Wonderful Winter Break Getaways in Florida for Families

WHERE TO GO FOR WINTER BREAK IN FLORIDA WITH KIDS

While the rest of the United States is hunkering down with hot cocoa and bundling up in boots and scarves, we’re still sweating our butts off here in Florida. It’s almost November and I haven’t even thought about whether my kids even own pants or long-sleeved shirts in their current sizes. We’re just trying to survive this heatwave with 100-degree heat indexes.

While I wouldn’t mind a crisp, cool fall day once and a while, most of the country is already dreaming about beach vacations and getting a little more vitamin D. If that’s your family, then Florida is definitely the destination of choice for those upcoming winter breaks at school.

Though it can be the busiest time of year to travel, I always love using those extra days off around Thanksgiving and Christmas to fit a little more travel in.

Our family has road-tripped almost everywhere in Florida, and I can tell you from experience which places are the absolute best for a winter family vacation.

THE FLORIDA KEYS

If you want virtually guaranteed warm weather and tropical island vibes, a road trip through the Florida Keys ending in Key West is probably your best bet.

During our family’s Thanksgiving break last year, we enjoyed a Florida Keys vacation. Though the temps were beginning to cool off in Northern Florida, the Keys were hot, sunny, and wonderful.

We hit Miami, Key Largo, and Islamorada on our way down to Key West to help break up our time in the car with the kids. Along the way, we tried conch fritters, fed giant tarpon at Robbie’s Marina, and did a little souvenir shopping.

In Key West, you can see Ernest Hemingway’s home and writing studio (kids will enjoy meeting his cats’ descendants), wander Duval Street, pose at the Southernmost Point of the continental United States, join a Sunset Celebration in Mallory Square, or visit Dry Tortugas National Park, one of the most remote National Parks in the United States.

This is a great way to feel like your family has splurged on a tropical island vacation without having to get passports.

Further Reading: Key West Family Travel Guide ; Tips for VIsiting Dry Tortugas National Park with Kids

DESTIN

Destin, Florida is a popular beach vacation destination for a reason. The Emerald Coast has some of the most beautiful and family-friendly beaches in the state with soft white sand and generally calm waves.

Besides laying in the sand and soaking up the sun, you can go shopping at HarborWalk Village, dine with gators at Fudpuckers, or play the day away at The Track with an arcade, bumper cars, and mini-golf. There’s also a great museum and aquarium in the area, so you’ll find plenty of alternatives to the beach if the weather’s not great.

One of our family’s favorite Destin activities was going on a dolphin cruise. We used Southern Star Dolphin Cruises, and they also had a Pirate Cruise Option that is specifically geared toward kids. My children loved standing at the side of the boat searching for dolphins and cheering when they found some. We got to see lots of dolphins playing around the boat during our cruise, and the kids even got to sit in the captain’s chair and “drive the boat” for a bit.

If you do happen to get hot weather, you can rent a boat or take a shuttle boat and head out to Crab Island, a sandbar (now underwater) where hundreds of boaters drop anchor and party. There are inflatable water slides, an ice cream man that will bring ice cream right to your boat, and even floating restaurants. Because of the sandbar, the water is super shallow around Crab island, so you can even get out with little ones (of course in proper flotation safety gear).

Destin is a popular vacation spot for families for a reason!

MIAMI

Our family loves visiting Miami! It’s especially beautiful in winter when a little bit of the heat and humidity subside.

What I love most about Miami is that there is such a great variety of activities to choose from. There is an excellent children’s museum, lots of history and beautiful landscaping at Vizcaya Museum and Gardens, aquariums, beaches, walking & biking trails, and heritage neighborhoods like Little Havana and Little Haiti.

Don’t forget that there are 2 National Parks within driving distance of Miami, and one off the coast of Key West. If your family is trying to visit all of the National Parks, Miami is a great home base.

Check out my post on what to do in Miami with kids for more tips!

