The Ultimate Florida Winter Bucket List: 10 Things You Can’t Miss This Year! 

What do you have on your Florida winter bucket list? 

Not sure?

Well, look no further, because I’ve got you covered! 

While other parts of the country are bundled up staying warm and cozy indoors, Florida has the perfect winter weather to check off those bucket list-worthy experiences. 

From the famous Nights of Lights in St. Augustine and a one of a kind Mantee Festival to hitting the slopes—Florida-style, and living out your pirate dreams when Gasparilla takes over Tampa, the Sunshine State is the place to be this winter.  

So, let’s get ready to turn your Florida winter bucket list dreams into reality shall we! 

NikkyJ looking at Christmas tree doing holiday tour in St Augustine Florida. Keep reading to find out everything you need to know about the best Florida winter bucket list.

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1. Experience the Magic of Nights of Lights in St. Augustine, Florida 

If there’s one thing you have to add to your Florida Winter Bucket List, it’s the world-famous Nights of Lights in St. Augustine! 

St Augustine Christmas near downtown. Keep reading to find out everything you need to know about the best Florida winter bucket list.

This isn’t just another holiday light display. This is an out of this world magical experience that takes over the entire historic district of St. Augustine.

Why We Love This for Your Florida Winter Bucket List 

Every corner is twinkling in winter holiday magic from the historic rooftops to the gorgeous palm trees in over 3 million lights

Night of Lights St Augustine, Florida. Keep reading to find out everything you need to know about the best Florida winter bucket list.
Night of Lights in St Augustine, Florida

The businesses stay open late, endless photo ops for incredible memories and festive rides that will take you on a tour through the sparkling glow of St. Augustine 

Holiday with NikkyJ enjoying Christmas in St Augustine standing near the bay next to the fort. Keep reading to find out everything you need to know about the best Florida winter bucket list.
NikkyJ enjoying Christmas in St Augustine standing near the bay next to the fort

And the best part? This iconic event runs for two whole months straight giving you plenty of time to come out and soak in all the holiday magic until the end of January.  

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2. Ring in the Holidays at Mickey’s Very Merry Christmas Party at Walt Disney World 

You must add Mickey’s Very Merry Christmas Party at Walt Disney World to your Florida Winter Bucket List if you love Christmas AND Disney! 

Magic Kingdom Christmas Tree in Main Street USA. Keep reading to find out what are the best things to do on your Florida winter bucket list.
Magic Kingdom Christmas Tree in Main Street USA

This Disney Christmas Party will take place on select nights from the beginning of November until the last days before Christmas. It is the perfect way to kick start your winter holiday vibes.  

Why We Love This for Your Florida Winter Bucket List 

Disney Characters come alive in Mickey’s Once Upon a Christmastime Parade!

Snow falls on Main Street, U.S.A, there are seasonal treats galore, free milk and cookies throughout the party and so many magical Disney Christmas decorations. 

Cinderella Castle decked out in white Christmas Lights Magic Kingdom. Keep reading to find out what are the best things to do on your Florida winter bucket list.

It’s a winter wonderland of holiday cheer that is sure to lift your spirits this season. 

3. Get Your “Fair” Share of Fun at the Florida State Fair

Is there anything more epic than the Florida State Fair in Tampa, Florida!  

Ferris wheel glowing in all diffferent colors in the night. Keep reading to find out what are the best things to do on your Florida winter bucket list.

This annual celebration is almost 2 weeks of classic Florida fun in February honoring the spirit of Florida and its farming heritage.   

Nikky at Florida State Fair in Tampa. One of the best things to add to your Florida winter bucket list.
Our Editor, NikkyJ, at the Florida State Fair in Tampa, Florida.

Why We Love This for Your Florida Winter Bucket List 

Endless midway rides of thrills and laughs that will have you spinning with excitement, competitions, fascinating exhibits, live entertainment, and so many farm animals. 

Be sure to come hungry! There is no shortage of mouthwatering and fun foods to indulge in from huge turkey legs to deep-fried snickers and wild new creations to try.  

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4. Celebrate the Manatees at Blue Springs State Park 

The winter is the best time to see manatees in Florida and Blue Springs State Park does not disappoint.  

Crystal River Florida Manatee under water. Keep reading to discover what are the best things to do in the winter in Florida.

From mid-November to March these gentle giants flock to the perfect waters that remain at 72° year-round.  

Why We Love This for Your Florida Winter Bucket List 

Every winter, these lovable sea cows make their great migration to the warm waters and Orange City, Florida puts on a one-of-a-kind Manatee Festival to celebrate at the end of January. 

