11 Fun and Festive Things to Do in Key West in December

One of my favorite winter destinations in the United States is Key West, Florida, the last island in the Florida Keys.

This is a guide to visiting Key West in December. It will showcase some of the best things to do during December in Key West (and then some!). 

If you have any suggestions for things to do in Key West in winter, particularly in December, please let us know in the comments!

And click here if you’re looking for the best stops on a Miami to Key West road trip.

Why You Should Visit Key West in Winter

Florida’s Key West is a magical island where anything goes as long as it’s fun and peaceful. And you can find some amazing food (like key lime pie!) there.

Key West is the last island in the Florida Keys, a chain of islands that stretches south into the Florida Strait.

I have been to the Keys countless times, and it’s one of my favorite places in the US. It is also one of the cheaper places in Florida – if you plan your trip ahead!

Geographically speaking, Key West is the southernmost point of the contiguous United States and is closer to Cuba than it is to Miami.

Key West is connected to the mainland by US Route 1, a long highway that connects all of the Keys and runs up the entire US East Coast (and through my hometown in Virginia!)

Every year, Key West lures in over two million visitors—some tag on the trip along with a Disney trip, and others just come in conjunction with a trip to Miami.

And some just come to discover the best key lime pie in the Keys!

But almost everyone comes to enjoy its year-round sunshine and the party lifestyle that the island is renowned for. 

The vibe on the island is super chilled out with an ‘anything goes’ kind of attitude.

Duval Street, the city’s main thoroughfare, is crammed full of cool bars and eateries where you can enjoy everything from a Landshark beer in Jimmy Buffett’s Margaritaville to devouring a conch sandwich at one of the many eateries along the street.

Even though Key West is pretty much amazing all months of the year, if you are looking for an alternative place to spend some time during the holiday season, it is probably one of the best places you can go.

There are plenty of things to do in Key West in December and the rest of the winter.

The city and island pride themselves on their alternative way of living, as their motto is “One Human Family”. You can also find many LGBT festivals and many gay hotels in Key West, making the island the perfect getaway for all travelers.

Interestingly, there are 25,000 people calling the island home and you will even find roosters roaming the island freely. Welcome to the craziness of Key West!

This guide will take you through the best things to do in Key West during December. If you feel I have forgotten anything, please leave a comment below! 

Weather during Winter in Key West

Key West has a tropical climate where temperatures remain pretty stable throughout the year, with only a few degrees difference between the hottest and coldest months of the year.

In Key West in December, you will find comfortable temperatures with an average daytime high of 76°F (24.5°C).

This temperature is perfect for chilling out on the beach or hanging out on the terrace of a bar, sipping a cocktail.

December also falls outside of hurricane season which runs until the end of November (though late hurricanes can occur).

The month of December also falls outside of the rainy season despite the likely possibility that you may experience infrequent showers that can occur in the morning or evenings in many tropical places.

How to Get to Key West

There are three main ways to reach Key West: by plane, boat, or car.

The most common way and, in my opinion, the best way is to take the 165-mile Florida road trip from Miami through all of the Keys, where you can stop off on each of the different islands and enjoy what they individually have to offer.

The drive to Key West is also incredibly stunning as you go from island to island over bridges that cross the water between each.

The journey is doable in a day, including a stop-off on one or two of the islands.

READ MORE: Best stops in the Florida Keys on a Miami-Key West road trip

Alternatively, from some airports in the US, you can fly to Key West. Do check flight availability, as it can be seasonal.

The Key West Airport is small and supports only domestic flights, despite being referred to as an international airport. Only smaller passenger planes can land at the airport, as the runway is relatively short.

If you are on a cruise from Miami, many ships will stop off at Key West as they head down into the Caribbean.

Since the city and island are small and compact, it makes for a great port stop because you can experience a lot that the island has to offer in such a short time. I still advise staying there a little longer, however.

Best Things to Do in Key West in December

1. Celebrate New Years

There are many places to celebrate the coming of the New Year in the US, but none are quite as weird and wonderful as Key West.

As those in the northern states have to endure frigid temperatures and awful weather, Key West is bathed in warm sunshine, meaning you can spend the early part of your day chilling on the beach or having a few pre-game drinks in the heat.

During the day, there is also the annual dachshund march, where hundreds of little sausage dogs saunter down the street.

While destinations such as Times Square in New York have the traditional ball drop, Key West has its own take on these holiday traditions, and that is pretty cool.

At the Bourbon Street Pub, you will find the first alternative ball drop where ‘Sushi’, the famous local drag queen, is lowered to street level in a giant, red high-heeled shoe.

At the historic harbor, the New Year’s celebrations involve the dropping of a Pirate Wench.

Finally, at Sloppy Joe’s, you can see the lowering of a conch shell, completing the trio of outlandish ways the New Year is announced.

The party continues into the wee hours of the morning in the streets and bars… all with nighttime temperatures averaging at a pleasant 67°F (19°C)!

2. Lighted Boat Parade

The annual Lighted Boat Parade is Key West’s fun and alternative take on festive lights and decorations.

