Tokyo to Osaka transportation

I have decided to go to Japan next month to utilize expiring paid leave. This is my first trip and there's only few weeks to plan. It will be 7-9 days trip to Tokyo and Kansai (Osaka/Kyoto). I thought of getting a round trip ticket to Tokyo, but it means I have to make a trip back to Tokyo. I heard by Shinkansen it will take 2-3 hrs by train to Osaka. I was planning to get 4/5 days in Tokyo and 3/4 days in Kyoto.

Kindly share some suggestions how shall I plan the transportation e.g. return trip to Tokyo (means round trip train to Tokyo), or taking domestic flight, or getting outbound flight from Osaka.

I will bring a 24" luggage + maybe 1 extra travel bag/folded travel bag for the shopping goods.

It's up to you. If you leave in/out of Tokyo but are going to Kyoto/Osaka, look into the Japan Rail Pass, as that will save you a little on the roundtrip shinkansen ticket.

Or just leave out of Osaka instead.

Thank you. Actually I'm thinking on the time spent. 3+3 hrs of return trip, not sure if it is expected on trip in Japan. May I know why you recommended to skip Osaka altogether?

Also, is getting JR Pass only advisable if I use shinkansen to travel across city?

Night bus(need booking) cheapest and operate a lot daily.
Fare is harf of Shinkansen.
Shinkansen is no mid night operate.

No Hitchhiking?
http://youtu.be/p1W3Ss2xVlE

Moccy,

When scarreddragon said "leave out of Osaka," I believe she meant "flying out of Osaka (Kansai airport)" instead of flying out of Narita :)

If you can find flights flying into Narita then flying out from Kansai, that would give you the maximum time in both Tokyo and Kyoto/Osaka, with least rail travel.

And 7-day Japan Rail Pass makes sense if you are making at least a return trip between Tokyo and Osaka/Kyoto within a 7-day period, for example. JR Pass generally is good for long-distance, meaning inter-city travels, (between Tokyo and Kyoto/Osaka, Kyoto/Osaka and HIroshima, etc.).

AK, thank you for the clarification :)

I am now thinking to go directly to kyoto from Haneda. Is it possible, or is it a good idea at all? I will reach Haneda on 2pm. I'm planning to book a ryokan in Kyoto, so upon arrival I can immediately rest and have dinner.

Yes AK, that's what I meant! Sorry it wasn't clear OP.

You can definitely go from Haneda to Kyoto in time for dinner, but it would need to be a later one, like 7-8pm depending on the ryokan location. Be careful though, some don't allow dinner that late. One option would be to opt out of dinner the first day and just get it around the station or the area instead, or to find a ryokan that allows it that late. They can sometimes hold dinner if you let them know in advance.

Thank you scareddragon.
I have booked the flight, both inbound and outbound will be at Tokyo and arrival is at 9am. But it's good to know that ryokan may not serve the dinner late.

Check with your ryokan and see if they can push it back for you. They can often be accommodating if they know in advance... but if you just show up late, then they definitely aren't going to be able to serve!

When you book, breakfast and dinner times (if you have those options) should be made clear. If you know you can't make the times, contact them, explain, and see if they can do it later.