I'm planning a trip to Japan in November 2024. It will be about 2.5 weeks, including travel days, and I'm hoping to fly into Tokyo and out of Osaka. I'd like to see lots of autumn color. I know it's hard to predict the peak of autumn (especially planning this far in advance) but if I'm going to err, I'd rather be on the earlier side, with slightly warmer temperatures and greener landscape, than to be traveling past the peak of autumn as it's getting colder and the foliage is more sparse. With that in mind, is November 15th a good target date for the start of the trip?

After lots of research, I've built a fairly typical first-trip-to-Japan itinerary (there will definitely need to be follow-up trips; there is so much more I want to see!) My main question is whether or not to group the travel days as close as possible together to use a JR pass. Are the destinations on my itinerary ones that would make sense for a JR pass or should I be looking at regional passes? When it comes to transportation, what is the most cost-effective way to order the destinations? I know a few of you are really familiar with the rail system and have advised others, so I'm hoping you'll do the same for me. Here are the two options I'm considering; parentheses represent the number of nights I'm planning to stay.

Option 1:
Tokyo (6) > Hakone (2) > Kyoto (6) > Koyasan (1) > Osaka/Nara (1, depending on time of departure flight)
This itinerary breaks up the quick stays in Hakone and Koyasan with a longer stay in Kyoto; this is my preferred itinerary but it may not be ideal if I want to use a JR pass

Option 2:
Tokyo (6) > Hakone (2) > Koyasan (1) > Kyoto (6)
This itinerary groups most of the travel in the middle of the trip

Thanks in advance for your advice!

memejs,
My husband and I will be traveling to Japan for the first time this fall so I can only remark on your trip from my planning experience. I’d originally planned to go to Koyasan but decided against it after deciding the schlep factor just wasn’t something we wanted to do. Your option #1 is probably more realistic since you can more easily get to Koyasan from Kyoto and then return to Osaka by public transportation. Hakone to Koyasan is a much longer trip to coordinate.

With the amount of time you’re planning to travel, I might consider taking a day from Tokyo and Kyoto to add to a smaller place, though I certainly appreciate staying longer in one place, too.

Thanks progol . I can't wait to read your report once you've taken your trip!

Yes, getting from Hakone to Koyasan looks complicated. The only reason I proposed that is if it would save me a significant amount of money in transportation costs. I could send my suitcase ahead to Kyoto and travel light on a day of many inconvenient train transfers to Koyasan if that's what I need to do. If there's no cost advantage to putting those sites next to each other in the itinerary, I'll head to Kyoto first and then do Koyasan at the end of the trip. It doesn't look like the most convenient place to get to, but all of the Japan vlogs I've been watching have convinced me that it's a priority for this trip.

It is soooo tempting to take another day or two to add on another area. Originally I was trying to fit Takayama and Shirakawago into the itinerary, but I don't want to rush that area, and I just keep finding more and more I want to do in and around Tokyo and Kyoto. So I'm prioritizing really doing those cities "well" on this trip and planning to come back to explore other areas. Plus, the time I'm planning in Tokyo and Kyoto includes a couple of day or half-day trips (Mt. Takao from Tokyo and Nara, an evening in Osaka, and the Kurama to Kifune hike/walk near Kyoto) - so I'll have a good mix of city and nature.

@memejs,
It’s amazing just how much there is to see and do in Japan and how hard it is to plan. Deciding what not to do is the tough part! We, too, will be bookending our trip with 6 days in both Kyoto and Tokyo. It sounds like you have a good idea of what you want to do and, it’s true, with forwarding luggage, even longer journeys aren’t quite so difficult.

We’re now just a month away! Very excited!

You don't need a 7- or 14-day JR pass with either of those itineraries. There is a regional pass if you were planning to go outside of Tokyo area, like if you wanted to go to Kawaguchiko and Nikko (Tokyo Wide Pass) but it is only good for three consecutive days. The price is going up, from 10,180 yen to 15,000 yen. I have doubts that the new price is worth it.

>> My main question is whether or not to group the travel days as close as possible together
You asked that about the JR Pass (which you don't need) and my answer would be "no, don't do that". Same for the Tokyo Wide Pass, even if it was worth it as far as travel cost goes.

You do want the Hakone Free Pass. Use the Odakyu Romance Car from Odakyu Shinjuku Station to Hakone-Yumoto.

Your Option 1 is good. Instead of those two one-night stays at the end, it would be better if you spent the last 2 or 3 nights in Kyoto or Osaka.

Your Option 2 is not good because of the trip from Hakone to Koyasan. Too long, too complicated from Tokyo and a bit worse from Hakone.

Tokyo (6) > Hakone (2) > Osaka (2) > Koyasan (1) > Kyoto (5)
Tokyo (6) > Hakone (2) > Kyoto (5) > Koyasan (1) > Osaka (2)

When you leave Hakone you want to be careful to use a Hikari shinkansen to go on to Kyoto. Your other option would be shinkansen from Odawara to Shin Yokohama to transfer to Nozomi shinkansen to Kyoto/Osaka. The undesireable option is Kodama shinkansen.

