FROM “TERRIFYING” SOLO TRAVELS TO CURATING LUXURY VACATIONS, JESSICA GAYA
FOUNDER OF DETAILED TRAVEL DESIGNS, JESSICA SHARES HOW HER LIFE HAS TRAVELED IN UNEXPECTED DIRECTIONS TO HER DESTINATION OF TRAVEL ADVISOR.
Jessica Gaya, founder of Detailed Travel Designs, specializes in crafting custom travel itineraries as seamless as they are unforgettable.
When Jessica hired me to capture her brand photography, I knew we’d instantly connect. My husband and I are avid travelers and she did a wonderful job of curating our 10-year anniversary trip. I interviewed Jessica to learn how her background, expertise and passion combine to create curated travel experiences that stand out.
Her personal adventures, however, stood out the most.
Q&A with Jessica Gaya
Q: Give us a brief business overview. What do you do, who do you serve, and how do you serve them?
My business is called Detailed Travel Designs. I’m a travel advisor, which means that I work with my clients to craft personalized travel itineraries, as well as handling all the bookings, documents, and other details that travel requires. My goal is to make the planning process fun, easy, and stress-free, while also creating once-in-a-lifetime experiences my clients wouldn’t be able to find on their own. I work with all kinds of travelers, from solo travelers to families and groups. Basically, anyone who wants to travel but doesn’t have the time or the desire to do all the planning themselves. I especially love planning unique experiential, immersive travel as well as small, niche cruise experiences like river cruises and expeditions.
Q: What would you say is a common theme about your business or your life?
I’m an introvert who really enjoys working behind the scenes so that others can shine. I’ve owned several businesses and raised a family, and the most valuable skill I’ve picked up along the way is being a good listener and empathizer, and paying attention to what people in my life care about, what their needs are, and what makes their eyes light up. I love the feeling of finding the perfect gift for someone, cooking their favorite meal, or planning the perfect trip.
Q: What’s your “WHY”? What specifically drives you to do what you do?
My first experience with international travel was at the age of 19 when I terrified my mother by embarking on a solo backpacking trip through Europe. This, of course, changed how I saw myself and the world and instilled a love of travel, independence, and adventure. As I grew up, married, and raised a family, my opportunities for travel were limited, but my wanderlust persisted. As the kids grew older, I looked forward to traveling more with my husband. But, in 2021, just as my kids were finishing high school, I suffered from a mysterious illness (later diagnosed as an autoimmune disorder) that kept me in bed and basically immobile for 4 long months. During that time I had to focus my brain away from the pain and uncertainty, and one of the things I found myself drawn to was videos of travelers in all their many forms: travel blogs, cruise reviews–I even followed a YouTuber who reviews bathrooms on airplanes! Dreams of traveling the world sustained me while I was sick in bed and motivated me when I was able to start physical therapy and get moving again.
In 2023, I was back to my old self, and I decided it was time to embark on a new chapter. Most of my adult working life was spent developing and running various businesses and entrepreneurial ventures with my husband. But I decided it was time to do something on my own. That’s when it occurred to me that I could become a travel advisor and put my obsession to good use by helping others discover the joy and freedom that comes with an amazing travel experience. I really wanted to create an easy and fun experience for people who might feel overwhelmed or intimidated at the thought of doing it all on their own. I’m so glad I did because it’s really fun (and it gives me an excuse to travel more as well).
Q: Which fear(s) did you face head-on and overcome during your journey?
My fears are pretty common, and I think we’ve all been there: fear of failure, fear of rejection, fear of looking stupid. I wouldn’t say that I’ve overcome my fears, and I don’t expect I ever will, but I’m learning that I can (and must) do scary things in spite of them.
Q: What’s one thing you’ve learned about yourself during the journey?
Initially, I thought I would enjoy this work because I love learning about new destinations and experiences, and I’m also a logistical nerd. But ultimately, what has turned out to be the most rewarding aspect of my job is the satisfaction of getting to know a client well enough to match them to experiences that are a perfect fit, and making the process fun and exciting for both of us.
Q: What 2-3 pieces of advice would you give others based on what you’ve learned?
Remember, when you feel awkward or embarrassed, that everyone you work with, whether a client or a colleague, is a human being just like you. They all have fears, challenges, and things they are self-conscious about. Honest acceptance and acknowledgement of your imperfections are endearing to others and make you more likable and trustworthy. So don’t be so hard on yourself!
Pack light. Stay hydrated. Bring a snack. Hire a private car and driver to pick you up from the airport; it’s worth every penny.
When I’m in a foreign country where I don’t speak the language, my favorite question to ask is, “how do you say thank you in your language?.” This results in a hilarious exchange where we say thank you back and forth awkwardly in both languages. Give it a try!
Q: What’s something you wish more people knew about your industry?
Most people who haven’t worked with a travel advisor before are surprised to know that it’s even a thing. Travel advisors are similar to travel agents, but we offer a more personalized service in that we do more than just make bookings. Travel advisors have connections all over the world who are experts in their destinations and who can recommend and arrange experiences that only a local expert could. My job is to get to know you and what you value and expect in a travel experience, and then work with my partners in-destination to create your perfect trip. And, to top it off, we provide support while you travel in case things don’t go as planned.
Q: What’s your hope for the future?
Okay, this is a cheesy Miss America answer, but my hope for the future is world peace. Seriously.
Q: What would you say to someone hesitant to invest in this type of service?
For someone who is hesitant to invest in my services I would say hop onto my website and schedule a free consultation with me. There’s no obligation. We can chat about your travel goals and see if we’re a good fit for each other. If you’ve never used a travel advisor before, I think you’ll be pleasantly surprised. Imagine a vacation where all the details are managed for you, the hotels are vetted, the experiences are curated, you get treated like a VIP, and you get it all without having to do any of the tedious, time-consuming work that comes with planning your own vacation. You don’t know what you’re missing (and once you do, you’ll never go back to DIY again).
Q: Where can we learn more about you?
Website: www.DetailedTravelDesigns.com
Ready to Plan Your Dream Trip?
Jessica understands that a brand isn’t just about looking good—it’s about delivering an experience that matches the promise of those visuals. Stunning imagery may capture attention, but it’s her dedication to thoughtful, personalized travel planning that keeps clients coming back for more.
Through Detailed Travel Designs, Jessica combines her passion for creating unique journeys with a commitment to seamless service. For those ready to embark on their next adventure, she’s the guide who can make it unforgettable.