One of the best things about this Florida winter event is that there is a free shuttle bus to Blue Spring State Park to see the famous Florida manatees. 

Group of manatees in the water. Keep reading to discover what are the best things to do in the winter in Florida.

Here’s what you can expect at the Manatee Festival at Valentine Park in Orange County: 

  • World Famous Disconnected K9’s Frisbee Show 
  • Walk-on-water balls, rock climbing, balloon man shooting gallery 
  • Dancing and live entertainment 
  • Arts & crafts show with over 100 booths 
  • Children’s area with shows, face painting, games  
  • Environmental Conservation Displays 
  • Sand sculpting 
  • Rides and more! 

The festival is a fund raiser for the Orange City Community with the proceeds benefit the “Friends of Blue Spring State Park,” educational scholarships, and other Greater Orange City Organizations. 

5. Unleash Your Inner Pirate at Seminole Hard Rock Gasparilla Pirate Fest in Tampa, Florida 

Be sure to set aside the entire day and night for this Florida winter bucket list. The Seminole Hard Rock Gasparilla Pirate Fest is a full day and night swashbuckling adventure.  

Dog in Pirate Costume for Gasparilla Festival. One of the best free things to do in Tampa, Florida. Keep reading to discover what are the best things to do in the winter in Florida.

The festivities kick off with the Gasparilla Invasion Brunch at the Tampa Convention Center with a bounty of food and drink along with booming cannons from the Jose Gasparilla.  

Why We Love This for Your Florida Winter Bucket List 

Then during the Gasparilla Invasion, you have a mind-blowing flotilla of hundreds of vessels accompanied by the dramatic arrival of the infamous pirates of Ye Mystic Krewe of Gasparilla.  

Pirate with his macaw looking out over the pirate deck. Keep reading to discover what are the best things to do in the winter in Florida.

Next up is the iconic Gasparilla Parade of Pirates, where Tampa’s streets come alive in pirate pride and victory!

But the fun doesn’t stop there—the celebration carries on into the night with Gasparilla Pirate Fest stage performances at both Curtis Hixon Waterfront Park and MacDill Park.  

Tampa turns into a full-on pirate party you won’t want to miss! 

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6. Hit the Slopes at WinterClub Indoor Ski and Snowboard in Winter Park, Florida

Are you still waiting to cross skiing or snowboarding off your bucket list? Well, the wait is over and you don’t even have to leave sunny Florida to do it. 

The WinterClub in Winter Park, Florida, is the ultimate spot to experience the thrill of real skiing and snowboarding with a twist—virtual reality 

Why We Love This for Your Florida Winter Bucket List 

This virtual reality feels just like shredding real snow on their soft nylon tufts giving you all the excitement without the frostbite. 

They offer private or semi-private perfect for you and your bestie or even group sessions for all ages over 6 years of age, abilities and skill levels.

It even includes the instructor, boots, helmet, poles, skies and snowboards. All you need to bring is your sense of adventure.  

Don’t forget to check out Snowcat Ridge, Florida’s ONLY Alpine Snow Park!

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7. Step Into a World of Creativity at Epcot’s International Festival of the Arts 

Epcot’s International Festival of the Arts is the perfect blend of excitement for all your senses. 

2025 Epcot Festival of the Arts Disney World Spaceship Earth with NikkyJ. One of the best things to add to your Florida winter bucket list.

It combines the love of food, art, music and Disney all in one place! 

Why We Love This for Your Florida Winter Bucket List 

I love that you get a get a little Festival of Arts passport and you can explore the festival at any pace you want.  

2025 Epcot Festival of the Arts Disney World Pop Eats Food Tomato Soup and Grilled Cheese. One of the best things to add to your Florida winter bucket list.

Even if you aren’t into artwork, you will still love this winter festival in Florida!

You can eat your way through the festival with all the colorful cuisine, watch art defying gravity shows, hear Disney songs like you have never heard before and be amazed at incredible fireworks. 

2025 Epcot Festival of the Arts Disney World Rainbow Cake. One of the best things to add to your Florida winter bucket list.

For a no obligation, FREE Disney Vacation Quote you can fill out the form with The Park Prodigy by Clicking HERE!

8. Visit America’s Southernmost Point in Key West, Florida 

Winter in Key West brings comfortable temperatures, making it the perfect time to check it off your Florida winter bucket list. 

Key West, Florida Southernmost Point 90 miles to Cuba famous statue. Keep reading to discover what are the best things to do in the winter in Florida.
Key West, Florida

Stroll along Duvall Street that goes from Mallory Square to the Southernmost Point marker and snap a photo to remember at this famous spot.  

Step back in time to The Oldest House in South Florida, browse the shops and uncover unique treasures, go shark watching, or bask in the beauty of one of the gorgeous little beaches.   

