The Perfect Two Week Japan Itinerary: Tokyo, Kyoto, Osaka, and Okinawa

Japan is every bit as wonderful as it is different. It’s a country with immense history, stunning nature, and some of the best food in the world. The contrast between old and new, man made and mother nature, is like nowhere else on Earth. The big cities are modern marvels of technology as Tokyo’s Shinjuku district makes New York’s Times Square appear flat.

A quick high speed train ride away is Kyoto, home to centuries old temples and shrines. That’s where most people finish their trips, which wouldn’t be a bad trip by any means. However, the islands of Japan offer a completely different perspective. A third vantage point where the pace of life is much slower and technology has gone on break. Palm trees and tropical beaches dot the landscape and often times, I forget I was ever even in Japan.

This itinerary will focus on visiting the highlights of Japan. You can’t expect to see too much of the country in just two weeks but this itinerary will hopefully allow you to maximize your trip. Japan is a country I will return to often and by no means will this be the end!

 

Where I went in Japan


I visited in September which I found to be a very good time to visit. The weather is still warm but not unbearably hot like it is in June-August. Almost all visitors to Japan stick within the mainland because there is so much to do and see that even with two to three weeks, it may feel like you saw nothing in the end.

I wanted to go diving and read that the Okinawan islands of Japan offered just that. Further research helped me land on the island of Ishigaki, famous for its manta rays and stunning beaches. Who knew Japan had great beaches? Well, they absolutely do.

Kondoi Beach taketomi
Kondoi Beach on Taketomi Island

In total, this itinerary is for anyone that has 14-16 days to spend in Japan visiting the following places:

  • Tokyo
  • Kyoto and surrounding areas
  • Osaka
  • Ishigaki, Okinawa

If these places ring a bell and sound like the places you want to visit, this is the perfect itinerary for you! Japan’s public transportation system is amazing and ultra efficient which means there’s no need to plan for delays and whatnot.

Detailed Posts

Full Japan Itinerary


The itinerary starts in Tokyo, where most transpacific flights land, and ends in Tokyo. From Tokyo, I took the bullet train to Kyoto which passes through Mount Fuji for those looking to spend a few days. Then I spent a few days in Osaka making sure to eat more than I already have been, before taking a flight on ANA to the island of Ishigaki.

Day 1-4: Explore Tokyo


Tokyo is where most people will likely start their trips in Japan. It is by far the largest city in the country, and one of the largest in the world. Having been to so many cities in the world, Tokyo is that one city where I felt like I saw everything, yet nothing at the same time. It was overwhelming, yet strangely quaint. Chaotic, but in the most perfect of ways. The constant lights, sounds, and smells (delicious smells mostly) of the city made sure my senses were completely overworked.

Spending 4 days here will barely scratch the surface. I could easily have spent all 2 weeks of my trip exploring Tokyo. Tokyo is a massive city, one of the largest in the world in fact. It’s population of 30m knows no limits. Japan is an urban society and life revolves around its biggest cities. As real estate prices rise and the population grows, people move further and further out of town. They still commute into Tokyo everyday however turning the city into a mega metropolis. Thankfully, for tourism purposes, most of the action is focused in a much smaller and more manageable area.

harajuku
Harajuku district in Tokyo.

Most people arriving internationally will be coming into either Tokyo via Narita or Haneda. From the airport, take the ultra efficient JR train system to the city. Taxis are of course available but they are not budget friendly at over 20,000 yen for a transfer into the city.

Where to stay in Tokyo

This is purely preference, but I preferred the Shibuya district the most. It seemed a little less chaotic (although this is relative of course) and had more of a “neighborhood feel” if that is even possible in downtown Tokyo. Shinjuku is another popular district but it felt a lot like Times Square to me. Both areas are jam packed full of people and are well connected with trains. There’s plenty of hotels and Airbnb’s in these neighborhoods.

Shibuya crossing Tokyo
The famous pedestrian crossing in Shibuya. Watch from the second floor of the Starbucks for the best views!

All in all, it probably won’t matter where you’re staying unless you are opting out for the fanciest of accommodations. Tokyo is such a densely packed city with unlimited attractions that you’ll be spending your entire day walking the town and you’ll be coming home just to crash.

Sights to See

To be honest, I found just getting lost wandering aimlessly around the city to be some of the best sight seeing available in Tokyo. You might even discover some cool hidden gems that otherwise wouldn’t make it on to guide books. However, there are a few main attractions everyone should visit while here. Meiji Jingu Forest: Something similar to a Tokyo’s central park, the Meiji shrine is something all visitors should see. Located in Shinjuku/Shibuya, this is a great place to escape the lights and sounds of the city.