SANIBEL ISLAND

The winter months are among the best times to visit Sanibel Island. Hurricane season is over and the weather is usually in the mid-70s.

Driving over the causeway to Sanibel feels like entering another world. It’s quiet, family-friendly, and idyllic with palm trees swaying in the breeze and copious seashells lining the beaches.

If you’re sick of winter, this is the spot to sun yourself and soak up some vitamin D. You’ll love the casual atmosphere where you can wear cutoff shorts, sundresses, swimsuits, and flip flops. It’s a nice break from boots and winter coats for those of you who live up north!

There’s plenty to do in nearby Fort Myers if you need a break from the quiet of the island. However, my favorite activities in the area were going shelling shortly after sunrise, and island hopping because we got to spend the day on the water.

Check out the Bailey-Matthews National Shell Museum to learn more about the beautiful seashells you find in Sanibel, or take part in the programs at Sanibel Sea School to do a deep dive into the marine life and ecosystems you’ll find in the area.

Read my complete family travel guide to the beaches of Fort Myers and Sanibel.

TAMPA BAY

Tampa Bay was such a pleasant surprise for our family. I truly didn’t realize how much this big city had to offer. Not only is there plenty to do within the city itself, but it’s also within easy driving distance of St. Pete Beach and Clearwater, or even Disney World.

Winter is a wonderful time to visit Tampa. Warm sunny days and cool nights make for the perfect escape from snow and arctic temperatures.

Visit ZooTampa, ride roller coasters at Busch Gardens, wander the Tampa Riverwalk, take a ride on the Pirate Water Taxi, or play in one of the many splash pads around the city if you happen to get a hot day.

The city is walkable, scenic, and safe, full of young professionals and families.

This is also a great spot to plant yourself if you want to hit a few different cities while you’re in Florida.

Read more in my family travel guide to Tampa Bay.

CRYSTAL RIVER

Crystal River is one of the few Florida destinations our family hasn’t had a chance to visit yet, but I wanted to include it on this list anyway. It’s the only place in the United States where you can legally swim with manatees in the wild, and winter is the best time to do it.

Manatees spend their winter in the warm springs of Florida, and Crystal River is a spot where you can see hundreds (even thousands) of manatees.

Our family went to visit manatees at Blue Spring State Park outside of Daytona Beach, but you can’t swim with them at that location. If you want a once-in-a-lifetime experience, swimming with manatees in Crystal River might be a fun option for your family.

SOUTH WALTON

South Walton, if you haven’t heard of it, is the stretch along Florida’s scenic Highway 30A comprised of 16 individual beach neighborhoods. Some of the iconic destinations here include Seaside (where The Truman Show was filmed), Rosemary Beach, and Sandestin to name a few.

South Walton in winter might not be quite as warm as some of the other destinations here, but it’s definitely one of the prettiest beach destinations I’ve ever seen. Since it’s located on the Florida panhandle, temperatures in the winter are hit or miss. You might get some hot days in the upper 70s or low 80s, or you might get some chilly days in the 60s.

I can guarantee you that South Walton locals won’t be enjoying the beach, though, which means you’ll basically have it all to yourself! (We Florida residents are pretty wimpy when it comes to cold ocean water).

For white-sand beaches, idyllic beach towns, and lots of bike paths for families with older children, South Walton is the new Florida getaway of choice.

HOLLYWOOD / FORT LAUDERDALE

Fort Lauderdale, Florida is another perfect winter getaway. Located in South Florida, the temperatures are usually pretty warm year-round, and it’s a short drive from Miami.

Hollywood, Florida is a smaller city just outside of Fort Lauderdale known for its art scene, wall murals, and surf culture.

The biggest reason I recommend this area is because of one of our family’s favorite hotels of all time: The Diplomat Beach Resort. I would be perfectly 100% happy to spend an entire vacation on the property of this hotel and never leave. They have water slides for the kids, a heated pool, a larger non-heated pool, hot tubs, beach access with umbrellas and beach toys for guests, multiple restaurants, and a great convenience store and bakery.

