Ultimate round trip through Japan: personal tips for Osaka, Kyoto and Tokyo
If there is one round trip through Japan that should be on your bucket list, it is this one: from Osaka to Tokyo, with magical Kyoto in between. I have been there a few times now – and my love for the country is great. Perhaps that is also because my brother is married to a Japanese woman. They live together in Tokyo with my nephew and niece.
Our last trip – last year – started in Osaka. We flew directly with KLM from Amsterdam to Osaka, and flew back from Tokyo.
Osaka – starting point of your round trip through Japan
Osaka is a bit like the Rotterdam of Japan. More relaxed, rawer, more bourgondian. In the evening, the city really comes to life – full of neon, food stalls, and nightlife.
We stayed at the Mimaru Osaka Namba North, where we booked a family room. Ideal with kids and jet lag.
Another tip is the W Osaka: great hotel, but a bit more expensive.
Food tips in Osaka:
Warm soufflé cheesecake from Rikuro’s – soft, wobbly, divine.
Takoyaki: octopus balls on a stick. Typical Osaka.
Kuromon Ichiba Market: an indoor street food market where you want to taste everything.
Two nights here is fine – then you really get the vibe.
From Osaka to Kyoto – fast and affordable
We traveled with the JR Special Rapid Service to Kyoto. A regular train, but super fast: you’ll be there in 30 minutes. And very affordable.
Kyoto – highlight of your Japan trip
If Japan is enchanting anywhere, it is in Kyoto. Old, serene, stylish. Completely magical during the sakura season (usually late March to early April).
Biking tip: Kyoto is flat, quiet, and easy to navigate – perfect for exploring by bike. We stayed at the Cross Hotel, nice and central and atmospheric.
Must-do’s in Kyoto
Arashiyama Bamboo Forest – yes, touristy. But absolutely worth it. Go early, the street leading there is also so nice: boutiques, the Miffy Café, and the cutest and tastiest eateries.
Fushimi Inari-taisha – the thousands of orange gates with the most magical light ever. Go as early as possible, because it gets very busy there during the day. Be sure to walk high up, it’s beautiful and much quieter there. Don’t forget to purify your hands at the entrance, at least, I love traditions so I like to participate (Shinto purification ritual, see box below).
Kinkaku-ji – the Golden Pavilion, a beautifully covered temple with real gold leaf.
Kiyomizu-dera – you shouldn’t skip this one either, such a beautiful temple on a hill with panoramic views over Kyoto. Just the walk there is fairy-tale-like.
Gion – where parts of Memoirs of a Geisha were filmed. The famous bridge, locals in kimonos… everything is perfect here and super fun for some photos.
Spotting geishas in Gion
I’m not really a proponent of this myself, but honestly: I did it during my first trip to Japan. Note: they are NOT a tourist attraction. So: no selfies or chasing. Do you really want to talk to a geiko or take photos? Then book an official tea ceremony or dinner through a recognized cultural center.
There are about 100 active geiko and maiko (geishas and apprentice geishas) in Kyoto. The chance is small, but if you see one, it’s extra special. Gion Kobu is the most famous district.
Shopping in Kyoto
This is also so stylish, full of cozy streets and unique shops. Boutiques, ceramics, kimonos, stationery – you want to have everything.
Eating & drinking
Everywhere you find the cutest restaurants, sake bars, and coffee shops. We had coffee at the Ace Hotel – tip: because it’s super cool.
Shinkansen from Kyoto to Tokyo – speed and comfort
The shinkansen (bullet train) took us to Tokyo in no time. Book seats D/E on the left side: on clear days you can see Mount Fuji glide by. Tip: book online in advance, everything runs smoothly (like everything in Japan).
Tokyo – hyper-modern, chaotic, and perfectly organized
Tokyo is an experience. Shibuya, Shinjuku, Daikanyama, Ginza – each district feels like its own world. We stayed at the Sequence Hotel in Shibuya: everything nearby and right in the action.
Highlights in Tokyo
Shibuya Sky
The spectacular observation tower in the heart of Tokyo, right above the famous Shibuya Crossing. Book your tickets online in advance. The best time is during sunset. You can see Mount Fuji from here.
Shopping & vintage heaven
Tokyo is the largest shopping paradise I have ever been to. Beautiful shops everywhere: big, clean, neat, fun, civilized – everything. But what I didn’t know is that Japan has a mega cool vintage culture. Every few shops you find the best of the best in vintage stores. Japanese people will never buy fake items and therefore this culture is very clear: everything you see is real and clean.
Daikanyama & Tsutaya Books
Daikanyama, this mega cozy boutique shop area is a must-visit. Everywhere you see charming streets and super cool coffee shops and boutique stores. Be sure to visit Tsutaya Books as well. The building itself is a true design icon, often praised in magazines like Wallpaper and Monocle, and is always featured in lists of the “most beautiful bookstore in the world.”.
Gotoku-ji – the Lucky Cat Temple
Visit the cutest Lucky Cat Temple. It is located in the middle of a residential area, but it is really worth it. Thousands of Lucky Cats in meditation pose. According to legend, a cat once saved a samurai from a storm here, and out of gratitude, he had this temple built. Since then, people come here to ask for luck, prosperity, and a touch of magic – by buying a Lucky Cat, making a wish, and leaving it among the thousands of other figurines.
