Upcoming Trip Advice: Ishigaki, Osaka/Kyoto, Atami Onsen, Tokyo

I’ve been following this sub for a few months to help plan for upcoming trip with my wife (both mid 30s, traveling from NYC). We like to move a lot when we travel, so I know many will say we are trying for too many places in only 12 days, but it’s a pace that’s worked for us before. That said, bigger cities like Osaka, Kyoto, and Tokyo feel like they have endless options, so seeking any big suggestions or feedback on my plans… also any food recommendations for these cities that would fit our open dinners/lunches. In addition, we may be there in peak season so trying to manage around the chaos of tourist surge we may see in places like Kyoto.

I’m including plans for first day in Taipei (direct flights on EVA, which is supposed to have unreal business class that we booked on credit card points), but will go light on that itinerary.

Some of my biggest questions:
– I have 2 nights in Osaka and 1 night in Kyoto, mostly because food in Osaka is supposed to be great and hotels and are much cheaper. It’ll be peak season in Kyoto. Should we do 1.5 days in Kyoto + 1.5 in Osaka? Or 2.5 in Kyoto (one as a day trip from Osaka)? Might mean replacing Arashyama with Osaka sights.

– Does anyone have experience with Ishigaki/Taketomi/Iriomote? Does my plan make sense? Should I try for both Taketomi and Iriomote in one day? Os Iriomote better than Taketomi?

– Any ideas for best ways to go out and see some fun bars in Osaka and Tokyo? Want to try sake, whiskey, and local beers.

– Any experience in Atami for Onsen? It’s pricey and I’m hoping worth it.

– For Tokyo fish market, any suggestions on tsukiji vs. toyosu?

Tues March 28: Arrival in Taipei, Taiwan @5:15am
– Leave bags at TPE overnight (anyone done this before?)

Wed March 29: Fly TPE > OKA > ISG and arrive in Ishigaki at 3pm
– Check in and grab beers/relax at Ishigaki Beach Hotel Sunshine
– Dinner: Akebono

Thurs March 30: Taketomi Day Trip
– take ferry to Taketomi and rent bikes
– Dinner: Funakura No Sato

Fri March 31: Ishigaki eBike Exploration
– reservation for Gorogo bikes
– visit attractions on Ishigaki Island
– Dinner: OPEN

Sat April 1: Fly ISG > KIX
– Check in (Swissotel Nankai Namba)
– Dotonbori explore for dinner

Sun April 2: Kyoto Day Trip OR Osaka Exploration
– If Kyoto: Arashyama
– If Osaka: Osaka Castle + other sites? And Airbnb bar crawl in locals neighborhood
– Ship bags to Tokyo hotel (have overnight backpack for Kyoto + Atami)

Mon April 3:
– Take early train to Kyoto
– Nijo Castle
– Golden Temple (will be mobbed, but worth it right?)
– check into Westin Miyako Kyoto
– Dinner: OPEN
– Evening: see temples lit up in South Higashyama

Tues April 4: Half Day Tokyo + train to Atami
– Fushiki Inari
– Philosophers Walk
– 1pm train to Atami and check in to Watei Kazekomichi (onsen in room + kaiseki dinner)

Wed April 5: train to Tokyo
– breakfast at Watei Kazekomichi
– train to Tokyo, check in to AC Hotel Ginza
– Lunch: OPEN
– Asakusa
– Dinner: Sushi Yuu (omakase)

Thur April 6: Shibuya + Harajuku
Any suggestions for what to do here aside from obvious (scramble, etc)?
– All meals open

Fri April 7: Tokyo (last day!)
– fish market (any suggestions on tsukiji vs. toyosu?)
– TeamLab Planets
– Lunch: OPEN
– Shinjuku
– Dinner: OPEN

Sat April 8: 10am flight back to NYC