Good morning! I’m writing this before I head off to Washington, DC, for a conference I’ve been looking forward to for months, with nearly 100 women in media who inspire me deeply. I’m so grateful to Hitha Palepu for nominating me (and Departure!) to be in the room alongside them this year, and I already know I will leave energized and brimming with ideas.
From there, I’ll hop over to Seattle to celebrate my best friend’s birthday. (This is also, admittedly, a mileage run, as I am very close to Delta status for the first time.) My husband will be joining me in the Emerald City—his first visit—and I’m looking forward to a few days of fall in the Pacific Northwest.
Before getting to this week’s interview, I wanted to thank each and every one of you who reached out after last week’s edition. I was flooded with DMs, texts, voice memos, and comments, where many of you shared your own doubts around growing your career and growing your family. At first, I wrote “growing your career vs. growing your family,” but as everyone’s outreach reminded me, it’s that these can complement each other, rather than be at odds with one another. Let both journeys continue on, and we’ll figure it out as it comes.
I’m thrilled to welcome Drea Sobieski as my guest interview this week—she’s the definition of a multihyphenate who’s turned her love of travel into her career. She first reached out to me professionally a year ago, but we became fast friends. We’ve had drinks in New York City, we regularly text about our lives, and she’s a part of what I’d call Departure’s Advisory Circle.
As a PR director, I was curious how it feels to go from traveling the world to working in the business of it, the challenges around real storytelling as brands work with creators, and how she was ahead of the “slow travel” curve by almost a decade. I’m truly honored she made the time—you’re going to get so much out of her perspective.
Drea, you’re the PR Director at Black Tomato, and you also ran an editorial platform called ELSEWHERE that you are relaunching soon. Tell us a bit more about who you are.
I’m a writer, publicist, brand strategist and founder. I moved to NYC last year after thirteen years in Los Angeles to pursue my dream job as PR Director at Black Tomato. I build relationships with writers, creator journalists, and tastemakers, finding new ways to tell stories about why we travel and what we carry home.
My background is in brand marketing, PR and storytelling, from shaping influencer strategies for lifestyle brands to creating hotel partnerships and experiences. Connection has always been at the heart of it, whether between a traveler and a place, or a brand and its audience.
I founded ELSEWHERE (@elsewhere on IG) in 2012, and it grew into an independent travel platform and creative consultancy. It gave me a place to explore travel through art, design, food and the people who give a place its character. We weren’t interested in guides, or prescribing the definitive way to experience somewhere. I’ve always been more curious about how someone “else” sees the world, through what they make, the stories they tell or the places they send their friends. At my core, I believe travel is one of our greatest teachers. It expands our sense of what’s possible, including who we might become.
Outside work, those interests spill into pretty much everything I do! I love cooking, exploring art and design, collecting things I have no practical reason to bring home from my travels, and introducing people I think should know one another. I’m also devoted to my sourdough. I’m happiest at the gym or at yoga, and being an auntie to my five (!!) nieces.
I’m relaunching ELSEWHERE soon, with a fresh perspective and the same curiosity about people and place that started it all. I’ve learned a lot since the first iteration, and I’m excited to give those stories a new home.
Travel is one of our greatest teachers. It expands our sense of what’s possible, including who we might become.
You founded ELSEWHERE back in the 2010s, when traditional travel media was more highly polished and aspirational—like flipping open a print magazine and seeing a breathtaking spread of a destination, followed by a caption that said, “Rooms start at $695/night.” What motivated you to start building ELSEWHERE at that time, and to take the lens of more authentic, slow travel—similar to the ethos of Departure? Did you know you were ahead of the curve, so to speak?
I don’t think I was consciously trying to get ahead of anything. I was following my curiosity and making the content that I wanted to read but that didn’t exist at the time.
I loved beautiful travel photography and a gorgeous hotel as much as anyone, but I wanted to know more about the life around it. Who lived there? What were they making? What did they do for work? Did they have a family? Where did they take their friends for dinner? I was interested in the details that helped you understand a place, and in recommendations that felt deeply trusted and personal. Nothing on a “top 10” list.
ELSEWHERE became a way to bring those interests together. We could tell a story through a designer’s relationship with their hometown, the people behind a small hotel, or a tradition that might make you reconsider something in your own life.
Beauty was absolutely part of it. One of travel’s great pleasures is discovering, with your own eyes, something (or someone!) you didn’t yet know you loved. But I wanted the stories to make people curious enough to go, ask questions and form their own relationship with a place.
Looking back, there’s a lot of overlap with what people now call slow or intentional travel. At the time, I was finding an editorial language for the things I cared about. That’s something I recognize in Departure, too: a curiosity about how travel becomes part of your life, well beyond the trip itself.
