2 Perfect Weeks in Japan: Travel Guide & Itinerary

2 Perfect Weeks in Japan: Travel Guide & Itinerary

Ever notice how everybody’s Japan itinerary looks exactly the same? Tokyo, Kyoto, and maybe Osaka if they’re feeling a bit adventurous. And even in those places, the same spots pop up over and over again. But here’s the thing. Japan has so much more to offer than just those places. After helping tons of travelers plan Japan trips and having a 20-year relationship with the country itself, I’ve seen how some of the best experiences often happen when you step off the beaten path. What if I told you there’s a way to still do iconic Japan where you’ll spend less time on trains, deal with fewer crowds, and come away with stories that don’t sound identical to everybody else’s Japan trip or have to photoshop 100 people out of your photo. So, let’s dive in and plan a trip that’s actually worth taking your vacation time. But planning a trip to Japan for the first time? Where do you even start? Don’t worry, I’ve got you covered with my free travel guide in the links in the description. All right, before we jump into the specifics of the itinerary, let me give you a quick run through the tools that’ll make navigating Japan an absolute breeze. First, grab an IC card. at the moment you land. They came back in 2024 and they make paying for everything from trains, convenience store snacks to unsolicited items. Maybe not the last one. Completely effortless. It’s your basic I’m not completely lost card. Here’s a pro tip for you, too. So, you can now actually download the IC card app onto your phone, which is super convenient if you prefer traveling light. Most people in Japan use IC cards on their phone these days. Next up is Pocket Wi-Fi. traveling internationally, normally you can use your phone plan. But what about those times you’re in a place where the signal isn’t so good for uninterrupted connectivity? Especially if you’re in a restaurant with like 50 menu items and you’re trying to Google search. Nothing beats having your own Wi-Fi device. So, I personally download two apps. Google Maps for the basics and also pair it with Nav Time for those train connections that Google sometimes does miss along with Google Translate. I guess that’s three. You’ll be able to navigate Japan like you’ve lived there for years. But here’s a question that might cross your mind. Once you’ve got this stuff, once you’ve got these tools, where exactly should you be heading first? You might be wondering, is it actually possible to explore some of the main cities in Japan and some more rural areas in just 2 weeks without destroying your wallet or your sanity? So, our trip begins in a city where you’ve got some ancient temples that stand in the backdrop of some crazy skyscrapers, where you can find ancient traditions and cutting edge technology within just blocks of each other. It’s a place that somehow manages to be exactly what you expected and nothing like you pictured at the same time. Look, I’m not going to tell you to skip Tokyo. That would be absolutely wild. The city is absolutely incredible and deserves a spot on your itinerary. But there’s a world of difference between experiencing Tokyo like 99% of other tourists and discovering the city that locals and long-term residents actually love. Tokyo isn’t just a city. It’s a place that’ll make you question your life choices. Like, why don’t I live here? After having spent years studying Japanese in Shinjuku, I’ve discovered some spots that most tourists completely miss while they’re busy going between the same three recommended places. So, this first day begins with a morning visit to Shinjuku National Garden, Shinjuku. While everybody else is still snoozing, you’ll have one of Tokyo’s most beautiful parks almost to yourself. It’s so peaceful that honestly, you’ll forget you’re in the world’s largest city until you see the skyscrapers hanging out over the trees. Nice try, nature. After stopping by the garden, make sure to grab lunch at Cafe Labo. La Labo, I think. I don’t speak any other languages other than Japanese and English, so sorry. But this is the actual restaurant that was featured in the the hit anime film, Your Name, or Kima, which is just a short walk from the park. Getting a chance to eat here, I did it with my language school teachers when I was still in school right around the corner. Shout out to KCP. And even if you haven’t seen the movie or have no idea what I’m talking about, it’s it’s definitely worth checking out. As the afternoon continues on, you can head to the eastern side of Shinjuku for some shopping. You can find literally everything from super high-end fashion items to the perfect pair of socks. As the evening starts to approach, check out Kabukicho. Yes, this is technically Tokyo’s red light district, but it transforms into something completely different as the night starts to set in. By this point, you might be getting a little hungry, so I’d make my way to Takito Ramen. Specifically, the annex. Not not hating on