She flies one way NYC to SFO or does a multi leg fare from NYC to Japan and back with a stop in SFO on the way over.

Thanks for your response.
right that’s the plan but it’s hard to search for the flights with these parameters. Spent quite some time this morning doing a lot of trial
and error on Google Maps, SkyScanner and my Chase Sapphire Travel Portal

I guess calling the airline as an earlier post suggested could be the move. Funny I’ve never done that, but not opposed.

Have you tried using Google Flights? You can select a connecting airport, and even select the layover duration time if you want to stay overnight in San Francisco before flying out.

I did the same in wanting a flight from Chicago to Tokyo, via Vancouver, SFO, and LAX to break up the long flight. I didn't want any flights connecting in Detroit or Toronto, Montreal, etc. Good luck!

Also, you may or may not find Hokkaido difficult to incorporate into your trip, but wanted to weigh in on that. Because if you wanted more nature and hikes, I really believe you'll find more than enough in Honshu. I've been north to Memanbetsu and also to Sapporo. Memanbetsu reminded me a bit of downstate Illinois, actually. Sapporo was a city like other Japanese cities, though there were some mountains to look at in the far distance. It was nice enough, but I don't have a hankering to return as I do other parts of Japan. I'm no expert on Hokkaido, so maybe watch some YouTube videos to help you decide. For a first time visit, it's not often where travelers go. Though for winter sports, I know it can be a destination for American skiers.

First time visitors usually do Tokyo-Kyoto with trips to Osaka, Nara or Hiroshima, maybe adding on Miyajima. They're popular for a reason, and the infrastructure is in place for foreign visitors, too.

August really is a hot month over there. I find carrying a parasol, or a light colored umbrella, does help. And the Japanese have lots of cooling gadgets for sale, too. Also, their sunscreens are great so maybe buy there at a Don Quijote (youtube for info on that). Even as healthy as you and your partner are, do be careful. You can get a load of steps in within a city, too. Kyoto has lots of walking and uphill paths. My family and I were there just in June of last year, and we were all about the Pocari Sweat. (Though, we were on Okinawa, too, which is wonderful, but again, maybe not in August.)

Have fun planning!

You get a roundtrip NYC-SFO for Aug 9 to 24
Both of you get roundtrip SFO-Japan Aug 10 to 24

You could fly to Tokyo from SJC

[QUOTE=ChgoGal;17584910]Also, you may or may not find Hokkaido difficult to incorporate into your trip, but wanted to weigh in on that. Because if you wanted more nature and hikes, I really believe you'll find more than enough in Honshu./QUOTE]

I totally agree with this. You don't have much time to take advantage of Hokkaido natural beauty compared to that of other places much closer which may be just as stunning. Every airport or long train trip takes a good deal of time and energy. Japan Guide is your friend.

To update, we will fly into Asahikawa Tues morning, land at 9am, rent a car and drive 30-40mins to Daisetsuzan Park. Spend the whole day plus next morning there. We will drive to Furano the next afternoon and drop the car in Sapporo. The following day, Thursday, we will train early to Hakodate and spend the day and evening there before flying back to Tokyo early Friday morning.

Ok, so you are spending Wednesday night in Sapporo?

Two options:
1) Spend a second night in Sapporo.You can spend a full day there.instead of spending hours to travel to Hakodate.
2) Drop off the car at CTS and fly to Hakodate on Wednesday. ANA nonstop 35 min for 75 bucks

Hakodate is an interesting historic city, very low key. It’s one of the ports that was allowed for international trade in the mid 1800’s once Japan opened to the West like Yokohama and Nagasaki. As such the Motomachi district has some historic buildings from that period. The night view from Mt. Hakodate reached by a rope way tram is considered one of the premier night views in Japan. There is a famous hot spring onsen, Yunokawa if that interests you. There is enough there for a one day visit should you choose to. Food as everywhere in Japan is excellent.

Hakodate is low key. I visited there for one night 20 years ago and my main thought was that the city had seen better days. Also thought the night view was nice but it is not Victoria Peak. imho, it is not worth 3.5+ hours on a train and 9000 JPY to visit there for one night given that the day starts in Sapporo. Especially when Hakodate would be the third one-night stay in a row.

For a night view, there is:
Mount Moiwa - Sapporo Travel (japan-guide.com)

Nice view from Sapporo TV Tower, among other points of interest:
Sapporo Travel Guide - What to do in Sapporo City (japan-guide.com)

The charm of Hakodate is in its uniqueness as a Japanese city and its historical importance. Like Nagasaki it has European roots and was one of the last bastions of shogunate resistance in the Japanese civil war. I contrast it to Sapporo, which is nice enough for a Japanese city of similar size but one I found to be rather uninteresting other than the famous snow festival

If you’re passing through Hakodate on your journey anyway, it’s a worthwhile one day visit. But if time is of the essence then flying obviously makes more sense.

>> If you’re passing through Hakodate on your journey anyway

Yes!
It is just not worth going out of your way to visit on a fast-paced itinerary. That is what I did and I recommend not doing that.

The OP actually did mention something of interest in Sapporo. It was a brewery (not Sapporo beer) IIRC. That was to been done after dropping off the car at CTS and before the early morning train to Sapporo the next day. Meanwhile, Hakodate was "interesting" but "not required".

But, this is a YMMV situation, not my trip. I did have some interesting experiences in Hakodate

Tropical Storm Maria is over Hokkaido/Tohoku. It might have been in OP's flight path to Japan but I think it didn't cause any late arrival or cancellations..

Historically about 1-5 typhoons hit Japan every year in August and most of the time not directly. Hokkaido almost never used to get hit but recently storms have made their way more northward. So if traveling in Japan in August for two weeks there is a good possibility one will be affected for a day or two mostly with just rains and wind.

Another typhoon. shinkanen ops suspended, hundresd of flight cancelled.

‘Very strong’ Typhoon Ampil set to approach eastern Japan on Friday - The Japan Times

Brandon, your trip sounds amazing, and definitely doable even on short notice! Japan during Obon can be a unique experience, with some areas quieter and others buzzing with local culture. Bigger cities like Tokyo and Kyoto might be less crowded, which could work in your favor. Your itinerary looks well-balanced, and visiting Hokkaido for the natural beauty is a great idea. The Shinkansen is a scenic and efficient way to travel, giving you a glimpse of the countryside. Go for it—this sounds like a trip of a lifetime!

Brandon, your trip sounds amazing, and definitely doable even on short notice! Japan during Obon can be a unique experience, with some areas quieter and others buzzing with local culture. Bigger cities like Tokyo and Kyoto might be less crowded, which could work in your favor. Your itinerary looks well-balanced, and visiting Hokkaido for the natural beauty is a great idea. The Shinkansen is a scenic and efficient way to travel, giving you a glimpse of the countryside. Go for it—this sounds like a trip of a lifetime!