When I got back from my long-awaited first trip to Japan, everyone naturally wanted to know how it was. Honestly, when the conversation turned to Tokyo, I found myself completely lost for words. The reason was simple: the city doesn’t leave you with one cohesive impression. Essentially, it’s made up of many smaller cities, each with its own character and rhythm.
I went through all the stages — from regretting dedicating an entire week to it, to making a “next time” list before I’d even left. Now I’m convinced that anyone who didn’t like Tokyo just wasn’t doing it right. It’s one of those places you can’t explore on autopilot: without a solid plan and a few personal ground rules it can feel overwhelming. But once you figure out how to approach it, the city unfolds beautifully, filling your trip with the kind of memories that stay with you.
In this guide, you’ll find my personal observations, conclusions and recommendations on how to navigate Tokyo — and genuinely enjoy it:
Travel light
If Tokyo is the first (or only) stop on your route, be realistic about what you actually need and pack light. You really don’t need much, because even mid-range hotels usually supply you with everything from a toothbrush to pyjamas and shoe deodorant.
If your Japan trip starts elsewhere, resist the urge to shop too early and save your splurging for Tokyo. Don’t miss out on authentic local finds, but wait with big chains like Uniqlo or Muji. Trust me, one short walk from the train station to your hotel with no escalators and a heavy suitcase is enough to make you rethink every single purchase. And if it’s already too late for that, let someone else deal with it. Ask your current hotel reception about luggage delivery — they can usually send your bags to another city within a day or two for a fair price and save you the frustration.
Accommodation matters
In Tokyo, choosing the right hotel in the right neighbourhood is one of the most important decisions you’ll make — and for good reason.
First, the city is massive. Your location will define how much time and patience you’ll spend commuting. Second, no matter how much fun you have, by the end of each day you’ll be both physically and mentally wiped out, so it’s crucial to come back to a place where you can properly unwind and recharge for the next round.
Here are my tips for choosing a hotel in Tokyo
- Start with your itinerary. Draft a rough plan of what you want to see and do, then mark where these spots are on the map. Check which metro stations connect them easily — that’s your cue to look for accommodation nearby.
- Pick residential neighbourhoods over touristy ones. It’ll instantly upgrade your experience and give you the peace and quiet you’ll crave after elbowing your way through Shibuya. I stayed in the northeast of Chuo City and honestly, it was a turning point in my logistics genius. On one hand, it offered easy access to most of the places on my list; on the other, it was full of charming, non-touristy corners and tiny family-run restaurants with no English menus whatsoever but incredible food and warm conversations. Bonus: there’s an airport shuttle bus terminal nearby. Tip: If you ever find yourself in that area, stop by Nagomi Gyoza for the best gyoza of your life and a little chat with the owner.
- Stay close to a metro station. It can easily save you up to an hour of walking (and several emotional breakdowns) a day.
- If you find a hotel that ticks all the above boxes and has an onsen, spa or aromatherapy bar — book it immediately. After thousands of steps around the city, a little wellness ritual in the evening feels downright heavenly.
- Don’t fall into the tiny room trap. Many hotels in Tokyo offer micro-sized rooms as their standard option. Unless you enjoy mild claustrophobia and plan on buying absolutely nothing, upgrade if you can.
- Think logistics (again). Getting to Tokyo with your luggage is one thing, leaving it without losing your mind is another. If you’re flying out, make sure you’ve got easy access to an airport shuttle. If you’re heading to another city, pick a spot near a train station. Future you will thank you.
Dose the activities
It’s wise to set one simple rule for yourself: one day — one neighbourhood or experience. Mute the FOMO and don’t rush to tick off ten things at once. If you actually want to stay sane (and not come home needing another holiday to recover), pace yourself.
Don’t take chances — secure them
When it comes to eating out or visiting popular attractions, spontaneity rarely works in your favour. Do your research, shortlist your must-visit spots and book ahead whenever you can. For restaurant-hunting and queue-dodging tips, check out my separate travel guide for Japan first-timers.
Try local experiences
As much as I love hunting for local brands and products, I still think the best souvenir is a skill or a unique experience. Tokyo has one for every interest, from sushi-making workshops to coffee tasting sessions, and even an earthquake simulation at the actual disaster prevention centre. Just pick what speaks to you.
Buy now or regret later
I know, I’ve mentioned shopping several times already but that’s because it’s impossible to leave Japan empty-handed. If you see something you love, buy it then and there. Don’t assume you’ll “come back for it later.” You either won’t fancy crossing half the city again, or you will, muttering curses at your past self for not doing it sooner.
Embrace bad weather and off-hours
Some of my favourite moments in Japan happened during rain, off-hours or public holidays when most places were closed. Why? Fewer crowds, quieter streets and a rare chance to enjoy cultural sites in peace. Even a bit of drizzle is enough to keep people indoors, so grab a rain jacket and enjoy — you might get Tokyo’s beauty all to yourself.
Accept imperfections
There will be moments when Tokyo leaves you tired, lost or exasperated — that’s part of the deal. Try not to fixate on the less-than-perfect bits. Japan is a unique country and Tokyo perfectly captures its blend of heritage and hypermodernity.
Just take it as it comes and embrace whatever the city throws your way.
**********
See more about Japan here in Dispatches’ archives.
Read Oxana’s post on Japan for first-timers here.
Oxana Skibun
Oxana Skibun is a fashion and lifestyle editor who has crafted her stories for print and digital media outlets across Europe, the Middle East and Russia. Raised in Moscow, she now lives in Amsterdam, where she continues writing for international audiences.
