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We took DS to Thailand and Cambodia last spring when he was 29 months. I've never been to Japan but I imagine it is wildly different from SE Asia. We had to be careful with water and food hygiene but luckily we didn't have any problems. There were no car seats anywhere except when we hired one or two taxis to take us long distances. It was also very hot and humid, but that's to be expected. Other than that, I found those places to be relatively easy with a young child. We took our Maclaren stroller, Ergo and Baby Bjorn crib since we stayed in an apartment for about half of the trip.

I took LO to Seoul when she was 11 months. One thing I noticed was that many restaurants didn't have high chairs, as sitting on the floor is quite common. So just be prepared for that possibility. Also, strollers aren't used by as many parents as they are here in the US. I'm not sure what people with toddlers do but I wore LO in the beco gemini most of the time. Have a great time!

ETA: You might want to bring enough diapers to last you the entire trip. I had to buy some Pampers when we were there, and they are really really expensive there!

I live in Hong Kong and took my daughter to Japan (where we lived for almost 4 years before she was born) when she was about 16 months old. It was a fantastic experience. Everyone was SO, SO, SO nice to us - particularly the elderly people. Two examples - one, we went to a carnival at our local park near closing time. They were shutting down the games, and the operators were inviting kids to come play/take prizes free of charge. My daughter wasn't great at fishing bouncy balls out of the pond with the little paper net, so they helped her out...and then, thinking she hadn't gotten enough prizes, a grandpa came over to her with another bag of balls he'd scooped up for her and played with us for a bit. SO sweet!

Second, we were roaming around Asakusa (an old-fashioned historic area) one day and I wanted to go to a really local tempura spot. I tentatively asked the proprietor if it would be okay to come in with the baby and she all but dragged me in the door cooing over DD! Seriously people were literally coming out of shops to say hi to her, try to give her a treat, etc. She basked in all the attention. The birth rate in Japan is very low (actually to the point it may become a problem), and I think children are really treasured there for that reason, even if they're not Japanese children.

As for restaurants, we left our umbrella stroller outside or folded it under the table. We didn't encounter a single place where DD wasn't welcome. We carried a TotSeat fabric highchair that attaches to any chair with a back to help deal with the issue of small spaces (most restaurants, the good ones anyhow, are tiny), and lack of high chairs in restaurants.

If you can ergo/bjorn your child, definitely have that as an option. Many subway stops DON'T have an escalator or elevator, and while people were always willing to help us, it was sometimes easier not to have to drag a stroller up and down the steps. An umbrella stroller rather than a big clunky one is a must.

No need to bring diapers if you don't want to - local brands Merries and Mammy Poko are both fine, so you don't have to splash out on Pampers from the international stores. There is also baby food available in vacu-pack envelopes, but the flavours are a little different (ie Curry Rice) so your kiddo may not be a fan.

Lastly, any little bit of Japanese you can learn before you go will go such a long way. My skills have faded since we moved, but it is still so appreciated when you can say hi, please, thank you, etc. in the local language.

What part of Japan are you going to? I can give you recommendations for Tokyo or for skiing if you'd like! Wherever you go, have fun! It's an amazing country - very clean, efficient, friendly, and culturally interesting for sure!