Flying South for the Winter: Why I Spend my Holidays Roasting in Florida

The idea of holiday cheer invokes a certain mental image: sleigh rides through soft snow flurries, sipping scalding hot cocoa to cure rosy cheeks, waking up to icicles and frozen wonderlands. My version of the holidays is a bit different – the only reason you’ll have rosy cheeks is if you forget to put on sunscreen before hitting the beach.

Flying South for the Winter: Why I Spend my Holidays in MiamiTo celebrate the holidays, I always head south to Miami, Florida.

Journeying down to one of the southernmost destinations in the country started out as a quick seven-hour trip down to my hometown during my college years, but it has since become the only place I could imagine celebrating Christmas. It’s more than just seeing my family and old friends – a hot, humid holiday has become my favorite annual escape.

For the next week, I’ll be climbing at Rumbling Bald in North Carolina. It’s going to be beautiful, but I’m already dreading life in the van in freezing weather. That whole winter wonderland thing is totally void when it’s 28º in your van and you wake up with dripping sheets of frozen condensation above your head. Changing into freezing cold underpants and socks in an unheated tin tube is not a joyous occasion, folks.

But it’ll all be worth it, because at the end of the week, I’m making the 11-hour, 800 mile trek down to a place where I’ll spend Christmas Eve eating dinner under palm trees and sleeping with the windows open to catch a breeze.

This year, I’ve got a few outdoor to-dos I’d like to tick off while I’m enjoying winter in Miami:

Boating from Matheson Hammock Marina

When I return home, one of the first things I ask my dad is, “how are the boating conditions?” On a bad year, it’s just a bit too chilly and windy to hit the water – but on a good year, it’s game on. We load up the cooler with sandwiches and fruit, tow our boat out past the mangroves at Matheson Hammock, and jet out into the bay for a day of cruising. That first day of feeling the salty air rush past my face while we speed towards No Name Harbor is one of my favorite moments of freedom (in any season).

Cinnamon roll and a chocolate milkshake from Knaus Berry Farm.Strawberry Picking at Knaus Berry Farm

If you haven’t tasted a homemade cinnamon roll or sipped on a freshly blended strawberry milkshake from this charming farm down in Homestead, you haven’t lived – Knaus Berry Farm is the real deal. A world-famous destination, this family-run institution draws Saturday morning crowds that wait hours for a box of cinnamon rolls. You could catch some sunshine just by standing in line, but I like to make it an outdoors experience by enjoying my milkshake while combing through rows of strawberry bushes and picking my own. If the season is right, you can pick your own tomatoes too.

I really love Knaus Berry Farm because everything is done with old fashioned way. They only accept cash, the family bakes and harvests everything fresh, and you can taste the love in each bite.

Hiking at Everglades National Park

While winter wildlife for most might involve herds of elk and moose sightings, my wintertime animal encounters will take the form of alligators, great blue herons, and manatees. There won’t be any elevation gains during hikes through the swampy terrain, but the sunshine is still enough to make you break quite a sweat. While I adore mountainous landscapes, there’s something special about the tropical waterfront scenery at the Everglades.

Bonus points: Stop at the historic Robert Is Here fruit stand on the way to the park for excellent milkshakes and local produce. You can even knock out some last-minute gift shopping with a large selection of locally made jams, dressings, and edibles.

Biking in Coconut Grove

For years, the first thing I did upon returning to Miami was hopping in my little hatchback and taking a drive down the canopied Old Cutler Road. It’s a fairytale roadway lined with enormous Banyan trees that often create an enclosed tunnel over the pavement. These days, the idea of wasting all that gas seems a bit rude, so I’m trading four wheels for two and riding my bike down my favorite scenic drive. Along the way, Wayside Market provides the ideal pit stop to cool down and refresh.

Napping in my hammock is my favorite outdoor recreation in Miami.Napping in a Hammock

Okay, so maybe this isn’t the most adventurous activity on my winter holiday itinerary – but this is a crucial to-do. Especially enjoyable in the late afternoon when the sun begins to ease up a bit, there’s nothing that relaxes me quite like a long nap on the hammock that sits beside my pool. This is also an excellent opportunity to reflect on all the folks up north who are shoveling snow from their driveway. Ha! 

* Y’all, I’m noticing a trend here – I really like adventures that involve making stops for milkshakes and snacks. Oops!

For most people, winter holiday travel is a suitcase jammed with puff jackets, wool scarves, and thick thermals. For me, it means not forgetting to pack a swimsuit.

Spending the holidays in shorts and sandals isn’t exactly the conventional way to celebrate the season, but boats, hammocks, and beaches have become my version of an annual tradition. It wouldn’t be Christmas if it wasn’t in Miami. My yearly adventure to my hometown has become a sultry solace in a season I otherwise spend shivering and bundled up begging for warmth. Plus, seeing Santa in swim trunks and a Hawaiian shirt is just too good.

Where do YOU head for the holidays?
Do you flock towards snowy destinations, or escape to the south?

*This post sponsored by Nature Valley.

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7 thoughts on “Flying South for the Winter: Why I Spend my Holidays Roasting in Florida

  1. Jillian Bejtlich says:

    I’d just like to say that all of this sounds incredible! I haven’t been to Florida in many many years, but I think you just planned my next trip there for me. Milkshakes, snacks, and the warm outdoors sound so good right about now (it’s 17F out with a foot of snow).

    I’ll personally be taking to the ski slopes on Christmas. So cold and snowy it is, but there will definitely be some hot beverages. =)

  2. Heather Balogh (@AColoradoGal) says:

    Obvi, I’ll fight you on this all day 😉 My parents are headed to Hawaii to spend the holiday with my sis, and I’m staying behind. I couldn’t miss the snow flakes and chilly temps that signal Christmas for me! (But, you did make me want to come visit you and your dad and hang out on the boat!)

    • Katie Boué says:

      How’d I know you’d be the first one to defend a snowy holiday? 😉 And lady, you are always invited to come hang out with my pops and I on the van – you two would get along great. He’s even cooler than I am, haha.

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