Best Things to do in Key West in December

One of the best times of year to visit Key West is over the Holiday season. From Thanksgiving to New Year’s the island offers a lot of activities and fun. But, what are the best things to do in Key West in December?

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Holiday lights start to go up around Thanksgiving. The palm trees are in full glory around the Historic Seaport and Key West Bight. Other areas of the island follow suit. Make plans to grab a cocktail and stroll the streets to see all of the wonderful decorations. Each year, the residents, and businesses, go all out to show off their holiday spirit.

So… let’s dive into some of the fun you can have while visiting Key West

Holiday Historic Inn Tour

Come check out historic homes all decorated with lots and lots of Christmas lights. Tour includes treats and cheer at each stop and trolley transportation is provided, but feel free to walk or bike to each home. Tickets are required (more info here)

Year Round Historic Walking tour (self guided)

Lighted Boat Parade

Schooner Wharf Bar hosts the lighted boat parade every year. It is a crowd favorite for sure. This family fun event starts early (plan 6pm). Head over and enjoy a stroll through the Historic Seaport, shopping the stores and tasting the wonderful food from the many restaurants. But stay for the parade, it’s the Florida Keys and Key West’s tropical tribute to the season. (for date and time)

wreath on light pole

Mallory Square

Of course, no trip is complete without a trip to Mallory Square. Traveling with kids, or a kid at heart? Then plan to visit Santa during the day. As the sun starts to set, head over to shop the local artists’ booths and see the world famous Key West sunset celebration.

Trolleys and Trains

A great way to explore Key West is by one of the Conch Train or Old Town Trolley Tours. These are offered year round, but they have fun themed ones during the Holiday season. Explore the most decorated neighborhoods and maybe even a bit of caroling!

Buy your tickets here

Looking for more fun? Check out the official calendar of events.

Key West Hometown Holiday Parade

So much fun! Floats, bikes, music and so much more. The parade kicks off at Bayview Park, down Truman Avenue, and then Duval Street. Who knows who you might see in the parade!

Holiday Classic Car show

Head over to Conch Republic Seafood Company for their annual car show. Run by the Florida Keys Southernmost Car Club, you can see cars decked out for the holidays.

Parade of Paws

Held annually at Higgs Beach this event supports the Florida Keys SPCA. Costumes are encouraged!

Concerts at the Key West Theater

Offering concerts and events year round, but expect special performances over the holidays. Check the schedule and buy tickets here.

Rudolph Red Nose Run 5k

A great annual event. Who else can say they have run a 5k at the southernmost part of the continental United States? Register here.

Key West Artisan Market

Looking for a great place to Christmas shop? Then look no further than the Artisan Market. Held Sunday mornings, this is the place to see locals selling amazing stuff from gifts to food. You will want to plan your trip around this artisan market. For times and location click here.

Historic Home tours

Be sure to check out the Oldest House and the Women’s Club on Duval St. During the holidays they offer special tours. So cool to see the inside of the Women’s Club all decorated with trees and lights.

Water Activities

I know, you’re saying what?? It’s December. Well, if there are no cold fronts you can plan to spend some time on the water. Parasailing, snorkeling, dolphin watching, and so much more. Take advantage of the sunny days and be out on the water.

Not sure you want to go in the water? One of the best ways to see the coral reef is by glass bottom boat.

The Best Key West Glass Bottom Boat tours

Looking to enjoy a beautiful sunset cruise?

Best Sunset Sail in Key West

Other amazing water activities

what not to miss key west sunset cruise

New Year’s Eve

A very popular night in Key West is New Year’s Eve. Parties, fun, music and so much more can be found. Key West is so popular that CNN broadcasts live from Duval Street every year. Instead of watching the fun… plan to be there in all of the action. There are four ball drops to choose from to ring in the New Year.

  • Conch Shell Drop – outside of Sloppy Joe’s, in the heart of Old Town and Duval Street the party is in the street.
  • Pirate Wench Drop – want to see a Pirate Wench lowered from a schooner mast? Then head over to Schooner Wharf for the fun.
  • Red Shoe Drop – As seen on CNN, Sushi will be lowered in a large red shoe outside of Bourbon Street. A lot of fun!
  • Key Lime Wedge Drop – Sunset Pier drops a giant Key Lime wedge to ring in the New Year.

Oh my… so many choices… I’m thinking you will need to plan multiple vacations to experience all that Key West offers for the Holidays and New Year’s. But, what kind of weather can you expect?

Weather – What to Expect

Well… since Key West has never experienced snow, you can probably bet it will feel very tropical. But, the evenings can be a bit brisk so plan to bring a light jacket. I always check the weather forecast before traveling to make sure my clothes match the expected weather. However, I have been caught and had to go shopping (or did I plan that on purpose???) Either way, no need to pack boots, hats, and gloves for this tropical destination.

Key West weather is very moderate for December. During the day, the average temperature is in the mid-70’s while at night dropping to mid to upper 60’s. It is less muggy in December than in the summer months. Rainy days are a bit behind us (with hurricane season ending in November – but there could always be an outlier) On average, December sees about three rainy days. The water temperature is in the mid-70’s. Overal, warm temperatures, a few days of sunny skies and a bit of cloud cover. Sounds perfect right?

How to Get to Key West

We’ve planned your events and talked about the weather, but let’s plan how you are getting to Key West. Best way is to fly into Key West International Airport and take a cab to your hotel. Parking spots can be really hard to find and probably will have a daily fee. If you need to drive, then plan to be near a public parking garage/lot and plan to pay for parking.

Ultimate Road Trip from Miami to Key West (Best places to stop)

Best Breakfast Places in Key Largo

Key West is one of the best places to be in December. The warm weather, live music, and fun activities are some of the best reasons to escape to one of the warmest places in the winter months. I would even say… it’s the most wonderful time of the year.

key west in december christmas lights at bight

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