outgoing

This is really helpful. Yes, we know about International Drivers License and we want to drive around to "holes in the walls" (like the local markets that Nagasaki Joe writes about in his review). How is English on the main island vs. Miyakojima vs. some of these even smaller islands. Is it that the smaller places/restaurants only communicate in Japanese or is US military presence large enough that English is better there than on the mainland. We want to avoid Hilton Chatan b/c Chatan is apparently very western. I do speak some very very basic Japanese but it is limited to asking for help or some really simple stuff in stores/restaurants. More memorized phrases than being able to have even basic conversation.

Also is the breakfast comped at RC for Platinum+? I'm Titanium and RC Kyoto breakfast was comped (despite this is not a published benefit) and absolutely amazing!

Nagasaki Joe

I was expecting a counterpoint, and I agree with many of your points about Naha, but in my experience, the negatives you mention mainly pertain to the southern half of the island, not the north. The Ritz-Carlton, is in the Nago area, where many other large resorts are located. These resorts are isolated, and you may well feel like you're "in the middle of nowhere" during your stay, as there are not that many restaurants or much at all in close walking distance to them unless you have a car. In fact, my mother-in-law complained about the isolation and lack of nearby restaurants and shops, as most Japanese, unlike you, seem to prefer a Waikiki Beach type of experience to a "middle of nowhere" experience. I really don't see Naha (the city) as the "happening place" as you stated, but rather a sleepy poor man's Honolulu, actually not like Honolulu at all, but more like Guam. I don't recommend staying at resorts in the southern half of Naha such as Chatan, where you will be more exposed to the US military presence and the negatives you mentioned. As for Ishigaki, I too like traveling off the beaten path, but I just think that if you are going to stay at a large resort hotel like the Intercontinental, you have certain expectations, but for me, those were not entirely met at this resort or by the island experience itself. Actually, there are not that many resort hotels in Ishigaki, as I think many Japanese go the airbnb route here for a vacation that lets them explore the island at their own pace and cheaper (though the IC is not expensive off-peak), which may be the best option for travelers here. To each his own.

I think you'll find more and better English spoken in Naha (not just the city) than you will in Ishigaki or Miyakojima, but much of the IC Ishigaki staff do speak English and they also have some native English speaking foreign staff. I would not expect many of the smaller restaurants on Ishigaki or Miyakojima to speak much English, but you may find they offer bilingual menus in some places.

The breakfast at RC Okinawa was not comped for Platinums when I was there, but since it has moved up to a category 8, that may have changed. I would advise checking reviews on tripadvisor.com for recent information about that.

joakgarp

All three islands Okinawa main island, Ishigaki and Miyakojima have their own charm. If you want a chill relaxing stay then Ishikigaki or Miyakojima is preferable. If you want everything in one island with beaches, tourists places, lots of different hotels, huge aquarium, children friendly activities then I think the main island is a better choice. We have done them all. When my little 1 month old daughter gets older I want to visit them all three again with her but I recommend 7-9 days for the main island. Ishigaki or Miyakojima are so tiny that 5-7 days is enough.
The main island Okianwa is pretty big. And rental is necessary on all three islands or you will get bored out.
Time period has always been august (peak season and very expensive hotel nights) and september (low peak season, cheaper hotel nights but chances of typhoons).