My itinerary went like this:
24th May - Arrive in Narita Airport at 11am, train to Tokyo Disneyland (bought Starlight Passport available for weekends only, entrance from 3pm till closing. Priced at JPY5000/adult, is available for purchase online). Night bus to Osaka by Willer Express
25th May - Arrive at Umeda at 8:30am. Trained to Namba. Shopped at Dotonbori and Shinsaibashi Suji, which are kind of interlinked so it was easy to walk to each street. Stayed at Hotel Le Botejour, semi double room without breakfast was JPY6500/night on Rakuten.
26th May - Kuromon Market and Doguyasuji. Trained to Kyoto. Stayed at APA Hotel Kyoto Eki Horikawa Dori, semi double room without breakfast was JPY5500/night on Rakuten.
27th May - Fushimi Inari Shrine, Kiyomizudera Temple.
28th May - Nishiki Market. Night bus to Tokyo by Willer Express.
29th May - Tsukiji Market, Asakusa Temple, Shinjuku. Stayed at Nishi-shinjuku Hotel MyStays. Standard Double room without breakfast, weekday at JPY9100, weekend at JPY9900.
30th May - Harajuku, Shibuya.
31st May - Back to Singapore!
I did my homework before travelling and printed the necessary maps for finding my way. Though there many said free wifi, I was not able to connect, so for those of you who really need your wifi connection, your best bet might still be to rent a wifi router. All in all, if you did your homework well enough, you wouldn't be lost or end up at some place during their off days. Definitely check up on the opening hours of places you wish to visit.
While Japan is known for their complicated train tracks and platforms, I feel that there are enough signs to let you know which platform you should be heading to. Much like our 'Marina Bay' platform or 'Joo Koon' platform, just find out the name of the last station for the line you are traveling on and head to that platform. Every station has a map of the track at the area where people top up their IC card, you can check if you are at the right station by checking that map. And if all else fails, just ask the staff working at the station! Traveling from Tokyo city to Narita Airport, there is the special line called Narita Express (N'EX). Do check carefully as the train does not stop at every station. I booked my ticket the night before I have to travel to the airport. Ticket price is JPY3190/adult/way. From Narita Airport to the city, I think they were having a 50% off promotion. Unfortunately I was travelling straight to Disneyland at Maihama so there was no need for the promotion ticket for me. http://www.jreast.co.jp/e/nex/tickets.html
Night bus is a popular option with the locals, convenient and cheap. While journey on the night bus is pretty long, the driver usually finds a rest stop every 2 hours for the passengers to get a 15-20 minutes break. When you exit the bus, a number tag will be given to you and the driver will inform you the time to return back to the bus. If you happen to be awake, do take that break to visit the souvenir shops. As you will be stopping at random areas, you will be able to find souvenir from different areas of the country. I stopped at Hakone rest area once, and there were Mt Fuji shaped biscuits. Snacks and drinks are allowed on the bus but do not bring food that have a smell. The locals will be catching up on their sleep so do not talk or make any form of sound on the bus. Even whispering is not a good idea as the bus will be dead silent. Blankets are provided and depending on the type of seats you reserved, some comes with an overhead cover so people passing by will not see your drool-stained face. There are many overnight bus companies (Toyotetsu, VIP Liner) available but I tried Willer Express due to their English website. https://willerexpress.com/en/
If there are things you wish to clarify, do drop a comment and I will try my best to answer you~
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