Why We Love This for Your Florida Winter Bucket List 

Don’t miss the nightly sunset celebration at Mallory Square—it’s a Florida bucket list experience!  

Key West, Florida Santa Maria Resort pool area. Keep reading for the full guide to the ultimate Florida winter bucket list.
NikkyJ and friends having fun in the pool on their holiday in Key West, Florida at Santa Maria Resort

This iconic Key West tradition is all about soaking up those one of a kind sunsets while chilling in the laid back atmosphere of street performers, live music, and irresistible food vendors. 

9. Discover the Beauty of Florida’s Natural Springs

February is hands down one of the best months to hit up Florida’s gorgeous springs

Crystal River Florida Three Sisters Springs Drone Shot. Keep reading for the full guide to the ultimate Florida winter bucket list.
Three Sisters Springs

With fewer crowds and water temperatures not too cold, you’ll have the perfect chance to cross this off your Florida bucket list. 

It’s the ultimate time to soak in the natural beauty, make some unforgettable memories, and snap some incredible photos without the crowds getting in the way. 

Why We Love This for Your Florida Winter Bucket List 

Florida has an abundance of natural springs to escape to. There is Silver Springs in Ocala, Weeki Wachee Springs, Rock Springs Ginnie Springs in High Springs and Devil’s Den Prehistoric Spring in Williston. 

Ichetucknee Springs Florida. Keep reading for the full guide to the ultimate Florida winter bucket list.
Ichetucknee Springs

Ichetucknee Springs is an epic place to go tubing, so much so that the Travel Channel made it “Florida’s Best Tubing River.” 

Kayaking on Three Sisters Springs, Florida. One of the best things to add to your Florida Winter Bucket List. Keep reading for the full guide to the ultimate Florida winter bucket list.
Kayaking on Three Sisters Springs, Florida

One of my personal favorites is Crystal River and Three Sisters Springs. It’s not just the manatees that make this spot epic but the breathtaking natural beauty too. 

Kayaking on Three Sisters Springs, Florida. One of the best things to add to your Florida Winter Bucket List. Keep reading for the full guide to the ultimate Florida winter bucket list.
Kayaking on Three Sisters Springs, Florida

I recommend renting a kayak since the waters are so calm and crystal clear, it’s like gliding on glass through some far away tropical paradise.  

10. Savor the Sweetness of Florida at the Strawberry Festival

If you’re looking for a sweet way to end your Florida winter then the Florida Strawberry Fest in Plant City, Florida may just be the celebration you are looking for.  

Strawberry Picking at Southern Farms Orlando Florida Clermont. Keep reading for the full guide to the ultimate Florida winter bucket list.

There will be rides, youth livestock shows, The Neighborhood Village with handcrafted and homemade items.

It all feels like pure Americana and a throwback to the days of celebrating harvest, fun and festivities. 

Baby Goat Yoga at Wildflower Farm Orlando Florida. Keep reading for the full guide to the ultimate Florida winter bucket list.

Plus, there’s live entertainment, parades, marching bands, and, of course, all the strawberry goodness you could ever dream of! 

Why We Love This for Your Florida Winter Bucket List 

This Florida Winter Bucket List event is totally worth the trip, just to catch all the insanely fun and unique contests. 

Best Restaurant in Brandon, Florida Datz Strawberry Pancakes. Keep reading for the full guide to the ultimate Florida winter bucket list.

Deep-Fried Strawberry Pie on a Stick Relay, Strawberry Pizza Pie Eating Contest to a Shoebox Float Contest and baby contests of decorated diapers, diaper derby and a baby parade, they’ve got it all and then some. 

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Wrapping Up Your Perfect Florida Travel Itinerary for the Winter 

Well, there you have it Hipsters! 

Key West, Florida with NikkyJ in front of the beautiful blue water and ocean
NikkyJ enjoying the beautiful blue water in Key West, Florida

It’s time to make those Sunshine State dreams come true! I hope this Florida winter bucket list has you excited for your next adventure. 

Best Things to Do in Florida for the Winter
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What’s your favorite thing to do in Florida during the winter? Let us know in the comments section below.

Until next time, Happy Florida Travels Hipster! 

Sarah Jordan Theme Park Writer and Florida Travel Expert Writer

About the Author

Sarah Jordan is a solo traveler enthusiast, professional travel writer, and proud mama to her rescue dog Coconut.

With a love for destinations across the globe, she made Epcot her first theme park and still treasures her EPCOT World Showcase passport to this day.

After finally following her inner wanderlust, she discovered the freedom and empowerment that solo travel brings. 

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