We’re always curious to learn more about women’s stories, their expertise and secret tricks for navigating through the world — and our favorite trick for discovering said tricks? By asking someone they are close to. Here, a conversation between two traveling pros: former Conde Nast Traveler Editor in Chief Pilar Guzman and YOLO journal founder + former CNT Creative Director Yolanda Edwards. At the start of fall, we caught Pilar on a rare break at home and asked her old, dear friend Yolanda to send her a few questions…
In Yolanda's words:
“Professionally Pilar Guzmán is known and adored for her masterful magazine editing (Cookie Magazine, Martha Stewart Living, Conde Nast Traveler) and today as a writer, speaker, and founder of a brand consultancy firm…but part of what makes her so uniquely good at what she does is her great curiosity, generosity, and kindness. She has this superpower to laser in on people and their potential, and within 5 minutes she's got a job, diagnosis, or maybe even a date for them. She trusts her gut, she takes chances, and she loves to share.
We've known each other since college days—I would borrow her art history notes, and try, unsuccessfully, to convince her to come to the nightclub I was promoting. Fast forward a couple of decades and we reunited in the magazine world when she was launching Cookie and asked me to come on board. We've been work wives ever since, and, living a couple of blocks from each other for most of our parenting life, we've raised our families together as well. Pilar is one of my favorite humans, but she also has a way she travels that I envy...I am an overpacker, an overplanner, and she is...well...see below!”
Yolanda: You've always been a traveler—since you were little and traveling with your mom and sister for your mom's work. Can you share more?
Pilar: My mother was a professional singer and stage actress. My sister, myself, my mother’s pianist Pearl, and Pearl's two daughters traveled with her for work all over the world, piggybacking family trips onto work trips. While my mother was (and remains) the world’s most inefficient packer—she traveled with a fleet of wheel-less Louis Vuitton hard leather suitcases—she was also the most fearless. She would ask stagehands and other behind the scenes theatre staff where, say, the best local barbecue was in Fort Worth, or best Cuban sandwiches were in Miami. She would venture into any neighborhood at any time of day or night.
She to this day walks up to strangers in restaurants and dives, asks them what they are eating. Invariably, and now to the horror of her longtime companion Don, she will be offered and accept a bite of whatever food they are eating. She also risks for the sake of adventure that other parents of that generation wouldn’t. I remember going up in a tiny float plane over Glacier National Park in Alaska when I was 8 and my sister was 11. I never felt at risk; we always felt girded by her own assuredness. She is perennially at home in the world.
Who is a traveler you've always admired, and why?
Not surprising, especially given my last answer, I would have to say my mom. While she is pretty scattered about just about everything else, she is one of the most curious, most rigorously researched, and fearless travelers I know, She also taught me never to waste any experience: To this day she will leave a restaurant (politely) if she suspects it’s not going to be the best, most authentically meal we can possibly have in a place (usually based on the quality of the bread or if she sees that the pasta seems overcooked). She also treats everyone the same way, whether they are the bellman or the owner of the hotel.
I learned early on that, apart from the obvious Golden Rule goodness, being nice to everyone only deepens a travel experience. It opens you up to the wisdom and generosity of strangers in a strange place. I can’t tell you how many people’s homes we’ve been invited into: We’ve gone as guests to both a stage dresser’s family picnic in a public park on Long Island and to the Tony Pacific Union Club in San Francisco with a theatre benefactor. Guess which one we enjoyed more.
Since everyone assumes you are the most perfect traveler, can you share some vulnerable travel moments?
Far from it. When I was a student studying in Florence for the year, I traveled somewhere almost every weekend usually with little planning. It was the early 90s and much of Central Europe was just opening up as relations between the US and the Soviets began to warm. I convinced my roommates to do a whirlwind tour of Prague, Budapest, and Krakow over one of our breaks. While my winging-it strategy worked well in the first two places, we’d arrived in Krakow too late to be let into the youth hostel. Accommodations were few and the jewel of a town wasn’t yet ready for prime time. We ended up having to sleep in the train station, which was, as it turns out, pretty safe back then.
And on the flip side, what are some of your travel hacks? You are the master of the no-check bag. Please share your secrets.
It’s true, we only carry on. If you’ve ever had a piece of luggage get lost, you too will never check again. I’m one of those people who doesn’t mind wearing the same thing over and over—of course with clean undergarments and shirts. I think people make the mistake of imagining a different version of themselves in different places. (Granted, fantasy dressing is another matter; when going on a sexy trip to St. Barths you have full permission to pack as many fun dresses as you can fit in your bag).
I would remind people to pay attention to their own dressing patterns and home. How many of us wear a pair of jeans for a few days and just change out our shirt? Same rules apply for most travel. Pack multiples of things that don’t take up much room like shirts and dresses. Shoes are the killer. Wear the shoes or boots that take up the most room on the plane. Pack a pair of flats and a pair of heels that are neutral enough to go with everything. My friend and former colleague, fashion editor Sarah Meikle, taught me to pack in a palette so things can be mixed and matched: camels, greys and blushy pinks one trip, navy, grey and white for another.
My biggest hack is pulling kids out of school for a couple of days over Thanksgiving and traveling that week somewhere outside of the US. Fares tend to be cheaper and you get that Friday through the following Sunday.
You're the best listener in the world. Are there any airplane seatmate stories that stand out?
I once sat next to a fascinating guy: A Stanford professor who was developing a new sustainable form of LED gallery lighting. He gave me an education on the history of lighting over the course of our flight from London to New York. Most of what he was working on was way over my head, but he patiently broke things down and used some of the most poetic metaphors to explain things. I kept telling him, “Pretend you are explaining this to a fourth grader.” We’ve stayed in touch a bit since then.
I haven't heard this story firsthand since we have been separated this summer...but did you travel 3 hours to go have lunch on your recent trip to Italy? Worth it?! And what are other meals you dream about and would literally get on a plane, or drive extensively for?
While I am usually pretty go-with-the-flow when it comes to a road trip with my husband or with friends, on a recent drive from the Salento region of Italy to the Amalfi Coast, I was on a mission to eat lunch at Antichi Sapori in Montegrosso. It's basically the OG Slow Food Mecca where everything is made in house or with painstaking care from vendors close by. It’s one of those places that, despite its intense rigor, is totally unassuming and doesn’t take itself so seriously.
...It was, however, about three hours out of our way and meant not hitting Matera or the ceramics factor that my husband had his heart set on. When we arrived after a long hot drive, we were seated next to a couple and their screaming toddler, which we are normally pretty good at tuning out...but once we moved and tucked into our first glass of wine and the simplest, most delicious orecchiette pomodoro, my husband understood what we were doing there.
Is there any trip that stands out to you as The Best Trip Ever?
The best trip I ever took was with my family to Egypt last November. We sailed down the Nile from Luxor to Aswan on a traditional dahabiya. It was at once the most culturally rich (in that cradle of civilizations sort of way) as well as the most relaxing. Something about the pace of sailing slows everything down. Plus, there are still so few tourists that you feel like you are seeing that part of the world as the Victorians did.
Talk about your travel planning--your issues with it, what paralyzes you,
Believe it or not, I hate booking flights more than anything on earth. That and deciding where to go: There are so many places I want to see. I have such FOMO, it’s embarrassing. I am keenly aware of the fact that choosing one place means unchoosing another.