Niseko Hokkaido: A Winter Escape for the Traveling Entrepreneur

When you blend work with the thrill of travel, every trip becomes a story worth telling — a saga of balancing duty with the joy of discovery. My December 2024 venture to Niseko, Hokkaido was no exception, and it surely packed the best of both worlds.

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The Journey to Niseko

Our journey began with an 8.5-hour flight via Japan Airlines from NAIA International Airport Manila, with a brief layover at Haneda Airport. The flights were smooth yet tiring, and as usual, I found myself working amid bustling terminals. It’s practically a skill at this point — or, should I say, a survival tactic.

Landing at New Chitose Sapporo Airport, we hopped into a private transfer, trading urban sceneries for a 2.5-hour snowy drive to Niseko. It was as if we were transported to a winter wonderland with snowflakes dancing around us — pure magic! Our Airbnb in Niseko Village was second to none, offering a mesmerizing view of snow-capped mountains and the stunning Mt. Yotei.

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Our Stay in Niseko Village

We had the whole apartment to ourselves, featuring two bedrooms, an attic, and not one, but two bathrooms with bathtubs. Throw in a living room, a dining area that seats six, and a kitchen that could accommodate a culinary tour de force. For just the two of us, it was like living in luxury with an abundance of elbow room!

The next day, we ventured out to pick up our snowboard and ski gear and stocked up on groceries. With our equipment ready for the following day’s lessons, we were all set for some winter sports action. To my delight, my coach’s feedback was motivating, apparently, not everyone makes it to the chairlift on their maiden glide. Although my second lesson was benched due to some sore muscles, I promised myself a longer stay next winter to master the slopes.

Side Trips to Sapporo

Before diving headlong into skiing, we did a quick return to Sapporo. The trip featured shopping and a visit to the Sapporo Beer Museum, Japan’s only beer-dedicated museum. Though we skipped the tastings, the nostalgia of the museum was beautifully captured in our souvenir tins of Sapporo beer.

Speaking of enchantment, Shiroi Koibito Park was another highlight. I highly recommend a 4–5 hour stay to truly indulge in its offerings: touring the Ishiya Chocolate Factory, baking shiroi koibito cookies, and unwinding in their delightful lounges. Our schedule constrained by our private pickup, allowed only a brief visit, yet the charm of the park left a lasting mark on us.

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Finding My Work Rhythm

Back in Niseko, after tackling some client tasks, we headed to an old haunt, the Arabica Niseko mobile café. Their Kyoto Latte with Oatmilk remains a favorite — something I can never quite get enough of. Returning the ski gear to Rhythm Hirafu was made easy by the convenient shuttle buses cruising around the village.

My subsequent days in the cozy Airbnb were a mix of work, relaxation, and preparation for departure. The tranquility combined with a rigorous home workout and a luxurious hot bath exemplified the balance of travel and thrive. The essence of this journey.

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The Long Journey Home

The return trip was longer, clocking in at 13 hours, yet Chitose and Haneda Airports provided ample amusement with scrumptious Royce chocolates and indulgent soft-serve ice cream. Obviously, or rather yet again, airports became my office during the layovers. As we took our much-coveted fire exit seats on the plane, fatigue quickly took over, and sleep ushered me back to Manila.

Reflections on Remote Work and Travel

Traveling as a freelancer isn’t about constant motion, it’s about creating balance. Niseko reminded me that it’s okay to slow down, to work a little, wander a lot, and still find meaning in both.

For those planning their next work-and-travel adventure, Niseko Hokkaido is more than a destination, it’s a reset. A mix of quiet mornings, snow-dusted streets, and that sweet spot where productivity meets peace.

To all traveling entrepreneurs and remote workers, how do you find your balance between deadlines and daydreams?