Two weeks in Japan is the sweet spot for a first visit: enough time to experience Tokyo, Kyoto, and Osaka in depth while adding day trips and rural detours. This itinerary moves efficiently without feeling rushed.
Days 1–4: Tokyo
Day 1: Arrival, recover from jet lag. Evening only: Shinjuku neon and Memory Lane. Day 2: Asakusa (Senso-ji, Skytree), Ueno museums, evening izakaya. Day 3: Harajuku (Meiji Jingu, Takeshita Street), Shibuya Crossing, Shimokitazawa evening. Day 4: Day trip to Kamakura (Great Buddha, Hase-dera, hiking trails) — 55 minutes from Tokyo.
Days 5–6: Hakone
Take the Odakyu Romance Car from Shinjuku (85 min, ¥2,170). Two nights at a ryokan with private rotenburo — this is the trip's onsen experience. Day 5: Hakone Open Air Museum, Owakudani ropeway, Lake Ashinoko pirate ship. Day 6: Morning Mt. Fuji view (clear days only in winter/spring), Hakone Shrine, afternoon travel to Kyoto by Shinkansen from Odawara (2 hours, ¥10,440).
Days 7–9: Kyoto
Day 7: Eastern Kyoto — Fushimi Inari (6:30am), Kiyomizudera, Gion evening. Day 8: Northern Kyoto — Kinkakuji, Ryoanji, Arashiyama bamboo and garden. Day 9: Nara day trip (deer, Todaiji Great Buddha, Kasuga Shrine) — 45 minutes from Kyoto.
Days 10–11: Kyoto to Osaka
Day 10: Morning in Kyoto (Philosopher's Path, Ginkakuji, Nanzenji), afternoon Shinkansen to Hiroshima (2 hours, ¥11,090 with JR Pass). Peace Memorial Museum, Hiroshima Castle. Overnight in Hiroshima. Day 11: Morning Miyajima Island (Itsukushima Shrine torii gate, Mt. Misen ropeway), afternoon return to Osaka (2.5 hours by JR, covered by JR Pass).
Days 12–14: Osaka
Day 12: Osaka Castle morning, Kuromon Market, Dotonbori canal evening and Shinsekai kushikatsu dinner. Day 13: Free day — Kobe day trip for beef (20 min), or explore Osaka's neighborhoods (Tenma, Nakazaki-cho). Final izakaya evening. Day 14: Depart from Kansai Airport (45 min from Namba by Nankai Express, ¥1,450).
JR Pass Calculation
This itinerary's intercity routes: Tokyo–Odawara (¥1,520), Odawara–Kyoto (¥8,920), Kyoto–Hiroshima (¥11,090), Hiroshima–Osaka (¥5,720), Namba–Airport (¥1,450 by Nankai, not JR). Total without pass: approximately ¥28,700. A 14-day JR Pass costs ¥70,000 — not worth it for this itinerary. Buy individual tickets or use the Icoca IC card for local transport and pay intercity fares separately.