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Meiji jingu forest tokyo
Meiji Jingu Forest within the city of Tokyo.

Sensoji Temple: Located in Asakusa, this is Japan’s oldest Buddhist temple, and one of its most significant.   Tsukiji Fish Market: Tokyo’s largest and most famous fish market where fresh Tuna is auctioned off every morning before being carved into delicious sushi. The tuna auction starts around 4:30am every morning but there is limited entrance space so 3:30am is the latest you should get there. Aside from that, this fish market is old school, with fresh fish hanging from the ceilings and being openly gutted in the stalls. I love these types of places but it may not be for everyone. What is for everyone however, are the many delicious no-frills restaurants and stands serving the freshest seafood around at 6am. Make sure to pack light, bring cash, and stay out of people’s ways!

tsukiji market fish
Tsukiji market restaurants serving sushi at 6am in the morning
tsukiji Fish market
Inside the Tsukiji Fish market

4 days will inevitably feel like a blur between bright colorful lights, and endless amounts of delicious Japanese food. I have no idea where I even ate because all the names are in Japanese, and almost every restaurant is of the highest quality. The Japanese pride themselves on being the best they can be in whatever job they are in. Take a train at rush hour: Take/observe a busy train at peak hour (Shinjuku station between 7am to 8am). If you’re lucky, you’ll see people actually be stuffed into an already packed train. You will see the impossible become possible. The Japanese probably don’t take pride in this, but somehow they remain so calm and civilized as their personal space evaporates, something that would inevitably start riots in any other country. Just watch the video below: https://www.youtube.com/watch?v=E7kor5nHtZQ

Eat, eat and eat

This seemed to be the theme in all of Japan. Food is amazing here. Not just Japanese food but anything. The Japanese work ethic is so dedicated and meticulous that anything they touch is the best version of itself in the world. I thought I would eat a lot of sushi in Japan, but I spent most of my time in the countless ramen and izakaya shops around town.

ramen machine tokyo japan vending
Most ramen restaurants forego the waitress and put the ordering process in these vending machines. Just hand the receipt to the chef and your ramen will come to you.

But when you want to try sushi, make sure to do something like this:

Day 4-7: Kyoto and surrounding areas


The next step is Kyoto, Japan’s ancient capital. There are many iconic and picturesque temples and shrines in Kyoto, many of which you’ll likely have seen in some magazine or Instagram photo. From Tokyo, take the JR bullet train to Kyoto from the Shinagawa train station in central Tokyo. The cost of the ticket was ~12,000 yen but this price may vary. These trains aren’t cheap like the trains in Europe but they are an attraction in their own right given how fast they are. It’s also the best and fastest way to reach Kyoto from Tokyo.

Higashiyama district in Kyoto next to Gojo district
Higashiyama district in Kyoto next to Gojo district

The train is impossibly quiet even while traveling at speeds of almost 300 km/hr. The train will pass through Mount Fuji and those that want to hike can stop along the way for a night or two. Often times, the volcano is covered by clouds, which was the case for me unfortunately, but the surrounding scenery is fantastic nonetheless.

Where to stay in Kyoto – traditional Ryokan

Kyoto has no shortages of name brand hotels to satisfy even the most luxury seeking individual. However, I’d recommend another type of accommodation here unique to Japan, the Ryokan. Ryokan’s are traditional Japanese Inns that originated in the 8th century AD. They are hotels at their core, but they offer a unique and cultural experience that you just can’t get at a big hotel.

They are scattered all over Kyoto but  you’ll find most of them in the more quiet and local neighborhoods (which itself is part of the charm) like Gion. Like western hotels, there is a wide range on the price and luxury scale. Some of the more expensive ones look absolutely amazing like the Mugen and Kyomachiya Ryokan Sakura Urushitei ryokans!

ryokan kyoto
Inside of the Ryokan. Obviously this can be as luxurious and outlandish as you’re willing to pay for

Lastly, it’s a traditional Japanese inn, so naturally the bed is on the floor on tatami mats. This is likely a deal breaker for many Westerners but I found sleeping on the ground to be quite restful. They say it’s how you should be sleeping and I’ll believe it.

