Travel in Japan

I have the following itinerary (10days trips) and need some help on the most economy train tickets to buy:

1. I want to travel from a) Narita to Hakone (28 Feb), then from Hakone to Shimodo, then from Shimodo to Disneyland Tokyo (final stop).
2. Should i buy a combination of Hakone free pass and Izu free pass and 18 kippu ticket (we have 2 pax travelling)?
3. Or should I buy only Hakone free pass and Izu free pass and get the rest tickets ala carte?
4. Or should I just buy the JR east pass?
Thanks.

I would think to get a JR East pass and stay the journey to shimoda from Narita. Since the pass last only 5 days, you should think of leaving the area on the fifth day and heading kahone area. For me, I would find a hotel etc that has a pick up service from a JR Station. For there, you have to figure out what to do or when to go before getting a second pass.

I never try free shuttle service on Hakone Hotel but done so on a few other areas in Japan to save a huge sum of transportation.

Don't buy a JR East Pass! The round trip to Shimoda even by the most expensive train costs only around 13,000 yen by regular tickets! And a Seishun 18 Kippu makes no sense as explained in a different thread.

The cheapest way of travel is by taking local trains as opposed to limited express trains and shinkansen. And by taking Odakyu Railways between Tokyo and Odawara instead of Japan Railways.

Inside Hakone, a Hakone Free Pass is likely going to pay off if you do typical sightseeing.

Get a N'EX + Suica roundtrip deal (5,500 Yen):

http://www.jreast.co.jp/e/nex/suica_nex.html

Take the N'EX to Ofuna, transfer to JR Tokaido Line and take that to Odawara (650 Yen, about 32-45 minutes by regular train). Present your N'EX ticket at a manned ticket gate and use the Suica Card to pay for Ofuna-Odawara section of your journey.

Depending on your length of stay in the Hakone area and what you plan to do, get a Hakone Free Pass for 3,900 - 4,000 Yen at Odawara.

Odawara to Izukyu Shimoda station via JR Limited Express Odoriko, 3,730 Yen.

Izukyu Shimoda to Tokyo Disney (Maihama station), Take JR Limited Express Odoriko to Tokyo and transfer to JR Keiyo line, around 6,500 Yen.

Maihama to Narita, using your return N'EX ticket take Keiyo line to Tokyo and transfer to N'EX. 0 Yen.

Total: Under 20,000 Yen and you will still have 850 Yen credit on the Suica card for and short trips you might make in Tokyo.

Hey, thanks for the help. I have one more question, would it not be cheaper for me to get the 18 kippu to travel from Odawara to Shimoda and from there to disneyland? I can share the ticket with my partner. Or will it not cover the routes?
Thanks.

You can only go as far as Ito in Izu on the Seishun 18 ticket because Ito to Shimoda is a different railway company, Izu Kyuko. Even if you don't have to change trains, the station staff at Shimoda will ask you to pay the cost of the Ito to Shimoda section. I haven't checked the exact costs but this may well make it not worth it to use the Seishun 18 ticket.

The places you could use the Seishun 18 ticket would basically be Odawara-Ito and Ito-Maihama, the total fare for these two trips would be less than 2,900 Yen using local trains. So less than 6,000 Yen for both of you against 11,500 Yen for the Seishun 18 ticket. You would still have the cost of the private railway between Ito and Izukyu Shimoda, over 3,000 Yen roundtrip for each of you.

So, using local trains only with the Seishun 18 ticket and private railway will cost nearly 18,000 Yen for both of you. Using single ticketing using only local trains will cost about 12,000 Yen for both of you and using Limited Express (faster and less changing of trains) will cost you about 22,000 Yen for both of you.