Living the Seasons of Japan: My Year Across the Islands

I first arrived in Niseko in November 2017, taking up the role of Tour Desk Manager for Niseko Central. Winters in Hokkaido are magical, with snow blanketing the ski slopes and a crisp, invigorating chill in the air. The mountain scenery is breathtaking, and the hospitality of the locals made even the coldest days warm. Managing tours during the ski season taught me early on about Japanese precision, planning, and dedication to excellence.

After the ski season, I spent April 2018 travelling through Tokyo, Nagano, Hakuba, Kanazawa, Kyoto, Hiroshima, Himeji, Osaka, Nara, and Hakone. Each region offered something unique: the hidden alleys of Kanazawa, the historic thatched farmhouses of Shirakawa-go, the spiritual depth of Kyoto’s temples, and the poignant reminders of history in Hiroshima. I was constantly learning, exploring, and documenting experiences that many travellers might miss if sticking to a standard itinerary.

In Tokyo during May and June, I had the unusual but incredibly fun role of a tour guide for MariCar — yes, the go-karting tours dressed as Mario Kart characters! Driving around the city, meeting tourists from all over the world, and discovering secret streets and local eateries gave me a playful perspective on one of the busiest cities on earth.



Then came Okinawa, from July to September, where I worked as a deckhand for the Seasir scuba diving centre in Naha. The waters there are crystal clear, the marine life spectacular, and the slower pace of island life a refreshing change. Scuba diving became one of my favourite ways to explore Japan, and Okinawa’s relaxed culture contrasted beautifully with the bustling urban energy of Tokyo.

Unexpected Encounters: The Heart of Japanese Hospitality

One of the moments that sticks with me most happened in Asakusa, Tokyo. I was standing in the middle of the street with a tourist map, completely unsure of which direction to go. Out of nowhere, a complete stranger approached me. They spoke no English, yet they insisted on helping. Through a friend who could speak English, they ended up touring me around Tokyo for two hours, showing me hotspots, hidden gems, and sharing insights only a local would know. It was a humbling reminder that sometimes the most memorable parts of travel come from the kindness of strangers.

Navigating Challenges: Language, Culture, and Work

Adapting to life in Japan wasn’t always easy. Not speaking Japanese fluently presented daily challenges, from reading menus to understanding public transport announcements. Working within the traditional hierarchy of Japanese companies as a Westerner required patience, humility, and an understanding of unspoken rules. But overcoming these obstacles taught me resilience, adaptability, and how to appreciate the nuances of a deeply respectful and structured society.

Tour Managing the Rugby World Cup: Adventure Meets Logistics

Perhaps one of the most intense experiences of my time in Japan was tour managing groups during the Rugby World Cup. Following England from Sapporo to the final, I witnessed the incredible enthusiasm of fans, the meticulous planning of the tournament, and the vibrant energy of cities across Japan. The biggest challenge came midway, when Typhoon Hagibis hit while we were in Tokyo. Keeping large groups safe while the country faced heavy rain and flooding required quick thinking, creativity, and a lot of patience. We ended up running pub quizzes and indoor activities at the hotel for 48 hours — and despite the circumstances, the group remained cheerful and engaged. Experiences like these taught me the importance of flexibility and maintaining a positive spirit under pressure, which translates directly into how I now plan and manage holidays for others.

Why Japan Makes the Perfect Holiday Destination

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Hidden Gems and Off-the-Beaten-Path Adventures in Japan

While cities like Tokyo, Kyoto, and Osaka are must-sees, some of my favourite experiences came from lesser-known spots:

• Kanazawa and Shirakawa-go: Traditional thatched roof farmhouses, quaint streets, and local crafts offer an intimate glimpse into rural Japan.
• Okinawa diving: Swimming alongside colourful reefs and exploring remote islands.
• Food markets: Seeking out local delicacies in smaller towns rather than sticking to tourist-heavy spots.

A Japan holiday isn’t just about ticking boxes; it’s about discovering what resonates with you personally. That’s where thoughtful planning, local insight, and flexibility make all the difference.

Philosophy: Crafting the Perfect Japan Itinerary

For me, a holiday to Japan isn’t just a trip — it’s a carefully designed experience tailored to individual interests, time, and budget. Some travellers want cultural immersion and off-the-beaten-track destinations like Shirakawa-go, while others seek historical depth, visiting sites like Hiroshima. By understanding what each person values most, I can construct itineraries that balance must-see highlights with hidden gems, ensuring every moment feels meaningful. Overpacking schedules, cookie-cutter tours, or chasing a rigid plan is never the goal — it’s about depth, quality, and serendipity.

Practical Tips from My Personal Experience

Having lived and worked in Japan, I’ve learned a few things the hard way. Here are some tips for anyone planning a Japan holiday:

• Language: Learn basic phrases, but apps like Google Translate are invaluable. Most younger Japanese people speak some English, but patience is key.
• Transport: Consider a Japan Rail Pass if you’re moving between regions. Trains are punctual, efficient, and comfortable.
• Cash & Cards: While cards are accepted in many places, some rural towns or smaller restaurants still prefer cash. ATMs at 7-Eleven or post offices are reliable.
• Etiquette: Remove shoes where required, bow appropriately, and observe local customs at shrines and temples.
• Packing: Pack light and versatile clothing — layers are key if travelling across multiple regions and seasons.

About Your Endless Travel

That’s exactly why I founded Your Endless Travel — to bring the richness of Japan directly to travellers in a way that’s authentic, personalised, and stress-free. With years of local experience, trusted contacts across Japan, and a deep understanding of what makes each destination special, we create tailor-made holidays that allow travellers to explore Japan beyond the guidebooks. From hidden gems to must-see landmarks, our focus is on crafting meaningful journeys that match every client’s interests, time, and budget.

Your Journey Awaits

A holiday to Japan is more than a destination — it’s a journey that will leave you inspired, amazed, and connected to a culture that balances tradition, innovation, and natural beauty like nowhere else. From the bustling streets of Tokyo to the tranquil villages of Shirakawa-go, from powdery ski slopes in Hokkaido to crystal-clear waters in Okinawa, Japan offers endless discovery.



If you’re ready to experience Japan in a way that’s perfectly tailored to you, pick up the phone or book a call today. Let’s create a Japan holiday that’s not just a trip, but an unforgettable adventure.