Your vibe,
translated to a place
I'm Ashley Theis, and I've spent the last decade building a travel practice that starts with one question: Who are you? Because I can plan the perfect trip, but if you and the location aren't a good fit, why board the plane? The best trips match your rhythm to a place so it feels like a homecoming, even if you've never been there before.
Before I launched The Constant Wayfarer in 2017, I spent years as an events coordinator and project manager in Charlotte—juggling logistics, keeping multiple stakeholders happy, making sure nothing fell through the cracks. Turns out, those skills translate perfectly to travel planning. Same obsessive attention to detail, just with better wine and fewer spreadsheets. (Okay, still plenty of spreadsheets.)
But my real education came from travel itself. My first solo trip happened by accident—I'd meant to go to London with a friend, but her plans fell through and I ended up wandering the city by myself for a week. I got lost on purpose, dipped into pubs, and fell in love with the in-between moments: conversations with strangers over a pint, spontaneous museum visits, and the realization that travel can shift how you see yourself and the world.
Years later, I spent two weeks on safari in Botswana and everything I thought I knew about luxury got flipped on its head. Luxury wasn't the lodge or the thread count. It was sitting in absolute silence watching elephants drink at sunset, then coming back to camp under a sky so thick with stars it felt like a celestial blanket. Safari does something to you. It strips away the noise and reminds you what actually matters. Those two trips taught me everything about the kind of travel I wanted to create for other people.
I started noticing how most travel advice had lost the plot: packed itineraries, must-see checklists, restaurants chosen because they went viral instead of because they're actually good. Travel became about feeding algorithms, not people's souls.
So I built something different. A practice where the trip starts with understanding who you are, then finding where your personality and a destination's heartbeat intersect.
I've been to 25+ countries, planned 600+ trips, and spent nearly a decade building relationships with hoteliers, guides, and chefs who greet my clients like returning friends. I'm proudly a Virtuoso advisor, which gives you access to perks and connections you won't find online.
I'm equal parts logistics obsessive and people reader. I love a good spreadsheet and a spontaneous picnic. I always try to know the bartender's name by the end of the night. My whole life, I've been the person in the group project everyone trusts to handle the important stuff. Your travel counts as the important stuff.
“Fill your life with experiences, not things. Have stories to tell, not stuff to show.”
– Abhysheq Shukla
Words to live by. Words to travel by.
My father taught me to value experiences over stuff.
My work continues that legacy.
How I Build Trips that Fit Like Your
Fave Jeans
Before I design anything, I want to understand you. Not just where you want to go, but who you are.
I make your quirks my compass. I pick up on the details most advisors miss: you're a late riser who needs that first hour alone with coffee, or you'd rather eat street food with locals than sit through a Michelin tasting menu, or you're traveling with a teenager who needs their own adventure so you can actually enjoy yours.
Then I tap into a network I've spent nearly a decade building. Hoteliers who save the corner room with the view. Guides who read your energy and know when to talk and when to give you space. Chefs who'll teach you to make pasta in their grandmother's kitchen. Drivers who double as historians and know the best place to stop for gelato.
My trips are built on relationships so you never have to feel like a transaction. When you show up, you're greeted like a returning friend, your shoulders soften, and streets you never thought you'd walk down become the neighborhood you suddenly feel right at home in.
01.
Trips THAT LEAVE A MARK
I plan trips to be two things: ridiculously fun in the moment and yet also rearrange something inside of you. I want you to be able to savor the memories of your trip for years to come.
What You Get
02.
LOGISTICS SO SMOOTH, YOU FORGET THEY EXIST
I sweat the timezone changes, restaurant reservations, backup plans for rainy days, and everything in between. You show up and it just flows.
03.
Space to breathe AND TIME TO SIMPLY EXIST
I leave blank spots on purpose. Time to nap, wander, chase a street musician, or sit with a view and think about the wild sweet ride of life.
04.
The right amount of structure
Your trip has a narrative arc, an emotional pacing. It builds, it settles, it surprises you at the right moments. It feels like it unfolded like a great book.
Recent Press Appearances
PODCASTS
TV
My joy & privilege
Real luxury isn't thread counts and Michelin stars. It's lingering over espresso because the light's hitting the plaza just right. It's the bartender remembering your name. It's realizing you haven't checked your phone in four hours because you're too busy being alive.
It's a trip built around how you move through the world—not how Instagram says you should.
THAT'S WHAT I BUILD. TRIPS THAT FEEL LIKE SOMEONE ACTUALLY KNOWS YOU.
BECAUSE SOMEONE DOES.
My Logistics
HOME AIRPORT
CLT
Countries visited
30+
miles flown
500K+
lost bags
0
clients served
600+
trips planned
800+
Favorite country
GR
FAVORITE CITY
LHR
I've been called a "grandma hobby enthusiast" by more than one friend, and honestly? I'll take it. If loving to needlepoint while watching the Red Carpet coverage makes me a grandma, then pass me a dirty martini and let me sit in my comfy chair.
This is Alyssa Darden, my Itinerary Coordinator. She's been with me for over a year, handling the details that keep your trip running smoothly like dining reservations, spa bookings, hotel coordination, and double-checking every last thing so nothing slips through.
Before The Constant Wayfarer, she managed operations at a coffee shop, which means she's a pro at staying calm, juggling multiple requests, and making sure everyone's taken care of. She's traveled to Kenya, the Philippines, Hawaii, and Jamaica, and she's a natural planner who loves learning.
If you get an email from Alyssa, you're in excellent hands.
Meet My Right Hand
