From Tokyo to Naoshima in under 6 hours?

We are flying into Tokyo at approximately 4 pm on a Thursday and would like to know if it is possible to end up in Naoshima the same day, preferrably at a reasonable hour. (We are getting the JR pass.) How late does the ferry service from Uno to Naoshima run? Thank you in advance.

The last ferry departs Uno at 21:45. It seems close to impossible to catch this ferry if you arrive at Narita Airport at 16:00.

You could catch a flight to Osaka's Itami Airport at 17:55, arriving in Osaka at 19:10.

But, in order to make the last ferry, you would have to catch the shinkansen from Shin-Osaka Station at 19:51, which is near impossible to do. Then you would have to change to local trains at Okayama Station.

Thanks for your help. We'll research other options.

Dear Uji, based on your previous response we are considering spending the night in Okayama, and then catching a train to Uno and a ferry from Uno to Naoshima on Friday. If we leave Okayama station at about 9 am, what time would we arrive in Naoshima? Would you happen to know of any links with timetable for this itinerary? Thank you in advance.

Train schedule for trains from Okayama to Uno:
http://grace.hyperdia.com/cgi-english/hyperWeb.cgi

Ferry departures from Uno to Naoshima are shown in the first column of the first table on the following page:
http://www1.biz.biglobe.ne.jp/~shikoku/diyaN3.html

(6:10, 6:30, 7:20, etc.)

Dear Uji, Thank you so much for your help. One other question. We are flying into Narita airport on Oct 4th at approx. 16:00. We would like to use our JR pass right away to go to Okayama from the airport. We want to confirm that the "Exchange Office" at Terminal 2 would be open at that time, and that we can catch a train directly from Narita Termain 2 to Okayama. Can you help? Which train would it be and what time does it depart? Thank you in advance.

Yes, the ticket office is open.

In order to get to Okayama, you have to transfer once at Tokyo Station. An additional transfer at Shin-Osaka might speed up the trip depending on the time of travel. You can look up schedules here (select the "excepts nozomi" option):
http://grace.hyperdia.com/cgi-english/hyperWeb.cgi