A "ball-park" idea about Naoshima island for your travel planning.

Basically three areas, Chichu Museum, Art House Project, and Benesse (House) Museum. A 30~40 min walk apart from each other. 10-20 min if you take bikes (few steep slopes involved). Or a public bus (about once in 30 min) can be used. However you like. See maps below.

Chichu Museum - Ando Tadao's signature design, James Turrell, Water De Maria and huge Monet "Water lilies" collection + Chichu Garden - a replica of the garden Monet loved. Many visitors' favorite.
Open hours: 10 am - 6 pm (last enter at 5 pm), Closed on Mondays (except national holiday), 1 hour earlier closing time from Nov - Feb. Ticket: 2000 yen (free under 15)

They may limit the number of people inside during a busy season. In that case, you may need to wait, occasionally for few hours.

Advanced reservations require following exhibits;
James Turrell's "Open Sky" - Night program - reservation

Art House Project - James Turrell, Ando Tadao, Senju Hiroshi, Miyajima Tatsuo, Sugimoto Hiroshi, Ohtake Shinro, Suda Etsuhiro. Honmura port area's 6 different house project, plus advanced reservation only Kinza reservation
Open hours: 10 am - 4:30 pm, Closed on Mondays (except national holiday)
Ticket: 1000 yen (free under 15)

Again some houses limit the number of people inside at a time. Quite often you have to wait in line for a while.

Benesse (House) Museum - Ando Tadao design, built in 1992, the first museum on the island, 350 art collections.
Open hours: 8 am - 9 pm (last enter at 8 pm), Open 365.
Ticket: 1000 yen (free under 15)

And the last year's new addition (and it's become very populer!)
Naoshima Bath (public bath): I ♥ 湯 (I love YU-hot water) at Miyanoura port
Open hours: Mon-Fri 2 pm - 9 pm; Sat, Sun, holiday 10 am - 9 pm; Closed on Mondays (except national holiday)

Lee Ufan Museum - Naoshima's latest addition, designed by Tadao Ando. (located between Chichu and Benesse Museum, not on the map below)
Open hours: 10 am - 6 pm (last enter at 5 pm), Closed on Mondays (except national holiday), 1 hour earlier closing time from Nov - Feb.
Ticket: 1000 yen (free under 15)




Got a rough idea how long it may take for you?  Start strategizing your day on Naoshima and then you'll be a happy visitor, totally relaxed, just enjoying the art-experience, rather than always wondering where and when to go next!

Few tips:

• There are passenger boats going directly to Honmura port - right by the Art House Project area, besides the main ferry to Miyanoura port. see Naoshima ferry timetable
  

• Some "shoe-free" exhibits here and there. You can practice lacing your shoes, or just don't wear them.

• Occasionally some or all those museums and house projects are closed for maintenance at rather short notice. Please double check with the Benesse Art Site Naoshima official site for the opening days/hours.