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Jamie · Updated Sep 8, 2016 · Guides

Journey to Japan: Addressing the Challenges and Joys of Group Travel

AnimeChicago hit a huge milestone this year – we visited Japan! Nine members signed on for a 10-day excursion in early May, right before the chaos of Anime Central. As the lead organizer with prior travel experience, I did tons of research, hostel booking, AirBnb reviewing, and managing of expectations. Here are three challenges and three joys that I experienced, which I hope help you, should you find yourself in a similar role.


Challenge #1 – Ensuring everyone is happy with travel arrangements

Vacation itineraries usually contain items like “read book” and “bask in the sun.” Ours was a whole higher level of planning. I constantly pored over spreadsheets and research websites to ensure we’d hit as many points of interest possible, while maintaining feasible travel schedules and staying within the accepted budget. Admittedly, this process swapped some of my excitement with nervous anxiety.

However once we arrived, all travellers were on the same page and very few disagreements came up as a result during the trip. We collectively made some concessions, but that’s a given when you face unexpected factors such as hours of operation, construction, weather, and language barriers.

This master plan did a lot of heavy lifting amid the chaos. I do not recommend visiting Japan without an itinerary, because the Fear of Missing Out is a major concern for every traveller.

Challenge #2 – Balancing dependence with autonomy

An interesting challenge emerged because of our diverse interests: what do we do as a group, and when can people strike out on their own? Many of our travellers were new to Japan, so their level of comfort with autonomous travel only manifested in the last leg of our trip. We had been going non-stop for 5 days with another 5 days left and a designated Free Day on Day 8.

My Free Day was primarily spent doing laundry at the AirBnb, walking around Shimokitazawa, eating poutine (yeah, in Japan), curry, and the most delicious purin I will ever have in my entire life. Other travellers had similar personalized experiences that day: one travelled to the Kuroki Goishi Ten, another made a friend with a local at Ueno Park, while yet another discovered a specialty card dealer’s shop.

Knowing what I know now, a second Free Day for solo exploration in Tokyo would have been worth the loss of time. I recommend earmarking 20% of your trip as Free Time.

Challenge #3 – Bending time to your will

Much like Chicago, many Tokyo landmarks seem to be 20 minutes away. However, that adds up quickly when you’re visiting several small destinations. A group our size only had the energy for 3–5 points of interest a day, so it’s crucial to research what’s in the area to maximize enjoyment of the region without burning out on trains.

Then there’s the unique challenge of closing time. Most Tokyo hangouts shut down with the last train at midnight, which is a very strange phenomenon when you’re ready to paint the town on vacation. In rural areas, tourism spots and restaurants close as early as 6pm because it’s quiet in those regions.

For seasonal activities such as Hanami and Sumo, you’re already constrained within the confines of your plane ticket. This is especially important when it comes to airfare. Expect it to be rainy, humid and miserable during summer months, and kind of chaotic, yet manageable, during holidays like Golden Week.

Drafting a solid itinerary means being aware of these time limitations and being flexible when you hit a snag.


Joy #1 – Discovering new interests

Japan is a big place with a rich heritage, numerous tourism opportunities, and the largest megacity on Earth. Tokyo has 3 times the population of the Chicagoland area, with 23 smaller cities, or special wards, housed within. Many tourists have visited Japan several times and still have more to explore with each visit, simply because its vastness is incomprehensible.

I’m extremely grateful my fellow travelers researched the restaurants, stores, and landmarks they wished to visit. If it weren’t for them, I would know nothing of Japan’s rich craft beer scene, the joys of Shimokitazawa, or about the extensive collection of manga at the Kyoto International Manga Museum. I wouldn’t have tried Ninja cuisine, or enjoyed a relaxing evening drink at the bank of the Kamo River. Their interests and wonder influenced my second trip to Japan in a way that felt like I was experiencing the country for the first time again.

Group travel isn’t just about your plans. Sharing time with your fellow travellers results in a richer experience with lots of memories. Be open to this!

Joy #2 – Enjoying meals together

Japanese cuisine can be challenging to an American palate, but I personally think sharing the experience makes it that less peculiar. There was always someone willing to pass their plate around when they had an interesting dish, and someone to take the fried sardine when you can’t handle a second bite.

We made it a point to make reservations for a traditional kaiseki dinner, get a taste of Osakan okonomiyaki, and experience a traditional tea ceremony together. Even rushing the nearest konbini was a sight: nine foreigners with an insatiable taste for canned coffee, onigiri, and melon buns definitely caught the eye of a local or two.

Eating is a communal activity, and it’s worth scheduling meals together for these unforgettable moments.

Joy #3 – Unexpected adventures

After our trip to the Sumida Sky Tower, we realized our JR Pass wouldn’t cover train fare back to our hostel in Asakusa. We didn’t have anything else planned and agreed that walking to the closest JR station wouldn’t be an unreasonable endeavor. And there we were on the bridge walking over the Sumida River when it started to pour, with the lights of Tokyo glistening in the background. Those 20 minutes felt like an adventure, seeing the locals run under canopies to get out of the rain, and the construction workers flag cars around open manholes.

It’s these moments that can leave a lasting impression. Somehow, despite the unwanted detours and the frustrations of incorrect train fare, everything will pan out, plans have come to fruition, and everyone’s connected to the world around them. Adventure is a powerful thing.


I’m proud of our club trip to Japan. Should the odds be in our favor, we might do this again in 2018. Thanks to all of my travel-mates for an entirely unique experience, and for being so patient with me as first-time tour guide. I hope you can pay it forward by showing someone else the joys of Japan!