Go cheaptickets.sg or some other site to find the cheapest ticket to Japan. Tokyo has 2 airports, Narita, Haneda. Haneda is nearer to Tokyo (about 20 min train ride). Direct flight is about 6~7 hours. Depending on traffic, customs might take 30~60 minutes.
Fastest way from Narita to Tokyo (Ueno) is via the Keisei Skyliner (about 40 min train ride) but a bit more expensive. You can buy 2-way tickets online at their website for a slightly discounted price.
From my experience, best is to land in the morning/afternoon. Most hotel’s check in time is 2pm. If you arrive early, you can ask the hotel’s concierge to keep your luggage until you come back to check in. If you leave on a late night flight, you can also ask the hotel’s concierge to temporarily keep your luggage after checkout.
If you plan to travel outside of Tokyo for a few days during your trip, it would be good to spend the last 1~2 nights in Tokyo if your flight departs from here. It would be risky and too much of a rush to travel from Kyoto back to Tokyo for your flight.
And if you plan to stay at the same hotel after returning back from outside of Tokyo, you can ask the concierge to keep your luggage at a small fee per day. Then just travel out with a lighter luggage.
Remm Akihabara is a not bad hotel (their elevator system is a little annoying though). Can book online at hotels.com. At off-peak periods, a night’s stay can be around $100 SGD. Akihabara Washington is also near by and pretty good. Both hotels are right next to JR Akihabara station.
Get a SUICA card (similar to our ezlink). Can buy from their ticket machine. Most machines should have a button on screen to switch to English. Might need a deposit. If I’m not wrong, the card expires 10 years from the date of the last transaction. You can use SUICA at most convenient stores and trains throughout Japan. Just show them the card to indicate you want to pay using SUICA. This will help you reduce the amount of loose change.
Get a data SIM card (https://rental.cdjapan.co.jp/ or at the airport). No eSIM as of the time of this blog post. Google maps is pretty reliable there. Can help you find directions and even tell you which train to take, and give you suggestions on what places to visit and dine at.
As for amount of money to bring, 10,000 JPY for every day you are there is safe. But if you don’t shop a lot, 5,000 JPY/day should be enough. This amount includes travel, food and some shopping. Use the meal prices at McDonald’s to gauge if a restaurant’s food is expensive or cheap.
Compared to my first trip to Japan, more places accept credit cards now. There are some cards like YouTrip or DBS’s Multiplier account that helps you make payment in foreign currencies at lower transaction/exchange fees. If you go this route, you can bring less JPY cash. Cash is still needed at some places. Topping up your SUICA for example.
JR Pass is only good if you plan to take Shinkansen out of Tokyo. Have to buy it here in Singapore (JTB), then exchange for the actual pass at a train station or airport when you’re there.
Don’t get from Chan Brothers. When I wanted to get a 14 day pass, they tried to sell me 2x 7 day passes which is more expensive.
Once exchanged, you will have to go through a manned gate at every JR station. Just show the staff your JR pass and you will be allowed to go through. You cannot use the JR pass for metro lines. They are both different train operators.
You can also make reservations for the Shinkansen at certain stations that have a counter only for Shinkansen travellers. I would a list of dates and times and the train number, departure and destination, and make those reservations as soon as possible. If you are unable to make a reservation, there are free-seating carriages so just arrive early and queue up.