the main location, but the annex is my favorite. Quick story. So, actually, when I was in language school, my friend and I would slip away between classes for what I still consider some of the best miso ramen I’ve had in Tokyo. And you pair that with some good old umesu, some plum wine, and some beer. We told ourselves it was a bit of cultural immersion. And even though I would only have one omeu or or maybe one beer, you you probably shouldn’t go drink beer between your classes. It’s probably falls under the category of bad study habits. But the ramen was absolutely worth the questionable academic choice. Or if you didn’t want to check out Kapukich Cho, you can finish your day by exploring the west side of Shinjuku, a side of Shinjuku that most tourists don’t actually get to see. Western Shinjuku has some incredible cafes where you can chill and just watch the city sort of transition from that busy Japanese workday to a more evening kind of calm. So now you’ve experienced one of the main areas of Japan, something that you normally would see on an itinerary. But Tokyo has so many different flavors. So when you’re done with one of the main tourist drags, what should you do next? There’s a whole other side to Tokyo that not everybody gets to see. So day two leads you to Tokyo’s coolest neighborhoods, Shimokazawa and Coeni. Shimokazawa has a bunch of really cool vintage record shops and thrift stores. Um, I once met a young woman who was studying abroad in Canada. She was Japanese. She got to meet my daughter, my wife. These types of small connections often become some of the most memorable parts of your trip. Henzi, on the other hand, is Tokyo’s underground sort of music haven. The street art alone is definitely worth checking out. They’ve got really cool small live houses and record shops that give Coenji a really unique character. Do you have a favorite Tokyo neighborhood? Drop a comment below. If you discover something that I haven’t mentioned, I’m always looking to expand places to go and recommend. All right, so after 2 days of exploring the city, you might be just wanting to get out and have some fresh air and enjoy a bit of nature. Tokyo’s concrete jungle has its charms, but sometimes you need to escape the crowds. There’s a few day trip options you can take from Tokyo to either places that are just on the outskirts of Tokyo or what some people would consider the greater Tokyo area. Although this next place is technically in Kanagawa. Day three gives you a chance to catch some of the fresh air at Mount Oyama. While there are a lot of tourists who visit Mount Taka, you’ll have a chance to enjoy Mount Oyama’s peaceful trails with a lot fewer people. You can take the cable car to save some energy. Then you can head to Afford Shrine for some gorgeous views. The cable car is perfect for people who want the hiking experience without the whole hiking thing. The real magic happens along the Komasando, which is the traditional street, and it’s got souvenir shops and ins and restaurants. After about 3 days in and around Tokyo, again, that last place was in Kanagawa. You’ve sort of gotten a taste of modern Japan’s energy and gotten out to nature in a little bit. But what if you wanted to explore a little bit more of Japan’s traditional side? This next place can feel like Japan’s bestkept secret. It’s a city that didn’t suffer from some of the bombing during World War II, which actually left a lot of its traditional districts completely preserved. It’s not just a destination. You can kind of get to time travel a little bit and see what life was like. It’s a place where traditional beauty meets unexpected creative energy. And you can walk ancient streets in the morning and then in the afternoon explore one of the most cuttingedge art installations. You can get to Kanazawa from Tokyo by bullet train in about 3 and 1/2 4ish hours. And on this first day, I’d explore the Higashi district. The streets of Higashi align with these preserved wooden tea houses that sort of make you feel like you’ve stepped into an old edeto period drama. These aren’t just pretty places either. There’s living history where you can see Kanazawa’s geisha still perform and walk around. And no, just like Kyoto, you can’t take photos of them. They’re not Disney characters. They’re not Mickey Mouse or Donald Duck or Goofy or, you know, they’re not in Disneyland. For lunch, head to Omito Market where you can try some absolutely fire seafood. Seafood doesn’t get any better than this. Then the 21st century Museum of Contemporary Art. Imagine stepping from those ancient streets into these modern cuttingedge art installations. There’s a famous swimming pool exhibit where visitors appear to be underwater and it creates some really cool photos that’ll have you and your friends questioning the laws of physics itself. I’d start this next day at Ken Rukuan Garden. Get there early. It’s ranked as one of Japan’s three most beautiful gardens. Let’s be honest, for good reason. Every season transforms the landscape of