Each winter, when the cold settles in across upstate New York, we start to feel it.
The snow, the gray skies, the long stretches of winter—it’s beautiful in its own way, but it also makes us want to get out and explore something different.
So each year, we do.
Not by booking a vacation, but by planning a trip.
Because for us, there’s a difference.
We don’t look for one destination to settle into—we look for a journey. A route. A series of places that unfold along the way. And each year, we choose somewhere new.
We also drive for a reason.
It gives us the freedom to take our time, to follow the kinds of roads that aren’t always on a typical itinerary—and just as importantly, it lets us bring our bikes along. Getting out for a ride, exploring a new place on two wheels, and staying active along the way has become part of how we experience each trip.
This winter, that journey took us south.
We made our way from New York through the Shenandoah Mountains, down through the heart of Georgia, and into Florida—eventually reaching the Keys, the Everglades, and the quiet coastal town of Apalachicola.
But what stood out most wasn’t just the destinations.
It was everything in between.
The back roads.
The farmland.
The places we didn’t expect.
To avoid the traffic of I-95 over President’s Day weekend, we chose a different route—following Route 81 through the mountains and continuing south through the center of the country. It turned out to be one of the best decisions of the trip.
Somewhere along the way, the landscape began to change.
The mountains gave way to open land.
The open land stretched into farmland.
And Florida revealed a side of itself I didn’t even know existed.
This wasn’t the Florida of beaches and resorts.
This was something quieter. More rural. More real.
And that became a theme of the entire trip.
Southeast Region Travel Guide
This stop was part of a larger journey through the Southeast, where we explored everything from the tropical landscapes of the Florida Keys to the quiet coastal towns along the Gulf. If you’re planning a similar trip or looking for inspiration beyond this destination, visit my Southeast Region Travel Guide, where I’ve pulled together our favorite stops, scenic routes, and travel insights from across the region.
Route Overview: How We Traveled South
Rather than taking the fastest route south, we chose a path that would give us a better experience along the way.
Traveling around President’s Day weekend, we wanted to avoid the heavy traffic along I-95. Instead, we followed a more inland route—one that turned out to be one of the most memorable parts of the trip.
We headed south on Route 81, driving through the Shenandoah Mountains, where the scenery shifted from snow-covered landscapes to rolling hills and open views. From there, we continued through the center of Georgia and into the heart of Florida.
And that’s where things really started to change.
What surprised me most was just how much land there is in this part of Florida—and how much of it is dedicated to farming. It’s not something you often associate with the state, but mile after mile, we passed wide-open fields and agricultural areas that felt completely different from the coastal image most people picture.
One of the most memorable stretches was around Lake Okeechobee.
Instead of staying on the main highways, we took back roads that gave us a closer look at the landscape. It felt quieter, more rural, and far removed from the busier parts of the state.
From there, we continued south into the Florida Keys, where the scenery shifted again—this time to turquoise water, bridges, and the feeling of being surrounded by the ocean.
Main Stops Along the Way
This trip wasn’t about one destination—it was about a series of places, each with its own character:
- Key Largo – Coastal views, biking, and unexpected quiet moments
- Big Pine Key – Wildlife encounters and the unique experience of seeing Key deer
- Everglades National Park – Vast landscapes, subtle beauty, and a different side of Florida
- Nike Missile Site – in Everglades National Park
- Apalachicola – A small coastal town with a working waterfront and authentic charm
On the way back north, we made a few stops to visit family and friends in Georgia and North Myrtle Beach, adding a personal ending to the trip.
The Journey South: Discovering a Different Side of Florida
Before this trip, I had a certain picture of Florida in mind.
Beaches. Palm trees. Coastal towns. Maybe a few busier areas filled with resorts and traffic.
But driving through the center of the state told a completely different story.
As we made our way past Lake Okeechobee and continued south on back roads, the landscape opened up into something I didn’t expect—miles of farmland stretching in every direction. Wide, open spaces. Agricultural fields. Long stretches of road where it felt like we were the only ones out there.
It didn’t feel like the Florida most people talk about.
It felt quieter. More rural. More grounded.
And in a way, more real.
That feeling stayed with us as we continued the trip.
Later, on the drive toward Apalachicola, we saw it again—this side of Florida that exists away from the coastline. Small towns, working land, and roads that don’t show up on most travel itineraries.
It made me realize how much of a place you miss when you only see the highlights.
There’s an entire layer of the country that exists in between destinations—the parts you don’t always plan for, but end up remembering just as much.
And for this trip, that became one of the biggest takeaways.
Not just where we went.
But what we discovered along the way.
Featured Stops from the Trip
While the journey itself was a big part of this trip, the places we stopped along the way each brought something different to the experience.
Rather than rushing from one destination to the next, we took our time—exploring each stop in a way that felt unhurried and intentional.
Here are a few of the places that stood out most.
Key Largo
Our first stop in the Florida Keys offered a mix of coastal views, quiet moments, and time to slow down. From biking along the area to relaxing by the water, it set the tone for the rest of the trip.