Oh, and timing. You would want to be heading to Kyoto by the 16th.
Fall colors are more predictable than cherry blossoms.

>> Hakone (2) > Koyasan (1)

Ok, am warming up to that idea because you can get from Odawara to Namba in three hours to get the Nankai train. (there are other options). Might be closer to 5 hours than 6 hours.That is in the range of don't want to do it but willing to bite the bullet in this case and relax when I get to Kyoto for that long stay.

Kyoto will be extremely popular at that time. They have started taking over-tourism countermeasures there. Dropping the bus day pass for starters.

Thanks for all of the great feedback! Since travel to Koyasan is going to be inconvenient either way, I'm also starting to think it might be better to just group Hakone and Koyasan together and end the trip in Kyoto. I'll have to look more closely at the different trains and put together different itinerary scenarios. What is the best website to use to plan out which trains to take?

I'll likely post again at some point asking for hotel recommendations. When is the best time (how far in advance) to start making hotel reservations - what the the sweet spot of hotels having their availability posted and getting the best price and maximum availability? I'm itching to get into the nitty gritty of planning, but it's still too early to start nailing things down!

The timing for booking can really vary a lot. Many hotels don’t accept reservations more than 3-6 months in advance, but not all. Some do accept reservations a lot sooner, particularly some of the larger hotels in Tokyo or Kyoto. OTOH, I made reservations at several places that were pretty strict about the time frame, not opening reservations until a specific date. I’d say, on average, it was about 6 months prior for most of the hotels I booked. And this also varies by location, with some of the more popular places booking very early. It can get confusing!

I booked directly with 3 hotels (including a ryokan). I used booking dot com for 2 hotels. And I used another booking site, Rakuten travel, for 2 ryokans. In fact, I attempted to book directly with one but was sent to Rakuten Travel to make the actual reservation.

Kyoto hotels will be quite expensive during your time frame. Tokyo too. We will be in Japan this November and I normally stay at the Westin in Tokyo and it’s gone up from $350/ night pre COVID to $570/night. Osaka hotels are quite reasonable. Staying in a Airbnb in Kyoto.

Option 1 was: Tokyo (6) > Hakone (2) > Kyoto (6) > Koyasan (1) > Osaka/Nara (1)

Option 3 could be: Tokyo (6) > Hakone (2)> Osaka/Nara (1) > Koyasan (1) > Kyoto (6)
would mean easier travel days and you could have that evening in Osaka. Your destination would be Osaka or Namba (Osaka). From Osaka station you would find your way to Shin-Imamiya to get the Nankai train to Koyasan. From a Namba hotel, you would get to Nankai-Umeda station to get the Koyasan train. Nankai has a faster train so look for that on the schedule (they call it a rapid express, i think)

Actually, anywhere in Osaka would work as well.

You can use this site to get an idea of the trip from Hakone to Osaka or Koya: Route Search - Japan Transit Planner | Norikae Annai (jorudan.co.jp)

Bur to actually plan the trip you would need to look at the transportation from:
1) wherever in Hakone you are staying to Odawara Station
2) Odawara to Kansai
3) Kansai to Koyasan

By Kansai, I mean Kyoto/Osaka/Namba/Nara.

Do a search for Hakone Free Pass and you will find information about transport in Hakone.

The origin of the JR part of the trip would be Odawara Station and you could use this website to find your way to Kansai area on JR West Japan Railway Company - Timetables, Route Maps, and Station Maps (westjr.co.jp)

You can find the Nankai Railway timetable somewhere.

Love the transport maps:
Osaka to Mount Koya: How to get to and around Mount Koya - Access, Transport and Orientation (japan-guide.com)

Kyoto to Mount Koya: How to get to and around Mount Koya (japan-guide.com)

Nara to Mount Koya: How to get to and around Mount Koya (japan-guide.com)

I meant Umeda where I wrote Namba in my last post. Namba should work too, tho.

Thank you for the suggestions mrwunrfl !

Osaka and Nara aren't really priority destinations for me. I originally had a night in Osaka (or Nara) in the itinerary because I wouldn't want to travel from Koysasan to Osaka the day of my flight home.

I used the Jorudan website to sketch out transportation for the various itinerary options, and while a full day of traveling from Hakone to Koyasan is doable, traveling several hours from Koysasan to Kyoto the next day isn't. (And most of what I've read says that 1 night in Koyasan is sufficient.) So I've gone back to the itinerary that breaks up the Hakone and Koyasan travel with a stay in Kyoto between those two shorter stays. I will still likely need to do a one night stay in Osaka at the end of the trip, but that is more to be in place for a flight home the next day rather than trying to fit in one last destination. If I decide I definitely want to visit Nara I will do that as a day trip during my time in Kyoto.

So all of that is to say I feel good about where my itinerary is at now; thanks to those who helped me think through it! Now it's just a matter of being patient for the next 6-7 months until I can start booking things and hoping I can find a good flight deal!