Although the Chinese believe that the Lucky Cat is Chinese, that is not the case. It may seem so because you see them everywhere in Chinese restaurants. But the maneki-neko originally comes from Japan, from the Edo period (17th century).
Azabudai Hills & teamLab Borderless
For a piece of next next level – as in: even cooler – I really recommend you go to Azabudai Hills: Tokyo's newest, most futuristic and luxurious urban district. Here you will find design, art, architecture, green roofs, next level concept stores, and the tallest building in Japan. In the middle of Azabudai Hills, you will find teamLab Borderless, an amazing digital art museum. This is exactly what I love. Truly amazing.
Make sure to buy your tickets online in advance, so at the right location (there are several): teamLab Borderless
Ginza – stylish and shiny
Yes, this is truly the high-end area of Tokyo. The Chanel of neighborhoods. Everything is shiny and styled to perfection. Think: Fifth Avenue meets Japanese minimalism. Flagship stores of Chanel, Dior, Loewe, Gucci, and Hermès – all in hyper-modern buildings that are themselves truly a work of art.
You will also find the most beautiful, cool, bizarre department stores in Japan here (hello Mitsukoshi, Wako, and Ginza Six). This is truly incomparable to anything in Europe. Even in their food halls in the basement, you can have Michelin-worthy lunch.
I was there on a Sunday – when the main street is made car-free. Super fun to see. Be sure to stop by Itoya Ginza – a stationery store with 12 !! floors. But also the department stores, that is incomparable to anything in Europe.
Cat Street
Cat Street is truly the cutest neighborhood. Especially if you love fashion, vintage, and a relaxed, creative atmosphere.
Cat Street is a charming and hip walking street that connects Shibuya with Harajuku. No real cats, though. The architecture is a mix of minimalist and creatively industrial – really super photogenic.
Cat Street runs from Harajuku to Shibuya and is a quiet, stylish shopping street full of Japanese streetwear, design shops, second-hand boutiques, and concept stores. Here you will find beautiful vintage designer pieces (think: Chanel, Acne, Hermes, Comme des Garçons, Loewe) that are truly authentic – because as I mentioned earlier, Japanese people do not buy and sell fakes.
Harajuku
Harajuku is perhaps the most famous district of Tokyo, especially when it comes to youth fashion, subcultures, and Japanese eccentricity. But Harajuku is more than just neon and hustle. I can honestly say: if you haven't been to Harajuku, you haven't really seen Tokyo. What's not to love.
Takeshita Street in Harajuku:
The most famous street in Harajuku – and perhaps all of Tokyo when it comes to youth culture. And, okay, you may not know me, but I was so happy here. Everywhere the cutest shops with Hello Kitty, My Melody, Eevee from Pokemon, and the most adorable accessories I ever dreamed of. Everything here is Kawaii: or in other words, too cute. It is busy, chaotic, and totally over-the-top, but you definitely don't want to miss this.
Omotesando (also known as Tokyo's Champs-Élysées)
From Harajuku, you walk straight into Omotesando – and it feels completely different right away. Just like the Champs-Élysées in Paris, Omotesando is a wide avenue lined with trees and spacious sidewalks. This part of Tokyo is high fashion at the highest level, with flagship stores of Balenciaga, Chanel, Louis Vuitton, Dior, Loewe, Prada, and Gucci – all located in minimalist architectural masterpieces. Here you will see by far the best-dressed people in the city.
Between Cat Street and Omotesando, you will pass the Medicom store. Here we bought a Bear Brick. You will find Bearbricks in all sizes, collaborations with Nike, Chanel, BAPE, Andy Warhol, and Star Wars.
Omotesando Hills
Omotesando Hills is a bizarre high-end shopping center, designed by the famous Japanese architect Tadao Ando. The building is architecturally amazing – sleek concrete, lots of glass, and a spiral-shaped walkway that winds through the complex like a catwalk. You will find stores like Maison Margiela, Alexander Wang, Yohji Yamamoto.
Omotesando Hills is much less hysterical than other malls, but all the more chic – it almost feels like you are walking into a museum.
In this article, I have taken you through my experiences in Japan. There is so much more to tell, as the country is bursting with unique experiences. Be sure to read my article about what not to do in Japan.
Japan will truly be a mega positive culture shock for you. It is the most civilized people I have ever encountered – and honestly, we can still learn a thing or two from them in the Netherlands.
Two more general travel tips:
Internet in Japan without hassle? Download Airalo
A tip that will make you so happy when you just landed: download the Airalo app (or another e-sim provider) before departure and buy an eSIM for Japan in it. This way, you have internet on your phone immediately upon arrival – without the hassle of loose SIM cards or searching for wifi.
You choose the number of days in the app, check out, and install the eSIM directly on your phone (works on most new iPhones and Androids). Within a few minutes, I was online and could just use Google Maps. I now use it for every vacation outside Europe.
By the way, for all distant destinations I recommend this eSIM app.
Tip for public transport: the Pasmo app (or card)
If you plan to travel a lot by metro or train in Japan – which you will almost certainly do – then the Pasmo app or card is what you need. You can buy this card physically, or, even handier, download the digital Pasmo app.
You load it with credit via your credit or bank card and check in and out quickly at every metro station, train station, and even at many buses and in stores. So, no hassle with loose tickets and such.
If you have any questions about Japan: feel free to email me!
