From Funky Town to Charleston Charm – Wrapping Up Our OBH7 Adventure

On the morning of April 6th, we said our goodbyes — to our friends, to Miramar Beach, and to One Big Holiday 7. The trip had been unforgettable, but we weren’t done just yet. Next stop: Charleston, South Carolina, where we’d spend the next three nights soaking in a different kind of rhythm.

We rolled into downtown Charleston around 5 p.m. and checked into The Lindy Hotel. After a long drive, we kept it simple — dinner and drinks at the hotel restaurant before turning in early for a well-earned night’s rest.

The next morning, we woke up feeling refreshed and ready to explore. I had already mapped out a walking route through the city so we could hit several sights in one loop. It was a gorgeous day — perfect for wandering.

We started with a walk to Brown Dog Deli to grab lunch, then carried it over to a nearby park where we found a quiet bench and enjoyed our food under the trees. From there, we strolled over to the Old City Jail, which unfortunately seemed to be closed. So we continued on to the Old Slave Mart Museum.

That visit hit hard. The exhibits were heavy, packed with the brutal reality of the slave trade and the inhumanity behind it. It was sobering — a reminder of how dark our history can be, and how important it is to remember it truthfully.

Afterward, we spent time at the Gibbes Museum of Art, which offered a needed shift in energy. The art was thoughtful and inspiring, and it was a good way to reset. We eventually wandered through the Charleston City Market, chatting with vendors and browsing the stalls before grabbing a drink nearby to plan our next move.

That night, we dined at Slightly North of Broad, where the food and cocktails didn’t disappoint. We returned to the hotel full, content, and grateful for the day.

The next morning, I was up early and off to Shadowmoss Golf Course for a solo round. My Uber driver was right on time, and I ended up being paired with a couple of great guys. The round was solid — and yes, I saw a few alligators — but none of them interfered with my backswing.

Later that evening, Nicole and I went exploring again and landed at The Swamp Fox Restaurant for dinner. The food was fine, but the atmosphere… well, let’s just say it had a certain “dated” charm. It made for a good story, if nothing else.

Finally, on the morning of our departure, we packed up one last time and made our way home — road weary, sun kissed, and full of memories.

From wild beach nights and purple tracksuits to Charleston museums and gator-filled fairways, this trip had it all. One Big Holiday 7 may be over, but the stories (and stickers) will stick around for a long time.

One Big Holiday 7 – Blurred Lights and Funky Nights

April 5th marked the third and final day of One Big Holiday 7 — and honestly, it all felt like a blur.

The day followed a familiar and welcome rhythm: more time on the beach with our friends, soaking up the last of the good vibes, salt air, and shared laughs. Then it was time to clean up, rinse the sand away, and get ready for the final night of music.

This night’s theme was Disco Ball Night, and while I kept things relatively tame, I still leaned into the fun. I rocked a silver sequin fedora, a disco ball necklace, and a “Mayor of Funky Town” t-shirt — a subtle nod to the spirit of the evening. It wasn’t the most outrageous outfit I brought, but it felt right.

The show itself? A flash of light, sound, and energy. Before I could even take it all in, it was over. As I stood there walking back to the condo, I remembered something Jim James once said about performing — how it’s all such a blur. One moment he’s walking on stage, and the next he’s walking off, not entirely sure where the time went.

I get that. Watching My Morning Jacket is like stepping into another dimension for a while — time doesn’t really move the way it normally does. It’s immersive, intense, emotional, and then suddenly… it’s done.

One Big Holiday 7 is officially in the books. And while the shows may be over, the memories — even the blurry ones — are here to stay.

One Big Holiday 7 – Cloudy Skies, Beach Vibes, and Cat Shirts

Day 2 of One Big Holiday — April 4th — started early. I ordered breakfast through DoorDash, and before long, we were hauling ourselves and all our beach gear out to the sand. Luckily, with an oceanfront condo, we could still see our place from our beach chairs.

The weather wasn’t exactly perfect — mostly cloudy with a steady salt spray that clung to everything — but we made the best of it. At one point, a few of us wandered down the beach to check out the One Big Holiday sticker exchange, and I walked away with some great finds after trading a few of my own.

