All About Holiday Fest in Key West

With the holiday season quickly approaching, you’re likely considering how you’re going to spend this particular time with the ones you love most. You could stay home to celebrate, but most of the United States experiences frigid temperatures that make you want to snuggle up at home instead of heading out to see your family. Instead, why not retreat to our Key West luxury rentals and enjoy the holiday season in the warm Florida sunshine?

When you spend the holidays in Key West, you don’t have to worry about giving up any of your family traditions. You can come here to build brand-new traditions that everyone is sure to love! One of the best ways to spend this time in Key West is by attending the Holiday Fest. Read on to discover why this is easily one of the most popular Key West events in the winter!

What is Holiday Fest?

Holiday Fest is your ultimate opportunity to experience how magical Christmas can be in Key West. During this Key West festival, you’ll be able to explore the island, mingle with the locals, and attend a wide range of festivals that guests of all ages are sure to enjoy. Holiday Fest Typically spans throughout December and even goes a little bit past Christmas Day, so no matter when you’re visiting during the holiday season, you’ll be able to take part in the festivities. Best of all, since there are so many different events happening on other days, you can easily fit them into your itinerary and don’t have to feel pressured to attend every single happening.

Holiday Fest Event Schedule

What things to do in Key West can you expect during Holiday Fest? The 2021 schedule has been officially released, so let’s check out what you can expect!

No holiday festival would be complete without a parade, which is why you should make every effort to attend the Key West Lighted Boat Parade on December 11 at 8:00 pm at Schooner Wharf! This incredible event isn’t your typical parade; instead of watching the traditional floats head down the street, guests flock to the water to watch themed boats float down onto the Key West Bight and Harbor. There’s no doubt that this is one of the most unique and creative events you can hope to attend in Key West, and it’s one that kids and adults alike will love! This will be the 28th annual installment of this event, so be sure to come out and support this local staple.

key west christmas tree with sign reading "gone to the beach..."

Are you attending a more traditional parade? Key West has that, too! The Hometown Holiday Parade is a free event that draws locals and visitors alike to see the incredible floats and, of course, Santa Claus himself! Typically, this parade will start on Truman Avenue at White Street, proceed down to Duval Street, and end at Eaton Street. This year, the Hometown Holiday Parade takes place on December 04!

If you want to see a bit more of the downtown area, consider joining in on Old Town Trolley’s Holiday Light and Sights Tour a variety of weekends throughout December including, December 12 – 17, 20 – 23 & 26. This holiday tour typically lasts one hour and takes you all across the island, allowing you to see the most beautiful lights of Key West as you roll down the street. If your schedule permits, this could be a great way to start your vacation since you will be getting a look at the island as a whole.

Photo from Unsplash

If you’d instead explore the area on your own time, consider coming out to the Harbor Walk of Lights with begins on November 24. This event allows you to walk along the Key West waterfront as you please, look at the gorgeous lights along the water, and get to know a little bit more about Key West and its history. In 2020, the Harbor Walk of Lights featured a fascinating nautical theme that truly got to the heart of the maritime history of Key West.

There are quite a few Holiday Fest events that are typical installations that you can expect to see. For instance, many of the most popular local restaurants tend to have a Christmas celebration of their own. In the past, there has even been a Holiday Classic Car Show, which takes place this year on December 5 at the corner of Greene and Elizabeth Streets! There is also an excellent chance to attend incredible musical performances, a fun Christmas-themed market, and a holiday movie screening. If you plan to visit Key West this holiday season, do some quick research beforehand to see what events will happen during your trip. 

How to Attend

We’ve talked about many fun events that you have the chance to attend this winter, but how exactly do you do so? That’s the best part! You can pick and choose exactly which events you want to attend, and many of the events are either free or have a very minimal entry fee. For instance, attending any one of the parades in Key West is a free endeavor. If you’re planning to participate in an event at a restaurant or another private venue, check with that establishment about admission fees.

No matter what event you’re planning to attend, consider if you can get there without driving your car. Often, parking can be a challenge, and it will be less of a headache if you can find another mode of transportation. Luckily, our Key West rentals are often within walking distance of the most popular things to do during Holiday Fest! Otherwise, you might consider renting a bike or a golf cart to get around the island.

Plan Your Next Stay

If you’re planning to head South for the winter, consider staying with us on the gorgeous island of Key West. We can help make sure your family has a holiday celebration that they’ll never forget! To learn more about our Key West vacation rentals and start planning the ultimate holiday getaway, contact us today!

Stay with Key West Vacation Homes

No matter what your holiday celebration in Key West might entail, Key West Vacation Homes is here to help make sure that you have the time of your life with the ones you love most. Your comfort and safety are our number one priority, which is why we’ve especially designed our places to stay in Key West with our guests in mind. You’ll always have access to incredible amenities such as spacious bedrooms and bathrooms, high-speed Internet access, multiple flat-screen TVs, and more. We use thorough cleaning processes between every booking and are happy to answer any questions you might have about our properties.

In addition to all you can find in our vacation rentals, you’ll also have access to the most dedicated passionate customer service team in Key West. We love where we live and work, and we are happy to spread our knowledge and recommend the best things to do during your trip. If you ever have a question or concern while staying with us, our team is never more than a phone call away.