The Edit: Intercontental Oskaka & Bellustar Tokyo.

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6 night Japan Trip.

AA 35K per for 3 in economy on Japan Airlines - JFK-HND, then HND-KIX. 14 hour 1st leg wasn't bad on JL. Good enough leg room.

AS 37.5k per for 3 in economy on AA metal. 12 hour flight sucked ass, but they fed us well with free alcohol.

3 nights Intercontental Osaka:

$1,888 for 3 in Premium Room 2 twin beds.

65,532(redeemed at 2.5x) in points $250 edit credit net $0.

Upgraded to city view.

Room was really nice. Deep tub. Good enough room for what I here about Japan hotels.

Service immaculate. 2 adult free breakfast, half price for my child covered by the $100 edit credit. Wife spent the rest on matcha lattes. Buffet breakfast was amazing.

Location about 10 min walk to Umeda Osaka station. Area had enough going on in a 20 min walking distance to keep you occupied.

Paid $28 hotel tax at checkout.

Bullet train to Tokyo.

3 nights Bellustar Tokyo:

$2,041 for 3 in Junior Corner Suite Twin, 2 twin bed.

68,340(redeemed at 2x) in points, $250 edit credit and $250 Pan Pacific credit net $174.

Upgraded to City View.

Room was small, but really nice again with a deep tub. View to die for!

Service immaculate. Located in the heart of Shinjuku. 10-15 min walk to any Shinjuku hot spot. Train station right up the block. 2 adult free breakfast, half price for my child covered by the $100 edit credit. The exclusive ala carte breakfast was ass. The breakfast buffet was good. No bill at checkout.

Notes:

I didn't know both hotels were going to give an extra 3rd bed for my child as most things online said the hotel expects the child to sleep with you. Not choosing a king bed room I think hampered my upgrades.

My opinion, unless you are into the origin of Japanese culture and civilization, stay the whole time in Tokyo. You can do day trips to most of Japan if you really wanted to.. Tokyo has so much to do and see as a first timer to Japan.