Back at our chairs, the mood was light, and I floated the idea of having pizza delivered directly to the beach. I found a good place online and placed the order — though they wouldn’t deliver to the beach itself, so I made a plan. When I got the notification, I hiked back up to the condo building, and wouldn’t you know it — as I walked into the lobby, the delivery guy walked in, too. I grabbed the pizzas, spun around, and was back at our chairs in under five minutes. Everyone was impressed — and amused — by the lightning-fast turnaround.

We ate, we laughed, we relaxed. It was one of those afternoons that makes you grateful for good friends, good food, and shared music ahead.

Eventually, it was time to head back up, clean up, and get ready for the night’s festivities. For the evening, I went full tropical-retirement-chic: white linen pants, loafers, and a bright yellow button-down shirt covered in black cats. I thought I looked sharp — and honestly, I still do.

The show itself was stellar. My Morning Jacket never disappoints, and that night was no exception. The performance was electric, but as always seems to happen with these moments — just as it was getting going, it was suddenly over. Another unforgettable day wrapped up, and another chapter added to the OBH memory bank.

One Big Holiday 7 – Reunions and Retirement Tracksuits

We woke up on April 3rd with that unmistakable feeling — today was the day. Not only was it Day 1 of One Big Holiday, but we were about to reunite with our friends who we hadn’t seen since the last OBH in Mexico.

Nicole and I packed up, loaded the luggage cart, and checked out of our hotel in Panama City Beach. From there, we headed toward the condo we had booked together for the event. Finding the parking lot turned into a bit of an adventure, and I couldn’t help but think I was lucky my truck wasn’t any bigger — the fit was tight.

Rob and Sallie had already beaten us there, having stayed nearby the night before, and were already settled in. It felt great to see them again and kick off the week properly. As the day wore on, though, we started to get concerned about Michael and Christina — their flight had been delayed, and it became clear they wouldn’t make it in time for Night 1 of the show. A definite bummer.

Still, Nicole and I decided to dive into the spirit of the event. We’d packed a few themed costumes for the week, and tonight’s look was straight out of your granddad’s Florida retirement fantasy — 1980s style. We suited up in matching purple tracksuits, complete with headbands, wristbands, pixelated sunglasses, and even an inflatable gold boombox. Yes, it was as ridiculous (and amazing) as it sounds.

By the time we got back from the show, Michael and Christina had finally arrived. We all spent the next couple of hours catching up, laughing, and settling in — a little reunion years in the making. Eventually, we called it a night, ready to recharge for Day 2 and everything it had in store.

One Big Holiday 7 – Into the Panhandle

We woke up on April 2nd feeling well-rested and ready to hit the road for the next leg of our trip. Our destination: Panama City Beach, Florida — just about an hour east of Miramar Beach, where One Big Holiday would officially kick off the next day.

After checking out, we said goodbye to Santee and cruised south before heading west into the Florida Panhandle. The drive was mostly smooth, though we did run into some construction that slowed us down, especially where the expressway ended. I was struck by how rural the region felt — more open and undeveloped than I’d expected. Unfortunately, in several places, the forests had been completely stripped away, leaving barren patches of land. It was a jarring and disheartening sight, to say the least.

We eventually made it to the hotel in Panama City Beach, eager to unwind and grab something to eat. Naturally, I pulled up trusty old Tripadvisor, and one name jumped out: Dat Cajun Place Cafe. I was surprised — and a little impressed — when Nicole agreed to give it a shot.

The place was absolutely slammed. Standing room only, with a swarm of people waiting outside. They quoted us an hour wait, and we decided to go for it. We grabbed drinks at the bar, then wandered outside for some fresh air and a little room to breathe.

When we were finally seated, it was more than worth the wait. I went all in: gator bites, baked oysters, and jambalaya with green beans and Texas toast. Holy crap — it was good. So good, in fact, that Nicole joked she might have to roll me out of there. She wasn’t entirely wrong.

Getting an Uber back to the hotel took a bit, but we eventually made it. Full bellies, tired feet, and another day of memories in the books — we both slept like rocks.