Japan is one of those countries where the planning matters as much as the trip itself. Get the route wrong and you spend half your holiday on trains. Get it right and you’ll feel like you saw the whole country in two weeks without rushing.
This is the route I send first-timers on. It works in any month — I’ll tell you what changes by season.
Before You Go
When to visit. Late March to early April for cherry blossom. Late October to mid-November for autumn colors. December to February for crisp weather and lower crowds. Avoid June to August unless you’re fine with humidity.
Money. Carry ¥10,000 to ¥20,000 in cash daily. Cards work in hotels and chains; small restaurants and shrines often won’t.
Transport. Get a Suica or Pasmo card on day one. The JR Pass is no longer a no-brainer since the 2023 price hike — only worth it for three or more Shinkansen rides.
Tattoos and onsen. Most onsen still ban visible tattoos. Search for tattoo-friendly options before booking a ryokan.
Pace. Don’t pack more than 3 sit-down activities per day. You’ll log 15 to 20 km on foot daily without trying.
Days 1–5: Tokyo
Tokyo deserves five days. Anyone telling you three is enough hasn’t actually seen it.
Day 1 — Land soft, stay west
Base in Shinjuku or Shibuya. After checking in, walk Shibuya Crossing, explore Miyashita Park, and end the night barhopping in Golden Gai or Omoide Yokocho. Don’t nap. Power through to reset jet lag.
Day 2 — Asakusa & old Tokyo
Senso-ji Temple before 9am to beat crowds. Walk Nakamise Shopping Street. Afternoon: Kappabashi Street for Japanese kitchen knives, then a Sumida River walk with Skytree views.
Day 3 — Akihabara & Ueno
Tokyo National Museum in the morning. Ameyoko market for cheap eats. Akihabara for electronics, anime, and arcades. Karaoke after dinner if you’ve got the energy.
Day 4 — West Tokyo culture
Ghibli Museum if you booked tickets a month ahead — they sell out fast. Otherwise: thrift shopping in Kichijoji, vintage cafes in Shimokitazawa. Evening: teamLab Planets in Toyosu (book your time slot).
Day 5 — Pick your fighter
DisneySea (only exists in Japan), Harry Potter Studio Tokyo (more chill), or a day trip to Kamakura.
Eating in Tokyo
Tokyo has more Michelin stars than Paris. You don’t need to chase them — a ¥1,000 lunch can be life-changing if you know where to look.
Ramen
• Ichiran (Shibuya) — solo booth tonkotsu, the famous tourist one, still genuinely good
• Afuri (Ebisu) — yuzu-shio, citrusy and lighter than tonkotsu
• Nakiryu (Otsuka) — Michelin-starred tantanmen, queue 90 minutes, worth it
• Tsuta — the world’s first Michelin-starred ramen shop
Sushi
• Sushi Dai or Daiwa Sushi (Toyosu market) — pre-dawn queue, omakase ~¥4,000, breakfast of legends
• Numazuko (Shinjuku) — kaiten-zushi (conveyor belt), affordable, fresh
Tonkatsu, tempura, yakitori
• Gyukatsu Motomura — beef cutlet you finish on a hot stone yourself
• Tonkatsu Maisen (Aoyama) — pork cutlet in a converted bathhouse since 1965
• Tempura Kondo — two Michelin stars, lunch ~¥6,000
• Toritake (Tsukiji) — yakitori counter where salarymen hide after work
Convenience store eating (don’t skip)
• 7-Eleven egg sandwich (tamago sando) — internet-famous for a reason
• Lawson karaage-kun — fried chicken nuggets, perfect drunk food
• FamilyMart famichiki — crispy chicken, ¥220, life-changing at 2am
Drinking
• Golden Gai — 200 tiny bars in 6 alleys; walk in if you see “ENG OK”
• Omoide Yokocho — yakitori smoke and cramped counters under the train tracks
• SG Club (Shibuya) — World’s 50 Best cocktail bar
• Hoppy Street (Asakusa) — locals’ open-air drinking street
Days 6–7: Hakone
Hakone is where you slow down. Mountain town, hot springs, lakes, Mt. Fuji views.
Day 6
Romancecar from Shinjuku — about 85 minutes. Buy the Hakone Free Pass; it covers every transport in the area. Hakone Ropeway up to Owakudani for sulfur-vent views. Pirate Ship across Lake Ashi to Hakone Shrine for the famous lake torii photo.
Day 7
Hakone Open-Air Museum in the morning. Pola Museum in the afternoon. Evening: kaiseki dinner at your ryokan, then onsen.