Ryokan Kyoto
Beautiful Ryokans in Kyoto

Wake Up Early for Kyoto Sightseeing

One of the things that seemed abundantly clear to me was avoiding peak times of the day is essential to avoiding the crowds in Kyoto’s main sights. Most of the famous temples and monuments here are open early in the morning and close around 5-6pm. The best times are to go first thing in the morning, or at the very end of the day. All hours in between will inevitably be met with hordes of tour buses.

The Top sights of Kyoto

This is by no means all the top sights in Kyoto, but merely the sights I was able to visit in my limited time there. Four days might seem like a lot, but the time will fly by.

  • Golden Temple: Otherwise known as Kinkakuji temple, the Golden Temple is one of Japan’s most iconic and most visited sights. For good reason. It is absolutely beautiful. I came here when it was about to close. The trick here is to stay until the very end (around 5pm). Most people start to leave but the security guards will let you hang around for another hour or so before kicking you out.

    Golden temple kinkaku ji kyoto
    Kinkaku-Ji, or better known as the Golden Temple in Kyoto!
  • Kiyomizu Dera: One of the most celebrated temples in all of Japan affording the visitor with outstanding views of Kyoto.

    Kiyomizu Dera kyoto temple
    Kiyomizu Dera, one of Kyoto’s most famous templs
  • Arashimaya Forest: Probably one of the most Instagrammed places in Japan. In reality, this forest doesn’t look as secluded as it does in pictures but get there early in the morning and it will feel slightly more mysterious.
Bamboo forest japan kyoto
The Bamboo Forest. Come here in the morning and you might get views like this. Otherwise, expect it to be filled with people!
  • Fushimi Inari: Kyoto’s iconic park filled with red torii gates that straddle the entire shrine

    Fushimi Inari morning empty
    Walking through Fushimi Inari in the morning. No one else with us which was such a relaxing experience
  • Downtown Kyoto: Plenty of restaurants, bars, and shops here that allow for a great night out

    Shijo bridge kyoto
    Shijo Bridge in downtown Kyoto.

Visiting Nara and Todai-ji:

Nara is a small town located about 40 minutes south of Kyoto. It makes for a great half day to full day trip from Kyoto. Todaiji temple is the star attraction here. It is the largest temple in all of Japan and the largest wooden building in the entire world. Inside the temple, the Great Buddha Hall houses the largest bronze buddha statue in the world.  I was in awe standing in front of the Todaiji as its size dwarfed every other temple I saw in Kyoto.

Todaiji Temple Nara Japan
Todaiji temple

Be on the lookout or the Nara deer that know no separation from humans in this town. They go about their business among the tourists and locals.

Visiting Yamazaki Distillery:

Any serious whiskey drinker out there will know that Japan creates some of the finest whiskey in the world. Suntory is one of the most well known brands in the world. They own the Yamazaki brand which has consistently won top awards around the world. The town of Yamazaki is a 40 minute JR ride from Kyoto and makes for an excellent afternoon trip from the city. The town is very small and quaint, with this distillery being the star attraction. They offer tours twice a day but only in Japanese. We reserved two spots well in advance (make sure to do this!) and brought up the rear of the tour with our English headsets.

Suntory whiskey japan 25y
Sampling some 25y Japanese whiskey is never a bad thing. Quite cheap for a tasting considering the bottle sells for $1000+

After the tour, we got to sample various whiskeys and could even purchase a tasting of the world class Yamazaki 25y and Hibiki 30y blends. These bottles are well over $1,000 (if you can even find them) but I was able to taste them for 2,500 yen which was quite reasonable! All in all, this was a great break from all the temples and shrines in Kyoto.

Day 7-9: Osaka


Located 2 hours from Tokyo and 1 hour from Kyoto, Osaka is every bit as cool as Tokyo. Osaka is Japan’s second biggest city and is surprisingly attractive and energetic city that is often overlooked by tourists. Osaka is like Tokyo’s food obsessed little brother. There are dishes native to Osaka that are must tries including a variety of fried street foods like Okonominyaki and Takoyaki.

Okonominyaki osaka
Okonominyaki being cooked in front of me

While I didn’t spend nearly enough time here, I made sure I ate everything I could think of. I’m talking sitting for an Okonominyaki feast, followed by an all you can eat Yakiniku (Japanese BBQ) feast a few hours later. It’s hard to fathom that Osaka is famous for its food when there’s perhaps more ramen restaurants in Tokyo than the rest of the world combined but even my Japanese friends agreed.

ebisu bridge osaka downtown night
Downtown Osaka and the Ebisu bridge

There isn’t much of a secret to finding good food here. It’s Japan and most restaurants adhere to a certain quality. Walking through the Dotonburi district with its famous Ebisu bridge will yield countless dining options. I ended up going to Tsuruhashi Fugetsu for my okonominayki but there are literally hundreds of places serving this local dish. Unless you’re an okonominayki connoisseur, any of these places will do!