Each year, the boat owners, no matter the size of the boat or type, select an individual theme and deck their boats with lights and decorations to create a fantastic, floating parade.

From kayaks to schooners, they each float past a panel of judges in an attempt to win the award for the best lights. Spectators of the event can enjoy an evening of joy and fun.

The evening starts off with viewing the lights of the harbor with a walk along the waterfront. Once the parade starts, the party atmosphere kicks off with boat owners sailing past while throwing beads and candy out to spectators.

In the warmth of the tropical evening, a calypso band will play classic Christmas songs and the boats will shun traditional Christmas norms for festive manatees or dolphins.

3. Holiday Historic Inn Tour

Throughout Key West, you will find some fantastic historical buildings built in interesting architectural styles. During the holiday season, these lovely buildings take on a whole new level of beauty as they deck themselves out with lights and decorations for the festive period.

Over two nights, you can visit each of the buildings and enjoy their lights, along with some little treats and festive cheer.

Each night features a different selection of buildings, with free transport available between them, although you can also transport yourself between the locations for a nice bike ride or walk to fully appreciate the warm evenings.

There is a small fee for participating in the tour, but the money raised goes to helping to keep the buildings in good shape and any spare change supports projects within the local community. 

Tour date: check back later for 2024 dates!
Price: ~$40 per person

4. Stock Island

While much of the US freezes and outdoor food markets and festivals have shut down until the spring thaw, Key West’s Stock Island springs into action to fill the void.

The main part of Key West focuses on tourism and the stereotypical party scene, but Stock Island is the more rustic, residential backbone of Key West.

Often referred to as the Brooklyn of Key West, the area was historically a shipping-focused, working suburb of the city, where trading ships would dock.

Now, it is more focused on the fishing industries with the fishing boats and trawlers landing their catch there.

Like Brooklyn, this area is becoming an artistic hub with creative studios popping up. Take a self-guided mural tour or pop into the many artists’ studios and antique shops. There is also an amazing food scene there, so make sure to grab a bite while you’re there.

Take a Key West Day Trip

5. Visit Bahia Honda State Park

One of the most beautiful places in the Florida Keys is Bahia Honda State Park, a remarkable Florida state park and my favorite place in the Florida Keys.

Just a short drive from Key West, it makes for the perfect little getaway from the craziness of Duval Street.

Spend time wandering through the island, checking out the unique nature and stunning beaches. The waters around the island are ideal for swimming since the water stays warm all year round.

The pristine waters are also a great place to enjoy snorkeling, with plenty of marine life calling the shores around the island home.

Alternatively, you can scour the island trying to spot one of the many iguanas that call it home. Even though they are there, they are not always easy to see.

My favorite thing to do in Bahia Honda is to find a place to chill away from others and fully enjoy the beauty of the island and the vibrant blue waters that surround it.

Contrasting to the beautiful nature, you can find large sections of the old railroad that once was built in an attempt to connect Key West with the mainland before being destroyed by a hurricane.

The park is open from 8 AM until sundown. Click here for more info about Bahia Honda.

In addition, if you walk all the way over to the edge (southern) edge of the island, you can view the old bridge which has a part taken out.

There is a concrete wall there that now has a fence on it where you can sit and you will often see iguanas on land and stingrays and various fish in the sea. 

I used to sit here and write for hours during the day long before they put a fence up.

6. Day Trip to Islamorada

Halfway between Key West and Miami, you will find the area of Islamorada, a town that is spread out over six of the Keys. There are many things to do in Islamorada that make it a worthwhile day trip!

Islamorada is the perfect place to enjoy a Key West day trip, or as a way to break up your journey as you travel to and from Key West.

Despite its small population of just over 6,000 people, the town packs a punch when it comes to things to do.

Spend time exploring the Indian Key Historic State Park– the island is accessible by boat and is home to an interesting collection of relics from the 1800s salvaged from wrecks that lay off the coast of the Keys.

Alternatively, Islamorada is world-famous for sport fishing with a huge number of fishing vessels available.

Take a break from exploring and fishing at the Islamorada Beer Company where you can enjoy some refreshing, local craft beers. 

The Florida Keys Brewing Company is also located in Islamorada. Also, Wahoo’s Bar and Grill is fantastic and cheap for seafood tacos.

7. Day Trip to Marathon

In the middle of the Florida Keys and spread over 13 of the islands, you will find the small city of Marathon.

The little city is another great place to escape the craziness of Key West and enjoy some laid-back island life on one of the many beaches or waterfront restaurants.

Along with beautiful beaches and lovely parks, Marathon is home to some of the best water-based activities in the Keys.

From sport fishing to scuba diving, there is plenty to do out in the ocean. The reefs around the city are teeming with life with plenty of fish and loggerhead turtles frequenting the area. The latter uses some of the beaches around the city as their nesting grounds.

On the islands themselves, you will have plenty of other life with some unique and rare birds frequenting the skies and trees in the parks throughout the city. It is one of the best places to spot the cute little Antillean Nighthawk.

A day trip to Marathon from Key West is definitely a great option for something to do in Key West in December (or any time of the year!)

I often stay there when visiting the Keys to save some money.

