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

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One of my favorite winter destinations in the United States is Key West, Florida… the last island in the Florida Keys.  The weather is fantastic, the vibe is chilled and carefree, and there are so many things to do there.  This is a guide to 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!

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

Florida’s Key West is a magical island where anything goes as long as its fun and peaceful.  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.

Things to do in Key West in December - Winter in Key West guide for Travelers (Florida)

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. 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.

Things to do in Key West in December - Winter in Key West guide for Travelers (Florida)

The city and island pride itself on its alternative way of living as its motto is “One Human Family”. Interestingly, there are 25,000 people calling the island home and you will even find chickens 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 please leave a comment below. 

Do You Need a Visa for the United States?

If you’re a passport holder for nationalities needing a US visa in order to enter, do be sure you get your paperwork and documents in order far ahead of time so you don’t miss your Key West trip!  Getting a US visa can be a cumbersome process and you need to ensure you go through the right agencies to do so.

If you have visa-free access to the US, make sure you still get your ESTA.  This ridiculous registration basically makes the US NOT visa-free, but I hear we are expected to do the same in Europe in the future.  I guess that is what we get for making things difficult for other nationalities.

Things to do in Key West in December - Winter in Key West guide for Travelers (Florida)

Do You Need Travel Insurance for the United States?

YES.  I highly recommend getting travel insurance for the US.  The reason?  If something happens, you don’t want to be stuck with $160,750 in bills from a simple ambulance ride (okay, that is an exaggeration, but we all know that US healthcare bills are astronomical).  We recommend SafetyWing, a Norwegian company that offers affordable coverage with widespread policies.  We use them ourselves and love them!

>> Click here to get a USA travel insurance quote

Weather in Key West in Winter

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 24.5°C (76°F).  This temperature is perfect for chilling out on the beach or hanging out on a terrace of a bar sipping a cocktail.

Things to do in Key West in December - Winter in Key West guide for Travelers (Florida)

December also falls outside of hurricane season which runs until the end of November (of course, 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 road trip from Miami through all of the Florida 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.

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 the airport being referred to as an international airport. Only smaller passenger planes can land at the airport as the runway is relatively short.

Things to do in Key West in December - Winter in Key West guide for Travelers (Florida)
The old road to Key West

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

Renting a Car in Florida

If someone were to ask me what my favorite road trip in the US is, I would l likely say the route from Miami to Key West.  In order to do this, you need to rent a car!  I have done this several times and it is a blast!  Gas is cheap in the US, too, so it makes the process rather easy and affordable for all travelers.  

If you rent a car in the US, you generally need to be 25.  Some companies will let you be slightly younger though.  

>> Click here to check rental car rates in Florida

Things to do in Key West in December - Winter in Key West guide for Travelers (Florida)

Celebrations and Festivals in Key West in December

Celebrate New Years

There are many places to celebrate the coming of the New Year in the US, but none 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.

Things to do in Key West in December - Winter in Key West guide for Travelers (Florida)

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 heel 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 night time temperatures averaging at 19°C (66.9°F).  Not bad.

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 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.  

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.

Things to do in Key West in December - Winter in Key West guide for Travelers (Florida)

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 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. 

I Love Stock Island Festival

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.

Things to do in Key West in December - Winter in Key West guide for Travelers (Florida)

Like Brooklyn, this area is becoming an artist hub with creative studios popping up. There is also an amazing food scene there. The I Love Stock Island initiative decided to enhance the creativity of the residents and showcase them in the I Love Stock Island Festival, which takes place on the second weekend of December.

Throughout the weekend, there are various events showcasing the fantastic food available from both food trucks and brick and mortar restaurants. There are also spaces for local artists to showcase their work or perform for the crowds. The festival is a great way to see a different side of Key West and fully appreciate the talented locals.

Take a Key West Day Trip

Day Trip to Bahia Honda State Park

One of the most beautiful islands in the Florida Keys is Bahia Honda, a remarkable 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.

Things to do in Key West in December - Winter in Key West guide for Travelers (Florida)
Things to do in Key West in December – Winter in Key West guide for Travelers (Florida)

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 connected Key West with the mainland before being destroyed by a hurricane.

INSIDER TIP:  There is an entrance fee of $8 per vehicle to enter onto Bahia Honda.  It is so worth the fee.  The park is only opened from 0800-1700, however.  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 that 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.

Things to do in Key West in December - Winter in Key West guide for Travelers (Florida)
If you look over the edge and just wait, stingrays and fish pass by in large numbers

Day Trip to Islamorada

Halfway between Key West and Miami, you will find the area of Islamorada, a village that is spread out over six of the Keys. 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 village 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 an interesting collection of relics from the 1800s which were salvaged from wrecks that lay off the coast of the Keys.

