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Self Drive Trip to Ireland for Mom and Me

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I will be taking my mom to Ireland for a self-drive trip and am just strating the planning. We are going in October and will have 11 days on the ground (I am not counting the travel days). We are flying in to and of Dublin and planning on driving across country to Galway, down to Dingle, Kilkenny and then east to Cork, Killarney and back to Dublin. We are going to stay in a hotel in Dublin and then B&B's with perhaps two castles in there somewhere. Lastly, we are looking to see historic sights but also take in the local culture. We like taking things slow and going off the beaten path.

So here are my beginning questions:

1. What is the weather like in October? Are we talking jackets or coats? (I am Floridian so cool weather is always great for me)
2. How is driving in Ireland? Basically, how hard is it to drive on the left side of the road? And is it safe for two women to drive through Ireland?
3. Does our itinerary sound like a good route?
4. Any suggestions to start off our planning with?

We have traveled Europe but have never done Ireland so this is all new to us. We are good independent travelers. Any pointers or suggestions would be most welcome.

Thank you all!

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