I think you missed that the OP is redeeming points at major hotel chains.

My Japan experience was 15-16 years ago and was similar (6 nights in Tokyo, 6 nights in Osaka). I also redeemed points (Hilton Tokyo and Hilton Osaka), though I did have Hilton status (useful for getting breakfast included, etc.). Yes, navigation of the subways can be a challenge, and back then, I didn't yet have a smartphone, but if I could manage it, then you'll probably do fine. ;)

One question (maybe you answered this but I missed it): did you consider an open jaw trip, i.e., fly into Tokyo/NRT and out of Osaka/KIX? I did that myself to save a train trip back to Tokyo.

That would have been my preference, but I'm a DL/SkyTeam flyer and the options out of KIX aren't good, so I need to return to Tokyo to fly out of HND.

Tokyo is definitely a city that rewards aimless serendipity. I had some memorable moments just wandering over the course of my visits.

That is poetic, I like it

I’m glad to see you chose Westin Kyoto. I’m heading there for three nights in April on points and then two nights at the RC Kyoto as Titanium. Why didn’t you pick Ritz? I could have got five nights at Kyoto but I just cannot pass Kyoto without staying at the best RC in the world (per flyertalk forum).

They are both very well located — not inside Gion, mind you, but walkable and honestly, having stayed at a Japanese inn last time right in Gion, I rather stay outside of it. It was a bit too touristy (as in way more tourists out on the street there than local folks).

Tokyo I would choose Hilton using points and I’m gold.

Osaka I’m probably choosing Hyatt using points (got no status though).

My entire Japan trip this April is on points, and I’m traveling alone too (a woman)!

There were a few reasons I picked the Westin. The RC is a lot more points and there's no lounge (although it looks like I would get breakfast as a Titanium). I know that shouldn't be a dealbreaker, but particularly when I travel alone, I tend to use hotel lounges most days for a drink, a snack or chatting with other guests. I just spent five nights in Paris at a hotel without a lounge and found I really missed having that option. Also, I'll be there in early September, which will be very hot and humid and I think the Westin, with a shuttle to the train station (and other drop off points) will mean less walking than if I stayed at the RC.

I was considering the Hilton but I have no status and booking a room with lounge access was a crazy amount of points and more than I have available, whereas at the Hyatt, I could book a club room for a very good redemption rate.

:) :tu:
I'd love it if you could report back after your trip; since all my hotels are booked with points, I can still change my reservations.

Hilton Diamond? Amex Aspire ... 150k points + 250 Airline Credit + $250 Hilton Resort Credit + Free Weekend Night ... a lot of value for $450 a year
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Note - Google Maps has updated their app to include the best entry/exit numbers (even highlighted in yellow to simulate the real world signs) for your route and they've also added the aforementioned EXPERT MODE, which will tell you the best train car to ride in to minimize time/distance to transfer lines or exit a station. Otherwise, each station will have charts on the wall to give you this information, but unfortunately they don't have English on them... YET.

Thanks for sharing that about Google Maps. I tend to do all my planning via the Google Maps website and will sometimes try to figure out which cars/platforms/exits beforehand, but it is nice to know ahead of time that they have added it to the app version.

The best exit number is absolutely huge. Paid attention to that on my most recent trip last week and it was just HUGE!

Of course as a male I risk much blame saying this, but there is probably no better place in the world to visit as a solo female traveler than Japan. Unless you just naturally go to sleep very early, I would definitely walk around Tokyo and Osaka at night to see the sights, visit an izakaya, and eat a bowl of late night ramen. ;) Kyoto also has a nice little nightlife-ish area around Kyoto-Kawaramachi Station (probably elsewhere too).

Don't forget being groped on a crowded subway.

Perhaps a bit of a stereotype? While there is little doubt there is lots of sexism in Japan, I don't think it is something foreign visitors would encounter. The groping issue in particular is a concerns during rush-hour trains and I highly doubt foreigners would get targeted. It also is not a real risk for the particular issue I was addressing; venturing out at night in downtown Tokyo or Osaka.

Good grief - there must be a term for this. How about Japan-man-splaining?

It is a risk, it does happen, but it is so prevalent everywhere that one might not feel more at risk in Japan than one does in one’s home country or where one has previously visited.

“I don't think it is something foreign visitors would encounter” - yes, I’m certain you do think that and won’t be changing your mind soon. I happen to know differently.

I have no problem with you saying it - it's not the first time I've heard that and as a woman who often travels alone, I know some places feel more comfortable than others.

FWIW, I'm a native New Yorker, I've been using mass transit my entire life and the subways here when I was growing up in the 70s were not so safe, so I tend to naturally be more defensive than most people. My plan is to avoid rush hour as much as possible, but at the moment, I'm more concerned about a spreading virus than gropers.