Things to do in Key West in December - Winter in Key West guide for Travelers (Florida)

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. 

INSIDER TIP:  Islamorada Beer Company sells beer and growlers to take with.  Grab some!  They are super refreshing.  Also, Wahoo’s Bar and Grill is fantastic for seafood tacos.

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 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 of something to do in Key West in December (or any time of the year!)

INSIDER TIP:  If you’re looking for a cheaper alternative of where to stay in the Keys but still be within a ‘shortish’ drive of Key West, Marathon has much cheaper accommodation.

Things to do in Key West in December - Winter in Key West guide for Travelers (Florida)

Activities and Excursions in Key West

Snorkeling

The Florida Keys are home to North America’s only living coral 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 Double Dip: 2 Stop Reef Snorkeling Trip is an amazing tour where you will be sped out to the reef on a luxury catamaran, stopping at two different points in the reef to see as much of it as possible. You will be fitted out with some of the best snorkeling gear on the market prior to your first swim.

Things to do in Key West in December - Winter in Key West guide for Travelers (Florida)

On your second swim, you will experience a slightly different, but equally as beautiful snorkel site where more fish will come out and greet you as they swim amongst the coral. As you return to land, you can enjoy complimentary drinks with both alcoholic and nonalcoholic options available.

Refreshments are included throughout the trip but alcohol cannot be consumed until both snorkeling sessions have been completed. The tour is only suitable for those who are able to swim, if you cannot swim, you will not be allowed into the water.

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

Dry Tortuga National Park

Off of the coast of Key West is one of the most naturally beautiful National Parks in the US, Dry Tortuga. Dry Tortuga 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 Fortress, the largest masonry building in the western hemisphere.

The national park is only accessible via boat or seaplane. From Key West, you can take a fantastic boat tour to Dry Tortuga National Park. Visiting Key West in December is wonderful because the tropical heat isn’t as strong in winter as it is during the summer months.

During the 10-hour day trip to Dry Tortuga, you will be taken to the National Park aboard a luxury catamaran where you will have the chance to enjoy breakfast as you cruise through the Gulf of Florida. An onboard guide will talk you through everything you cruise past, learning all there is to know as well as enjoying the epic scenery.

Things to do in Key West in December - Winter in Key West guide for Travelers (Florida)

Once you dock, there is a guided tour of Fort Jefferson.  This will give you the chance to see the unfinished structure. After exploring the fort, you will have free time to peruse the beaches, swim in the sea, and admire the diverse wildlife in the area.

During lunchtime, you can head back to the boat for a buffet lunch that can be enjoyed on the boat at the dock. After lunch, you’ll spend more time exploring before heading back to Key West. 

>> Click here to check rates and availability for a day trip to Dry Tortuga National Park

Sunset Cruise

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 sun rise and the sun set. However, the sunset might be the most spectacular as the sun lowers into the sea 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 aboard a boat that can take you out into the turquoise waters that surround the island. I wholeheartedly recommend booking a sunset sail on a Schooner where you will be taken out to the open sea on a luxury sailboat.

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!

Things to do in Key West in December - Winter in Key West guide for Travelers (Florida)

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

Dolphin Watching 

The waters that surround Key West are a haven for marine life and one of the most majestic animals in the world, the bottlenose dolphin. The dolphins inhabit the area around the Keys year-round and ethical tours are available to go and view them from a safe distance so you will not impact on their daily lives.

The dolphin watching and snorkeling tour from Key West is the perfect way to witness the dolphins in their natural habitat. After spotting the dolphins, the boat will take you to one of the best snorkeling spots on the reef around Key West where you can get acquainted with the other animals that call the waters around Key West home.

On the way back to port, enjoy cold alcoholic and non-alcoholic beverages in the warm, winter sun.

>> Click here to check rates and availability for dolphin watching and snorkeling

Things to do in Key West in December - Winter in Key West guide for Travelers (Florida)

Waterfront Brewing Company

There are several little breweries in Key West where you can down a festive beer. The Waterfront Brewing Company 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 Brewing Company, check out First Flight Brewing Company, 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.

Key West Tours Mentioned

I mention a few worthwhile tours of Key West above that might be worthwhile.  Here is a quick reference of the tours that you should take in Key West in December:

Things to do in Key West in December - Winter in Key West guide for Travelers (Florida)

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:

You have made a brilliant choice is you’ve added Key West in December to your holiday agenda.  Seriously… it is one of my favorite places on the planet and has been for two decades!  Please let us know if you have any additional questions by leaving a comment below.

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