Cycle Osaka bike tour

Given our limited time, we elected to take a bike tour of the city. We did the half day tour that visited many of the highlights including Osaka Castle, Nakanoshima Park, and Tenmun-gu. If I could go back and do it again, I probably would have opted for something a little more engaging like the Mario Kart tour of Osaka that seems both ridiculous and absolutely amazing.

Osaka Castle cherry
Osaka Castle with the cherry blossoms

Kobe Beef dinner in Kobe

If there is one thing I can recommend without hesitation in Japan, it is a Kobe beef dinner done teppanyaki style. Kobe Beef is Japan’s most well famous and well known beef (there are more expensive and higher rated beef than Kobe in Japan!). The town of Kobe, home to Kobe beef, is located 40 minutes outside of Osaka by train and is the perfect place to experience this mouth watering delicacy.

Kobe Beef Ishida
Eating Kobe Beef in Kobe, Japan

The trick here is to visit for lunch. Prices are half the price as dinner and you get the same amount of food. I made the mistake of going to dinner but even with a price of over 10,000 yen per person, I still regret to this day not eating more beef. Read my detailed Kobe beef post for more about that experience.

Pachinko Rooms in Japan

If you want to end your night on a more relaxed note, then you should head over to any Pachink room in your vicinity. These parlours resemble land-based casinos since they are loaded with slot machines. However, being inside will bring you one step closer to the Japanese culture. In modern Pachinko rooms, you will be able to find both digital and mechanical slot machines.

But, many modern players in this country are turning to online gambling sites. So, if you want to experience this kind of entertainment from the comfort of your room, you can explore any online casino Japan. It might not offer the same atmosphere as the one found in any Patchinko parlour, but it will give you the chance to see which online casino games the Japanese enjoy. 

Day 10-15: Ishigaki, Okinawa


Okinawa never makes it on to people’s itinerary when visiting Japan and I can understand why. There is so much to see on the mainland and pictures of idyllic sandy blue beaches aren’t the typical images that people think of what they think Japan. I’m here to say, it’s definitely worth considering and visiting. Mainland Japan and island Japan might as well be two different countries. The language, culture, food, and climate are all different. Okinawa is the region to Japan’s south encompassing hundreds of small islands. The island of Okinawa is the biggest island in the region. I wanted to go diving in Japan, and I stumbled across the island of Ishigaki which is famous for their manta ray migrations. A little bit of research and a few Google images later, I was sold. I settled on the island of Ishigaki, the largest island within the Yaeyama archipelago in the most western region of Japan. I immediately received street cred from all mainland Japanese when I told them I was going to Ishigaki. Seems like this place is as special to Japanese people as it is unknown to tourists.

Downtown Ishigaki
Downtown Ishigaki

There are regular flights to Ishigaki airport from Osaka and Tokyo on numerous airlines at very reasonable prices (10,000 yen one way). I flew out from Osaka and flew back into Tokyo Narita airport. There are many things to do on Ishigaki so read the detailed post for a full recount of that trip. Ishigaki is a tropical island and there are no fancy trains here. A bus connects the main points of interest in the island and only leaves once an hour! Talk about a polar opposite experience from the mainland. It does always leave on time however.

Ishigaki Beef
Delicious amazing Ishigaki Beef in Ishigaki. Much cheaper than Kobe and just as delicious

There are also many different types of accommodations on the island in all price ranges.

Kabira Bay

Kabira Bay is one of the most photographed areas of Ishigaki. The view is truly impressive, and not one which you’re likely to tire of quickly. It’s not just the bay which is of interest; casting your eye further afield you’ll be able to see Mt. Omoto clearly in the distance along with the Hirakubo peninsula which extends to the north on the other side of Ishigaki island. Swimming isn’t allowed here however as strong currents and jellyfish are present.

