  • Island City House Hotel
  • Amsterdam’s Curry Mansion Inn

The innkeepers are on hand to share fun stories about the history of their inn, along with appetizers and holiday libations. Guests are free to start at any participating property. Trolleys provide transportation between stops.

Advance tickets are recommended. A limited number of tickets are also available for pick-up after 5:00 pm at the tour’s first stop.

2) Christmas In Key West At Bayview Park

Get into the holiday spirit by attending the festive Christmas tree lighting in Bayview Park. This annual event takes place after Thanksgiving Day, no matter how many decorations the retail stores put out sooner than that! Check the calendar for exact dates.

During the tree lighting event, holiday music is playing, and Santa pays a visit to really get the season started.

If Christmas tree lighting is not your thing, there is also an annual Lighting of the Menorah Ceremony at Bayview Park. At sunset on the first day of Hanukkah, the menorah is lit to usher in the beginning of the eight-day Jewish Festival of Lights. Blessings are offered by a Rabbi from a local Jewish congregation.

Christmas In Key West - Festive  Christmas Tree

3) Key West Christmas Jet Skiing

No one ever said that Christmas time would be boring in Key West! Do something a little different this year and celebrate the holidays with a jet ski tour in Key West.

Reserve a jet ski tour that is led by a knowledgeable local guide who can show you the Florida Keys National Marine Sanctuary. Most jet ski tours are 1.5 hours and will go completely around the island of Key West.

You’ll see top spots like the Boca Chica Sandbar, the famous Southern Point, Key West Harbor, and, of course, the Florida Keys Wildlife Sanctuary.

Most jet ski tour operators do not charge for the second rider when you ride together, so couples can save some money by cuddling on one jet ski.

Great Holiday Escape - Jet Skiing In Key West

4) Christmas In Key West At Duval Street

Let’s get this holiday season started! If you are lucky enough to be visiting Key West in early December, then you can watch one of the best small-town holiday parades you’ll ever see.

The Key West Christmas parade starts on Truman Avenue and makes its way to Duval Street, ending at Eaton Street. You’ll see festive floats, church groups, happy kids, and of course, Santa is there to ring in the season. Groups of adults, children, elves, and costumed reindeer add to the merry band of celebrators.

Bring a paper bag with you to bring home the loot as paraders toss candy to spectators along the way.

Santa In Old Town, Key West

5) Key West Southernmost Point

No matter what time of the year you are in Key West, no visit would be complete without stopping for a photo opportunity at the iconic Southern Point Buoy.

The large concrete buoy marks the southern point in the continental United States. The buoy reminds us that it is only 90 miles to Cuba from this point.

Visitors wait in the queue for a turn to stand in front of the buoy and have a picture taken. This year’s family picture at the buoy might become next year’s family holiday card.

Southernmost Point Of The Southernmost City

6) Key West Waterfront

Spend an afternoon walking along the waterfront restaurants, enjoying the colorful decorations and lively atmosphere. You can walk from the Gulf of Mexico to the Atlantic Ocean!

On the gulf side, you’ve got the Bight Marina, Historic Seaport, and Mallory Square. As you make your way to the Atlantic side, you’ll see the Southernmost Point of the Continental US, Higgs Memorial Beach Park, the Key West Nature Preserve, and Smathers Beach.

During the day, the area is a laid-back fishing village with interesting boats bobbing in the harbor. Around 5:00 pm, the town comes to life as locals and visitors alike enjoy happy hour at one of the bars and restaurants overlooking the water. Join in the fun and have some holiday cheer.

7) Mallory Square Key West

Need to buy a few Christmas gifts while you are celebrating Christmas in Key West? The shops at Mallory Square have just what you need and more. You’ll find the historic square next to the cruise ship port, just west of Duval Street.

There are interesting shops, art galleries, exhibits, and places to eat here. From the beginning of December until just before Christmas day, there is an added surprise.

Kids of every age can visit the North Pole located upstairs to see Santa and share their holiday wishes. There are added activities for kids, including letter-writing stations and a mailbox to send letters to Santa.