the garden completely. After the garden, you can do some more exploring and check out the Nagamachi Samurai district. The Nomra Samurai House offers a glimpse specifically in how some of the elite families live during this time period. Spoiler alert, much better than everybody else. You can wrap up your day in Kanazawa with enjoying something that’s really unique to the region itself. Gold leaf ice cream. And no, it’s not just like a brick of gold and ice cream like sitting next to it. It’s actually wrapped in a thin layer of gold leaf so that you can eat it completely. Kanazawa produces 99% of Japan’s gold leaf. It’s the only time that eating something shiny is socially acceptable unless you’re planning on going to the hospital. So, now that you’ve done Kanazawa, our next stop takes us deep into the Japanese countryside to a place where traditional life hasn’t just been preserved, sort of like in a museum, but it’s still being lived. The village itself is so unique that it became a world UNESCO heritage site. There’s these really cool steep roof houses that have with the centuries of crazy heavy snowfall. They’re the same way that they’ve been since hundreds of years ago. It’s like stepping into some sort of fairy tale where time moves completely different. Shirakawagago offers an experience unlike anywhere else in Japan. To be honest, from the time you arrive, you’ll understand why people travel from across the world just to see it. The Gasho Sukuri farm houses are amazing. They withtood centuries of heavy snowfall. The people who built these are basically like ancient geniuses who figured out snow engineering. While in middle of Europe, people were still trying to figure out how to keep their castles from flooding. No disrespect, Europe. You can get to Shirakawagago from Kanazawa a few different ways, but the best way to probably do it is an express bus from Kanazawa to Shidikawagago. I start that first day at the Wada House, which is the village’s largest gashuki building, and it’s a designated national treasure. It was once home to the village’s most prosperous family, but now offers a real close look at traditional rural life. It’ll make you really grateful for modern conveniences like, you know, uh, indoor plumbing. Do not go in there. For some really gorgeous views, you can hike up to the Shiroyama viewpoint. You can take time to cross the Deay Bridge that spans across the Shokawa River for a different perspective or different view of the village. For more spiritual context, you can visit Mioenji Temple and Shiakawag Hashiman Shrine. One of the truest Shirakawagago experiences comes from staying overnight at one of the houses. As the day trippers leave, the village becomes something even more special. You can sit around one of the old Eidori hears and enjoy a home-cooked meal with local mountain vegetables and heat of beef. And it’s an opportunity to share stories with the people that are staying with you or hosting you. Again, creating some of those memories that not everybody gets to get. So, after experiencing this amazing mountain village, you might be wondering if there’s any more traditional Japan that you can see. Is there any other different perspective on some of Japan’s past? There’s another historic gem that’s just waiting to be explored in this next place. This place prospered once as a really wealthy merchant town and was strategically positioned on an ancient trade route that cuts through the mountains. Here in some ways that are similar to Kazawa, you’ll find streets lined with wooden buildings that have stood for centuries. Morning markets that have been operating continuously for 300 years or so and a craft tradition that’s remained unbroken since the Edeto period. Takayama is where Japan’s traditions aren’t just preserved, they’re celebrated with pride. It’s a town where the past feels very present. To get to Takayyama from Ishira Kawagago, your best bet again is probably going to be an express bus. Noticing a theme here. So, this first day brings you to the Sam Machi Suji. It’s Takayyama’s beautifully preserved old town. The streets are lined with wooden merchant houses from the Edeto period that feel so authentic that you’ll forget what century you’re in. You can look for these cedar balls that are hanging outside of different sake breweries. And that’s your invitation to taste some of Japan’s best rice wine. It’s crafted using pure mountain water. So, it’s not that you might need an excuse to drink before noon, but they got you covered. you now have a cultural excuse to do so. You can spend your afternoon at the Matsuri no Morti where Takayyama’s famous festival floats are displayed year round. And these aren’t just parade decorations. There’s superdetailed works of art that feature mechanical dolls and carvings that really show some amazing craftsmanship that’s been passed down through the centuries. This next day, I’d start with the morning markets along the Miagawa River, where farmers and artisans have gathered for over hundreds