More than a few readers have their own passion projects like ELSEWHERE or Departure and want to move into the travel space full-time—how were you able to translate your past experience into your current PR work? What advice would you have for fellow women who aspire to work in the travel industry in some capacity? Did you know in your gut that your love of travel would lead to a career in it?
The thread is so much clearer looking backward! First, for anyone building something: Keep building. Don’t give up. You never know where your stories will lead you, who they’ll connect you with, or what doors they’ll open. Every part of it expands your world, your confidence and your sense of what’s possible, even before you can see how it all connects.
My career has moved through fashion, editorial, brand strategy, marketing, PR, partnerships and community building. Across all of those roles, I was learning how to find a story, understand an audience, and bring the right people together. Those skills travel well (pun intended).
Building ELSEWHERE gave me a way to put them into practice around something I cared deeply about. Alongside the publication, I built a creative consultancy, so I was working on both the editorial and commercial sides: developing stories, pitching ideas, building partnerships and figuring out how to make the work sustainable. That experience is incredibly relevant to what I do at Black Tomato, where I work with writers, brand partners, creators and other voices to help tell our stories.
For women hoping to move into travel, I’d start by asking: What can you already do that this industry needs? Writing, producing, operations, design, relationship building. Loving travel gives you the motivation, but being able to articulate what you bring gives someone a reason to hire you.
And give your passion project credit. When you’re building something yourself, you’re making decisions, managing relationships, solving problems and developing a point of view. Learn to explain that work with the same confidence you would a salaried role.
Travel was clearly a pull for me early on and it was something I knew I was born to do. ELSEWHERE was one way I made room for it before it became my full-time work. I think there’s value in following that curiosity without needing to know exactly where it will lead. Truly so many of my best friends and business relationships today can be traced back through my work with ELSEWHERE.
You’ve also had experience with brand relationships and influencers, and I think sponsored and brand-led content is a real tension in travel media. Readers are really smart and savvy, but there’s a (sometimes intentional) blurring that makes it harder to distinguish what’s authentic vs. paid. How has the relationship between travel brands and creators changed—and maybe more importantly, how should it?
Having worked on both sides, I appreciate that tension and I have a lot to say on this. Here’s my TL;DR: Good storytelling takes time, money and work, and partnerships can make stories possible that otherwise wouldn’t get told. And, it’s important to tell stories! They shape what we notice, whose knowledge we value, and how we understand places we’ve never been.
Donna Haraway writes, “It matters what stories make worlds, what worlds make stories.” I think about that in the context of travel: the stories we encounter shape our expectations before we arrive, and those expectations influence how we behave when we get there. There’s a responsibility in that, whether you’re a publication, a creator, or the brand funding the work.
In today’s digital era, we all know that partnerships help fund independent media. That’s part of how this world works. Writers and creators deserve to earn a living, and thoughtful commercial partnerships can support incredibly valuable work. Readers deserve to understand who paid for what, and how that relationship shaped the story.
The word “authenticity” gets thrown around so much that it can start to mean very little. To me, it means there’s an honest relationship between what you experienced, what you actually think, and what you tell your audience. You can be paid and be sincere. You can also pay for your own trip and tell people exactly what you think they want to hear.
What matters is whether someone’s judgment remains their own. Would they recommend this to a friend? Can they say who it’s right for, and who it might not be for? Is there room to share something unexpected, or admit that part of the experience didn’t resonate?
For me on the brand side, that means choosing people for their perspective and giving them room to use it. If everyone comes home with the same photographs and the same talking points, you’ve missed an opportunity. The interesting part is what someone notices that you wouldn’t have thought to put in a brief. The beauty is perspective.
As I think about relaunching ELSEWHERE, those are questions I’m asking myself, too. What partnerships serve the story and the reader? How do you make the commercial relationship clear while protecting a point of view? I think trust depends on being willing to answer those questions openly.
You just got back from Egypt, Portugal, and Italy (the jealousy is seeping through my pores), but those are three places that carry a lot of visitor expectation and a lot of foot traffic. Where did a place feel authentically itself, and where did you feel like it was more of a “performance”? Was there a tell?
For me, the tell is whether there’s room for spontaneity and surprise. Can a conversation wander off-script? Can the person hosting you take things in a direction you totally didn’t expect? Or does everything feel arranged to recreate a photograph you’ve already seen on Instagram?
I’m a little hesitant to declare somewhere “authentic” after spending only a few days there. Places are complicated, and people don’t owe us a particular version of themselves because we’ve arrived with an idea of what a place should look like. Someone having visitors as part of their livelihood doesn’t make the encounter less meaningful, either!
