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"Should I sit on the right or the left on this bus?" 9 things I ask AI when traveling abroad

Traveling abroad is full of mysteries. No matter how many times I travel, I'm always left wondering about something.

"Should I sit on the right or left side of this bus for the best view?"
"How much should I exchange?"
"Is there a mistake in the itinerary I put together?"
"Will I stand out if I use an umbrella in this country?"
"Should I sleep now or stay awake to prevent jet lag?"

Looking things up in guidebooks, maps, and translation apps can be part of the fun of traveling, but I don't always have the energy for that. Besides, there are some minor questions where you wonder, "Is this really worth searching for?"

Lately, I've started asking generative AI about these things. Whether it's asking for advice on a problem, confirming a worry, or asking about a "What is this?" I found while walking around town. It's less about getting the perfect answer and more like having someone I can bounce questions off of at any time.

In this note, I'll summarize the things I often ask AI, divided into two categories: "When preparing for a trip abroad" and "When walking around the destination."

Preparation Edition

Itinerary Planning

Once I have a candidate country or city in mind, I start by consulting on the itinerary.

・What is the classic sightseeing route in this city?
・What kind of itinerary would minimize the use of paid leave?
・What are the must-see tourist spots?
・If I'm going to spots A, B, and C, what is the recommended route and how long will it take?
・What are some recommended cities for a day trip from the capital?
・In which area are the hotels for tourists concentrated?

As an office worker, I often travel abroad for short periods, so I'm particularly concerned about "how many days I need to go."

If a model plan in a guidebook is 5 nights and 7 days, I usually travel for 2 nights and 3 days. I just don't have the time. So, it's also okay to ask specifically, like, "I want to leave Tokyo on Friday and be at work by Tuesday morning. Create a realistic itinerary under these conditions."

Of course, I don't expect a perfect answer from the start.

"I'm confident in my physical strength, so sleeping at the airport and on the plane is fine."
"I'm not interested in that spot, so I want to cut it."
"I prefer trains over buses, even if they cost a bit more."
"I'm carrying a backpack, so I can walk for up to 2 hours."

By repeating this exchange, I expand my image of the trip.

I don't necessarily adopt it as is, but it's much easier than starting from scratch.

Getting from the airport to the city

Getting from the airport to the city (hotel) is still the biggest hurdle. When I think, "I want to visit this city," before opening a guidebook, I use AI to gather some light information.

・What are the access options from the airport to the city?
・Does the airport bus run 24 hours a day?
・Are there ride-sharing services available?

I start choosing the city and flights after confirming these points. Especially for a woman traveling alone, the travel budget and schedule change depending on the safety and travel time of the transportation.

For example, if I find out that the only safe way to get around is by taxi, I might decide, "This is a bit over budget, so I'll go to this city when I have someone to split the costs with."

If the bus from the airport runs 24 hours a day, flights arriving or departing early in the morning or late at night become options. Choosing a hotel might prioritize "proximity to the bus stop."

Double-checking and organizing the itinerary

I'm the type who wants to see as many new sights as possible while minimizing the use of paid leave, so I don't stay in one city for very long. People might find it intense, but this level of movement is standard for my trips.

I am working on 2/26

With an itinerary like this, a single mistake in booking a flight or hotel can be a disaster. I use AI to do a quick check like this.

Is there any flaw in this itinerary? Please check it carefully, taking into account overnight travel and time differences.

Next, I give the following instructions to have it organized into a format that is easy for me to check myself.

Summarize the itinerary day by day in the following format:

🗓 February 20 (Fri) | Tokyo → Tashkent (Uzbekistan Airways: HY528) 11:05 Depart Tokyo Narita (NRT) ✈️ 9 hours 05 minutes 16:10 Arrive Tashkent (TAS)

The more travel involved, the more tedious the organizing and checking process becomes. To lighten that burden, I proceed with arrangements using the following steps.

① Have AI do a quick check
② Have AI organize it into an easy-to-read format
③ Check it thoroughly myself
④ Confirm the bookings
⑤ Have AI write out the final itinerary
⑥ Check the written-out itinerary against the booking confirmation emails
⑦ Paste the itinerary into my "Travel Guide"

▼ Click here for the "Travel Guide"

Local money and payment situations

I often ask AI about local money and payment situations because they are constantly being updated.

・Is it a cash-based society? Or can I use a credit card everywhere?
・Can I use contactless payment for subways and buses?
・Is there a tipping culture? What are the standard rates?
・Are public restrooms paid?
・I want to do these things; are there situations where I will need cash?

I don't know the common sense regarding tipping habits

It's a different story for countries that use dollars or euros, but for countries with other currencies, you need to be especially careful. After all, it's a problem if you don't have enough cash, but it's also a problem if you have too much left over.

The idea is to gather information first, then think, "Okay, how much cash should I carry?"

Choosing clothes and belongings

Choosing clothes is also something that works well with AI.

AI knows my wardrobe and also knows information like, "I'm a backpacker traveling with only carry-on luggage. I want to reduce my luggage, but I get cold easily and sweat easily, so I need extra cold-weather gear and changes of clothes."

With that in mind, I ask questions like this.

