Best way to travel to Okinawa

Hey everyone me and my family are planning a 2 week vacation to Japan and we would like to start in Okinawa, to be exact were hoping to fly from USA and start in Iriomote, move on to Okinawa Island, and then move on to Miyako island, over the course 4-5 days before moving onto Osaka on the mainland and site seeing on the mainland before leaving from Tokyo. What would be the best way we would be able to do this or would it be better to start on the mainland and continue on to Okinawa.

Iriomote is reached by taking a flight or ferry to Ishigaki Island, then a ferry to Iriomote. With the exception of a few flights from Taiwan a day, there are no International flights to/from Ishigaki. Therefore you'd have to fly into a different Japanese airport (such as KIX or Narita/Haneda) then catch a flight to Ishigaki, then the ferry to Iriomote.

It's fine to do that first, but you'd probably end up pretty exhausted, plus depending on where you're flying from in the US, the timing of catching a domestic flight after an International one could be difficult to pull off. You may end up staying the first night around whichever airport you flew into, then taking the flight to Ishigaki the next morning.

Basically, you'll have to work out your flight times and see what is do-able and what fits with your travel pace/style.