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Need help filling out my itinerary

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As some of you may remember I spent several weeks last year traveling around. This year I wanted to explore other perhaps a little less traveled parts if that exists.

The reason I am going back to Kyoto there were too many things I never got to see, the same for Osaka. This is the itinerary so far. I am flying from Matsuyama to Fukuoka on Nov 2 and have purchased that ticket. Will probably spend 5 days or so there in order to see the Karatsu festival as well as the Saga Balloon festival and other side trips.

Where do I go after Takamatsu before Matsuyama?

Thur Oct 12 JFK Eva Airway BR 29

Fri Oct 13 Taipei
Sat Oct 14
Sun Oct 15

Mon Oct 16 Hualien
Tue Oct 17

Wed Oct 18 Taipei

Thur Oct 19 Osaka Jetstar 721
Fri Oct 20

Sat Oct 21 Kyoto
Sun Oct 22
Mon Oct 23
Tues Oct 24
Wed Oct 25

Thur Oct 26 Naoshima
Fri Oct 27
Sat Oct 28 17.00-18.15 Chichu Art Museum nightshow

Sat Oct 28 Takamatsu

Also am a little confused by the e-mail I received confirming my reservation at Chichu art museum.
This is how it ended:
・Others : We recommend to reserve a taxi, as there is no public transportation after the program. Please take care on your way back if you are planning to walk or to use a bicycle. There are not many streetlights.
Naoshima Taxi 087-892-3036
※click below for ferry schedule.
※No more ferry to Takamatsu by this time.

According to the ferry schedule there is one at 19.15 going to Takamatsu. What am I missing here?

Also need to clarify that I am now 1 year older, have just undergone spinal surgery. Do not drive nor ride a bicycle otherwise I'm fine, or will be in a few weeks.

In case you want to get a sense of how I travel here is my TR from last year.

Thanks in advance for your great help and advice.

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