Kabira bay, Ishigaki
Kabira Bay, Ishigaki

Taketomi Island

For perhaps some for some of the best beaches in all of Japan, head to Taketomi island’s Kondoi beach. Home to shallow waters, white sand, and turquoise waters that seem to go out forever, this is an amazing little place. Thanks to preservation efforts, the small village on the island consists almost entirely of traditional style, one-storied houses, which are surrounded by stone walls, and covered with red tiled roofs and ample lion-like shiza statues to ward of evil spirits. Some of the village house’s even serve as accommodation options.

Taketomi water buffalo
Water buffalo carts pulling tourists through the village of Taketomi.

The ferry from Ishigaki is only 20 minutes and visits Taketomi island multiple times a day making for the perfect day trip.

taketomi island japan bike
Biking around Taketomi Island
Taketomi kondoi beach
Kondoi beach taketomi

Iriomote Island

Iriomote island is located 1 hour west of Ishigaki by ferry. It is more sparsely populated than Ishigaki. It’s well known for its beaches, jungles, and just generally being completely off the grid. It makes for a great day trip from Ishigaki.

Iriomote Beach
Star sand Beach on Iriomote!

Japan Two week itinerary Day by Day breakdown


Day 1 – Tokyo: Arrive in Tokyo, explore Shinjuku Day 2 – Tokyo: Meiji Jingu, Harajuku, Shibuya Day 3 – Tokyo: Sensoji Temple, Tsukiji Fish Market, Tokyo Museum Day 4 – Tokyo/Kyoto: Ginza, Train to Kyoto Day 5 – Kyoto: Kiyomizu-dera, Philsopher’s walk, Golden Temple Day 6 – Kyoto: Fushimi Inari, Nara Day 7 – Kyoto: Arashimaya, Suntory Distillery Day 8 – Kyoto/Osaka: Downtown Osaka, eating constantly Day 9 – Osaka: Osaka bike tour, Kobe Beef dinner in Kobe Day 10 – Osaka/Ishigaki: Flight to Ishigaki, explore Ishigaki Day 11 – Ishigaki: Scuba Diving Day 12 – Ishigaki: Scuba Diving Day 13 – Ishigaki: Iriomote Island Day 14 – Ishigaki: Taketomi Island Day 15 – Ishigaki: Flight back to Tokyo

What I would do differently

I will definitely be back in Japan soon. There is so much more to explore in the country. If I could have changed it up, I would have booked one night at a high end Japanese Onsen for the night. An Onsen is a Japanese hot spring. There are plenty of them throughout the country with many surrounded by luxurious Ryokans offering some fantastic views of the Japanese countryside. Would be the perfect place to visit during the late fall and winter months.

onsen japan
Onsen Japan
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Johnny

I'm a dual Canadian-American from NYC that moved to South Africa for work and ended up traveling all through the continent. I'm currently living the expat life in Frankfurt, Germany and traveling the world as much as I can. I'm a bit obsessed with scuba diving, churning credit cards so I never pay to fly, and eating the most questionable of foods in the most peculiar of places. My bucket list is the world, and some day I might make it there.

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    • Hi Ciara, I think without the international flight, it cost me about $2000 per person. I did spend a lot of money eating Wagyu and omakase dinners so this adds up quickly. Otherwise, I think you could do this trip for cheaper.

  1. This will be my first visit to Japan and I was looking for a two-week itinerary that included Okinawa — i like getting some beach time in during my ‘big trips’ so this is perfect! Will read more of your posts in a bit, lots of helpful info. Also planning to go in late September (traveling out of NYC).

    • Hi Dani, unfortunately didn’t have time for Mt Fuji! However, I know plenty of people that make the stop for a night when going from Tokyo to Kyoto so it is totally doable.

  2. I loved my visit to Kyoto but didn’t visit Okinawa. And I’m an island person, how could I have missed that! :O 😀 Will definitely visit it next time I’m in Japan. Thanks for the write up! Was a good read.

  3. wonderful itinerary. I am planning the cities/places, was wondering if it would be too much but seems doable. What time of the year did you go to? We are planning for August/Sept. which I hope we get hot weather in Okinawa!!

    • Hi Vanessa! I went in September and the weather was perfect. It was hot but not unbearably so in Ishigaki and was pleasant in the rest of the country.

  4. Love all of this, especially the part about Okinawa. Going to definitely check out Okinawa after seeing what the area looks like. Would be fun to try scuba diving too. Thanks for sharing all of this info!

  5. Hi Johnny, thanks for writing this up. I was looking for an itinerary that included Okinawa and am glad to have found yours. I am actually going to stay in Hotel Olive in a few months time in Ishigaki! Very excited!

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