Japan Itinerary and Obon Travel Questions

Hi Japan Travel Experts,

This will by my first trip to Japan and I'm heading there July 29 with my wife and then-to-be 15 month old son. We are experienced backpackers in Africa, Asia and Europe mostly but we did bring our 3 month old to Cuba for 3 weeks last summer. While I usually do not plan out so much in advance it seems that traveling around the time of Obon and with an infant/toddler and with a very short trip (18 days!) I'll need to book some accommodation and reservations on trains beforehand. I think I've finally done enough research to ask specific questions of the expert travel community. My itinerary so far is as follows:

July 30- arrive Narita airport 1:30 pm
July 31-August 1- Two full days in Tokyo
August 2- Bullet train Tokyo -> Hakodate + Train to Sapporo
August 3- Pickup rental car in Sapporo and begin Hokkaido drive.
August 4 -Hokkaido drive day 2
August 5- Hokkaido drive day 3
August 6- Hokkaido drive day 4
August 7- Hokkaido drive day 5 back to Sapporo + Train down to Hakodate
August 8- Long travel day: bullet train Hakodate --> Tokyo --> Kyoto
August 9- 11- Three fully days in Kyoto
August 12- Kyoto --> Magome
August 13- Walk Magome --> Tsumago --> Matsumoto
August 14- Visit castle in Matsumoto --> Tokyo
August 15- Tokyo
August 16- Flight from Narita 7pm

Questions:
1. August 12 --> 14 is a weaker part of the itinerary. I originally had this planned for two days (Kyoto --> Magome --> Tsumago + Tsumago --> Matsumoto --> Tokyo). Now that I've made it three days it feels like too much. Is there somewhere else anyone would recommend in central Honshu that we should visit maybe between Tsumago and Matsumoto or between Matsumoto and Tokyo? Or else would people recommend another day in Kyoto over a day in Nagoya or anything else I haven't thought of yet?

1. From what I can tell, Obon 2018 will have its heaviest travel days on August 15. That is why I tried to get us back to Tokyo before that. If we take a step-wise approach to returning to Tokyo from Kyoto through Nagono as in the itinerary, will we run into as much Obon travel mayhem? Is it true that by not trying to get back August 15 we will miss the busiest time? Are there other ways to make sure we aren't stuck without transportation?

2. I haven't decided yet if I should get a 7 or 14 day rail pass. With a 7 day pass we could get up to Hokkaido and back down to Kyoto with this itinerary. Then the rest of travel can be pieced together and may end up cheaper than the extra 7 day pass. With a 14 day pass, everything is covered even the trip back to Tokyo, provided we take trains and not buses. However, the big question is around making train reservations on bullet trains around the Obon season. Do I need to make reservations as soon as possible for the August 2 and August 8 bullet train trips? If so, I think I can make them as far as 1 month early if that is correct. I found a website that would allow me to make the reservations from abroad if I'd already purchased a rail pass. Does that sound plausible? If not, how do I make sure that we are able to get the trains in the itinerary and are not stranded somewhere during peak travel times?

I'm sure I have more questions like tips on rental cars (can I get a car seat for the boy?) and where to go in Kyoto, Tokyo and Hokkaido. But for now I'm thinking about the big 3 questions above. Thanks for any input, criticisms or other feedback!

Evan

Did you consider flying to/from Hokkaido?

Three full days for Kyoto is not much time, particularly if it is in-between long travel days and if you are with a small child. Could well add a day or two there. Also most people visit Nara from Kyoto and it is IMO well worth it.

If you can do train reservations in advance, I'd certainly do that. I believe from outside Japan you can only reserve on JR East, i.e. Tokyo to Hokkaido and back.

I agree with bamse, consider flying. The train up there and back is going to be costly and long. No use spending big bucks on rail passes only to rent a car and not take the train.

Your time in Kyoto is indeed very short, particularly if trucking around a 15 month old.

where to go in Kyoto, Tokyo and Hokkaido

I'd figure this out before I start setting most of the itinerary in stone. If you dont know where to go in these places; how can you figure they need 3, 3, and 5 days of your time respectively?

Thanks Bamse and rpbourne for replying so quickly.

I definitely considered flying to Hokkaido. I researched the cheapest specific flights on days that made sense. I made a spreadsheet and considered 9 transportation permutations. When compared to a rail pass, flying both ways might seem to save about $60 per person but that doesn't include transport to and from airports nor checked bag fees. In the end it felt about the same. I thought the convenience of staying near a train station and getting on a bullet train would be easier than trying to cart the family back to Narita hours before the flight and then doing something similar when trying to get to Kyoto when landing in Kansai.

The way I understood it, getting around Hokkaido was definitely best with a car. This also is easy for the family as we only take out what we need when we reach our destination. Do you think that it would be pretty convenient and easy taking public transport? I'm not 100% sure where we want to go so maybe planning that should be next. My brief research made it seem that there was lots of national parks (Shikotsu-Toya, Daisetsuzan etc) and other beautiful and rural areas. The point of visiting Hokkaido was to beat the heat and rain of summer on Honshu, get out of the megalopolises to see a more rural side of Japan, visit an onsen or two, go for a hike or two, and see some natural beauty. I figured there could be easily 5 days work of places to visit so I hadn't yet worried about that detail.

Similar with Kyoto. I figured there was just too much stuff to see and so I would make a list later and just see what we could in 3 days. Maybe instead we make that 4 days though since I have some time built in. But I'll also do some research on Nara as well.

Thanks for the feedback!

In Hokkaido you might very well want to skip Sapporo altogether and just rent a car from/to the airport. Also, there are several airports on Hokkaido, and depending on where you want to go, flying to somewhere other than Chitose, could actually save you time.

As for convenience, going by car certainly has advantages in rural parts if travelling with a child.

Hokkaido certainly has excellent nature, but you need to check how accessible it is in your situation. Are you able to hike for x kilometres to see something amazing or are you more looking for places not too far from the road?

Also I would not exclude Honshu completely. Temperatures in the Japanese Alps should be fine, onsen are everywhere and normally it does not rain every day either. Also, you have very accessible nature/rural areas just in the outskirts of Kyoto or Tokyo. Could go there as a day trip on a good weather day, doing city sightseeing things on bad weather days instead.

Basically what I am saying is, that if you are a very outdoorsy type, it could make sense to go all the way to Hokkaido. If you are only looking for mixing the concrete/sightseeing with some nature, you could do this equally good (and cheaper/less time consuming) closer to Tokyo/Kyoto.

bamse- Amazing feedback. Thank you. I have a lot to consider! Ill get some more research into staying on Honshu the whole time and get back to the board with more questions as they come up!

Thanks again!!

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