Japan, According to Me 🇯🇵
Osaka → Kyoto → Tokyo in 9 days.
Not a “see all of Japan” itinerary — just a very solid first trip built around food, bars, neighbourhoods, a little chaos and a few places worth planning properly for.
For this route, I’d do 3 nights in Osaka, 2 nights in Kyoto and 4 nights in Tokyo. It gives you enough time to actually experience each city without turning the entire holiday into a luggage transfer exercise.
The Route
Day 1–3 — Osaka
Stay: Fraser Residence Osaka
Arrive in Osaka, check in and use the first couple of days to explore the city properly.
Osaka is the fun, easy part of the trip — street food, bars, shopping and a lot of wandering.
Day 2 — Universal Studios Japan
Keep an entire day for Universal Studios Japan.
The big note here: buy your Express Pass in advance. This is not the day to arrive and hope for the best.
What I’d Do in Osaka
Dotonbori
Yes, it’s touristy. Go anyway.
Neon everywhere, food everywhere, people everywhere — it’s one of those places that looks exactly how you imagine Osaka should look.
I’d come in the evening when everything is lit up.
Kuromon Ichiba Market
Go hungry.
This is the kind of place where I wouldn’t schedule a proper lunch afterwards because the whole point is to stop, eat, keep walking and repeat.
Shinsaibashi-suji Shopping Street
For shopping, wandering and conveniently losing several hours of your day.
Easy to combine with Dotonbori.
What I’d Eat in Osaka
Mizuno
One of the food stops I’d save for Osaka.
Wanaka
Another easy one to keep bookmarked when you’re moving around the city.
Rather than trying to make every meal a major reservation, Osaka is where I’d leave room to eat as you go.
The Bars I’d Save in Osaka
Osaka has a surprisingly strong cocktail scene, so I wouldn’t make every evening about food.
Bar Nayuta
One of the first bars I’d bookmark.
Bar K
For a more classic cocktail-bar experience.
Bible Club Osaka
A moodier, more atmospheric option.
Craftroom
Another one for proper drinks rather than a giant night out.
Bar 1979
Add to the bar-hopping list.
Bar Masuda
Another Osaka bar worth keeping saved.
My approach here would be simple: pick two bars in the same general area rather than trying to conquer the entire list in one night.
Day 4 — Osaka to Kyoto
Take the train from Osaka to Kyoto.
The journey is short — roughly 15–30 minutes, depending on the service — so there is absolutely no need to sacrifice half the day to travel.
Stay: Ace Hotel Kyoto
I’d make Ace part of the Kyoto experience rather than just treating it as somewhere to sleep.
Check in, drop your bags and keep the first day relatively open.
Day 4–5 — Kyoto
Kyoto is the part of the trip I would intentionally keep slower.
After Osaka, you don’t need another 48-hour checklist.
Use these two days for:
Walking
Neighbourhoods
Temples and older streets
Long meals
Coffee
A little shopping
Actually looking around rather than running to the next pin on Google Maps
I’d resist trying to “complete Kyoto.” Two nights will only ever give you a taste, so pick the things you actually care about.
Day 6 — Kyoto to Tokyo
Take the Shinkansen from Kyoto to Tokyo, roughly 2–2.5 hours.
This is one of those journeys where the transport itself feels like part of doing Japan properly.
Stay: Hotel Groove Shinjuku
Shinjuku is a very fun base because you can walk straight out into one of the busiest parts of Tokyo.
And importantly for this itinerary, you’re also perfectly placed for late-night food, bars and places like Golden Gai and Omoide Yokocho.
Day 6–9 — Tokyo
Tokyo is where I’d save the majority of the serious reservations.
You could spend weeks here, so four nights is absolutely about choosing your version of Tokyo, not trying to see the entire city.
Mine would heavily involve food and bars.
The Tokyo Bars I’d Actually Save
Bar VirtĂą
One for a more polished cocktail evening.
The SG Club
A very strong Tokyo bar save and one I’d definitely make time for if cocktails are a proper part of your trip.
