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Planning your trip to Japan: Tokyo, Osaka, Sapporo Itinerary

Updated: Oct 24, 2022

Tokyo, Osaka, Hokkaido Travel Itinerary

Japan is one of my favourite places in Asia because of its amazing food! Think: the freshest sashimi, sushi, endless ramen stores, et cetera... Over the past two years, I've been fortunate enough to visit the Kanto, Kansai, and Hokkaido prefecture! There's still a lot more to explore in Japan such as the Kyushu regions of Okinawa and Fukuoka, but I'm bringing you itineraries of the more popular three cities: Tokyo, Osaka, and Hokkaido. Even if you are not heading to all three prefectures, these itineraries would also give you a good plan of what you can do for each of these cities.

How many days are needed for each city?

Mt Okurayama Ski Jump, Sapporo, Japan

We did 5 days for each prefecture and felt that it was just enough to cover the sights although having more time would allow you to experience more of Japan.

However, if you are planning to travel from one prefecture to the next (e.g. Osaka to Tokyo), we do recommend you to plan for either 7, 14, or 21 days. Reason being is because the JR pass that allows you unlimited travel on the trains have passes for 7, 14, and 21. You could also slot in an extra day is necessary for your transfers to and fro the airport.

We do know that sometimes the number of days aren't quite determined by you because #worklife and it really depends on the number of leave days you can get off work. Just do keep in mind the following JR pass options and the rest of the days which are not covered by the JR pass can be spent at a particular city, using their local trains. For instance, if you can only head to Tokyo for 10 days, get the 7 day JR pass and spend the rest of the 3 days touring Tokyo.

How to get cheap tickets to Japan?

The reason why we've been to Japan so many times the past two years was that we managed to snag cheap tickets. We flew to Tokyo on Singapore Air and paid roughly 570 SGD per pax, Hokkaido was a crazy last minute Singapore to Sapporo non-stop promotion by Scoot which we paid roughly 200 SGD each, and finally Osaka was another promotion on Scoot and we paid about 440 SGD per pax.

Otaru, Hokkaido, Japan

You may also be interested in our blog post on:

How I spent below 900 SGD (including air tickets) on a 5D4N trip to Hokkaido.

Before you purchase your tickets, read also our guide on Travel Hacks to find out: How to score cheap flight tickets from Singapore?

Also, if you do really intend to take the Shinkansen and travel to various prefectures in Japan, buy a multi-destination ticket! What that means is that if you fly in to Osaka, choose to fly out either from Tokyo or Sapporo so that you won't have to make the round back to Osaka to fly out of Japan. This saves you time and allows you to use that time that you'll have to travel back to explore more of Japan. Plus, sometimes, there's not much of a difference in the prices even if you were to buy a round trip ticket.

Now that you've figured out where you are flying in to and how many days you are spending in Japan, pick from one of these travel plans: 5 days, 7 days, and 14 days itineraries.


5 Days in Japan (Tokyo vs Osaka vs Sapporo)

If you only have 5 days, you will need to choose if you are visiting Tokyo, Osaka, or Hokkaido. With only 5 days, you may also want to make these cities as base and travel only in the day. Should you wish to move from city to city, it may mean a lot of luggage moving (even if you are only travelling with one bag pack).

Read these blog posts as a form of inspiration as to which cities you should visit:

- 12 must-eat dishes in Tokyo, Japan

- 26 things to do and eat in Osaka, Japan (including day trips)

- Hokkaido (Sapporo/Otaru) Travel Guide

A. 5 days in Tokyo Itinerary

Hakone, Tokyo, Japan

Day 1: Transfer to Hotel + Explore City

Airport to City

There are two airports in Tokyo, the Narita Airport and Haneda Airport. While Narita Airport is the main International Airport in Tokyo, Haneda is slightly closer to the city. Depending on your airline, you may be able to choose which airport you land in and depart from.

