Two weeks in Japan hits the sweet spot — enough time to see Tokyo, Kyoto, and Osaka properly without feeling like you’re on a forced march, plus room for day trips to smaller places that first-timers often skip but shouldn’t.
I’ve done this itinerary twice, once during cherry blossom season and once in October, and refined it based on what actually works versus what looks good on a Pinterest board. The biggest mistake first-timers make isn’t visiting the wrong places — it’s cramming too many places into each day and spending half their trip on trains instead of experiencing where they are.
This itinerary assumes you have a Japan Rail Pass and are arriving at either Narita or Haneda airport in Tokyo.
Days 1-5: Tokyo
Five days in Tokyo sounds like a lot. It isn’t. Tokyo is enormous — a collection of distinct neighborhoods that each deserve at least half a day. Trying to “see Tokyo” in three days means seeing the inside of a lot of train carriages.
Day 1: Arrival and Shinjuku
Arrive, get to your accommodation, and spend the evening in Shinjuku. Walk through the neon chaos of Kabukichō, find a tiny yakitori joint in the alleys of Memory Lane (Omoide Yokocho), and eat grilled chicken skewers at a counter with six seats. This is your introduction to Tokyo — overwhelming, delicious, and completely unlike anywhere else.
Practical: Pick up your Japan Rail Pass at the airport exchange office. Get a Suica or Pasmo IC card for local trains — it works like a tap-and-go transit card and is also accepted at convenience stores and vending machines.
Day 2: Shibuya, Harajuku, and Meiji Shrine
Start at Meiji Shrine — arrive early (before 9am) when the forested approach is quiet and the shrine feels genuinely sacred. Walk through Harajuku’s Takeshita Street for the fashion and people-watching, then head to Shibuya for the famous crossing. It’s best experienced from the Starbucks overlooking the intersection or the Shibuya Sky observation deck.
Eat: Harajuku’s back streets have excellent small restaurants. Skip the crepe shops on Takeshita Street and find a ramen place on the side streets instead.
Day 3: Asakusa, Akihabara, and Ueno
Sensō-ji temple in Asakusa is Tokyo’s oldest temple and worth visiting despite the crowds. The Nakamise shopping street leading to it is touristy but fun for picking up small souvenirs. Walk to Ueno Park for the Tokyo National Museum — the best museum in Japan for understanding the country’s art and history. If you have energy left, Akihabara’s electronics shops and anime culture are a 10-minute train ride away.
Day 4: Tsukiji Outer Market and Teamlab
The inner wholesale fish market moved to Toyosu, but Tsukiji’s outer market remains one of the best food experiences in Tokyo. Arrive at 7am for the freshest sushi, tamagoyaki (Japanese omelette), and seafood on sticks. Spend the afternoon at Teamlab Borderless (now in Azabudai Hills) — book tickets online at least a week ahead, as they sell out consistently.
Day 5: Day Trip to Kamakura or Nikko
Kamakura (1 hour south): A coastal town with the Great Buddha statue, beautiful Zen temples, and hiking trails between shrines. The Daibutsu hiking trail connects the main sights through bamboo forests. Finish with a walk along Yuigahama beach.
Nikko (2 hours north): Ornate Tōshō-gū shrine in a mountainous cedar forest setting. Less crowded than Kamakura, more dramatic scenery. The shrine complex is one of Japan’s most lavishly decorated.
Days 6-9: Kyoto
Take the shinkansen from Tokyo to Kyoto — 2 hours and 15 minutes, covered by your JR Pass. Kyoto is Japan’s cultural heart: over 2,000 temples and shrines, traditional geisha districts, and a food scene that rivals Tokyo’s.
Day 6: Eastern Kyoto
Start at Fushimi Inari Shrine — the famous orange torii gate tunnel. Go early (7am) to beat the crowds on the lower paths. The full hike to the summit takes 2 hours and gets progressively emptier. In the afternoon, walk through the Higashiyama district: Kiyomizu-dera temple (stunning hilltop views), Ninenzaka and Sannenzaka lanes (traditional shops and teahouses), and the narrow streets of Gion where you might spot geiko (Kyoto’s term for geisha) in the evening.
Day 7: Western Kyoto and Arashiyama
The Arashiyama Bamboo Grove is iconic but crowded by mid-morning. Arrive at 7:30am when the light filtering through the bamboo is magical and the paths are nearly empty. Visit Tenryū-ji temple next door, then cross the Togetsukyo bridge. In the afternoon, visit Kinkaku-ji (the Golden Pavilion) — genuinely as stunning as the photos suggest.
