Jaunt by Journeys USA Travel: September 2026

Some trips are about discovering somewhere new. Others become meaningful because of who is standing beside you when you experience them.

Our annual family vacation to Charleston became the latter.

I had been to Charleston before, but this visit felt different. I was traveling with my daughter and my father, now 82, and my mom over the course of the trip we encountered pieces of American history, African American history and our own family history in ways I hadn't anticipated.

Charleston is a city that makes it difficult to separate those things.

Returning to a Changing Charleston

We stayed on King Street, which gave us a wonderful vantage point from which to experience the city.

What struck me immediately was the growth. Charleston's historic architecture and unmistakable Southern character remain, but alongside them is a city continuing to develop—new businesses, hospitality, restaurants and people discovering the region for themselves.

We wandered through the historic Charleston City Market and took a horse-and-carriage tour with Old South Carriage Company, allowing us to slow down and experience the streets rather than simply move through them.

That pace suited this trip.

There was nowhere we particularly needed to rush.

A Return to a Special Table

One evening brought me somewhere I'd been before for an entirely different reason.

We returned to the restaurant where I had celebrated my anniversary in February.

There can be something bittersweet about returning to places attached to another moment in your life. But this wasn't.

The memories were good.

I could appreciate what that dinner and that time represented without needing the present to look exactly like the past. Now I was there making another memory, this time as part of our family vacation.

Travel has a funny way of doing that.

Places become bookmarks in our lives.

Fort Sumter—and a Moment I Won't Forget

The highlight of Charleston for me was our visit to Fort Sumter National Monument. Fort Sumter is inseparable from the story of the Civil War, but the history of the site reaches beyond the familiar story of the first shots fired there. Enslaved people were among those whose labor was used in the construction of the fort.

Standing there as a Black family therefore carried its own weight.

But then history became personal.

My father is a retired United States Marine. At 81 during our visit—and now 82—he was given the opportunity to help lower the American flag.

I watched him help fold and roll it.

A Black man. A Marine. A father and grandfather. Standing inside a fort constructed in part through enslaved labor, participating in the care of the flag of the country he served.

And his daughter and granddaughter were there to witness it.

There are moments you plan on vacation.

And then there are moments you could never have planned.

That was one of them.

There is something uniquely revealing about returning to a city you once called home.

You remember the streets a certain way. The restaurants. The neighborhoods. The people. You remember who you were when you lived there. And then you return years later and discover that while the city has changed, so have you.

That was Dallas for me this summer.

I didn't return simply for a getaway. I came back during a season of transition—personally and professionally—and found a Dallas that felt both familiar and entirely new.

A Different Dallas

Dallas has always understood ambition. But the city I returned to felt more sophisticated, more textured and decidedly more cosmopolitan than the one I remembered.

There is still that unmistakable Texas confidence, but now it sits alongside a growing design culture, elevated hospitality, interesting culinary experiences and neighborhoods that feel increasingly distinct from one another.

The evolution was especially noticeable because I wasn't experiencing Dallas as a resident this time. I was seeing it as a traveler—and perhaps that gave me permission to notice things I once took for granted.

It reminded me of one of the reasons JAUNT exists in the first place: sometimes travel isn't about discovering somewhere completely foreign. Sometimes it's about returning somewhere familiar with entirely new eyes.

Checking In at Virgin Hotels Dallas

For this return, I made Virgin Hotels Dallas my home base, which made the airport DALLAS LOVE FIELD the smarter choice flying in. A quick 15 min ride and we arrived!

Located in Dallas' Design District, the property felt appropriate for this particular trip: contemporary, energetic, design-conscious and decidedly social.

But what mattered to me wasn't simply having a beautiful hotel room.

I needed a place that could become part of the experience.

My suite wasn't just where I slept. It became a place to gather, talk, entertain and reconnect. Instead of creating another formal networking event, I wanted something much more intimate—a small salon-style gathering where people could have cocktails, enjoy light bites and actually talk to one another.

That's increasingly how I think about access.

The most interesting conversations don't always happen on stages or inside enormous ballrooms. Sometimes they happen with eight or ten people sitting around a room, sharing ideas and discovering unexpected connections.

And Dallas gave me an opportunity to create exactly that.

Coming Home to Old Friends

Perhaps the greatest luxury of returning wasn't the hotel at all.

It was the people.

There is something grounding about reconnecting with people who knew you in another chapter of your life. They remember versions of you that your newer relationships never experienced.

But returning also gives those relationships an opportunity to evolve.

We weren't simply reminiscing about what had been. We were talking about businesses, families, investments, ideas, opportunities and what comes next.

That's an important distinction.

Nostalgia can take you backward. Relationship can move with you.

And increasingly, I recognize that some of the greatest assets we accumulate over a lifetime aren't sitting in financial accounts. They're the relationships we've nurtured over decades.

That made returning particularly reflective.

GUICE Foundation: Where Another Chapter Began

Dallas also carries another significance for me.

It is where I launched the GUICE Foundation. Where my first board member lives and signifies fertile soil to which my nonprofit will be engaged.

That made returning particularly reflective.

What began as an idea about philanthropy and creating greater impact has continued evolving alongside the broader GUICE ecosystem. Today, my work increasingly sits at the intersection of wealth, philanthropy, access, experiences and legacy.

And in many ways, being back in Dallas allowed me to see the connective tissue between those things more clearly.

Wealth isn't simply what we accumulate.

It's what we're able to build with it.

It's the businesses we create, the people we employ, the communities we support, the experiences we share and eventually the legacy we leave behind.

That philosophy has become central to how I think about both GUICE and the Foundation.

So returning to the city where part of that journey began while contemplating where it goes next felt remarkably full-circle.

Moving Into a New Season

There was another layer to this trip that was harder to photograph.

I was changing.

Sometimes you don't recognize a transition while you're living through it. You simply know that things that once fit don't fit quite the same way anymore.

Dallas gave me enough distance to see that I was moving into another season.

Not abandoning what came before.

Building from it.

There are friendships I want to carry forward. Businesses I want to grow. Places I want to revisit differently. Ideas that are finally ready to become something tangible.

And there are things I'm increasingly comfortable leaving behind.

Maybe that's another form of travel we don't talk about enough.

We think of journeys geographically—New York to Dallas, Dallas to Charleston, somewhere familiar to somewhere new.

But some of our most important journeys happen internally.

You arrive somewhere as one version of yourself and leave understanding the next one a little better.

The JAUNT Take

Dallas surprised me.

Not because it had become unrecognizable, but because it had evolved without losing the character that made it Dallas in the first place.

Perhaps that's why this particular return resonated so deeply.

I could relate.

Virgin Hotels Dallas gave me a stylish home base from which to rediscover the city, entertain friends and create new memories. But the real story of this trip wasn't a hotel review.

It was returning.

Returning to a city that helped shape me.

Returning to friendships that have survived different seasons.

Returning to the birthplace of an idea that became GUICE Foundation.

And returning with enough perspective to recognize that both Dallas and I had moved forward.

Sometimes the best trips aren't escapes at all.

They're reminders of how far you've traveled. Until next time...