１）Henro is in Shikoku, one of the 4 island of Japan and your closest direct flight is KIX Osaka.
2) Accomodation has 3 options
Delux 17000 Yen to 8000 yen hostel or Temple’s inn(Syu ku bo)
Economy about 3000 yen hostel or Syukubo
Cheap 0 yen (called “zen kon yado ” or “Tsu ya do”)
3) you need to telephone in Japanese to make a reservation, which might be the hardest part for you.
4) The list of accommodation is listed here (use google translation)
https://pilgrim-shikoku.net/lodgingsforshikokupilgrimsatatemple-list
5) Most people walk about 20 km a day… but it is up to a person.
6) According to the average, most people start their 1st day, walking 18 km, vising 6 temples, and the last temple called “Anrakuji” provides accommodation.
https://shikoku6.or.jp/shukubo/
7) Anraku ji temple also has a free accommodation but you must bring your own sleeping bag.
https://pilgrim-shikoku.net/anrakuji-tsuyado
8) The rest, goes on and on. You can probably get assistance from the people you stayed the night before, to get a next day’s reservation… if you can make yourself understood.
Japanese required is “ The next day” = tsugi no hi
“stay” = To ma ru
telephone = den wa
here = ko ko
adult = O to na
one person = hi to ri
bed prefered = bed ga i i
how much = i ku ra de su ka?
9) You will fly SF to Osaka, then from Osaka to Tokushima by bus( about 5500 yen 2.5hour) or a ferry(about 2000 yen, about 2.5 hour) , then Tokushima downtown to No1 temple Ryouzenji temple.
Google map of No1 temple Ryouzen ji
https://goo.gl/maps/omf3fNGe4xqa35U3A
Photos
https://www.jisyameguri.com/chiiki/tokushima/shikoku01-ryozenji/
so before you start you might like to stay one night in Osaka and(or) Tokushima downtown.
9) You may like to stop by the Information desk in Tokushima downtown so you have an emergency contact. When you get in trouble like a stolen wallet or something, or simply your taxi driver doesn’t understand you…