Japlanning

OUR ADDICTION TO PREPAREDNESS

Back in December 2024, a few of my medical school buddies floated the idea of group international travel. I had only traveled with one of them previously, and have been looking forward to a bigger trip as a group. Given the strength of the dollar to yen this past year, we decided on Japan—following suit with the flocks of people before us.

For me and Peter, this will be our first big international trip together. Up until now, we’ve had multiple small trips together so we’re excited to see how we’ll do flying across the world.

When originally planning the trip with my friends, it was meant to be only 1 week long with an emphasis on the Hokkaido region and maybe a few days in Tokyo. We were keen on having a ryokan experience as a means of just slowing down and catching up with each other.

Set for August 2025, this trip isn’t happening at the most popular time of year. Admittedly, going off-season has its perks of cheaper airfare on top of the generous conversion rate. Peter and I saw an opportunity to capitalize and make an even bigger trip out of this. So, we planned for an additional week in Japan for the two of us. He and I could then explore Japan more privately and enjoy the trip as a couple before we re-grouped.

Planning for an international trip can be daunting. Even planning for a small domestic trip can be a tall order as I am a maximizer when it comes to experiences. There is so much rich culture and history to explore in Japan that even 2 weeks feels inadequate. As we were already going to hit Hokkaido and Tokyo with my friends, Peter and I planned on visiting Kyoto and Osaka during our first and private leg of the trip.

The first week of our trip was planned to end conveniently in Tokyo where we would spend a day before the big rendezvous with my friends. I excitedly took to planning the first leg of the trip as it would take more active coordination with my friends for the second leg of the trip.

Peter’s mode of traveling is the complete opposite of mine. He generally has no preference on activities or food. Rather, when traveling, he allows others to plan while he tags along—provided it is reasonably priced and convenient.

Though happy that I get to plan the entirety of the trip to my liking, this also meant tackling the task singlehandedly. I started the process by slowly saving locations and activities I wanted to visit across various social media platforms. The list ballooned quickly, and I soon started plucking and plugging events into a Microsoft Word document, organized by cities and prefectures. Aghast, Peter exclaimed at how inefficient and laborious my process was.

In usual Peter fashion, he created a very comprehensive Google sheet decked out with formulas that streamlined the entire process. The base of this Google sheet was having separate tabs for (1) potential activities, destinations, and food options, (2) notes, addresses, and price points, (3) day by day organization in 30 minute increments. I was always one to organize trips into 30 minute or hourly increments, filled to the brim with activities. After all, I’d rather have an overly ambitious trip than to idly waste precious vacation time.

We had an organizational tab where I would dump all the activities, destinations, and restaurants along with a short description, their price point, and address, all neatly sorted by column. This was segregated into the 4 main cities/areas we’d be visiting in Japan. On the main itinerary tab, with rows separated by increments of 30 minutes, I then copy over the activity.

When copying over the activity, it also pulled it all of it’s associated descriptors so we would know exactly what to expect. Once this itinerary was filled out with activities, the sheet also provides a guesstimate of the cost of our travel in sub-categories (e.g., food, activity, shopping, etc) as well as in total. Embedding addresses into the itinerary also makes it easy to navigate from one place to the next with an easy tap that would bring us directly to Google maps.

While I was busy making lists of all my favorite things including shopping districts, matcha, temples, and scenic trails, Peter helped out tremendously on top of designing such a smart sheet to help organize.

He took care of all the hotel reservations, flight planning, and ironing out any major kinks in transportation. In other words, he managed all of the logistics of the trip so that my puzzle pieces fit seamlessly together. It helped that both of us have been to Japan before, so we could apply our respective experiences to streamlining this upcoming experience.

Peter had just a few requests to incorporate into the trip, all of which were easily accommodated for by my generous flexibility. We looked for hotels with gym facilities and a close proximity to train stations. We did not want to splurge on hotels because we intended to be exploring for the vast majority of our time there. We just needed a place to sleep at night.

We also looked for proximity to laundry facilities so that we could pack fewer clothes for a 2 week trip, effectively cutting our luggage space consumption by half (and doubling the space available for shopping)!

As we did some financial planning a few weeks prior, we also had a specific budget we wanted to stay under. With this in mind, we could be intentional in the food options as well, ranging from some nicer restaurants (mainly to appease me), street food, and more affordable options. After all, who can resist the temptation of convenience store food when in Japan? Planning our meals ahead allow us to be mindful of our dietary intake even while on vacation, albeit with a slightly larger allowance of indulgence.

Brainstorming and organizing for Japan has been months in the making but we’re so excited. We’ve focused our planning on experiences and enjoying our time there together rather than on luxury amenities and accommodations. We both find those to be personally unnecessary, especially when it comes to more premium plane seats or hotels. However, we do also want to be comfortable while we travel, so it took some negotiation to find a sweet middle ground.

At the end of the day, we wanted to travel happily within our means while making the most of our resources. And though we’ve only exerted maximum control over our private portion of the trip, we look forward to spending time with my friends. We hope to share some of our favorite memories with you in our coming blogs!

XOXO,

Howard and Peter