Real Talk : Q&A with Mrs Jenna Swan

Tell us a little about yourself—who are you beyond the job titles?

Being a mom and a wife are the job titles I am most honored to have, and take the most pride in. Luxury Travel Advisor is a title that fulfills my desire to be a lifelong leaner. Beyond that, I am a loyal friend who deeply values authentic connection. A cheerleader to peers, who believes there is room for everyone to succeed. I am a creative who loves to celebrate and thrives with a theme. I’m a wellness nerd who believes that clean food and therapy are equally important. I’m fun and funny but also serious. I cry at movies and speed on the highway. As long as everything is exactly the way I want it, I can be totally flexible!

How did you get into luxury travel planning?

I was a wedding planner for over a decade and took a break from work when I had my babies. I loved staying home with them for the first several years. During that time, I knew I eventually wanted to go back to work in some capacity, and I knew I didn’t want to return to the event world.
We continued to travel as a family, and after one particularly special family trip to Mexico, it became clear to me that my next move was to plan travel. I had an itch to share all of the hidden gems I’d been finding and experiences we’d been having along the way. Shortly after returning from that trip, I reached out to Embark Beyond, my host agency, and the rest is history.

What’s your favorite part of planning a trip—for yourself or for clients?

My favorite part of planning a trip for myself and my family, is the research in where to eat, and the shopping (even if from my own closet) for what to wear. When I plan a trip for my clients, it’s a bit different. I love sending clients to a property they haven’t been to, that I just know will perfectly suit their style. It makes me feel like a bit of a match maker, and it’s such a fun part of my job! I am also a huge fan of publishing a clients complete itinerary. When we have the pre-trip call, and they can see every single detail of their trip listed in the easy-to-read app, it’s a beautiful culmination of my work and their dreams.

You’re known for coordinating your outfits with the destination—where did that start, and why is it important to you?

First and foremost, I really do have fun with it. I enjoy the planning, the shopping and the styling. I have always felt that how you present yourself, the clothes you wear, the way you speak, your poise and posture, is a form of self-respect. On a deeper level, when I travel abroad, I feel like I am representing The United States of America. Showing the rest of the world that the US citizens can be elegant and graceful, is important to me. You simply cannot convey that if you’re wearing dirty tennis shoes and kids are in charter tees.

How do you balance motherhood, marriage, and a career in travel?

To be honest, I don’t always feel like I balance it evenly. My instinct is to say that my family, my kids specifically, will always come first, but I think I do a good job at prioritizing my own needs. Am I allowed to say that? Does that make me sound selfish? I understand that you simply can’t pour from an empty cup, so I am sure to keep mine full.
I am a hands-on Mom, and a supportive wife. I find joy in being there for my family. I structure my schedule so that I am able to chaperone filed trips, I feel accomplished after cooking homemade meals. I don’t let the mundane “tasks” cloud the fact that I am lucky to be able to be present with them.
I value the services I provide to my clients, and I make myself available when necessary, but through the genuine relationships I form with them, they know that I am a mom and a wife, and that comes first. You won’t often find me at my computer after dinner, because that doesn’t fill my cup.

What’s your dream destination—and what would you wear there?

I wouldn’t consider my list to be of dream destinations, but rather experiences, or specific properties. Currently, number one on my list, is to experience the Venice Simplon-Orient Express, a Belmond Train through Europe. I am memorized by the opulence of train travel in the 1920’s and would love the opportunity to step back in time and have even a taste of what that might feel like. I know how well Belmond executes the details, and their service is impeccable.
When I do get to experience a train voyage like this, I imagine that I will wear a fair number of vintage pieces. I will draw inspiration from the past and choose looser silhouettes, and neutral colors. I will not shy away from pearls around my neck, gloves at dinner and the occasional headpiece.

Any travel tips you swear by for traveling with kids (and keeping it stylish)?

I swear by including my kids in the planning, and I swear by using packing cubes.

This goes without saying- I swear by a plan!
When the kids share their opinions in the planning process, it helps give them a sense of ownership of the trip. For them, knowing what to expect helps them look forward to the different experiences ahead, and keeps them present through the long and (potentially for them) tiresome days.
To me, packing cubes are a no brainer. They keep things neat and organized, and they take the guess work out of getting ready each morning in a hotel room. The packing cubes ensure that the outfits that are slated for certain activities are clean and available. They also let you get more into your carry on because they act as a sort of compression bag.

What’s always in your carry-on, no matter where you’re going?

My supplements and my makeup, for no other reason than replacing them while on a trip would be annoying and time consuming. I would happily shop for an entire vacation wardrobe while traveling (not that I am manifesting a lost suitcase!) but shopping for magnesium and nontoxic face powder is not how I want to spend my time. I will also always have ChapStick, socks and Werther’sOriginal within reach. While on a plane, there is nothing worse than dry lips or cold feet, and I have a deep love for those little caramel creations.

What’s one destination that completely surprised you—in the best way?

Peru! I was looking forward to Peru before I went, but I was not prepared for how much I would love it. The people are kind, the colors are bold, the food is delicious, and the shopping is endless. I loved every step I took in that wonderful country and cannot wait to return.

Favorite travel memory as a family?

Gosh, I have so many. Last year we were in Florida for Spring Break, and on one of our beach days, all four of us were hip deep in the ocean. The break was calm, the sun was shining, and we were so carefree laughing together while we jumped in the water. Knowing lunch and a spicy margarita was only one ask away while the attendants on the beach monitored our lounge space absolutely had something to do with my breezy state of mind, but the ocean with my kids and my husband is what I will remember forever.

How do you define “luxury” when it comes to travel?

For me, luxury means easy and hassle free. There is no bigger hassle than waiting. Waiting in line, waiting for it to be 3:00 so you can check into your room, waiting for the cold water you asked for. Waiting can ruin the mood and push back the (carefully curated) schedule. You can be at a beautiful property, but if you’re left to wait, the experience does not feel luxurious.
When you book with a luxury travel planner, and stay at luxury properties, they work together to eliminate the waiting. The details are planned and in place to ensure that no time is waisted waiting for something.

Do you plan your outfits first or the itinerary first? Be honest!

I always plan the itinerary first. Always! No doubt that certain outfits or styles inspire destinations I want to visit, but the itinerary inspires what I’m going to shop for and pack. More specifically, the itinerary determines what I will wear each day. If I know I will be having a picnic at the Eiffel Tower, I don’t want to wear a short dress that day.

What can readers expect to find on your blog?

I am excited to share a bit more of myself and my knowledge as a luxury travel advisor. You can expect my take on travel with kids, how I structure itineraries, and what I’m wearing. I will write about my personal experiences with my own family, as well as insider news from within the travel industry.
I know nothing I share will be earth shattering, but I do hope you find it entertaining!

What’s next for you—personally or professionally?

Publishing this blog feels both personal, and like a next step professionally. I am excited to spend time in 2026 to continue to grow my travel business through deepening my relationships with suppliers around the world by attending prestigious travel symposiums.

My husband and I will remain committed to our health and wellness by continuing to explore peptide therapy and other modalities to keep us feeling like Benjamin Button.

My kids are as excited as I am to be heading to Scotland for our first time in April.