Meet Hilary Bendon | Travel Advisor & Concierge

We had the good fortune of connecting with Hilary Bendon and we’ve shared our conversation below.

Hi Hilary, what role has risk played in your life or career?
Risk is relative. When I was first out of university, I found a job and took off for Costa Rica. I spoke barely any Spanish, but I knew Italian, so I thought it would be relatively easy to learn. People said to me that I was so brave. I didn’t understand that — I didn’t feel brave or anything other than excited to be working abroad, meeting people, and learning about a new culture. As I look back after many years, I see now why people thought of my choice as risky, and I recognize many other risks I have taken in my life and career. I’ve spent most of my working life as an independent consultant, mediator, and fractional executive which has risk built into it. Interspersed have been roles as an employee, and, given my comfort zone, need for autonomy, and desire for independence, jobs seem more risky than branching out on my own.

In 2025, I took another risk and pivoted to a completely different industry and different kind of work — I left corporate America and am now designing, booking, and serving as a concierge for luxury and leisure travelers. This time, ironically, it feels like a risk because I have only so much of a runway to get this business off the ground. Because I want to mitigate the risk, I have allied myself with an experienced travel agency — Travel Savvy. I know this risk is well worth it. The excitement I feel when I’m designing an incredible travel experience for a client tells me I’m doing the right thing.

What should our readers know about your business?
I started out my career as an Administrative Assistant (when that was a thing) for an Italian bank in San Francisco. It was a fun job, more because, in imitable Italian fashion, my boss was as much into enjoying life as work, and he encouraged the same from us. From there I traveled to Costa Rica, returned to California for graduate school, worked in Connecticut and Armenia, returned to California, set up shop as a consultant and transitioned a few times from focusing on organizational and fund development for nonprofits to a corporate career in learning and development. I also have worked as a teacher for elementary and middle school bilingual and special education students, sold real estate, and coached individuals for personal and professional development. I’ve gone in and out of consulting, focusing on organizational and talent development, mediation and conflict resolution, and leadership coaching.

My career trajectory has not been linear and has involved many pivots. I’ve had the good fortune, and the not-so-good fortune in some respects, to have dabbled in many things. The biggest challenges I have faced in my career have been related to dealing with organizational politics at work. I am naturally a very literal person which causes me to take most things at face value. I have gained skills to be able to see below the surface by becoming a good listener and avid learner.

Last year I transitioned again and am designing and coordinating travel experiences. I’m passionate about my new focus because I love to travel myself. I’ve lived, studied, and worked abroad in Italy, Costa Rica, Guatemala, and Armenia and have traveled to many other places besides. Whether I am putting together a trip to Italy or China or Japan, I research and learn new things while also incorporating my own experiences and knowledge of local customs and traditions to curate memorable moments for clients. I’ve been to 5 out of the 7 continents and hope to add Oceania and Antarctica to my list soon. I’ve spent time in China, Ecuador, Israel, Spain, France, the Netherlands, Poland, and Portugal (including swimming with wild dolphins in the Azores) as well as having traveled throughout the United States, and I’ve enjoyed all the places I’ve been.

Once thing I love about my new role is that I get to combine my interest in travel with my natural curiosity about people — their backgrounds, culture, language, and life choices. I’m able to use listening skills learned from years as a Coach and negotiation skills honed as a Mediator to be an advocate for my clients.

The greatest lessons I’ve learned are to be ok with saying, “I don’t know, and I’ll find out” and to accept leading from behind, which, it turns out, is much more powerful. As a Travel Advisor, I strive to be resourceful — to find travel options best suited to my clients’ needs and desires. I pride myself on attention to detail, strong organizational skills, and a commitment to excellent customer service.

Any places to eat or things to do that you can share with our readers? If they have a friend visiting town, what are some spots they could take them to?
LA has so many incredible places to visit and enjoy, and some of my favorite places are close to home (Redondo Beach). I enjoy heading down to Riviera Village, hanging out in Manhattan Beach, and sneaking into El Segundo for a nice coffee or meal. I love the Rocke salad at the Rockefeller in Redondo, braised short rib at Tin Roof Bistro in Manhattan Village, and the savory salmon salad at the Hook and Plow, Redondo and Manhattan Beach locations.

Venturing farther afoot, I like to visit Pasadena and Beverly Hills. Pasadena also has some great restaurants — Union, Uovo, Smitty’s, and so many more. Old Town Pasadena is a great place to walk around.

Beverly Hills is always fun, whether it’s a trip to admire the delights at Louis Vuitton, enjoy a meal at the fabulous Il Pastaio, or ride in a Waymo to breakfast at Nate n’ Al’s.

For casual sushi whenever I am in Long Beach, I head to Sushi Kara, love their cucumber salad and spicy tuna on crispy rice. The sashimi is fresh, and my best friend swears by their spicy mayo on the popcorn lobster roll.

What I love about LA’s entertainment scene are the unexpected things that pop up — like the David Bowie photographs at the Santa Monica Art Museum, the Titanic exhibit, and the cool Muse/ique performances around town. Recently I took some friends to the Petersen Museum, and they were thrilled to see all the different kinds of cars and excited to explore the Back to the Future DeLorean .

There is so much to do, so many delectable cuisine delights, and such incredible beaches, it’s impossible to come up with any list that does LA justice!

Shoutout is all about shouting out others who you feel deserve additional recognition and exposure. Who would you like to shoutout?
My mom has always been an inspiration for my career even though I’ve traveled a very different road. She was a successful attorney, respected in her field, and she built a solid business when she went out on her own. I admire that.

I credit my friends, Marta, Lisa, Yvonne, and Kim, for the support and suggestions they offer as I have made multiple pivots over the years, and especially with my most recent transition to travel advising.

I also want to thank the many mentors I’ve had throughout the years…Pat, Susie, Rhonda, among others.

Website: https://www.travelsavvy.agency

Instagram: travelbyilaria

Linkedin: https://www.linkedin.com/in/hilarybendon

Image Credits
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