Heading to Japan for the first time for 2 weeks late Oct./early Nov. Flying into/out of Tokyo. Thinking to base the trip around Tokyo, Kyoto and Osaka, with day trips around those areas. Thoughts?

if you are not driving, then you may want to consider JR pass and you need to buy that quick as price increase of 70% is coming up shortly. JR pass is only available for visitors and you need to pre-purchase.

when i travelled japan in 2019 (osaka-kyoto-nara-tokyo-niigata-sapporo), the trains i wanted (shinkansen bet. osaka, kyoto, and tokyo), wasnt covered by JR. so worth looking into actual routes to compare which works out best for ya!
in early nov, ryokans will be LOVELY
also for food: kyoto has the best food in my opinion- esp with vegetable cooking. amazing pickles etc.
also enjoy many joys of convini stores- i found them authentic (locals use them heavily), and food's great. in my opinion, shelling out on food in tokyo aint best bang for the buck, esp if you can spend few days in smaller cities.

Internet - def get a pocket wifi or Sim card or such so you can access on the go. It'll make navigation etc much easier.
Tokyo - lots to do/see especially if you like city. It's also the easiest to revisit so if you think you might go back I'd spend less time here and just hit the famous neighbourhoods.
Kyoto - wonderful with lots of history. Some temples etc are spread out/take a while to walk so plan accordingly. Day trip to Nara. Maybe Himeji too. If trees are changing colours, will be extra picturesque!
Osaka - try their okonomiyaki. Great city with lots to do. If you extend past 2 weeks in Japan, also a great place to grab a cheap flight to other places in Asia.
If you're willing to go farther, would recommend Kobe (food and can really see more international influence married with Japanese culture) and Hiroshima (besides the weighty history, Miyajima Island is lovely).
If you do the JR pass, plan to take some stops to see some other cities along the way to your main destinations!

We just spent 3 weeks in Japan and got a JR Rail Pass which made it very convenient to travel around. Around Tokyo you can do day trips to Hakone and Mt. Fuji. If you have time I would recommend 3 days in Kyoto as there is a lot to see. Nara is also very close to Osaka for a day trip. There a large park where deers roam around and the Todai-Ji Buddist temple located near the park is also a must see!

JR pass is jumping up in price in October so purchase ahead of time!

We spent 2 weeks in Tokyo and there is lots to do. You can plan for museums and buy tickets ahead like borderless and others from now as they are hard to get. We got the JR pass for 2 weeks and used it between Tokyo, Kyoto, Osaka, and Hiroshima, hakone and back to Tokyo. Osaka is great for food but not that much to do other than food, party, and shopping, and Kyoto great for old japan charm culture. Tokyo has so much to do that suits everyone. Comfy shoes to walk and more business casual clothes to blend in.

Following

My wife really loves Osaka. We've been twice. Lots of cool, little Kensington Market like places there like America Mura and Nakazaki-cho. Shinsaibashi is cool too. Haven't been to Tokyo, I'm not good with crowds and Osaka is crowded enough for me. Hit lots of great, little Kissaten. Did a day trip to Himeji Castle and spent a few relaxing days in Nara on this last trip. We did Kyoto on our first trip. Loved the old buildings, but wasn't a fan of the more stuffy, conservative vibe. Definitely less fun and more touristy than Osaka, but lots to see.

We did two weeks in Japan in 2019. If you can, try to fly into one city and out of another to maximize your time. We flew into Osaka and out of Tokyo. Osaka itself was okay, we liked Hiroshima better. Maybe consider going there if possible. Definitely get the bullet train foreigner pass before leaving, can’t get it there.

https://www.facebook.com/reel/254337447025902...
FACEBOOK
I hope these tips are useful while planning your Japan trip! Some thing to note, you can purcahse Shinkansen or Bullet train individually and also the suica or pasmo card can be purchase as an actual card but you have to put a 500 yen deposit while on the apple wallet you don’t have to. @places_in_sydney More content on my TT, IG, FB & YT with the same handle @adrianwidjy #placesinsydney #travel #japan #japantravel #traveljapan #pasco #suica #toptip #japantraveltips #shinkansen #jrpass #japanrailpass #traveltip #travelsmart #smarttravel

Echoing the suggestions above, but we also took a day trip from Tokyo to Nikko, which has some significant historical sites (Toshogu). If you have teens, the Robot Restaurant in Tokyo is super over the top fun, and the cooking class we took in Kyoto was fabulous (we'd take it again) - seriously awesome: https://www.cooking-sun.com/
COOKING-SUN.COM
Japanese Cooking Classes in Tokyo & Kyoto with Cooking Sun

Spend more time in Kyoto! You won’t regret