Back to Margaritaville: How a One-Week Trip Turned Into a Month-Long Stay
Opening
After our April 2025 trip to Latitude Margaritaville Hilton Head, something stuck with us.
It wasn’t just the sunshine, or the palm trees, or even the laid-back pace that makes you forget what day it is.
It was the feeling that we hadn’t quite experienced it all yet.
A week was enough to get a taste—but not enough to settle in.
The Shift From Visit to Stay
Not long after we got home, the idea started to take shape.
What if we didn’t just visit Margaritaville again…
What if we actually lived there for a while?
We already knew the rhythm. The morning walks. The easy evenings. The kind of place where doing nothing somehow feels like doing everything right.
So instead of planning another short trip, we started thinking bigger.
A full month.
The Opportunity
That’s when things started to fall into place.
The home next door to Alan and Carie—a Camelia cottage model—was available as a rental.
At first, we had our sights set on October. It felt like the perfect time to go back.
But sometime in mid-May, we got a curveball.
The owner mentioned he was hoping to rent the property for longer than just a month, which meant October might not be an option after all.
A Quick Pivot
So we took a shot.
Instead of waiting and possibly missing out, I asked if the home might be available earlier—specifically mid-June through mid-July.
It turned out… it was.
Just like that, the plan shifted.
What started as a “maybe someday” idea turned into something real.
Making It Happen
Once we had the dates, everything else started moving quickly.
We began making arrangements to rent the cottage, aligning schedules and drawing on our past month-long remote work trips as we figured out how to make another extended stay on the road work.
This wasn’t just another road trip.
This was something different.
We weren’t just passing through—we were settling in.
Closing / Transition
In the next part of the series, we’ll share how we planned the trip, packed for a month away, and mapped out the drive back to Margaritaville.
Because getting there is still part of the story.
🔗 Related Links
- Finding Our Own Margaritaville: A Road Trip Story That Changed Us
- The Trip That Started It All: Car Camping to Margaritaville
- What’s Not to Love? The Next Chapter in Our Margaritaville Story
- COMING SOON: One Month in Margaritaville
- What daily life there is really like
- Day trips to Savannah, Charleston, Beaufort, and more
- The road trip stops along the way
- And how the music became part of the story