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South Island trip in Oct.

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We will be in NZ Oct. 2 - 14. Wondering if we need to book places to stay for every night we will be on the South Island. We arrive in Christchurch the afternoon of Oct. 2nd pick up a car and drive to Gore Bay where we have a reservation for the night, the next day we drive on to Kaikoura and we have reservations for 2 nights there.
The only other reservations we currently have is 2 nights in Queenstown Oct. 12 and 13....we fly out to Sydney the afternoon of the 14th.
Not sure what our itinerary will be in between.....debating between going the Arthur's Pass route and then down to Queenstown, making stops along the way, or taking the eastern route and taking in Mount Cook on the way to Queenstown. Yes I realize that either way we are backtracking from Kaikoura returning to Christchurch, but we want to spend some time exploring that area. Also after reading some of the other blogs, may want to checkout Akaroa before continuing on to Queenstown by whichever route. Should mention that we would like to work in Milford Sound. We will have a car for our entire time.
We are in our 60's and like to hike, explore local sites/culture, but are not so much into city sights.
I know weather can still be very "iffy" in Oct. which is why we are reluctant to commit to a route... I don't think I would like the Arthur's Pass route in bad (icy/snowy) weather.
Any help will be appreciated.

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