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Crete - (2 Weeks in September Solo) Recommendations Appreciated

I have a 2 week solo trip coming up in September and would really appreciate some recommendations. My plan right now is to stay to the eastern side of the island of Crete. Flying in and out of Heraklion. Maybe 2 or 3 days in Heraklion, 1 day Lasithi Plateau, 1 day Kritsa or Agios Nikolaos, then make my way east towards Sitia, 1 day in Zakros, then start heading back west towards Ierapetra, then make my way following the coast to Gortys and up back to Heraklion. I'm thinking I'll only stay one night in most places as I'd like to keep moving to see as much as possible. My goals are to see archaeological/historical sites, hike a lot, hit some beaches, and eat+drink well.

A few questions I have:
Will I be fine renting a small car?
Which monasteries should I see? Is it possible to stay in them?
Hiking recommendations?
I like the idea of horseback riding one day, can anyone recommend this?
Any good wineries I should look out for? (I love wine.)
How easily can I communicate without knowing much Greek? (I am going to learn some in preparation.)

Any recommendations or ideas would be greatly appreciated!! I'm very excited and just want to make the most of my trip.

Thank you!

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