At night, about two hours before sunset, the area turns into a lively party atmosphere with street performers, musicians, vendors, artists, and food trucks. Everyone is waiting to see a spectacular sunset over the Gulf of Mexico.

Mallory Square Near Old Town, Key West

8) Historic Seaport Key West

See the historic Key West Seaport all aglow with festive lights and creative holiday displays during what they call “the night before Christmas.”

The Key West Bight is a bend in the shoreline on the northwest side of the island. The Key West Bight Marina becomes a lively Christmas scene, beginning in late November and lasting all the way through New Year’s Eve.

Holiday lights in this area have a nautical theme in honor of the maritime history of the historic waterfront. The Harbor Walk of Lights lines the seawall past Greene Street, William Street, and Margaret Street to the Key West Bight Ferry Terminal.

Holiday Decorations In The Conch Republic

9) Key West Christmas Lighted Boat Parade

One of the most popular holiday events in the Florida Keys is the annual Schooner Wharf Bar & Galley Lighted Boat Parade. The best view of the boat parade is at the Historic Seaport.

Dozens of sailboats, fishing boats, yachts, and catamarans parade along the waterfront at night, decorated with twinkling holiday lights.

The boat parade typically begins around 8:00 pm, but get there early to stake your place and enjoy the festive atmosphere. Local musicians play classic holiday music, and the Harbor Walk of Lights adds to the colorful holiday party.

Lighted Boat Parade In The Conch Republic

10) Visit The Harry Truman Little White House

The famous winter home of President Harry S. Truman is just a short walk from the Key West waterfront. President Truman enjoyed 11 visits here for a total of 175 days. As the frequent residence of the president, this historic home earned the title of The Little White House.

The Little White House is a top attraction in Key West year-round, but especially during the festive holiday season, as the house is elegantly decorated in beautiful Christmas decorations.

Over the years, other famous dignitaries came to rest and relax at Truman’s winter home, including Thomas Edison, Dwight Eisenhower, John Kennedy, and former Presidents Jimmy Carter and Bill Clinton.

Guided tours are available with knowledgeable guides who are well-versed in the house’s history and those who have stayed there.

Harry Truman's Little White House In Key West

11) Old Town Trolley Key West

Every year, a friendly competition occurs in Key West, where residents decorate their homes in all their finest Christmas regalia, adding even more color to this sunny paradise, in hopes of winning cash prizes for the best display. Neighbors work to outdo each other with outdoor decorations, and the results are fun to see.

Key West visitors can take an Old Town Trolley Lights and Sights tour to see the historic Key West homes adorned in colorful lights with front gardens that set the stage for some quirky and creative holiday displays.

The Old Town Trolley tours are guided by local Key West enthusiasts sharing fun facts and entertaining stories about the island.

12) Key West Harbor Walk Of Lights

Take a walk along the historic Key West Seaport in December, and you’ll know that Christmas day is coming soon.

The famous Key West Harbor Walk of Lights on the waterfront is a captivating postcard scene with over 61,000 festive lights and decorated palm trees.

Light sculptures include ship’s anchors, tropical birds, fish, pink flamingos, pelicans, manatees, animated sea turtles, and dancing dolphins surrounded by brightly lit holiday palm trees.

A few quirky Christmas traditions are on display, including the fishing buoy tree, a nautical Christmas tree, and the original Key West lobster trap tree.

Holiday Lights Tour Along The Decorated Palm Trees

13) Key West Boat Trips

For the highlight of any trip to the keys, take a sunset cruise in Key West.

Head to the sandbar and beyond with an experienced skipper at the helm. You’ll drop anchor at a sandbar, reaching deep enough for you to jump into water that is just above waist-high water and get some awesome photos with the sun setting behind you – it’s really something special.

See the holiday lights displays on the island, with the colorful sunset over the water. It’s a memory to last a lifetime.

Book your own private sunset cruise in Key West. We look forward to meeting you!

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