JAPAN – The best 14 days itinerary for Tokyo & Kansai Region: Kyoto, Osaka, Nara, Kobe

I love Japan: its efficiency, its century old culture and the food! I have visited Japan twice for just a few days in Tokyo. Last Christmas my family joined for a two-week Japan trip. This trip included just one day Tokyo and for the rest of the trip Osaka was the base to explore Kobe, Nara, and a few other places. As Kyoto is so beautifull I planned 3 nights there to have enough time to explore all the temples. This Japan itinerary is packed with culture but leaves also enough time to plan in activities and time to relax. I’ll take you to Tokyo and the Kansai region in this Japan itinerary; enjoy!

Japan Itinerary Day 1: Arrival

I love to fly business class and preferred with KLM and so does my family. When flights to Osaka and Tokyo were offered at just 50% of the miles they regular cost, I booked 4 tickets spending 400.000 miles. Of course, if you don’t have the miles, you can also book cheap business class tickets using my tricks. The overnight flight arrived on time in the morning after which I picked up the rental car I booked with Sunny Cars.

I like their business model as all insurances are included in the price, GPS is always included in the price and much more. Especially the GPS comes in VERY handy in Japan unless you can read Japanese road signs. Don’t be scared if the price is slightly higher at Sunny Cars because there won’t be any additional charges as would happen with many other car suppliers – it’s all-in. Driving in Tokyo is spectacular, on the left side, but you’ll get to see landmarks from a different angle like the Tokyo tower. Just two hours after landing I arrived at the Intercontinental Strings Hotel which would be my home in Tokyo.

Japan Itinerary Day 2 – 4: Tokyo

Tokyo is the capital of Japan and is a huge city with many places of interest. The three most important cultural heritage sites include the Imperial Palace, Meiji Shrine, and the Asakusa Temple. In the evening Roppongi Hills is my favorite but also Shinjuku, Shibuya, and the Ginza neighborhoods are great. I have visited most places of interest during my two previous visits to Tokyo. I recommend to plan at least take 2 days in Tokyo to see these places. The third day I highly recommend to go see the Tsukiji fish market and do a sushi workshop. With three days in Tokyo you’ll get a good impression but there is so much to see and do that you can extend this easily to a week!

Read more travel inspiration for Tokyo in the detailed day by day articles:
JAPAN – A very very short visit to Tokyo! Bleisure fun!
JAPAN – A day in West Tokyo: Skyscrapers & temples
JAPAN – Experience Tokyo: Tsukiji fish market & a sushi workshop
JAPAN – Top places to drink craft beer in Japan: Tokyo, Osaka, Kyoto & Kobe

Japan Itinerary Day 5: Snow Monkey Park & Tomioka Silk Mill

The snow monkeys of Japan are found in Jigokudani Monkey Park in Yamanouchi, about 3 hours’ drive from Tokyo. On the way, you’ll pass the Tomioka Silk Mill which is an UNESCO World Heritage Site since 2016. Both places are best visited on the same day and a car is required to achieve this. Make sure to hire a car with automatic transmission if you are not used to driving on the left side. That’s the most difficult part to get used to especially if you’re driving just a day.

The snow monkey park is best visited in winter when the monkeys seek warmth in the hot springs. It’s a lovely sight! The Tomioka Silk Mill shows the history of silk production and trade in the area and is a great stop about half way to the snow monkeys. I had a great day trip and can recommend to everyone who wants to escape Tokyo to add this to their Japan itinerary.

Read more travel inspiration for Tomioka & Jigokudani in the detailed day by day article:
JAPAN – Tomioka Silk Mill & Snow Monkeys in Jigokudani day trip from Tokyo

Japan Itinerary Day 6: To Kansai Region

What do you do if your daughter wants to fly a pink plane? Then you’ll make it happen and that’s exactly what I did in Japan. Peach is a local Japanese airline which offers flights within Japan and to a few surrounding countries. Their rates are cheap and their process from booking to boarding is very efficient. I flew with my family from Tokyo to Osaka which was a short flight and much more efficient as taking the train to the Kansai Region.

I’m a tall person and their seat pitch was enough for me to have a pleasant flight. I loved the fact that even 45 minutes prior to boarding you can drop your luggage, go to the gate and simply be on time. I flew in the morning from Tokyo so that I had half a day in Osaka to explore this huge city. In Osaka I recommend to buy an ICOCA smart card which is valid for public transportation in the Kansai area, you don’t need a JR Pass (expensive). I highly recommend to fly Peach in Japan.

Japan Itinerary Day 7: A day in Osaka

Osaka is the third largest city of Japan, the largest in the Kansai Region, and a great place to entertain yourself. There are some interesting temples, museums and of course the Osaka Castle too but Osaka is best used as a base to explore the Kansai region. It’s exactly what I did too; to make day trips (see the next days) to various places and return to Osaka for dinner, drinking and nightlife. Where to eat, and drink I’ll share with you later in a separate article. I stayed at the Intercontinental Osaka as it was located near the Umeda station which is one of the two big hubs for trains in Osaka.