The Diplomat is part of Hilton’s Curio Collection of boutique hotels, so it has the amenities of a chain like Hilton, but still feels unique and independent. I would highly recommend booking a stay here if you’re just looking for a break from the winter blues and want some sun and sand therapy.

If you do grow antsy, you can explore Hollywood and Fort Lauderdale and go shopping, sightseeing, and strolling along the beach promenades or along one of the many canals.

Check out what to do in Hollywood, FL with Kids, and why I think The Diplomat is the perfect spot for a family getaway.

ORLANDO

Yes, I had to include Orlando in my roundup of wonderful winter break destinations. It’s a popular and cliche spot to visit in Florida for a reason!

Disney World and Universal Orlando are probably the first things that come to your mind when thinking about what to do in Orlando during winter, and you wouldn’t be wrong! These two theme parks are both decked out for the holidays, and you’ll find so much to do with little ones to keep you busy for an entire week! Not to mention that if the weather’s a little cooler, it makes it that much easier to stand in line waiting for rides. (Central Florida in summer can be SWELTERING).

Besides theme parks, my kids loved Coco Key Water Park and the Crayola Experience in Orlando. There are also zoos, aquariums, museums, and 2 malls in the area, so you’ll never get bored!

One thing I love about Orlando is that even though it’s not on a beach, you can easily drive in either direction to quickly get to some of Florida’s most beautiful beaches. (Check out my 13 easy day trips from Orlando for ideas).

NEW SMYRNA BEACH

New Smyrna Beach is an under-the-radar beach town that locals absolutely love. It’s located just south of Daytona Beach, so you’re not guaranteed hot weather when you’re there in winter, but it should still be nice enough for outdoor activities, of which New Smyrna Beach has plenty.

My kids and I loved Smyrna Dunes Park. It cost $10 for our vehicle to enter the park, but it was totally worth it! We didn’t swim much when we were there, and you might not want to either since the water will be cold, but it’s a popular spot for surfers, and we had fun watching them while we built our sandcastles.

You can also drive vehicles onto the beach in certain spots, which might be appealing for families with young kids who don’t want to carry ALL of their beach gear to the sand. This is an actual concern at Smyrna Dunes since it took us about 20 minutes to walk from the parking lot to the beach. There is an intricate system of boardwalks set up over the beautiful protected sand dunes where you can view wildlife.

While in NSB, make sure to hit Flagler Ave when all the local food and drink hotspots are. Grab an ice cream or a smoothie, eat some fresh seafood, or do some shopping for souvenirs.

Don’t forget that New Smyrna Beach is just a short drive from Daytona Beach if you want to add some bigger city adventure to your vacation!

Read what to do in Daytona Beach with kids.

ST. AUGUSTINE

St. Augustine is an excellent winter destination in Florida because there’s so much to do there other than the beach. It claims to be the oldest city in the United States. so you’ll find a ton of historical and educational things to do with kids in town.

Visit the Fountain of Youth Archaeological Park where you can learn about Ponce de Leon’s quest to find the fountain, the local indigenous people, and even drink some of the water rumored to be from the Fountain of Youth (spoiler alert: it tastes like sulfur).

You can also check out Castillo de San Marcos, once used to defend the Spanish settlement against the English, or visit the Colonial Quarter and the Oldest Wooden Schoolhouse. History truly comes alive in St. Augustine.

Take a trolley tour or a ghost tour, stroll along the pedestrian-only St. George Street for some restaurants and shopping, climb the lighthouse, or visit the Alligator Farm.

And if you DO happen to get some beautiful weather in the winter, you can definitely still hit the beach, splash pad, and Anastasia State Park.

Side note: if you’re there around Christmas time (this year November 23 - February 2), you’ll get the pleasure of seeing St. Augustine Nights of Lights where the town is absolutely covered in millions of magnificent Christmas lights.

Read more about what to do in St. Augustine with kids.