Seatmates: Kayla Douglas
On working in luxury travel marketing, airline pajamas, and why life’s greatest luxury is returning to somewhere familiar
This interview is part of Seatmates, a Window Seat series where tastemakers, travelers, and creatives share how they move through the world—what they pack, where they stay, and the travel rituals that shape their lives.
Kayla Douglas has a knack for turning wanderlust into something tangible. As the Director of Content at SmartFlyer, a full-service luxury travel agency, she shapes the way we dream about (and book) high-end travel experiences. She writes not one but two Substack newsletters: her personal letter, The Sunday Series, and one dedicated to her monthly book club, West Village Book Club. Somehow, she makes it all look effortless.
Based in New York, Kayla moves between the worlds of editorial, community, and luxury hospitality with a rare sense of clarity and warmth. Whether she’s sharing her latest reads or crafting the perfect travel itinerary, her voice is one you want in your corner—and in your inbox.
Read on to learn how she scored her dream job by sending a cold DM, which island she’s visited for the past three summers, and her favorite spots in NYC’s West Village neighborhood.
Tell us a little about yourself.
Hi! I’m Kayla, a New Yorker deeply passionate about fostering connections between people and places through storytelling. My motivating forces in life are curiosity and creativity—fortunately, my personal and professional journey has allowed me to tap into both. Beyond being a writer, I’m an older sister, loyal friend, avid reader, reluctant runner, dedicated foodie, perfectionist Virgo, fresh flower enthusiast, long-time Swiftie, eager hostess, and discerning traveler.
Before becoming SmartFlyer’s Director of Content, you were a social media marketer and travel agent–all roles within the travel industry. How did you navigate this career path?
I graduated from college with an International Studies degree and zero clue what to do with it. Actually, I wrote about how my final college semester studying in India inspired me to find my first professional opportunity within the travel industry in a recent Substack. It’s been nine years since I started working as a travel agent fresh out of school, eight years since I pivoted to a marketing role in the agency space, and a million learning lessons in between. When I think back on those early years that helped me lay the foundation of my travel career at Flight Centre, I’m so grateful for the perspective I gained selling travel and working in a traditional corporate environment (think: uniforms!).
But I knew early on that I didn’t want to stay on the sales side, and with the help of a few internal champions, I pitched myself for a marketing role at the company’s New Jersey headquarters. I had zero marketing background at the time—I’ll never forget the CMO telling me that they interviewed ten external candidates who each had more qualified resumes than mine—but I was the only person who understood the brand from the inside after working as an agent. I moved to New Jersey without knowing a soul there to take the job. It was a wild time of transition, and I relished the chance to run social accounts for major travel brands just as platforms like Instagram were really beginning to be leveraged for business.
Without this answer becoming a novella, perhaps it’s poignant to share how much intuition led me to my next career move. By 2018, I began to crave a change. I was in the midst of following along as Erina Pindar, Managing Partner and COO at SmartFlyer, posted from Mexico City. Heavily influenced by the cheap prosecco I was drinking in the United Lounge during a flight delay, I responded to one of her IG Stories that I’d love to work for her if an opportunity arose. There wasn’t a job posted at the time, but I inexplicably felt magnetized to SmartFlyer. That DM changed my life; mere months later, I moved to New York and started my journey with the company. You can read the whole story here, but my point in sharing is: you should always shoot your shot. Have the subject expertise to back it up, of course, but never be afraid to put yourself out there. My first day working with SmartFlyer was at a Vegas pool party, and the intervening years have been just as dynamic.
You’ve been to over 30 countries so far. Is there anywhere you wouldn’t travel to again? Is there anywhere you’d visit over and over again if given the chance?
Oh, tough question! I need to update my country count, but to be honest, I stopped keeping track. Back in college, the idea of checking off a new-to-me country was so exciting; now, I find that life’s greatest luxury is to return to somewhere familiar and uncover a new layer. I’ve gone to Mallorca the past three summers—the Balearics are my happy place. I finally got to check out Menorca last year, too, and I fell in love with its slower pace and how wild the island felt. I want to go back and add on time in Formentera, where some fun new properties are cropping up. Finally, I’m a huge francophile and can never get enough of Paris. I just did a solo stint there in September and will be back in May with West Village Book Club! As far as somewhere I wouldn’t go back? Really nowhere. Namibia maybe? Not because I didn’t find it fascinating, but because it’s so specific and tough to get to—I felt like I had a really holistic experience there that couldn’t be topped.
As a resident of NYC’s West Village neighborhood, what are your favorite local spots to recommend to out-of-towners?
I love this question! For me, living in the West Village for the past three years has allowed me to have a small-town feeling within this bustling city. I’m definitely guilty of staying in my neighborhood bubble when I’m home, but I justify it because frequenting the same cafés, shops, restaurants, and bars means seeing familiar faces and, in turn, feeling more connected to my community. Below is a non-exhaustive list of some of my West Village faves, including some that are newer or more geared toward special occasions:
Coffee: Sogno Toscano, St. Jardim, Plantshed, The Elk
Breakfast: Dante, Buvette, Little Owl
Lunch/Dinner: Left Bank, Pastis, Don Angie, Via Carota, Joseph Leonard, Waverly Inn, Emmett’s on Grove, Roey’s, San Sabino
Drinks: b’artusi, Bar Pisellino, Katana Kitten, Do Not Disturb, Lavaux Wine Bar
A Little Treat: Magnolia Bakery, Gentile Gelateria, Barachou, Fabrique
Shopping: Casa Magazines, Three Lives & Company, Cursive, Madame Matovu Vintage, Big Night, Hudson Grace, Greenwich Letter Press
