Sometimes too much choice is bewildering. Just ask someone looking at the menu of 100 dishes. That can be the feeling with a Japan Rail Pass, as you can have over 100 itineraries with a 7-day pass, which will cost ¥50,000 from October 2023.
On the other hand, a 5-day pass covering West Japan for ¥10,000, strikes the right balance between choice and value. The following itinerary gives you good coverage of western Japan, and while it is a bit rushed, is a good taster for people who like to see the smaller cities and country areas of Kansai, as well as the ability to try the different trains offered by JR West. The hotels in smaller cities can be a bit cheaper, while this pass gives you a chance for day trips to the more expensive cities like Osaka and Kyoto.
Day 1 Kansai Airport to Takamatsu or Naoshima
The Haruka Limited Express is a comfortable option from Kansai Airport to Shin Osaka. It does not stop in Osaka, so for a taste of Japan's second-biggest city, get off at Tennoji Station if you want a mini-break. You can head up to the Harukas Tower for a bird's view of the city. At Shin Osaka, take the shinkansen bullet train to Okayama, where you can change for a train to Takamatsu with its beautiful Japanese gardens and delicious noodles, or one to Ono Port, with a ferry (not included) to the art island of Naoshima.
Day 2 Takamatsu or Naoshima to Okayama and Himeji
Okayama has one of Japan's top three gardens, while the black castle is a striking contrast. Himeji is known for its World Heritage castle. While Okayama is larger and has a quaint tram, Himeji has no shortage of shopping and restaurants and is more convenient for the journey north to the Sea of Japan.
Day 3 Himeji to Kinosaki Onsen or Amanohashidate
There are only 3 direct trains per day from Himeji to Kinosaki Onsen on the Hamakaze Express, so plan accordingly. It takes 103 Minutes. It leaves Himeji at 1044 with the second service leaving at 1325, the last service at 1921. A daylight train is best for this scenic route through some remote mountains, offering a different view of Japan. If you don't mind spending another hour or so on the train, take the private Matsu train onwards from Fukuchiyama to Amanohashidate (not included in the rail pass)
Day 4 Kinsaki Onsen or Amanohashidate to Kyoto
This is another scenic route over the Tamba mountains, with an optional pit stop at Arashiyama or Nijo (home of Nijo Castle, which is best reached by a subway from JR Nijo (subways are not included in the JR pass). Even if you get to Kyoto late in the afternoon, the back streets of Central Kyoto like Shishin or Gion are delightful places to be, day or night.
Day 5 Kyoto to Kansai Airport
This the most comfortable option from Kyoto to Kansai Airport, and faster than the bullet train. Alternatively, you can take the JR train to Uji or Nara, and then after a brief tour, continue on to Tennoji, where you can change again to the Haruka Limited Express or the standard JR airport express to Kansai Airport.
Tips
1. The Haruka Limited Express operates hourly during off-peak times, so it may be quicker to catch the standard JR airport express if you just missed the Haruka.
2. The standard JR airport express from Tennoji splits in two, with some cars going to the airport, while other cars going to Wakayama, so make sure you are in the correct carriage.
3. "Passengers bringing baggage with dimensions totaling more than 160 cm but less than 250 cm on three sides (oversized baggage) on Sanyo Shinkansen (between Shin Osaka and Okayama) are required to reserve a seat with a large baggage area. Shinkansen passengers with oversized baggage may use a reserved seating rail pass and a section ticket, or a separate Unlimited Ride Oversized Baggage Ticket (available for purchase at JR-West Ticket Offices in major JR-West stations) if using a non-reserved seating rail pass. Please ask a station attendant for more details." - source https://www.westjr.co.jp/global/en/ticket/pass/kansai_wide/
4. There is limited wifi on the Haruka Limited Express and at major JR stations. Suppose you need WiFi outside the major cities. In that case, I suggest renting a pocket WiFi from the airport, which will get you out of trouble if you are lost in regional areas, as well as help you translate as there are fewer English speakers than in the larger cities.
5. A free rental bicycle service is available in some railway stations on a first-come, first-served basis.
I'm intrigued by Takamatsu City with the castle, gardens, and Shikoku Mura.