8. Go Snorkeling

The Florida Keys are home to North America’s only living coral barrier reef and it is one of the must-see sights from Key West.

To make the most of the coral reef, I recommend taking a snorkeling tour out to the best locations on the reef where you can meet many of the fish that call this natural ecosystem home.

The Key West 3-hour coral reef snorkeling tour is an amazing tour that speeds you out to the stunning coral reef on a comfortable catamaran where you’ll have time to snorkel admiring the fish and coral. 

You will be fitted out with some of the best snorkeling gear on the market before your first swim. Refreshments are included throughout the trip but alcohol cannot be consumed until the snorkeling session has been completed.

The tour is only suitable for those who can swim, if you cannot swim, you will not be allowed into the water.

>> Click here to check rates and availability for a snorkeling adventure

9. Dry Tortugas National Park

Off of the coast of Key West is one of the most naturally beautiful and least visited National Parks in the US, Dry Tortuga. Dry Tortugas National Park consists of several islands, coastal waters, and stunning coral reefs.

Along with the natural elements of the park, there are some historical monuments and relics, such as the Jefferson Fort, the largest masonry building in the Western Hemisphere. 

Besides visiting the historic structures, you can also spend your time swimming, snorkeling, kayaking, fishing, birdwatching, or camping! The national park is only accessible by boat or seaplane.

Visiting Key West and Dry Tortugas in December is wonderful because the tropical heat isn’t as strong in winter as it is during the summer months.

Working Hours: open all week
Entrance fee: $15 per person, under 16 years of age – free

10. Sunset Cruise in Key West

Sitting at the end of a long chain of islands and fully surrounded by water, Key West is one of the best places to watch both the sunrise and the sunset.

However, the sunset might be the most spectacular as the sun lowers into the sea and turns into a ferocious orange ball turning the sky a range of colors. Trust me, I’ve experienced this several times!

One of the best ways to enjoy the sunset is to hop aboard a boat that can take you out into the turquoise waters that surround the island.

After setting sail, you will have the chance to enjoy drinks and snacks as the boat glides gracefully through the water.

Keep an eye out for various sea creatures such as dolphins and turtles while you’re on your journey!

As the sun sets, sip a glass of Champagne and take in the unbelievable beauty of the sun dropping into the sea and stars coming out in the clear night sky.

Under the light of the stars and the moon, you will sail back to the dock where you can carry on enjoying the festive party atmosphere on Duval Street.

>> Click here to check rates and availability for a sunset cruise in Key West

11. Waterfront Brewing Company

There are several little breweries in Key West where you can down a festive beer.

The Waterfront Brewery has one of the best ranges of beers on the island with rotating taps highlighting various limited-release beers along with some of their core line.

The harbor-side brewery is a great place to sit before the Lighted Boat Parade or to simply watch the sunset that day.

In addition to great brews, they serve up hearty food, including delicious seafood dishes. Tours of the brewery are available and you will get to try a range of beers that are in production and learn all about the brewing process.

If there is no space available at The Waterfront Brewery, check out First Flight Island Restaurant and Brewery, which claims to be the southernmost microbrewery in the US.

They also have a great range of core beers that they have spent time perfecting, along with a great selection of food.

Address: 201 William St, Key West

Where to Stay in Key West

There are several options of where to stay in Key West and I have crashed in multiple places there throughout the years. 

Here are some of my recommendations for where to stay for all budgets:

• Opal Key Resort & Marina (Luxury)
• Silver Palms Inn (Mid-range)
• Southwinds Motel (Budget)

December in Key West – Commonly Asked Questions

Can you swim in Key West in December? Yes, you can swim in Key West in December as the waters remain warm and the temperatures are still around 78F (or 26C).

However, storms can still pass through, making the weather more unpredictable.

What is there to do in Key West in December? Key West is still up and running in December and there are plenty of things to do.

You will have holiday festivals and light shows, as well as the usual activities you see at other times of the year.

How warm is the water in Key West in December? The water is around 72 °F in Key West in December and most of the winter.

This is warm enough for northerners to enjoy, but someone from a milder climate may find it too cold to swim in.

Is December a good time to visit Key West?

If you’re looking to beat the summer crowds but still experience Key West during a fantastic time of the year, yes, you should definitely visit Key West in December or during the winter months!

You’ll find so much to do from snorkeling, and checking out one of Florida’s most iconic lighthouses, to drinking a craft beer to ring the New Year in!

I have spent many winters in Florida and the beaches and warm temperatures help combat the winter blues – especially during the holiday season! 

We hope this guide helped encourage you to book that December Key West trip!

Please let us know if you have any additional questions by leaving a comment below! Click here if you are going to be making a stop in Key Largo along the way!

More South Florida Travel Guides

• Miami to Key West itinerary
• Best key lime pie in Key West
• Miami jet ski tour
• Islamorada attractions and places to visit
• Things to do in Marathon FL
• Things to do in Key Largo
• Day trips from Miami
• Best things to do in Miami
• Small towns in Florida
• Best Florida lighthouses
• Florida Keys golf courses
• Weekend in Key West itinerary

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