Eating in Hakone. Eat at your ryokan. Mid-range ryokans (¥25,000 to ¥40,000 per person) include kaiseki dinner — eight to twelve tiny seasonal courses, often the best meal of your trip. Don’t book a ryokan that doesn’t include dinner. For day visitors: black eggs at Owakudani — boiled in sulfur springs, one supposedly adds 7 years to your life.
Days 8–10: Kyoto
Shinkansen from Odawara to Kyoto (~2 hours). Sit on the right side, seat E or D, for Mt. Fuji views.
Day 8 — Northwest Kyoto
Ryoanji Temple (the famous rock garden), then Kinkakuji (Golden Pavilion). Walk the Kinukake-no-michi path between them.
Day 9 — Arashiyama, but early
Bamboo Grove by 6am. Yes, really. By 9am it’s a tourist scrum. Then Tenryu-ji Temple, the Iwatayama Monkey Park, Hozugawa river boat ride.
Day 10 — East Kyoto
Fushimi Inari Shrine at 5–6am — non-negotiable. The famous orange tunnels are unwalkable by 9am. Then Kiyomizu-dera, Yasaka Shrine, walk through Gion in the afternoon.
Kyoto’s Hidden Side
Most travelers do the same five spots. These are the ones they miss.
• Ohara village — 1 hour north by bus. Sanzen-in Temple in autumn is one of the most beautiful places in Japan.
• Philosopher’s Path at dawn — walk from Ginkaku-ji to Nanzen-ji before 7am. Empty, soft light, free.
• Pontocho alley after 9pm — find a tiny standing bar, point at what looks good.
• Kurama-Kibune — half-day hike between two mountain temples, ending in a riverside ryotei.
Eating in Kyoto
Kyoto food is gentler than Tokyo’s — refined, vegetarian-friendly, deeply seasonal. The country’s spiritual food capital.
Kaiseki and tea
• Kikunoi — three Michelin stars, lunch course ~¥12,000
• Giro Giro Hitoshina — modern kaiseki, no reservation needed for the counter, ¥4,500 for nine courses
• Ippodo Tea — 300-year-old tea house, sit-down matcha tasting
Casual Kyoto
• Nishiki Market — 400m of stalls. Don’t miss tako tamago (octopus stuffed with quail egg)
• Issen Yoshoku (Gion) — one-dish okonomiyaki since 1955, ¥800 a plate
• Omen — Kyoto-style udon, lunch ~¥1,500
• Arashiyama Yoshimura — soba with bamboo grove views
Sweets
• Saryo Tsujiri — matcha parfaits stacked like geological cross-sections
• % Arabica Higashiyama — coffee with a view of Yasaka pagoda
• Demachi Futaba — mame mochi, queue but quick
Days 11–12: Osaka
The food city. Different energy from Kyoto — louder, looser, more fun.
Day 11
Train to Osaka (~15 minutes from Kyoto). Drop bags, head to Dotonbori for the iconic neon canal. Abeno Harukas Observatory for skyline views. teamLab Botanical Garden in the evening.
Day 12
Osaka Castle morning. Shinsaibashi shopping afternoon. Osaka Aquarium Kaiyukan late afternoon — one of the world’s best.
Eating in Osaka
Osaka calls itself tenka no daidokoro — “the kitchen of the nation.” Locals say kuidaore: “eat until you fall over.” Take this seriously.
The Osaka Holy Trinity
• Takoyaki at Wanaka or Kukuru (Dotonbori) — octopus dumplings, eaten standing up
• Okonomiyaki at Mizuno (Dotonbori) — savory pancake, you grill it yourself
• Kushikatsu at Daruma (Shinsekai) — fried skewers, dip-once rule, ice-cold beer
Beyond the trinity
• Harukoma Sushi (Tenma) — best cheap sushi counter in the city
• Imai Honten (Dotonbori) — kitsune udon since 1946
• Kuromon Market — eat your way through; wagyu skewers, oysters, fugu in winter
Day 13: Nara
Train from Osaka (~45 minutes). Feed the bowing deer at Nara Park. Todaiji Temple — the giant Buddha is genuinely massive. Kofuku-ji for the pagoda. Hike Wakakusayama Hill if the weather’s good.
Day 14: Back to Tokyo
Shinkansen back to Tokyo (~2.5 hours). Use this last day for whatever you missed — last-minute shopping in Ginza, a final ramen, a relaxed coffee in Daikanyama. Don’t squeeze in a new neighborhood. Just enjoy.