Chasing Wanderlust with The Constant Wayfarer

constant wayfarer

Planning a trip to a place you’ve never been can be a uniquely time-intensive and stressful endeavor. And since trips are finite, the pressure is high to see and experience it the “right” way.

After years of working as an executive assistant and project manager, Ashley Theis found herself looking for a creative outlet and a way to work for herself doing something she was passionate about. In this search, she settled upon the perfect solution to others’ travel stressors.

“I love to travel and have been on many solo adventures… Finally, in 2017, I decided to venture into the travel industry.”

Ashley started her business, The Constant Wayfarer, slowly at first, while also still working a full-time job and spending a lot of time dreaming about what her business could be. Then, in 2020, officially transitioned to full-time, “despite the weird timing with the pandemic.”

constant wayfarer

Today, her luxury travel consulting services include all the research, booking, and support for clients before, during, and after their trip. She’s also able to provide access to the best travel suppliers in the world. This makes it possible for her to help plan trips big and small and to offer a yearly service for travelers who travel often, but who perhaps don’t have the time to plan all the travel on their own. 

From weekend getaways to longer vacations, or even just singular hotel stays or one-off luxury cruise bookings, Ashley as The Constant Wayfarer has positioned herself to take care of all the details so you, the traveler, can simply plug into enjoying the experience. Ashley answered some of our top questions about her work and her best advice for vacationing in 2022.

Have you always had your own love of travel? 

Yes, as a child I used to travel with my family often. In college, I went to Europe for the first time and fell in love with it. In 2007, I did my first solo trip to London (during Kate and Will’s royal wedding), and it changed everything for me. Travel is truly transformative when you can slow down and experience a destination. Meeting new people and seeing beautiful places helps us see the world with more empathy and perspective than just reading about a place or hearing about a place in the news. That’s why I love to travel so much. 

What are some of the major benefits to booking a trip through an advisor or agency like The Constant Wayfarer?

Now, years into a pandemic, the travel landscape has completely changed. I am on hand while my clients travel should they need to troubleshoot anything. But I am also walking them through what tests they need, entry forms to fill out, or travel insurance to purchase. I think a lot of travelers learned that you can’t rely on some of the big online travel agencies… My services are personalized, and I love becoming friends with my clients. Hearing about hobbies and interests and travel goals means not only can I curate a trip that really reflects who clients are and how they like to travel, but also have an ongoing relationship with them. Together, we can really build a travel portfolio of incredible experiences!

constant wayfarer

Using Charlotte as a homebase, what are some of the easiest places to travel to? 

Charlotte is a great location to get to several popular destinations: Charleston, Savannah, Asheville all being an easy drive away. There are so many places that are great and a relatively short plane ride away. New York, Boston, Miami and tropical destinations like Turks and Caicos and Mexico aren’t that far. 

Tell us: what can someone expect when booking travel through The Constant Wayfarer? 

We set up a time to talk through the details of their trip as well as questions about their previous travel experiences, hobbies, favorite trips, least favorite trips and the overall vision and vibe they are looking for. I send my clients a beautiful proposal, along with a video walk-through of the details. We can revise it until they are happy. And then I take care of booking all components and adding in the fun stuff like dining suggestions, extra activities, or spa appointments. All the concierge aspects are taken care of. All you have to do is pack your bags and have fun. I am on hand the whole time should clients need to troubleshoot anything. Then they come home, we recap the trip and start talking about the next one!

What’s a favorite memory shared from a client about their trip? 

I have had the honor of being a part of a surprise engagement in front of the picturesque Neuschwanstein castle in Germany for clients who then asked me to put together their Hawaiian honeymoon. Being a part of those big life moments in such a small way is the best part of my job. 

the constant wayfarer

What is your best travel tip? 

Pack your patience and be kind. Airports and hotels are short-staffed and have more work now than ever. Wait times are longer and plans change at a moment’s notice. You’ve got to be patient and flexible right now as plans can change quickly. But, that is even more reason to use a travel advisor. We know how to calm you down and give you some alternate options so you can still enjoy your trip. 

Is there anything else we should know? 

Travel for 2022 is insanely busy already. Popular destinations like Italy and Greece are already booked for the summer and availability is hard to come by. If you already know what your travel dreams are for this year, reach out sooner rather than later. In 2021, once people started traveling more, I had the same amount of trips booked for clients in 5 months than I normally do in a full year! It’s bouncing back maybe a little quicker than we realized it would and 2022 is going to be even busier.