(Narita Airport --> City)

1. By train (approx 60 - 90 mins)

There are various trains that would take you from the airport to Tokyo Station. The JR Narita Express takes about an hour and is the fastest way to get to the city. However, ticket prices aren't the cheapest. It costs 3000 yen for a one-way trip and 4000 yen for two-way, which makes it a no-brainer that you should totally get the round trip! The other option is the JR Sobu Line, it takes 90 mins and costs less than half the price of the JR Narita Express.

2. By Bus (approx 100 mins)

Buses are a great way as a transportation to and from the airport as you will definitely get a seat, plus you do not need to worry about any transfers (should you be staying at Tokyo Station) even though it takes slightly longer than the trains. You can purchase a limousine bus ticket online, or at the ticket counter at Narita Airport. Purchase the two way tickets if you are departing from the same airport to enjoy some cost-savings!

3. Private Transfers (approx 100 mins)

Should you be feeling like a Crazy Rich Asian, try the private transfers for a whopping 519 SGD.

(Haneda Airport --> City)

1. By train (approx 30 - 35 mins)

From Haneda Airport, you can board the Tokyo Monorail to Hamamatsucho Station and change to either the JR Yamanote or JR Keihin-Tohoku Line to your destination in Tokyo. Alternatively you could take the Keikyu Railway to Shinagawa Station and change to the same JR Yamanote or JR Keihan-Tohoku Line. Both ways cost roughly the same and the Keikyu Railway is only 5 minutes behind.

2. By Bus (approx 40 - 45 mins)

Buses from Haneda Airport to the city takes about 40 to 45 minutes, depending on the traffic situation. It does cost more than the train options but especially for families with children, sometimes having a seat and the fact that you do not need to squeeze is extremely helpful!

3. Private Transfers (approx 40 - 45 mins)

Should you be feeling like a Crazy Rich Asian, try the private transfers from Haneda Airport for 231 SGD.

Where to stay in Tokyo?

Wherever you decide to stay in Tokyo, you may want to consider staying in one of the areas close to the JR Yamanote Line. The Yamanote Line is a circular line that brings you to major attractions in Tokyo. For those like being in the middle of all the 'action', Shinjuku and Shibuya are great options.

We decided to stay in Shinjuku at the APA Hotel Shinjuku Gyoemmae. We chose this hotel because of the affordable pricing (53,460 yen = 660 SGD for 5 mights) and it was in a quieter region of Shinjuku. Especially for those going during the Sakura season, you'll be a stone's throw away from the Gyoemmae Park. The room is tiny, but all the amenities are available. They even have an onsen at the basement where you can enjoy soaking in, especially during the winter season!

Exploring Shinjuku

There's just so much to cover in Shinjuku and the night is still young whichever time you'll reach Tokyo. From its food to the countless of bars, there's always something to do in Tokyo's Shinjuku.

Day 2: Exploring Tokyo City (Tsukiji Fish Market - Sensoji Shrine - Meiji Shrine - HArajuku - Shibuya>

Start your day bright and early by visiting Tsukiji Fish Market. For those who really want to watch the tuna bidding, you'll have to be there as early as 4 am in the wee hours. Otherwise, just roaming around the outer market is really fun too!

Just look at the crowd! We were there in the early afternoon so it was already flooded with tourists and locals. If you can, you may wish to head over earlier where everyone's still in bed! When you're there, snack on the freshly shuckled and grilled seafood, or shop for the souvenirs at the variety of stores. For more of what there is to eat, head over to read our 12 must-eat dishes in Tokyo, Japan blog post!

After filling your bellies, visit the Senso-ji Shrine. The Senso-ji Shrine is recognisable by its large lantern in the middle. The shrine is extremely crowded so do be prepared to squeeze with the crowd. Nonetheless, there are still quite a bit to see and souvenirs to buy in the shrine grounds.

