Drea Sobieski
My work has always centered on connection – whether that’s between a traveler and a place or a brand and its audience. As Director of New Media and Influencer PR, it’s my job to build bridges between Black Tomato and the next generation of storytellers. It’s about amplifying our voice in new, culturally relevant ways while staying rooted in authenticity and emotion.
My background is in brand marketing, PR, and storytelling. I’ve worked programming brand partnerships for hotels, launching everything from Après cocktail takeovers with NYC bars to weekend retreats for tastemakers and media — all designed to tell a bigger story, not just sell a stay. Before then, I shaped influencer strategies for several leading lifestyle brands – and founded Elsewhere, which is my personal passion project. Naturally, it all comes back to travel.
Through all of this, I’ve been led by culture, community, connection, and curiosity – and these are the values I live by. In my personal life, that all comes through exploring art, design, cooking, running, Pilates, and Yoga – and being the best auntie to my four nieces.
'It was the kind of journey that reminds you why you travel in the first place'
A closer look at Sri LankaSri Lanka is one of those places that stays with you. One morning, I took a small boat across Koggala Lake, gliding through still waters and tangled mangroves that were alive with birdcalls. The air was heavy with the scent of cinnamon, and we stopped to meet local harvesters who showed us how they carefully peel and dry the bark — a craft passed down for generations.
Later, on the drive from Dambulla to Kandy, the island unfolded in layers of green. Tea hills, roadside fruit stalls, treehouses tucked into forests, and people greeting us with warm smiles. I spent an afternoon at an elephant sanctuary and bonded with a gentle soul named Madu, whose quiet strength and curious eyes felt all too human.
It was the kind of journey that reminds you why you travel in the first place — to feel small, connected, and entirely in tune with the world.
Explore Sri Lanka
“Using AI To Plan Travel: Black Tomato’s New Tool May Reinvent How You Book”
“The hardest parts of travel planning is getting started. The Feelings Engine makes that feel like a game worth playing”
“Many companies brag about offering once-in-a-lifetime experiences. But with Black Tomato it’s not hyperbole”
“Black Tomato is a super innovative company where the sky is the limit for their clients”
“Black Tomato prides itself on meeting customers every minor need or desires”
“Black Tomato has made it a mission to keep the world of travel fresh, responsible, and exciting”
“Tailor-made travel experiences that truly get under the skin of a country and its people”
