Road Trips
Chronological road trip stories and travel journals from our journeys across the country. These posts follow our routes day by day, sharing the experiences, stops, and memories that define each trip.
-
Revisiting Route 66: A Family Road Trip 11 Years Later
There are some trips you take because you want to see new places. And then there are the ones you take because you want to go back. This June, we’re heading west again—following stretches of U.S. Route 66 that we first traveled in 2014 and 2015. But this time, it’s different. Jameson is 15 now. And this trip? It’s about seeing it all again—through his eyes, a decade later. 🛣️ Then and Now on Route 66 On those earlier trips, Jameson was just a kid riding along as we explored roadside stops, neon signs, and small towns that still held onto pieces of the past. This time, we’re going back…
-
Living the Good Life at Margaritaville: Food, Friends, and Everyday Moments
When we arrived at Latitude Margaritaville, it was already dinner time. With the Bar & Chill right on site—both convenient and reasonably priced—it was the perfect choice. It gave us a chance to relax after the drive while still getting started on unpacking, which we finished the next day. We ended up dining at Bar & Chill many times throughout our month-long stay, but we balanced it with local restaurants, home-cooked meals, and plenty of dinner and game nights. During our remote work trips, we’ve found a rhythm that works well—enjoying new places while still keeping an eye on the budget. For Pat’s birthday, we headed to The Crazy Crab…
-
Margaritaville for a Month: First Stop in Pigeon Forge
Packing Up Packing for a month-long trip—especially one where we’d be working remotely—felt completely different than packing for a typical week-long vacation. We had to think beyond the usual travel essentials and consider what we’d actually need to live and work comfortably for a full month. That meant bringing along work tech, of course, but also things we don’t normally pack—like favorite cookware, utensils, and seasonings. We knew we’d be balancing dining out with cooking at home, just like we do in everyday life. And to fully lean into the Margaritaville vibe? We added a few tropical shirts to the wardrobe… and yes, we officially drank the Kool-Aid and bought…
-
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…
-
What’s Not to Love? The Next Chapter in Our Margaritaville Road Trip Story
Prelude Back in November and December 2024, we started talking with Alan & Carie about another visit to Latitude Margaritaville. It didn’t take long before the plans came together—April 20–25, 2025. As always, the destination was part of the excitement… but the journey getting there was just as important. Saturday, April 19, 2025 – Hitting the Road We kicked off the trip the right way—with a stop at one of our favorite local spots, Java Station 31. Coffee in hand, we headed south, picking up I-65 to I-265, then I-64 through Lexington before connecting to I-75. A must-stop along the way was Buc-ee’s in Richmond, Kentucky. It’s hard to pass…
-
The Trip That Started It All: Car Camping to Margaritaville (October 2023)
Before Margaritaville became something more to us… before the return trips, the music, and everything that followed… there was just one visit. At the time, it felt simple. A road trip to visit friends. 🏁 It Started at Indy 500 Weekend In May of 2022, during our annual Indy 500 weekend camp at our home in Speedway, Indiana, our good friends Alan and Carie shared some big news. They had sold their home in Ohio. They were living in their Airstream. And they were building a new home in Latitude Margaritaville in Hilton Head Island, South Carolina. At the time, it sounded exciting… but also a little hard to picture.…
-
Finding Our Own Margaritaville: A Road Trip Story That Changed Us
There are some trips you take… …and then there are the ones that stay with you long after you’ve unpacked the car. The kind you don’t fully understand while you’re in them. The kind that, over time, quietly become part of who you are. This is one of those stories. It didn’t happen all at once. There wasn’t a single moment where everything changed. Instead, it unfolded slowly—over a few years, a few visits, and a whole lot of time spent with good friends in a place we didn’t quite understand at first. But somewhere along the way… we found our own Margaritaville. It Started with Friends This journey really…
-
June 13-21, 2020: South Dakota
-
A Trip to Tulip Trestle
Indiana is full of many hidden treasure from the shores of Lake Michigan to the banks of the Ohio River. One of them is a little known train trestle in southern Indiana, southwest of Bloomington in Greene County. But “little” is the last word that should describe the Greene County Viaduct, affectionately known as “Tulip Trestle”. I first heard about Tulip Trestle some 15 years ago when a car club I was in made a trip to view the 2295 foot long structure. Tulip Trestle was completed in 1906 at a cost of $246,000, or over $6 million in today’s dollars. It was built by the New York Bridge Company using mainly…
-
2015 Route 66 RV Trip Overview | September 12–20 Road Trip Adventure
By September 2015, we were starting to feel comfortable traveling Route 66 with our RV, but we were still learning something new on every trip. Traveling the Mother Road in an RV is a very different experience than traveling by car and staying in motels. The pace is different, the planning is different, and the experience of the towns and the road itself feels different when you’re bringing your home along with you. This trip would take us west on Route 66 through Missouri, Kansas, Oklahoma, and Texas, before turning around and heading back east toward home. We planned the trip around RV parks along or near Route 66, which…