Everything you need to reserve, in the order you should do it. Items marked HIGH must be booked immediately or 1–2 months ahead.
| □ | What to Book | When to Book | Where | Priority |
|---|---|---|---|---|
| JR Pass (14-day Ordinary) ×4 passes — activate at Haneda on arrival |
Now — before departure. Cheaper overseas. | JRPass.com, KKday, or Klook | HIGH — DO NOW | |
| Tokyo Hotel (Shinjuku or Shibuya) 3 nights: Jun 18–21. 4-person room or 2 connecting rooms. |
Now — June fills up | Booking.com, Hotels.com | HIGH — DO NOW | |
| Hakone Ryokan 2 nights: Jun 22–24. Request dinner included. Min 2 rooms. |
Now — 2–3 months ahead minimum | Relux, Jalan, Booking.com | HIGH — DO NOW | |
| Kyoto Hotel 4 nights: Jun 24–28. Near Gion or Kyoto Station. |
Now | Booking.com, Hotels.com | HIGH | |
| Osaka Hotel 3 nights: Jun 29 – Jul 2. Near Namba/Shinsaibashi. |
Now | Booking.com, Hotels.com | HIGH | |
| Romancecar Shinjuku → Hakone-Yumoto Jun 22, ~9 AM departure. ×4 reserved seats (GSE panorama car if possible). |
1 month before Jun 22 = May 22 | odakyu-global.com (EMot Online Tickets) or Klook | HIGH | |
| Shinkansen Seat Reservations Odawara→Kyoto (Jun 24), Kyoto→Osaka (Jun 29), Osaka→Hiroshima→Osaka (Jun 30), Osaka→Shinagawa (Jul 2). Hikari or Sakura only (not Nozomi). |
1 month before or at any JR office in Japan | Japan Official Travel App, JR office at Haneda on arrival | MEDIUM — DO IN JAPAN AT JR OFFICE | |
| Nikko Pass World Heritage Area ×4 Jun 21. Pick up day before at Tobu Asakusa Tourist Info Center. |
Buy in advance online, pick up at Asakusa | Klook or tobu.co.jp | MEDIUM | |
| Hakone Free Pass ×4 (2-day) For Jun 22–23. Includes round trip Shinjuku↔Hakone + all transport in Hakone. |
Buy at Odakyu Shinjuku Station or EMot app | odakyu-global.com or Shinjuku Sightseeing Service Center | MEDIUM — BUY MORNING OF DEPARTURE | |
| Tea Ceremony (Kyoto) Jun 28, morning. Group of 4. |
1–2 weeks ahead minimum | Klook, Airbnb Experiences, or En tea-ceremony.net | MEDIUM | |
| Final Dinner Reservation (Osaka) Jul 1. Kaiseki, Wagyu BBQ, or omakase sushi. |
1–2 weeks ahead (or from Kyoto concierge) | TableCheck, Tableall, or hotel concierge | MEDIUM | |
| Suica / Pasmo IC Cards ×4 Load at Haneda on arrival. ¥5,000–¥10,000 each. Used for all metro, bus, and convenience store purchases. |
At Haneda Airport on Day 1 | JR/Keikyu machines at Haneda arrivals | DO ON ARRIVAL DAY | |
| Japan eSIM or Pocket WiFi Essential for Google Maps navigation. Get eSIM before departure or rent Pocket WiFi at Haneda. Need for all 4 phones. |
Before departure | Saily, Airalo (eSIM), or eConnect Japan (Pocket WiFi) | HIGH — DO BEFORE FLYING | |
| Japan cash (Yen) Japan is still very cash-heavy. Get ¥50,000–¥100,000 cash per person. 7-Eleven ATMs in Japan accept foreign cards reliably. |
Arrive with some USD, convert or withdraw at Haneda 7-Eleven | 7-Eleven ATM, Haneda currency exchange | DO ON ARRIVAL |
| JR Pass (14-day Ordinary) | ~$530 |
| Accommodation (15 nights, mid-upper range) | $1,200–$2,000 |
| Romancecar + Hakone Free Pass | ~$60 |
| Nikko Pass + local transport | ~$30 |
| Admissions (shrines, temples, museums) | ~$80–$100 |
| Food & drinks (15 days) | $600–$900 |
| Activities (tea ceremony, etc.) | ~$50–$100 |
| Souvenirs + misc | $100–$300 |
| eSIM / WiFi | ~$20–$40 |
| ESTIMATED TOTAL PER PERSON | $2,670–$4,060 |