After hosting dozens of first-time visitors to Japan over 25 years, I’ve learned that most 2-week itineraries fail for the same reason.
They try to pack in too much.
The guests who leave happiest are those who follow this slower approach I’ve refined through decades of trial and error.
Living in Nagoya since 2000, I’ve had the unique advantage of testing every route, timing, and connection with real visitors.
This isn’t theoretical travel planning.
It’s what actually works when you’re jet-lagged, carrying luggage, and trying to navigate a country where you don’t speak the language.
This 2-week Japan itinerary balances must-see destinations with the breathing room you need to actually enjoy them.
You’ll explore diverse wonders from bustling cities to peaceful temples, but at a pace that lets you soak in Japan’s unique culture rather than just photograph it.
Planning Your Trip
After watching countless visitors struggle with Japan prep over the years, I’ve identified the essentials that make or break a trip.
Here’s what to sort out before you go.
And the mistakes I see people make repeatedly
Securing the Essentials
Start by choosing when to visit.
Spring brings cherry blossoms, autumn offers vivid leaves.
Book your flights early for better deals.
Narita and Haneda are the main airports for Tokyo.
Buy a Japan Rail Pass before your trip if you’re visiting multiple cities.
It covers most long-distance trains and can save you money.
Travel insurance is a must.
Check visa requirements as many nationalities can enter visa-free for up to 90 days.
Understanding Public Transportation
Japan’s trains and subways are clean, fast, and punctual.
In Tokyo, get a Suica or Pasmo card.
These prepaid cards make travel simple.
If you’ll be exploring the city a lot, the Tokyo Subway Pass offers unlimited rides for a fixed period.
An eSIM makes mobile data easy to set up in advance, useful for navigation and translation apps.
Avoid rush hour when possible as the trains can get very crowded.
Tokyo: The Modern Metropolis
Having lived two hours from Tokyo for close to 3 decades, I’ve watched this city evolve dramatically.
What strikes every visitor I bring here is how Tokyo manages to blend old and new without feeling forced.
Skyscrapers stand beside historic temples, but there’s a rhythm to experiencing both that most tourists miss
Iconic Landmarks
Visit Tokyo Skytree or Tokyo Tower for sweeping views of the city.
Check out Meiji Shrine, nestled in a quiet forested area.
In Ueno Park, you’ll find museums, temples, and even a zoo.
Cultural Hotspots
Akihabara is ideal for tech and anime fans with shops packed full of gadgets and goods.
At Tsukiji Outer Market, enjoy fresh sushi and lively street stalls.
For youth fashion and quirky style, Takeshita Street in Harajuku is the place to be.
Shopping and Fashion
Ginza offers luxury brands and department stores.
For variety, Shinjuku is packed with shops ranging from souvenirs to electronics.
Kyoto: City of a Thousand Temples
I’ve brought more visitors to Kyoto than I can count, and their reaction is always the same: overwhelming beauty followed by temple fatigue.
Kyoto is known for history, gardens, and temples, but the secret is knowing which ones to prioritize and when to visit them
Historic Sites
Visit Kiyomizu-Dera Temple for great views and the Otowa Waterfall.
The Golden Pavilion reflects beautifully in its surrounding pond.
Stroll through Gion District in the evening for a glimpse of Kyoto’s traditional side.
Natural Beauty
Walk through the Arashiyama Bamboo Forest for a calm, scenic experience.
Fushimi Inari Taisha is famous for its winding path of bright orange torii gates.
End your day in a Japanese garden for quiet reflection.
Osaka: The Nation’s Kitchen
Living just two hours from Osaka, it’s become my go-to city for showing visitors what Japanese food culture really means.
Osaka is all about great food and fun city vibes, but there’s a difference between tourist food experiences and what locals actually eat.
Downtown Fun
In Dotonbori, bright signs and food stalls line the canal.
Try takoyaki or okonomiyaki for a local meal.
Shinsaibashi is a lively shopping street, while Kuromon Market is packed with fresh eats.
History and Landmarks
Osaka Castle offers insight into Japan’s samurai past.
Explore its museum and the scenic grounds around it.
Nearby shrines and temples provide a peaceful break from city life.
