Planning Your First Trip to Japan? Here’s What I’d Do (I Go 3x a Year)

How to Plan Your First Trip to Japan (Pro Tips!)

If it’s your first time going to Japan, I already know your Pinterest board is full, your TikTok saves are maxed out, and your brain’s spinning with all the places you think you need to see. As someone who visits Japan 2–3 times a year (and still finds new gems each time), let me help you actually plan a trip that’s not overwhelming, but unforgettable.

Here’s how I’d help you plan your first trip to Japan, from choosing between hotels and Airbnbs to navigating trains, food hacks, and what your itinerary really needs.

Accommodation: Hotel vs. Airbnb in Japan

Hotels in Japan are famously clean, efficient, and safe, but often compact (read: very small rooms). If you’re someone who doesn’t need much space and wants daily cleaning + reliable front desk support, hotels in Japan are solid, especially in cities like Tokyo, Osaka, or Kyoto.

Airbnb has come a long way in Japan too. You’ll find cute, minimalist apartments that feel like a home-away-from-home. Perfect if you want to cook, do laundry, or experience a quieter local neighborhood.

I always go for Airbnb because I stay longer every time, and I want a spacious place where I can work comfortably.

Pro tips:

Check if your Airbnb is licensed (a legal requirement in Japan)

Hotels near train stations are worth the price, trust me

If you’re staying in Tokyo, neighborhoods like Shinjuku, Asakusa, or Ikebukuro are central and easy to navigate for first-timers

Transportation: Mastering Japan’s Train System

The train system in Japan is as intimidating as it is legendary, but once you get it, it’s a breeze.

For first-timers, here’s what you need:

IC Cards: Get a Suica or ICOCA card for quick tap-in access to trains, subways, and even convenience stores.

JR Pass: Only worth it if you’re taking multiple long-distance Shinkansen (bullet train) rides. Otherwise, skip it.

Google Maps > Apple Maps in Japan, trust me on this.

Hack:

Download the NAVITIME or Japan Travel by Navitime app for train route planning in English, with platform numbers and fare info.

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Food: Convenience Store Food is Not a Joke Here

Yes, you’ll want to try sushi, ramen, matcha everything, and street food, but Japan’s convenience store food (7-Eleven, FamilyMart, Lawson) is chef’s kiss.

From onigiri to hot meals and even desserts, you’ll be shocked at how good “conbini” food is.

First-timer food tips:

Don’t be afraid to eat solo, Japan is solo-travel friendly (though I have never been solo yet in Japan)

Most restaurants have ticket vending machines (select, pay, eat) Ooppsss! You have never been to Japan if you have not tried ramen from Ichiran. It’s a different game!

Tipping is not a thing. Don’t try, it’s awkward.

Itinerary: What Most First-Timers Get Wrong

Most people cram in Tokyo–Kyoto–Osaka into one 7–10 day trip. While possible, it can feel rushed. Here’s what I’d suggest:

Option 1: Slow Tokyo + Day Trips

Stay in Tokyo 5–7 days

Do day trips to Nikko, Kamakura, or Hakone

Explore different neighborhoods: Shibuya, Shinjuku, Shimokitazawa, Nakameguro, Daikanyama

Option 2: Tokyo + Kyoto Split

4–5 days in Tokyo

2–3 days in Kyoto (beautiful, slower pace, more temples and nature)

Optional: Osaka overnight for foodies

Packing Hack:

Bring a small duffel bag or foldable tote; shopping in Japan is next-level.

Culture Tips for First-Timers

Trash bins are rare: Keep a small bag in your backpack for wrappers, etc.

Take your shoes off when entering homes or traditional accommodations

Use a quiet voice on trains. Talking loudly is a no-no.

Cash is still common. Carry yen even if most places take cards

Your First Japan Trip Doesn’t Have to Be Perfect

You’ll get lost. You’ll press the wrong button on a vending machine. You’ll say “sumimasen” a hundred times. And it’ll all be part of the adventure.

As someone who keeps coming back to Japan, here’s what I know for sure: You don’t need to see everything. You just need to be present where you are. The magic will meet you there.

So take the trip, try the matcha, ride the train, and let Japan surprise you!

Bookmark this if Japan is on your 2025 vision board. And feel free to send it to that one friend who keeps saying, “We should go to Japan someday.”

P.S. For more of my travel tales, work-from-anywhere moments, and real-time Japan snaps, come hang out with me on Instagram: @JenTravelTales ✈️🌍