How to Plan a BIG Trip

In May – July, 2017, I kicked off a solo trip to Asia. It was a huge planning project, and I would like to share my planning process for this trip in this blog post.

Choosing a Destination

For me, I did not even know where I wanted to go. I had a ton of destinations on my to-go list, but I had no idea which ones to pick, where to start, and how to arrange the route. The only thing I knew was that, I finally graduated, I needed to do a grad trip.

First, the most important question to ask is what is your purpose of this trip. Is this for exploring new cultures & local experiences, relaxation, or food? Do you like big cities, small towns, beaches, or mountains? Do you like to walk? Do you drive? How many hours would you feel comfortable to be outside? Usually, if you end up in a big city, then you’ll likely be taking the public transitions, so be prepared to know how to read their map and subway schedules, etc. If you end up in outdoors (e.g., national park), then you’ll likely be driving around, so make sure that you get your international driver’s license if necessary. Also, there’s a big difference between travel and vacation. Generally speaking, traveling is much more energy consuming and tiring, and requires long day walkings, while vacation typically involves relaxation, sitting by the beach reading a book, doing water sports, etc. Think about these questions and do some research online, and you’ll find that your endless list of destinations will shrink quite a bit!

For me, the purpose of my trip was to find myself — experience different cultures, get involved in local life, and taste unique local food. I’m not good at directions, so I might rent a car if I have trouble with local public transitions, so I got my international driver’s license beforehand. Given my purpose, I filtered my destinations by continents. As I said, I had no idea where I wanted to go. There are a 7 continents, and my thinking process was as follows:

  1. I have a huge amount of time, so I want to go to somewhere far. I’ve been living in North America for a long time. So definitely not gonna travel within North America or South America.
  2. Asia sounds very tempting. Also crime rate in Asia is relatively low. Sounds like a safe place for solo trips.
  3. Africa sounds very interesting. Might require some experience in travelling though. Some preparations would be required (getting vaccines, etc). Maybe next time.
  4. Australia is gonna be winter.
  5. Recently have been to Europe.
  6. Antarctica… sounds challenging.

Therefore, Asia it is!

Next question is: which countries in Asia? There are so many countries that I wanted to visit in East Asia and South Asia. What I did was that I filtered my destinations by climate. I knew that my trip was gonna be around May – July, so I would need to avoid places that are too hot or rain too much. For example, South Asia is going to be humid AND hot during those months, Tokyo & Seoul is going to rain a lot around June, and I’ll likely get cooked if I visit China in July, etc. Therefore, my destinations largely depend on which months are the best time to visit, and which months are to avoid. Also make sure you check the weather. It’s very possible that you’re in your destination city in its best season, but it happens that the one week you’re there it keeps raining.

Third question is: how to optimize the route? Ideally, I should start somewhere North, stop by a few countries, end somewhere South, and return to Canada before I get cooked by the ☀️. Therefore, that cut off quite a few destinations that would have conflicts in both route and weather.

How to Choose Dates?

I searched for each of my candidate destinations and wrote down places/attractions that I’d like to visit and the approximate time that I would spend there. In the end, I have a list of destinations with estimated time to be spent. Something like this:

Shopping (3 days)
Bukhansan National Park (1 day)
DMZ (1 day)

Because I have a lot of time, I added two days buffer to each country in case of jet lag, period, or any kind of random things that could happen. When you book the flights, you should also look around for similar dates, because sometimes flight fares differ a lot each day!

Best Apps to Use for Trip Planning?

Transportation: Google Maps. This is just my go-to app for routing. Works 100% time.

Accommodation: Airbnb. Airbnb offers many nice houses at convenient locations at a much cheaper price than hotels. You can choose to have a private room, a shared room, or an entire suite. Some hosts are very hospitable and are willing to share their stories. This is also a great way to get involved in a local culture.

Meeting local people: Meetup. I think one important thing to do when solo travelling is to meet local people and get involved in their culture. Meetup is a great app for meeting people with similar interests. Usually the Asian people who use Meetup are also very happy to talk to foreigners in English. Definitely give it a shout when you’re solo travelling!

Which Attractions?

I started planning 3 months in advance. My plan has undergone countless revisions — in fact, complete reconstructions! In the end I chose Korea, Taiwan, Japan, Singapore, and China to be my destinations. I don’t usually go on TripAdvisor or similar services to find ideas unless I know nothing about my destination. I do read a lot of travel blogs. I also like to associate places with stories. I got most of my ideas from literature and movies. Take a few famous but not quite iconic examples:

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Lotte World. It’s the largest indoors amusement park in Asia. Many famous Korean dramas were filmed here, including Full House and Stairway to Heaven.

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The piano from movie Secret directed by Jay Chou. In the movie, the main actress played this music sheet on this piano and travelled back to 20 years ago.