Japan Itinerary Day 8: Day trip to Nara

Nara is a city with over 13 centuries of history and served as the capital of Japan for a long time. Its historical remains are a UNESCO World Heritage Site and can be visited as a day trip from Osaka. Make sure you leave around 7AM from Osaka so that you have the full day to explore Nara; its the longest day of this Japan itinerary. There are basically two groups of temples of which I recommend to end in Nara Park. All of them are a must see in Japan as their structures are truly beautiful. It’s a long day to explore it all and it needs some planning which I’ll cover in the day article in more detail.

Japan Itinerary Day 9: Day trip to Kobe (Kansai Region)

I visited Kobe, which is a 20-25-minute train ride from Osaka, on the 1^st of January: I could literary walk over the people as it was really crowded. This also has its charm and throughout the city there were all kinds of activities organized on the streets. The main reason I visited Kobe was for the Kobe beef for which you need to make a reservation if you want to have the best experience.

Kobe is also famous for its sake breweries but as it was the 1^st of January they were unfortunately closed as were several museums. The main places of interest are the old European houses in the Kitano area, Chinatown and nearby temple, the port area around the Kobe Port Tower and I also suggest to go up with the ropeway to the Herb Garden. A day is more than enough in Kobe and if you need to shorten your Japan itinerary I suggest to visit Kobe only for the Kobe beef on the way back from the Himeiji Castle (see day 15).

Read more travel inspiration for Kobe in the detailed day trip report:
JAPAN – 1-day trip to Kobe from Osaka or Kyoto: What to do & where to eat Kobe steak

Japan Itinerary Day 10 – 13: Kyoto

Kyoto can be visited on a day trip from Osaka, but I suggest to stay there 3 nights so that you have enough time to explore this beautiful old capital of Japan. It is the most famous city in the Kansai Region. Kyoto has over 600 temples of which 17 are part of the UNESCO World Heritage Site of Kyoto. They are all worth a visit (the 17!) so you’ll need at least three days for that.

Most famous are probably the Golden Pavilion and the Fushimi Inari Shrine. The latter isn’t part of the UNESCO inscribed sites but it’s the icon of Kyoto with its famous orange arches. I’ll share in three separate day itineraries later which temples are a must see if you have a day, two days, or three days in Kyoto. One thing I can guarantee is that you won’t get bored during these three days in Kyoto and Kyoto should be on any Japan itinerary.

Japan Itinerary Day 14: Day trip to Horyu-Ji

Horyuji is located just a 25-minute train ride west of Osaka and is home to a large temple complex consisting of the oldest wooden structures in the world. It’s a UNESCO World Heritage Site. It’s a nice half day trip from Osaka and this was great as I explored it in the morning and in the afternoon the weather turned bad. That wasn’t a problem as the spa at the Intercontinental Osaka was a great place to spend the rest of the day. The temple complex is large but can be covered in about 2-3 hours so it doesn’t take up a full day in this Japan itinerary. There is one more pagoda a 45-minute pleasant walk through the city into the country side. I did take a taxi back from there so that I would arrive not to late back in Osaka.

Read more travel inspiration for Horyu-Ji in the detailed day by day article:
JAPAN – Horyu-ji day trip from Osaka/Kyoto: world’s oldest wooden structures

Japan Itinerary Day 15: Day trip to Himeji Castle

Himeji Castle is the most beautiful castle in the Kansai Region and for sure all of Japan and a UNESCO World Heritage Site. Himeji castle is reached by an hour train ride from Osaka and a visit takes about 4 hours including climbing the interior of the castle. I was really impressed by the beauty of this castle and I highly recommend to add it to any Japan itinerary, especially if you are travelling in the Kansai region. Next to the castle is a beautiful garden worth a visit, although in winter it wasn’t that impressing. In case you don’t plan a visit to Kobe, you can on the way back to Osaka stop in Kobe for the fine Kobe beef. It’s a must eat in Japan.

Read more travel inspiration for Himeji in the detailed day by day article:
JAPAN – Day trip to Himeji Castle from Osaka (or Kobe / Kyoto)

Japan Itinerary Day 16: Departure

The above 14 days (+2 days arrival/departure) are a sample itinerary for Japan with the capital Tokyo and the Kansai Region as focus. In my opinion the best Japan itinerary for a first-time visit. You’ll learn about the history and culture, eat the best food, and see the hectic city life. I’m sure you will enjoy Japan as I did and if you have suggestions for changes in this itinerary let me know in the comments. I do know I skipped Mount Fuji which could be an alternative for the Snow Monkeys. I did that as I know I’ll return to Tokyo again later and will then visit Mount Fuji.

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Did you visit Japan too or do you have questions? Please leave a comment at the bottom of the page. Love to hear from you!