Bar Benfiddich
One of the names I’d prioritise from this list.
This is much more about the bartender, ingredients and actual drinking experience than simply walking into a photogenic room.
Bar High Five
Another classic Tokyo cocktail-bar experience.
Albatross G
A very different mood from the serious cocktail bars.
Small, atmospheric and a fun one to fit into a Shinjuku night.
Golden Gai
Do Golden Gai at least once.
It’s a maze of tiny bars packed into narrow lanes in Shinjuku, and the fun is less about having one specific reservation and more about wandering until somewhere catches your eye.
Some bars are extremely small.
That is the point.
I’d pair Golden Gai with a few other Shinjuku stops and make a whole night of it.
Omoide Yokocho
Another Shinjuku classic.
Tiny alleyways, yakitori-style spots, smoke, noise and a completely different energy from polished Tokyo.
Do this before or after drinks rather than turning it into a separate sightseeing day.
An easy evening could be:
Omoide Yokocho → Golden Gai → Albatross G
Very Tokyo, very little unnecessary commuting.
The Tokyo Restaurants I’d Save
SĂ©zanne
This is one of the serious restaurant reservations on the list.
If you’re going to do one very polished dining experience in Tokyo, this is the kind of booking you plan the evening around rather than squeeze between activities.
Tofuya Ukai
A much more traditional-feeling experience and a nice counterbalance to Tokyo’s modern side.
Mumbai
Also on the food list — a useful save when you want a break from Japanese food.
Because yes, at some point on a long Japan trip, you may suddenly feel extremely emotional about Indian food.
Day 7 — Tokyo DisneySea
Give Tokyo DisneySea its own day.
And just like Universal in Osaka:
Book your passes in advance.
This is not something I’d try to casually add to an afternoon.
Go early, stay properly and accept that this is the itinerary for the day.
How I’d Break Up Tokyo
Rather than assigning 14 attractions to four days, I’d work geographically.
Shinjuku Night
Omoide Yokocho → Golden Gai → Albatross G
Serious Cocktail Night
Dinner → Bar Benfiddich / Bar High Five / SG Club
Proper Dinner Night
Sézanne or Tofuya Ukai → one great cocktail bar afterwards
DisneySea Day
DisneySea → return to hotel → late food if you still have a functioning body
That is enough.
My Japan Travel Rule
Japan is the sort of destination where you can become completely consumed by recommendations before you even land.
There will always be another:
ramen counter
cocktail bar
vintage store
café
neighbourhood
restaurant someone insists is “life-changing”
You cannot do all of it.
And I actually think this route works because the cities give you very different energies:
Osaka: food, nightlife, easy fun
Kyoto: slower, more traditional, beautiful
Tokyo: everything, everywhere, all at once
My Ideal 9-Day Japan Itinerary
Day 1 — Osaka
Arrive → check-in → explore → Dotonbori at night
Day 2 — Osaka
Universal Studios Japan
Day 3 — Osaka
Kuromon Market → Shinsaibashi → food → Osaka bar crawl
Day 4 — Kyoto
Train to Kyoto → Ace Hotel → explore slowly
Day 5 — Kyoto
Full Kyoto day
Day 6 — Tokyo
Shinkansen → Hotel Groove Shinjuku → Omoide Yokocho → Golden Gai
Day 7 — Tokyo
DisneySea
Day 8 — Tokyo
Explore → proper dinner → serious cocktail bar
Day 9 — Tokyo
Slow final day → shopping / food / whatever you missed → final drinks
My Japan Take
Don’t try to do 17 cities because you’ve finally made it to Japan.
For a first trip, Osaka + Kyoto + Tokyo gives you enough contrast without making the holiday exhausting.
Book the things that genuinely require planning — Universal, DisneySea and your major restaurant reservations — and leave space around everything else.
Because Japan is exactly the kind of place where the unplanned two-hour detour into a tiny bar or shop can end up becoming the thing you remember most.