of years. And this doesn’t just attract tourists. It’s an actual living tradition where locals still shop daily. While the market comes to life, man, treat yourself to some nice mitarashidango. Later, you can find peace on the Higashiyama walking course. It’s a path that takes you past 12 temples and shrines tucked into the countryside. Enjoy your Takayama day with a meal featuring the legendary hida beef. It’s usually overshadowed by Coobe. Takayyama’s Wagyu has marbling and flavor. It’s the kind of meat that ruins regular beef for you forever. So, sorry about any future barbecues. They might be ruined. Oh jeez. Well, that first batch might not be done for. You’ve now experienced some of Japan’s best preserved historical towns and villages. What about the places that connected them in the first place? Now, our trip takes us to a region that offers two different but equally fascinating experiences. One of Japan’s most impressive original castles and a remarkably preserved section of the ancient highway that once connected Tokyo and Kyoto. This next part of the trip allows you to literally walk in the footsteps of seami, merchants, and pilgrims who traveled these same stone paths centuries and centuries ago. Matsumoto combines history with a little bit of like countryside quirkiness and it creates a perfect contrast that keeps you really surprised. So to get to Matsumoto from Takayama express bus, a little bit of walking should take you about 2 and 1/2ish hours. This next day centers around Matsumoto Castle, nicknamed the Black Crow for its striking exterior. Unlike many Japanese castles that are completely rebuilt in concrete, this is one of Japan’s few remaining original wooden structures. When you’re climbing the interior stairs, you’ll be amazed at how these wooden beans withtood centuries of earthquakes and war. After the castle, you can try something that you probably wouldn’t have expected. Wasabi. Wasabi. The Dio wasabi farm is visually appealing and it has like these really cool streams. You can try wasabi ice cream, which yeah, I know I said wasabi ice cream. It sounds like a dare, but it’s amazing. This next day takes you to the Nakasendo Trail, which you can access by bus or taxi. Specifically, you’ll be checking out the preserved post towns of Simago and Mome. This historic route once connected Tokyo and Kyoto during the Edeto period, and walking between these two towns today feels like stepping through a time port. The Nakasendo Trail offers a rare glimpse into travel as it existed in Japan centuries ago. Postal runners once raced along these same routes carrying messages. Damio lords travel with their entouragees between the capital and their domains. Imagine being the postal worker who had to run up these hills. No wonder Japan’s train system is so good. You can stop at a traditional tea house along the way for matcha and wagashi sweets. The simple act of just enjoying the absolutely gorgeous view and looking at mountains that samurai once viewed centuries ago creates a sense of connection across time that I don’t think any museum can match. Speaking of historical capitals, you’ve probably guessed this. Your trip has been building up to one of Japan’s most famous destinations. Now, we arrive at a city that probably needs no introduction. Most people consider this place the cultural soul of Japan. It’s a place with over thousands of temples, hundreds of shrines, and a history that stretches back centuries, even a millennia. But while most tourists rush between the same handful of famous places, we’re going to discover a little more hidden side of this ancient capital. So, you’re going to get in to Kyoto from Sumagle. Train is one of the better options here. Yes, if it’s your first time in Japan, I don’t think you can go wrong putting Kyoto in your itinerary. But not just to check off the same temples that everybody sees before you immediately leave. This first day begins at a lesserknown temple that offer sort of a peace and tranquility that some of the other famous sites can’t match. The place I’m talking about is Otagi Nimbutsuji. features,200 stone statues, each with uniquely expressive faces carved by amateur artists. Walking along these statues almost feels like meeting a community that’s frozen in stone. One of the best parts about this is you can actually enjoy them without fighting through a bunch of people with selfie sticks, which is honestly a bit of a miracle in Kyoto. As evening approaches, you can visit what I consider still one of the best temples in Kyoto, Fushimi Inari. I would go in the evening because the crowds are a bit thinner or go earlier in the day. It completely changes the experience. The red Tory gates and the light look completely different. It’s really gorgeous. The next day, I would explore some of Kyoto’s highlights, but with more insider type timing. Arrive at Nishiki Market early in the day as vendors are just setting up. After checking out Nishiki Market, check out Nij Castle with his nighting gale floors that chirp