Hiroshima and Miyajima
These destinations balance powerful history and natural scenery.
Peace and Reflection
Hiroshima Peace Memorial Park and the A-Bomb Dome serve as moving reminders of the past.
The museum shares stories of those affected and encourages peace.
Visit Hiroshima Castle to explore more of Japan’s feudal history.
Island Experience
Take a ferry to Miyajima Island and see Itsukushima Shrine, which appears to float at high tide.
Ride the cable car up Mount Misen for sweeping views.
Watch out for the friendly deer roaming the island.
Day Trips from Major Cities
Japan’s efficient rail system makes short trips easy and rewarding.
Cultural Getaways
From Tokyo, visit Nikko for ornate temples or Kamakura to see the Great Buddha.
From Kyoto, head to Nara for Todaiji Temple and its friendly deer.
Outdoor Escapes
From Tokyo, explore Hakone for Mount Fuji views and a Lake Ashi cruise.
From Osaka, Mount Koya offers forest trails and temple stays.
Japanese Cuisine: A Culinary Journey
When I moved to Japan in 2000, I thought I knew Japanese food from sushi restaurants back home.
Now, I realize I hadn’t even scratched the surface.
Food is a big part of the Japan experience, but the real discoveries happen when you eat where locals eat, not where tourists are directed.
Must-Try Dishes
In Osaka, enjoy takoyaki and okonomiyaki from street vendors or small shops.
Kyoto’s Nishiki Market is full of local snacks and treats.
In Fukuoka, slurp up a rich bowl of tonkotsu ramen.
Food Experiences
Join a cooking class to learn the basics of sushi or tempura.
Try a multi-course kaiseki dinner.
Each dish is a visual and flavourful experience.
Outdoor and Nature Experiences
Japan is rich in natural scenery for every season.
Mountains and Valleys
In Nagano, try hiking routes like Kamikochi.
Nikko National Park in autumn is known for colourful leaves and scenic trails.
Beaches and Coasts
Okinawa has white sands and clear waters for snorkelling and diving.
In the Izu Peninsula, kayak along the coastline and keep an eye out for marine life.
Entertainment and Leisure
There’s plenty of fun for all interests.
Modern Fun
Visit teamLab Borderless in Tokyo for digital art you can walk through.
Theme parks like Tokyo Disneyland and DisneySea offer unique rides and shows.
At night, explore Shinjuku’s Golden Gai—tiny themed bars tucked into narrow alleys.
Cultural Performances
Watch kabuki or noh theatre for a look into Japan’s classical performing arts.
In Kyoto’s Gion, some tea houses host short shows with music and dance.
Shopping and Souvenirs
From local crafts to fun gadgets, there’s something for every taste.
Where to Shop
Tokyo’s Ginza is great for high-end brands, while Harajuku is perfect for youth fashion.
For tech and anime items, Akihabara delivers.
Kyoto has traditional items like fans and ceramics.
In Osaka, visit America Mura for funky streetwear.
Popular souvenirs include green tea, sake sets, chopsticks, and character goods.
Markets and Malls
Visit malls like Omotesando Hills in Tokyo or Namba Parks in Osaka for variety and convenience.
Don’t miss 100-yen shops or department store basements—they’re treasure troves for affordable finds.
Final Reminders
Wear comfy shoes and expect a lot of walking.
Bring a small towel for public bathrooms.
Learn a few simple Japanese phrases as the locals will appreciate it.
And carry cash as many places don’t take cards.
Stay quiet on public transport and try using chopsticks when eating.
Tipping isn’t common and often not welcomed.
Wrapping Up
After 25 years of calling Japan home and sharing it with visitors, I can promise you this.
Japan will surprise you in ways no itinerary can predict.
The moments you’ll remember most aren’t the ones I’ve planned for you.
They’re the unexpected discoveries that happen when you slow down enough to notice them.
This itinerary gives you the framework, but the real Japan reveals itself in the spaces between destinations.
Trust the process, embrace the unexpected, and remember that the best travel stories come from the moments when plans go beautifully wrong.
Safe travels, and welcome to the Japan that has been my home for over two decades.
