2 Week Itinerary (with emphasis on Tokyo/Osaka day trips)

My SO and I are planning a 2-week trip to Japan in the second half of October (can’t wait for the fall colors!). It’ll be our first time visiting, and we’re especially excited to build an active itinerary that includes a blend of hiking, nature, cultural sites, and food. We’d love to see multiple cities, so we definitely plan on getting the JR pass.

One complicating factor… I’ve saved up a good chunk of Hilton points and am able to use them to redeem 10 free nights split equally between Tokyo and Osaka (the redemption has to be 5 nights, so we have limited flexibility with our locations). Since we want to see many other locations, our current idea is to do a number of day trips using Tokyo and Osaka as home base (with a two-night stay in Kamikochi to break things up, plus one night in Hakone on the tail end).

Curious to hear if people feel that what we’ve outlined is feasible/reasonable, or if we should reduce the number of day trips and focus more on Tokyo and Osaka. The other big open questions in my mind are 1) are we shortchanging Kyoto by only spending one day 2) is it worth staying in Kamikochi itself (it seems like there are a ton more options if you take the bus in/out, but hotels in the valley are super limited) and 3) are we selecting the right day trips. Appreciate any input!

Here is what we have drafted so far:

**Day 1 – Arrive Tokyo**
Arrive at Haneda / Check into Conrad Tokyo / Dinner and a bit of walking
*Overnight: Tokyo*
**Day 2 – Explore Tokyo / Jet Lag Recovery**
Full Day to Explore Tokyo (Activities TBD)
*Overnight: Tokyo*
**Day 3 – Kamakura Day Trip**
Kamakura Day Trip (Hasedera Temple, Great Buddha of Kamakura, Zeniarai Benten Shrine, Genjiyama Park, Tsurugaoka Hachimangu Shrine, Komachidori Street)
*Overnight: Tokyo*
**Day 4 – Explore Tokyo**
Full Day to Explore Tokyo (Activities TBD)
*Overnight: Tokyo*
**Day 5 – Nikko Day Trip**
Nikko Day Trip (Kegon Falls, Ryuzu Waterfall, Senjogahara Marshland, Yudaki Waterfall, Lake Yunoko)
*Overnight: Tokyo*
**Day 6 – Transfer to Kamikochi**
JR to Matsumoto / Check out Matsumoto en route to Kamikochi / Bus to Kamikochi / Check-in at Kamikochi Alpen Hotel / Late Afternoon Walk / Fall Colors
*Overnight: Kamikochi*
**Day 7 – Kamikochi**
All Day Hike
*Overnight: Kamikochi*
**Day 8 – Kamikochi to Osaka**
Morning Walk or Bike / Fall Colors / Bus to Takayama / Explore Takayama en route to Osaka / Transfer to Osaka / Check into Conrad Osaka
*Overnight: Osaka*
**Day 9 – Kyoto Day Trip**
Kyoto Day Trip (Arashiyama, Arashiyama Bamboo Forest, Tenryuji Temple, Togetsukyo Bridge, Arashiyama Monkey Park, Fushimi Inari Taisha Shrine, Shinbashi Dori)
*Overnight: Osaka*
**Day 10 – Hiroshima and Itsukushima Day Trip**
Shinkansen Shin-Osaka to Hiroshima / Peace Memorial Museum / Peace Memorial Park / JR Shin-Hakushima to Miyajimaguchi / Explore Itsukushima
*Overnight: Osaka*
**Day 11 – Nara Day Trip**
Nara / Nara Park and Sites / Explore Naramachi
*Overnight: Osaka*
**Day 12 – Osaka**
Full Day to Explore Osaka (Activities TBD)
*Overnight: Osaka*
**Day 13 – Hakone**
Shinkansen Shin-Osaka to Odawara then Bus to Hotel / Check-in to Hyatt Regency Hakone / Explore Hakone (Hakone Open-Air Museum, Take Hakone Ropeway, Visit Sites Around Lake Ashinoko)
*Overnight: Hakone*
**Day 14 – Depart for US**
Transfer from Hotel to Odawara and on to Haneda

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1 comment
  1. > Nikko Day Trip (Kegon Falls, Ryuzu Waterfall, Senjogahara Marshland, Yudaki Waterfall, Lake Yunoko)

    The good news is that late October is peak foliage on the Chuzenjiko side of Nikko…The bad news is that the roads will be congested and I don’t see how all of this can be accomplished within a day trip. From Asakusa to Lake Yunoko for example is 3.5 hours on the fastest train.

    If it were me I would cut Hakone and stay overnight in Nikko, yes there are no good redemptions but a minshuku type lodging shouldn’t be too expensive and slumming it for one night between Conrads isn’t the end of the world.

    > Jet Lag Recovery

    TBH considering how much of your itinerary really rewards waking up early (Nikko as described above, everything in Kyoto, Kamikochi, Day 10 will require waking up very early to accomplish everything you want to do, etc.), coming from the US, you would actually want to keep the jetlag going as much as possible because this naturally makes you want to go to bed early and wake up early.

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