1. To get to Tokyo Bay, as long as you are not traveling with too much luggage the JR line is the best bargin. Get on the free hotel shuttle from the Hilton Tokyo to Shinjuko station. Take the JR from Shinjuko Station to Tokyo Station (there is some walking within the train stations as you make connections, up and down stairs/escalators and long hallways) and switch trains there to Maihama Station (which adjoins the monorail for Disneyland). From there you take a short monorail ride over the second stop (it's just a short circle monorail with only 4 stops -- see http://www.tokyodisneyresort.co.jp/t...fer/index.html for map of the monorail) and get on the Hilton Tokyo Disneyland bus (very cute buses) which basically carries you a few hundred yards to the hotel. All in all not too difficult without too many bags, but if you have luggage it may be more of a pain and you might want to consider a taxi (but $$$$).

2. From the Hilton Tokyo Disneyland to NRT the answer is extremely easy -- the NRT bus. There are buses leaving many times a day which go directly! The bus is really the easiest and cheapest way to get to/from the hotels to the airport. Typical greyhound-type buses.

The JR and subway lines interconnect and it can be difficult to read their maps and get around, but it just takes patience. E-mail me offline if you want a good map that shows them both.

Have fun!