Day 8: Nara Day Trip
Nara is 45 minutes from Kyoto by train. The friendly (aggressive) deer in Nara Park are the headline act, but Todai-ji temple — housing an enormous bronze Buddha inside the world’s largest wooden building — is the real reason to visit. You can see Nara’s highlights in half a day and be back in Kyoto for dinner.
Eat in Kyoto: Nishiki Market for street food tasting. A kaiseki (multi-course traditional) dinner is a splurge worth considering at least once — expect ¥8,000-15,000 ($55-100) for an experience you’ll remember forever.
Day 9: Slow Day in Kyoto
Visit a quieter temple — Nanzen-ji, Tōfuku-ji, or the moss garden at Saihō-ji (requires advance reservation). Have a matcha at a traditional tea house. Wander neighborhoods without an agenda. Kyoto rewards slowing down more than any other Japanese city.
Days 10-11: Osaka
Take the train from Kyoto to Osaka — 15 minutes on the shinkansen or 30 minutes on a local rapid train. Osaka is Japan’s street food capital and has a rawer, more energetic personality than polished Kyoto.
Day 10: Dōtonbori and Street Food
Dōtonbori is loud, neon-lit, and entirely about eating. The essentials: takoyaki (octopus balls) from a street stall, okonomiyaki (savory pancake) at a sit-down restaurant, and kushikatsu (deep-fried skewers). Osaka Castle is worth the walk through its park even if you skip the museum inside the reconstructed tower.
Day 11: Shinsekai and Kuromon Market
Shinsekai is Osaka’s retro entertainment district — less polished than Dōtonbori, more local. Kuromon Market is Osaka’s kitchen — fresh seafood, fruit, and the chance to eat uni (sea urchin) and otoro (fatty tuna sashimi) at breakfast prices.
Days 12-13: Hiroshima and Miyajima Island
Take the shinkansen from Osaka to Hiroshima (1.5 hours). This is the most emotionally heavy part of the trip but also one of the most important.
Day 12: Hiroshima Peace Memorial
The Peace Memorial Museum and the A-Bomb Dome are profound, sobering, and essential. Plan for at least 2-3 hours at the museum. The surrounding Peace Memorial Park is a quiet place to process what you’ve seen. Hiroshima itself is a vibrant, modern city — try Hiroshima-style okonomiyaki (layered, with noodles) for dinner.
Day 13: Miyajima Island
A short ferry from Hiroshima (covered by JR Pass) takes you to Miyajima, home of the famous floating torii gate of Itsukushima Shrine. At high tide, the gate appears to float on the water. At low tide, you can walk out to it. Both are worth seeing. The island’s friendly deer, mountainous hiking trails, and maple-leaf-shaped momiji manju pastries make this a perfect final full day.
Day 14: Return to Tokyo and Departure
Take the shinkansen back to Tokyo (4 hours from Hiroshima). If your flight is in the evening, spend the morning at Hiroshima or stop in a city en route. If departing the next day, use the afternoon for last-minute Tokyo shopping in Ginza or Nakamise.
Practical Tips for First-Timers
- Cash still matters. Many small restaurants, temples, and rural businesses are cash-only. Withdraw yen from 7-Eleven ATMs, which reliably accept foreign cards
- Convenience stores are excellent. 7-Eleven, Lawson, and FamilyMart have surprisingly good food — onigiri, sandwiches, and bento boxes for ¥200-500 ($1.50-3.50)
- Download Hyperdia or use Google Maps for train schedules. Both show exact platform numbers and train times
- Shoes off indoors. Temples, traditional restaurants, some hotels, and most homes require removing shoes. Wear shoes that slip on and off easily. A universal travel adapter is also essential — Japan uses Type A plugs
- Pocket wifi or eSIM. Get a pocket wifi device at the airport or an eSIM before departure. You’ll need data constantly for maps and translation
What This Itinerary Skips
Two weeks can’t cover everything. This itinerary skips Hakone (hot springs town near Tokyo), Kanazawa (beautiful Kenroku-en garden), Takayama (mountain town with morning markets), and the entire island of Hokkaido. Each is worth a trip of its own. Consider them for your second visit — because you will come back.