Japan Travel Itinerary

Hello here is my japan trip for september-october

🇯🇵 Japan Travel Itinerary ✅ Tokyo - Kamakura Day trip / 1-hour commute
✅ Kamakura - Tokyo 1 hour
✅ Tokyo - Nikko Going by train / 2-hour commute
✅ Nikko - Matsushima Heading there straight after Nikko / 3 hours by train
✅ Matsushima - Kyoto Going by night bus, 11 hours (Night bus might not be available)
✅ Kyoto - Gifu Day trip / 1-hour commute
✅ Gifu - Kyoto 1 hour
✅ Kyoto - Osaka 12 minutes 😝😝
✅ Osaka - Nara (About a half-day trip) 35 minutes 😼
✅ Osaka - Wakayama 1-hour commute
✅ Wakayama - Osaka 1 hour
✅ Osaka - Fukuoka (2.5-hour commute) ✅ Fukuoka - Kurume 12 minutes
❌ Kurume - Takachiho 2.5 hours
❌ Takachiho - Kurume 2.5 hours
✅ Kurume - Fukuoka 12 minutes
✅ Fukuoka - Beppu 2 hours
✅ Beppu - Miyazaki 3 hours
✅ Miyazaki - Fukuoka 4 hours
✅ Fukuoka - Tokyo 5 hours

i checked and marked it but i wanted to be sure, if i buy jr pass for 21 days does it cover all the places for my trip?

And when should i book the trains etc.?