In May, I went to an incredible restaurant in Lisbon called Isco Petisco (save it to your Google Maps!). I fell in love with the food, the hospitality, and the warmth of the place. Then I met the owner, and what started as a conversation became a connection that gave me a very, very good reason to return. This time, I was going back to see someone, and that changed how the whole city felt. Lisbon had become personal. I love that travel can do that: You go somewhere for dinner and leave with a reason to come back.
In Italy, I was leading a group through the Langhe-Roero region, where we met Paolo, an incredibly charismatic goatherd and cheesemaker. We spent time with his animals at dawn, learning about his work and understanding the connection between what we were eating and the people and land behind it. By our last night, we’d found ourselves at his nonna’s house for a spontaneous dinner with his wife and adorable daughter. Even the mayor of Monteu Roero showed up! A simple introduction to Paolo and his work became a welcome into his whole world, and that’s the part you can’t put on an itinerary.
The latter trip was part of my work developing The Keepers, a collection of Black Tomato journeys built around the question: What can other ways of life teach us about our own? Each journey brings travelers together with people whose knowledge is rooted in their land, seasons and community, to spend time with them and learn alongside them. With Paolo, that question became very tangible. How would I shop, cook or eat differently if I understood the people and work behind more of my food?
Both experiences—in Lisbon and Langhe-Roero—reminded me how much the people we meet shape our relationship with a place. You can plan a wonderful trip, but you can’t predict who will stay with you, or where that connection might lead.
Places are complicated, and people don’t owe us a particular version of themselves because we’ve arrived with an idea of what a place should look like.
“Slow travel” has become a bit of a marketing phrase. When a luxury company says it, what does it have to do for the word to be earned, in your opinion?
It has to be willing to leave some things off the itinerary. That sounds simple, but there’s a temptation in luxury travel to prove “value” by filling and stacking every hour. Another experience, another transfer, another reservation. Sometimes the most thoughtful thing you can do is give someone an afternoon back!
But it also has to land at the right time, and that takes expertise and emotional intelligence, aka understanding who’s traveling, how they want to feel, and when they’ll appreciate a little space. The care is in knowing when to introduce something extraordinary and when to let someone enjoy where they already are.
For me, slow travel means having enough time and attention to develop a relationship with a place. You return to the same café. You visit the same yoga studio. You have time to follow a recommendation someone gives you. That can totally happen on a four-day trip, but it needs room and intentional space.
A company earns the phrase through the choices it makes: fewer stops, realistic travel times, guides with deep local relationships, and flexibility when something is worth potentially lingering over. It also means respecting the pace of the people hosting you. A working farm or an artisan’s studio has its own rhythms, and being welcomed means adapting to them and respecting their schedules
The luxury is having someone take care of the details so you can be present. If you’re constantly watching the clock, I’d question how “slow” the travel really is.
Black Tomato is best known for its custom, deeply personal itineraries. How does the team translate something so tailored into a story that resonates with a broad audience…without also flattening it?
I say this knowing there’s a good chance my boss is reading, but truthfully, I’d been following Black Tomato for ten years before I joined, and there’s a reason it was my dream job. The team and the travel experts here “get it”. They’re curious about people, they care about the details, and they understand that two people can go to the same place and need totally different things from it.
When we’re telling those stories, we start with why someone wants to go. Someone wants to reconnect with their teenage daughter. Someone is returning to a country their family came from. A couple has just retired and is finally taking the trip they’ve talked about for twenty years. Someone wants to try something new and feel a little more like themselves again. I think we can all see ourselves in some part of that: wanting to feel closer to someone we love, understand where we come from, or make room for a part of ourselves we’ve neglected.
Then it’s about the details that make the experience uniquely “theirs”. What did their travel expert remember from an early conversation? What experiences were they most interested in? Who did they meet? What happened that they couldn’t wait to tell their friends about when they got home? That’s what makes a story feel human, and shows what went into creating the trip.
I think the mistake would be trying to make every itinerary sound like it’s for everyone. In fact, the more specific and particular it is, the more I think it resonates. The reader doesn’t need to want the same trip. You want them to recognize that their own hopes, dreams, and desires deserve that same level of curiosity and care. At the end of the day, they should stop and think, “Wow, I wonder what that could look like for me.”
And that’s what Black Tomato does best. (:
In a similar vein, you share this really gorgeous anecdote about your time in Sri Lanka, but often when we bring readers into someone’s craft or daily life, we need to be mindful of ethics. How does Black Tomato make sure the exchange isn’t extractive? How do the craftspeople or guides you work with benefit?
I think the first thing is recognizing that someone’s everyday life can be extraordinary to you, but it’s still their life. Being welcomed into it comes with responsibility. In Sri Lanka, watching cinnamon harvesters peel and dry the bark gave me an appreciation for knowledge and skill I’d never really considered. That expertise deserves to be valued in its own right.
