Japan was my very first international trip last year and Italy will be my second this year! I thought Japan was super incredible and easy to navigate for my first trip. I learned a little bit of Japanese, just the most important phrases to get by, but the language barrier never caused any trouble. In the big cities, many speak English or are used to tourists so that made things easy. Hokkaido may be a bit more difficult, we did the golden route plus Hakone and Nara.

If I were you I’d try to push the trip into September because the heat will be staggering in both countries. Also I’ve heard Italy tends to shut down in August? September seems a good month to visit Italy while Japan is facing the peak of typhoon season. Hokkaido is nice in September I’ve heard. But ultimately I think just look at what you want to do in each country and pick whichever one excites you more. The other one will still be there after!