Rob O’Leary

Sales Manager

Having grown up in a bed and breakfast on Ireland’s wild western coast, my living room was always filled with travelers sharing stories from their home countries. Inspired by our guests’ tales of the world, I dreamed about a life in travel. And to help it come true, I decided to become a teacher. I lived in the US first, then China, South Korea and, finally, Spain, teaching children from all walks of life whilst also learning so much about each country, culture, and language. I found that even learning very basic greeting words will get you a long way, although nothing could prepare me for being interviewed on live TV in China – in Mandarin.

As a Travel Expert at Black Tomato, I’m lucky enough to be able to draw on my experiences to help craft remarkable memories and trips for our travelers. Whether that’s letting them in on my favorite tucked-away izakaya (Japan’s answer to the pub) between the neon lights and chochin lanterns of Osaka, or the best places to spot bears in the wilds of Alaska. Really, it’s a conversation – a collaboration – between one traveler and another.

‘Eating pillar to post’

A closer look at Japan

One of my favorite places to go ‘out on the town’ has to be Osaka. One night, during a research trip, I went ‘food hopping’ from place to place, tasting plates of sakana and kimchi (and beer). After eating my way from pillar to post, I became fast friends with the owners of a small izakaya – one that fitted just seven people. When we left, they closed their own bar and followed us to the next one to keep us company. I felt like one of the locals.

If you’re looking for the best backstreets in the city, I know a place. Actually, several.

Discover Japan

“Using AI To Plan Travel: Black Tomato’s New Tool May Reinvent How You Book”

“The hardest part of travel planning is getting started. The Feelings Engine makes that feel like a game worth playing”

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“Black Tomato prides itself on meeting customers every minor need or desires”

“Black Tomato is the choice provider of mind-expanding vacations”

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“Black Tomato is a leading luxury travel company that provides innovative and inspiring experiences”