when you walk on them like an ancient security system. I’d escape out to the philosophers’s path. There’s a walkway alongside a canal where Japan’s most famous philosopher practiced meditation while walking. This next day takes you to Muk City, which is southwest of central Kyoto, but is super accessible by train. Here, you can get a chance to check out some really cool bamboo groves. It’s similar to Arashiamyama, but without the crowds. In the evening, you can return when they light up the bamboo forest, and it creates a completely different atmosphere. Have you discovered any other hidden gems in Kyoto that you think should be on the list? Drop your recommendations in the comments. Again, I’m always looking to add more places to explore in this amazing city. Our journey comes full circle as we go back to Tokyo, not to the city center with the huge skyscrapers and the litup districts that we explored a bit earlier. This time we’re going to take a look at the city’s historic heart. It’s a place where you can still glimpse those echoes of old Edeto, old Tokyo. The place I’m talking about here is Asaka. So once you get in to Tokyo, you’re going to get into Tokyo station, catch a train out to Asaka. So this next day starts with an early morning visit, not middle of the day, an early morning visit. Arriving before the crowds get here offers a really rare opportunity to experience this centuries old temple in a sort of quiet space that it deserves but doesn’t often get. You can watch shoppers along the Nakamise prepare for the day. It’s a sort of behind-the-scenes look at Tokyo while most people are still snoozing. For lunch, I check out Hoppy Street, which is named after a non-alcoholic beer that’s mixed with shou. If you love coffee, I’m a huge coffee person these days. Make sure you don’t miss a coffee for a really good cup. If you’re hunting for souvenirs, you should check out Kapabashi Street. Fun fact, it’s actually where a lot of Tokyo’s restaurants buy their supplies. When your friends ask you where you got that amazing knife, you can casually say, “Oh, I just got it from Tokyo’s restaurant supply district.” No big deal. Humble brag. This last day gives you time for some final exploration and a proper goodbye to Tokyo. You can take a really relaxing cruise along the Sama River for some beautiful views of the city from the water, giving your feet probably a muchdeserved break after two weeks of exploring. If you haven’t been yet, Akihabara, which isn’t far, makes for a great last minute shopping trip. Beyond the typical electronics and the anime merchandise that made it famous, the area has sort of evolved to include some surprisingly cool cafes and hangout spots for dinner. Consider returning to one of your favorite spots from earlier in the trip. Or you could be bold and try that one place you’ve been dying to try, or that one food you’ve been super curious about. But I think either way, try to make your last night in Japan memorable and really enjoyable. Now that you’ve done or planned this epic trip, what about the Japan Rail Pass? Is it worth it for this itinerary? Here’s how the math shakes out for this specific trip. Individual tickets cost about 49,000 yen, while the Japan Rail Pass runs you about 80,000. So, you’re looking at about 31,000 yen saved total. If flexibility matters more than saving money, then the Japan Rail Pass can still work here. But just keep that price difference in mind. But knowing your route in advance can really maximize your yen for the experiences that you think matter. So, this twoe trip blends iconic landmarks with hidden gems and I think can create a really unique personal experience of Japan. I’ve helped lots of people plan trips when people are able to get off the beaten path and see some of the iconic things and really enjoy some of those personalized experiences. The feedback’s always positive. But before you finalize your travel plans and try to do this trip, there’s one more crucial piece of information. Knowing what not to do in Japan. In this next video, I’ll reveal the cultural missteps that can turn your dream trip to very awkward very quickly.

Link to FREE travel guide → https://dezzy-d-s-dojo.ck.page/japanguide
The one money hack Japanese locals use to save $500+ per trip
→https://dezzydsdojo.com/savings2/
Plan your dream trip → https://dezzydsdojo.com/plan-your-trip/
Call→https://calendly.com/dezzydsdojo/jpitinerary

Video Sources:

Manpuku_gourmet24
All the anime
Roaming Japan
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Travel Japan 8k ( HDR TV )
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kurakama’s Japan travel & gourmet
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高山市公式YouTubeチャンネル
Nakatsugawa Official
Kiso Ontake Tourism Office
【京都市公式】きょうと動画情報館(City of Kyoto)
The KYOTO
京都府向日市
旅channel花鳥風月
Japan Night Walk
東京シニア夫婦チャンネル
We need dog and cat in the country.In Japan.
Walk in Japan 4K

Other Sources:

Shinjuku-Gyoen

http://www.togeihida.co.jp/

Daio Wasabi Farm

https://sukemasa.tokyo/