・Ulaanbaatar on August 1, 2026. High of 22°C, low of 11°C. Rain in the forecast. What kind of clothing do you recommend?
・I'm debating whether to bring both an ultra-light down jacket and a packable parka.
・How many T-shirts will I need for this itinerary?
・Will I stand out if I use an umbrella in this country?

Sometimes I ask quite specific questions like this.

I'm going in all Uniqlo.
For bottoms, I'm sticking with the brown jersey barrel-leg pants. For tops, a few black T-shirts. I'm bringing a packable parka and an ultra-light down jacket.
I can't do laundry locally.
How many T-shirts do I need for this itinerary?

Communication

When abroad, my personal rule is to greet people in the local language.

I have AI teach me these four phrases and their pronunciation. I make a note of them, set it as my smartphone lock screen, and cheat when necessary.

・Hello
・Thank you
・Excuse me (to get someone's attention)
・Delicious

Overseas, actions that are taken for granted in Japan might be interpreted in unexpected ways. Asking things like "Tell me what gestures I should avoid" or "What should I be careful about when riding trains or buses?" helps prevent trouble.

Local Edition

Dining, restaurants, and choosing souvenirs

AI is also reliable when it comes to understanding the local dining scene.

・What should I eat in this city? Tell me some places that are easy for a woman to enter alone.
・Does this dish contain cilantro?
・Can I get takeout at this restaurant?
・Are there any shops I can stop by along my sightseeing route?
・What do you recommend buying at a supermarket for souvenirs to give out at work?
・Is this yogurt locally produced? Which one is a staple in this country?
・If I were to buy food that doesn't require cooking at a supermarket in this country, what would you recommend?

In countries where I can't read the script at all, such as Russian-speaking or Arabic-speaking regions, I also use photos. I have the AI look at a photo of an entire supermarket shelf and ask, "Which products are locally produced?" or "Which one is yogurt and which one is milk?" and I get an answer in an instant.

How to spend time to prevent jet lag

On long-haul flights, I sometimes ask, "Given this flight schedule, when should I sleep to minimize jet lag?"

If I provide the departure and arrival locations, as well as the departure and arrival times, it will give me advice based on the time difference. This kind of calculation is a hassle, so it's quietly helpful.

Johannesburg to Hong Kong flight
The time difference was significant, so it was a big help.

Ask about everything you see in front of you, like "What is this?"

When I'm there, I just ask about everything.

It's not just for when I'm in trouble. If I'm walking around town and think, "What is this?", I ask right then and there, partly to keep a record.

[Trouble]

・How do I say "Please hold the cilantro" in the local language?
・Get the latest airport bus timetable for Ulaanbaatar from the official website.
・What floor of the building is this cafe on?
・I can't find the entrance to this tourist spot. Where is it?
・Where is a supermarket with a good selection near my hotel?
・The hotel door won't open, what should I do?
・I'm waiting at the airport for 6 hours until morning; where is a comfortable place to spend the time?
・Google Maps says this road is a 60-minute walk, but is it actually walkable?
・My hotel room is too cold. Is this a type where I can't change the temperature myself?
・Does this strike information affect my train?
・What does this notice say?
・The night bus isn't coming. What's the next option?
・Is there a free restroom around here?

Aren't hotel keys difficult?


[Curiosities]

・For the bus from the airport to the city, is the view better on the right or left side?
・Does the Islamic Adhan sound different depending on the location?
・Tell me 50 pieces of trivia to deepen my understanding of Islam.
・How big is this mosque compared to others in the world?
・When someone sneezed, the people around them said some mysterious words. What was that?
・There's someone in front of me with a hawk (?) on their arm. What's that about?
・There's a huge line at this shop; is it famous?
・The shop clerk keeps saying the same word over and over. What does it mean?
・What language is this cool-looking script?
・If you had to compare this city to a place in Tokyo, where would it be?

The "prayer app" used by Muslims
I only learned about it after AI told me
It also explained falconry
in an easy-to-understand way

Two reasons to keep "one thread per trip"

When traveling, I create a thread dedicated to that trip and keep using the same one for all interactions.

There are two reasons for this.

1. You get the answers you want immediately

Since it understands my movements, I don't need to explain the premise, like "I'm in Ulaanbaatar right now, and my hotel is here..."

Time is precious when traveling, and I don't want to be standing on the side of the road with my phone in my hand. In that respect, an AI that understands everything makes things faster.

Even without the prefix "in Ulaanbaatar,"
vague questions are fine

2. A travel log is created automatically

Reading this thread back after returning home is quite interesting.

I take photos and write a diary while traveling. However, interactions with AI record smaller events and thoughts that don't end up in those. It's funny to look back and think, "I was worried about things like that while traveling?"

Is there a one-drink minimum at Mongolian restaurants?
I was worried about things like that, but
I've forgotten by the time I write my diary
Reporting my actions with timestamps,
and having the log summarized after returning home is also fun

Things to ask AI, things not to ask

Of course, I don't trust AI's answers completely.

For information where mistakes could be problematic, such as entry requirements or airport bus timetables, I check multiple sources. My criteria are fairly simple: 'If I get this wrong, can I laugh about it later?' If I can laugh about it, I trust the AI's answer.

When traveling alone, there is no one to consult by saying, 'I'm in this situation right now, what do you think?' That's why, even today, I find myself asking AI things that seem trivial but are actually quite important to me, like, 'Should I sit on the right or left side of this bus for the best view?'

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