Getting Started

Hello everyone. I'm planning a trip to japan in April of next year for me and 3 other people. They visited several years ago, but this will be my first time, but they have left me to plan it (jerks). So I'm looking for a bit of guidance. Specifically, where to go. I will be there for about two weeks (April 2 - 18). My original plan is to start off in Okinawa (flight goes from texas to tokyo, then okinawa, stay for a few days, then back to tokyo, no extra charge). However, as I've never been, I don't know if I want to visit other places over Okinawa, such as Hokkaido. So this is my first issue, where to go. We will obviously spend time in Tokyo, but where else? Thanks for any help you guys can give.

You're travelling during cherry blossom season on the main island (around Tokyo and the Kansai area), so you'll need to make decisions quickly to start bookings. It would be a shame to travel at this time and not see the blossoms, so consider dropping Okinawa and Hokkaido and seeing the blossoms around Tokyo and the Kansai area.

So for where and what to see, you need to tell what you like.
Why go to Japan?
Have you been to other countries before and what do you like about them?
Why go Japan? If you cant answer that, we cant help you.

You can start from West ie Hiroshima, and go to the East and end your journey at Tokyo. Hiroshima/Miyajima - Himeji - Kobe - Osaka - Nara - Kyoto - Takayama - Hakone - Tokyo.
While Okinawa is good, it is quite far from the main island, and during cherry blossom season, it is better to visit cities where you can see the cherryblossom. Okinawa's cherry blossom is around January and Hokkaido is early May. You can check when the cherry blossom will bloom in each city at the cherryblossom report 2016 on this website.

Have you read the main japan-guide website? Or any other guidebook/website?

They are packed with ideas, example itineraries, etc.

Thank you all for the input. I'm sorry for the vague question. AS to what I enjoy doing, well, pretty much anything. The exception is I don't want to spend my time looking/doing something that I could do anywhere else (Like shopping at Old navy or something dumb like that). Here are a few things we've picked:

Fox Village
Nara Park
Bamboo Path (kyoto)
Uncle Rikuro's Cheescakes (Osaka)
Akhibara
Harajuku
Ryokan
Fushimi Inari Shrine hike.

Is it worth going to Okinawa or Hokkaido, and is so, which one? I do love the beach (I'm from Puerto Rico), but I also doing/seeing things I haven't before. We would spend a day at whichever place we went.

We would spend a day at whichever place we went.

Neither are worth the distance for a mere day. Skip them if you can't dedicate more than that... you can always use them as an excuse to come back!

So, I can spend more time in Okinawa (when I looked again I intended to arrive the night of the 3rd and leave on the 6th). Is Okinawa worth visiting? I read that Ishigaki might be better. Or should I just stick to the mainland?

Okinawa main island has beaches, but the main ones are a bit of a journey from the airport. Buses are infrequent but you could hire a car. Naha city itself is nice, but imho not worth a trip just to visit the city. You need to get around the island, which will take time...

Ishigaki is lovely, but again you need a car. You can spend a day or two driving round the island and stopping off at various lovely beaches, and the beef there is fantastic. But to go to Ishigaki, you need a few days and need to wrestle with internal flight timetables. This can be done, but will take planning. We were there last Easter and loved it. There are some questions on this forum with info (use the search function), if you want to explore further, and of course the main Japan guide site has good info.

If you're only going for two weeks, and this is your first time, then just stay on the main island IMO. Don't try to extend north into Hokkaido or south into Okinawa. Save that for your next trip.

For a full two weeks excluding travel time to and from Japan, I would start in Tokyo, go up to Takayama, Shirakawa, and Kanazawa. Then make your way down to the Kansai region (Kyoto, Osaka, Kobe), over to Hiroshima/Miyajima, back east to Hakone and finally back to Tokyo to fly out.

You can easily spend 4 days in Tokyo doing the typical tourist stuff like the Shibuya district, Shinjuku district, Imperial Palace, Tokyo Skytree, Odaiba, etc. In the Kansai region, you'll also easily spend 4 more days, 2-3 in Kyoto and another on a daytrip such as Osaka or Nara. Hiroshima/Miyajima will require 2 days to not feel rushed. Hakone at the end of the trip is strategic because it's an onsen town so you'll get a chance to relax and wind down, and also it's 30 minutes away from Tokyo which means you don't have to rush on your last day to get back to Tokyo/Narita for your flight out.

My advice would be to look up each of these cities on tripadvisor or here, jot down the points of interest that you like, and see which city appeals to you overall.

I would love to spend more time there, and I do have the time to do so, but hotel/food costs is what would stop me. My flights are free, and I can get a couple of nights of free rooms with points, but only so much. My initial reason for including Okinawa or Hokkaido is to maximize my free flights, as I could go to one without any additional cost.

I agree with the others. Two weeks and the first time in Japan, stick to the main Island Honshu. Okinawa is great, but as a autumn destination, maybe not worth the time. Up to you to really decide what you want from your own holiday.

6 days Tokyo/Kanto, 5 days Kyoto/Kansai and 2-3 days Hiroshima - and you have all the good cherry blossom places sorted and major Japanese drawcards sorted.

Sorry want I meant to convey regards Okinawa was that since you are already from a sub tropical environment, that Okinawa in autumn maybe not be anything new/special for you.