Itinerary Advice: Nagano > Okinawa > Osaka in Feb 2023

My group of 4 (including myself) is planning a trip at the start of February next year! Total trip length is 9 days. We are flying from Singapore.

The main struggle is deciding the order of visit as factors such as cost and efficiency plays a part too.

Currently, the plan is SG to Tokyo (Narita/Haneda) and take the Shinkansen in tokyo to Iiyama (Nagano) and taking a bus to the onsen resort. Main purpose is for skiing + onsen + Snow monkey park.
Then on the fourth day, head back to Haneda/Narita to take a domestic flight to Okinawa (Naha). Main purpose is water sports + visiting the famed aquarium and nearby beaches.
Then on the seventh day, domestic flight to Osaka (Kansai). Main purpose is visiting USJ and dotonbori.
Then finally on the ninth day, flight from Osaka back to SG.

I think there are many flaws to this due to
1) Nagano ski (cold) > Okinawa (almost tropical) > Osaka (cold again) does not make too much sense?

2) I would think going to Okinawa first makes more sense, but there does not seem to be a direct flight from SG, and it costs more compared to the planned flow.

3) From Nagano to Okinawa, I cant seem to find a direct flight from the nearby Matsumoto Airport?

Greatly appreciate any help and tips for a better itinerary flow and efficiency, thank you!

1 comment
  1. 1. It depend on you. For me, I would probably get sick with difference in temperature.
    2. You could just connect to Okinawa from Tokyo, then fly back to Tokyo/Osaka and task trains to Nagano.
    3. Matsumoto is a very small airport. No, there aren’t direct flight.

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