In the late afternoon, Meiji Shrine located at Shibuya, in Yoyogi Park. If there is one shrine to visit, you'll definitely need to head to the Meiji Shrine. there is quite a bit of walking required to reach the shrine. The start of the trail is marked by the large Torii gate. After you pass it, you'll somehow will be able to get away from the crowded bustling city sounds, and enter the forest trail. Do note, however, that the shrine is currently undergoing some renovations. As such, the treasure house is closed.

After all that walking, head over to check out Harajuku. This is where all the cool kids hang out! The popular shopping street is Takeshita Street and there's all sorts of interesting fast fashion and your Harajuku Crepes. You'll find popular eateries in the Harajuku area such as Luke's Lobster and Dominque Ansel as well.

You'll can then spend the night at Shibuya. There's the Shibuya Crossing, Hachikyo Memorial and several shopping malls like Shibuya 109 where the ladies can shop to their hearts content.

Day 3: Tokyo DisneySEA / Disneyland / Fuji-Q Highland

On your third day, you could head to popular theme parks like Tokyo Disneyland or Tokyo DisneySEA. Great for families with children, you'll have to make a pit stop to Disneyland. Otherwise, you could head to Fuji-Q Highland to try to catch a glimpse of the elusive Mount Fuji!

Read more about our Tokyo DisneySEA experience: Experience Tokyo DisneySEA.

Purchase Disney tickets along with bus transfers here.

Day 4: Day Trip to Hakone and Yokohama

For your fourth day, if you would like to get out of the hustle and bustle of Tokyo, a great day trip would be to visit Hakone. Especially for onsen lovers, you can even head to one of the onsens to get a soak. We manage to complete Hakone in half a day and decided to stop by Yokohama on the way back!

Read more about our Hakone Day Trip and Yokohama Day Trip.

Day 5: Flying Home + Last bits of Tokyo

On your final day, you could re-explore the Shibuya or Shinjuku regions before heading to the airport. Another attraction that you could head to is the Tokyo Tower. Just like the effiel tower, the Tokyo Tower is a communications and observation tower in Shibuya and is the second-tallest tower in Japan.

B. 5 days in Osaka Itinerary

Besides being the food capital of Japan, Osaka is a brilliant place to visit the Kansai region! Get a glimpse of everything in just 5 days!

Day 1: Transfer to Hotel + Explore Osaka's Vibrant Night Life

From the Kansai Airport, take the Nankai Line Airport Express to the JR Namba Station and transfer to your respective hotels. We stayed at APA Hotel Namba-Eki Higashi which was located close to the Namba Station and was in walking distance to the Dotonburi area. It was a small room but we had everything we needed!

We chose the location primarily for us to make full use of day and to explore bits of Dotonburi and Shinsaibashi each night when we were there! After you've checked in, head over to Dotonburi for some shopping and catch a glimpse of the Glico Man at the Ebisu Bridge. If you're there in the day, you can also head to Kuromon Ichiba Market!

Day 2: Day Trip to Kyoto

Start your day bright and early and head to Kyoto. One day may not be sufficient and those who are in Japan for a much longer time should consider staying one night in Kyoto. The old capital is simply beautiful and there's just so many attractions there like:

- Fushimi Inari Shrine

- Gion District

- Nishiki Market

- Yasaka Shrine

- Kiyomizu Dera

- Togetsukyo Bridge

- Arashiyama Bamboo Forest

Read more about how to get to Kyoto from Osaka and a bit more of each of these attractions in our Summer in Japan, 8 things to do in Kyoto, Japan.

Day 3: Day Trip to Nara + Osaka Castle

Besides the deers in Nara, there's a whole lot more to see. Besides, Nara is really just a couple of hours from Osaka. It is a great day or half day trip to enjoy the wild animals!

Read more about how to get to Nara from Osaka and 6 things to do in Nara, Japan!

If you still have energy after walking the entire day, stop by Osaka Castle! The Osaka Castle is rich in history and is a convenient stop while on your way back from Nara. But,