At Black Tomato, a lot of this starts with relationships built over years, and partners on the ground who understand the local context. We work with partners who prioritize local employment and training, and build opportunities for travelers to support local guides, businesses and artisans into their journeys. The benefit needs to be tangible: income, opportunities for local businesses, and ongoing demand for their expertise.
For me, the standard also has to include fair compensation for someone’s time and knowledge, a say in how they welcome visitors, and control over what they choose to share. The same care applies to storytelling. Agreeing to host someone shouldn’t be treated as unspoken permission to photograph or publish every part of your life.
When someone welcomes you into their home, workshop, or daily life, you have a responsibility to honor the trust behind that invitation.
In your years in travel media, whose perspectives and destinations were consistently underrepresented, and has that shifted? What level of intention was necessary for that change? And what do you wish readers knew about the PR of it all?
One of the biggest gaps has been who we treat as an expert. A writer visits somewhere for a week and becomes the authority, while someone who has lived and worked there for decades becomes a colorful character in their story. I’d love to hear more directly from the guides, makers, and women running small businesses whose knowledge makes those stories possible.
And with destinations, sometimes a place gets covered constantly, but through the same narrow lens. We know its resorts, its ancient history, or its political turmoil, but very little about everyday life. Who’s making art there? What are young people building? Where do people who live there actually love to go?
I do think independent publishing has opened things up in a great way. But it takes intention and thoughtful curation.
As for the PR of it all, I wish readers knew how many choices happen before a story ever reaches them. Who gets invited on a trip, who gets introduced to a journalist, which photographs are shared, whose business makes it onto an itinerary. It all shapes what we end up seeing.
That’s something I think about in my own work. Sometimes the most useful thing I can do is make an introduction, ask another question, or recognize that the person helping us tell the story has a much more interesting story of their own.
You’re very well-connected within this industry. Who’s inspiring you nowadays, and who are the tastemakers and curators we should be learning from?
Obviously Departure! It feels like talking travel with a very trusted, thoughtful friend.
Tori Simokov, who pens Window Seat, has such a good eye for travel and design. I like that she covers up-and-coming hotels and experience, not the mainstream, and she has thoughtful commentary and substance behind all of her recommendations. Not just glamourized content.
Sam Youkilis is incredible. His work is so human and relatable and makes you look deeper at the world around you. That’s a wonderful thing for digital storytelling to do—to make you more curious when you put your phone down.
There’s so much inspiration outside travel, too. I love Cabana and the editorial empire they’ve built around interiors, craft, and culture.
Alain de Botton is forever my north star. The Art of Travel was pivotal for me. I love how he explores what we bring to a place: our expectations, our moods, our capacity to pay attention. It helped shape how I think about why we travel, and its ability to change us.
And Anthony Bourdain, always. He showed how much you can learn by pulling up a chair, sharing a meal, and listening.
If a reader could only take one idea from all of your work on how to travel better, what would you want it to be?
Have your plans, but stay curious enough to let someone you meet change them.
💦 I’ve started a third journey in addition to career and family: one with tretinoin, as prescribed by my dermatologist. My skin has been dry and angry, and I know all this upcoming travel will only rile it up further. I’ve been relying on this SOS Rescue Spray, and it is truly a miracle product that soothes my skin almost immediately. 10/10 if you’ll be on a plane any time soon.
💳 If you consider yourself a fellow points aficionado, check out Rachel Lipson’s The Point. I found her work through the conference, and many other attendees were singing her praises. Easy to digest, thorough, and thoughtful.
🛳️ Did you know American Express has a Cruise & Yacht Collection? I didn’t, until it was freshly reintroduced this week. You can find upscale brands like the Ritz-Carlton and the Aman (for the most ambitious of us!), but their new partners include Virgin Voyages, too—which I tried out last year and enjoyed. There’s also a card benefit: “Eligible Platinum Card and Centurion Members can receive $100–$300 in onboard credit per stateroom or suite, plus a special amenity, on eligible sailings.” Not bad.
🌍 High on my bucket list is a National Geographic trip. In the meantime, I’ll have to settle for their “Best of the World” list for 2027, released earlier this week. Really appreciated their spotlights on community-led tourism in Puerto Rico and Mexico, specifically.
👀 Bilt just announced a new partnership with TrueBlue points, on a 1:1 ratio. If you fly JetBlue at all and want to earn miles on your rent or mortgage, definitely consider a Bilt card. I shared more about my Bilt strategy in this Points, Cards, and Travel episode, particularly how we’ve racked up tens of thousands of miles this year. Here’s a referral link if you’re considering applying.
See you next week! —Henah x
Beautiful interview ❤️ Love hearing from the always thoughtful Drea!
Finally meeting IRL and sitting with you has been the best part of my trip! I’m so glad you’re in this room!