Read more:
👉 Biking Key Largo/ An Easy Way to Explore the Florida Keys
Big Pine Key
One of the most unique stops of the trip, Big Pine Key gave us the chance to see Key deer in their natural environment and explore a quieter side of the Keys.
👉 Read more: Biking Big Pine Key/ Key Deer, Quiet Roads, and a Stop at No Name Pub
Everglades National Park
The Everglades offered a completely different experience—wide open landscapes, subtle beauty, and a sense of stillness that stayed with us long after we left.
👉 Read more: Everglades Highlights
👉 Read more: Nike Missile Site in the Everglades
Apalachicola
A quiet coastal town with a working waterfront, Apalachicola felt authentic and grounded—one of those places that doesn’t try to stand out, but does anyway.
👉 Read more: Apalachicola Florida
Why We Travel This Way
Trips like this remind me why we choose to travel the way we do.
For us, it’s never been about checking off destinations or fitting as much as possible into a set number of days. It’s about the experience of getting there—the roads we take, the places we discover along the way, and the moments that aren’t planned.
That’s the difference between traveling and vacationing.
A vacation is often centered around one place. You arrive, settle in, and experience what’s nearby. There’s nothing wrong with that—but for us, it’s the movement, the change in scenery, and the unexpected stops that make a trip meaningful.
Driving gives us that flexibility.
It allows us to take back roads instead of highways. To stop when something catches our attention. To spend more time in a place that feels right—and less in one that doesn’t.
And it lets us bring our bikes along, which has become part of how we experience each destination. Some of our favorite moments come from simply riding through a new place, seeing it from a different perspective, and slowing down even more.
This trip reinforced all of that.
The farmland we didn’t expect.
The quiet towns we hadn’t planned for.
The conversations and small moments along the way.
None of those were highlights you’d find in a guidebook.
But they’re the ones we remember.
Related Read
If this way of traveling resonates with you, you might enjoy:
👉 Traveler vs. Vacationer: What’s the Difference and Which One Are You?
What Stayed With Me
Looking back on this trip, it’s not just the destinations that stand out.
It’s the feeling of the journey as a whole.
The shift from winter to warmth.
The change in landscape from mountains to farmland to water.
The quiet moments in places we hadn’t planned for.
There wasn’t one defining highlight.
Instead, it was a collection of experiences—each one adding something different to the story.
Driving through farmland in central Florida, realizing how much of the state exists beyond the coastline.
Taking back roads that felt far removed from the busier highways.
Finding small towns like Apalachicola that felt grounded and real.
Even the familiar places felt different when experienced this way.
Slower.
More intentional.
More connected to the journey itself.
And maybe that’s what stayed with me the most.
Not just where we went—but how we traveled.
Because in the end, it wasn’t about escaping winter.
It was about discovering something along the way.
Trip Planning Tips for a Winter Road Trip
If you’re thinking about taking a winter road trip like this, a little planning can make a big difference—while still leaving room for the flexibility that makes trips like this so rewarding.
Choose your route intentionally
Avoiding I-95 over a busy holiday weekend made a huge difference for us. Taking Route 81 through the Shenandoah Mountains and continuing through the center of Georgia and Florida not only helped us avoid traffic—it became part of the experience. The scenery, the quieter roads, and the unexpected stops were worth it.
Leave room for flexibility
Some of the best parts of this trip weren’t planned. Stops like Apalachicola or even the back roads around Lake Okeechobee came from simply being open to changing the plan along the way.
Pack for more than one climate
Starting in upstate New York in winter and ending in the Florida Keys means experiencing very different weather. Layers are key, especially during the first part of the trip.
Bring what helps you enjoy the journey
For us, that meant bringing our bikes. It gave us another way to explore and stay active, especially in places like the Keys. Think about what adds to your experience and build your trip around that.
Plan your stops—but don’t overfill your days
Having a general idea of where you’ll stop helps with flow, but leaving space in your schedule allows you to slow down and enjoy each place without feeling rushed.
Look beyond the obvious destinations
Some of the most memorable parts of this trip came from places we hadn’t planned—rural farmland, quiet roads, and small towns that don’t show up on most itineraries.
Explore More
If you enjoy this style of travel—slowing down, taking back roads, and discovering places along the way—here are a few more stops from this journey:
- 👉 Key Largo Highlights: Coastal Views, Biking, and Hidden Gems
Turquoise water, quiet moments, and a different pace in the Florida Keys - 👉Biking Key Largo/ An Easy Way to Explore the Florida Keys
- 👉 Biking Big Pine Key: Key Deer, Quiet Roads, and a Stop at No Name Pub
A unique stop where wildlife and back roads come together - 👉 Everglades Highlights: Scenic Stops Along the Road to Flamingo
Wide-open landscapes and the quiet beauty of the River of Grass - 👉 Nike Missile Site: A Hidden Cold War Landmark in the Everglades
An unexpected piece of history tucked into the landscape - 👉 Apalachicola Florida: A Quiet Coastal Town Off the Beaten Path
A working waterfront town that feels authentic and unchanged
Stay Connected to the Journey
If you enjoy discovering places like these—the quiet roads, unexpected stops, and stories in between—I’d love to have you along for the journey.
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