Jioufen. Yubaba’s bathhouse from Spirited Away was inspired by this place. I see a lot of Japanese tourists here (yeah of course) 😂


Cafe La Boheme in Tokyo. It was the restaurant Taki works at in movie Your Name.

Impromptu Trip

As an old saying goes, plans are meant to fail. Sometimes, plans just will not work out. The craziest thing I did during my solo trip was probably an impromptu trip. I planned to stay in Taiwan for 2 weeks. Taiwan was flooded immediately before my arrival, and I was lucky that I missed it. A week after my stay in Taipei, my Airbnb host warned me that the local forecast predicted storms for the following week again. Therefore, I purchased my flight ticket to Tokyo 14 hours in advance. That was my first impromptu decision.

I purchased the one-way ticket to Tokyo in case I wanted to go to somewhere else during my time there, but then Bai told me that I would also need the ticket leaving Japan in order to enter the customs. I was like… if I purchase another one-way ticket from Tokyo back right away then it’s a terrible deal… (could’ve purchased a return ticket for a cheaper price). Therefore, I have to purchase a return ticket from a different city!!! So I purchased the return ticket from Kyoto 12 hours in advance. That was my second impromptu decision.

My friend suggested Kinosaki Hot Spring to me and advertised it as a must-go. I did some research later and figured that I wanted to visit this place. This place was 3 hours of high-speed train away from Kyoto. I decided to purchase the train ticket on the day of visiting. That was my third impromptu decision. It was not efficient obviously, and I only got to spend 2 hours there (the train ticket was expensive T T). But I’m still super glad that I did it! The hot spring was the perfect place to relax after so many days of walking. Made me feel like reborn 😀

Those days have been crazy. I planned everything one day in advance or on the fly. Bai and Yasunaka (met at Tokyo machine learning meetup) have helped me a lot. This experience pushed me to be more decisive, think about more things at the same time, and do stuff whenever I want to because there would not be much time for hesitation.

Make a Shopping List

For long trips like this, you probably would want to buy something that is 1) only available in your destination country, or 2) significantly cheaper in your destination country, or 3) is meaningful in terms of local culture, design, or histories. You probably don’t wanna bring back a huge luggage of stuff that is easily accessible from your home country. It is also important to look up online and make a detailed list of what is worth getting and where to get them before going shopping. When you’re travelling, you don’t have time to do price comparisons, so it would save you a lot of time if you do your homework ahead of time 🙂

Girls’ Problem — Luggages??

Like most girls, I love shopping too, and I have a lot of luggages… What should I do? How should I carry so many luggages myself?

Well, first of all, check if your Airbnb place has elevators. Some houses in Asia are very old — do not get surprised when they don’t have elevators! Well, I obviously did not do that, and I regret it. I spent about 30 min carrying my luggages downstairs from 4th floor during my stay in Taiwan… and it was not fun 😦 I also tripped over the stairs while carrying my luggages during my stay in Kyoto… it was actually sad. So make sure to check whether your place has elevators!

Also, flights within Asia have a big allowance for the limit weight of the luggages. Usually they allow 30+kg for each luggage. My suggestion is to try to put everything in one luggage and don’t worry about it going overweight. As long as you’re flying within Asia, you can pretty much stuff your luggage as much as you can. You can then purchase a second luggage/bag at your final stop and split your luggages (all airlines flying to the US only allows 23kg per luggage).

Post Trip

As an old Chinese saying goes, “It is equally important to travel ten thousand miles and to read ten thousand books” (读万卷书,行万里路), travelling has indeed enriched my knowledge and broadened my horizon, and I think it’s also important to do both at the same time. After I came back from the trip, I became particularly interested in the history of the countries that I visited, and I started to read history books. I hope I can take away the most out of each place: the best pictures, the best friends made there, and their best and worst stories.

That was how I planned my gigantic Asia trip. To learn more about my experience in Asia, please visit here. I hope this blog post was helpful if you’re considering planning your next trip. Please feel free to comment down below to let me know if you have any questions! 🙂


About me

Hello! I am Shirley, an ML engineer living near San Francisco, California. I was born in Suzhou, China, and immigrated to Toronto when I was 16. I earned my degree in Computer Science and moved to SF for work and living. When I am not working, you can find me playing music, traveling, reading, and writing in this space! I usually write in English for tech stuff and Chinese for everything else :)

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3 responses to “How to Plan a BIG Trip”

  1. […] All fantasies come to an end. This journey was truly amazing and special. Thank you all, for letting me have good stories to tell. ❤ For full gallery, please visit here. For tips on how to plan a trip, please visit here. […]


  2. Great post filled with great information!!


  3. Try out this travel planning site: TripHobo. They have so many itineraries for each city. You can edit those or create your own itinerary. See at:


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