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Advise on where to base in Ireland for 2 week trip

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Our family of 5 (kids are 9, 17 & 18) are planning to visit Ireland for 2 weeks. It looks as if we will most likely go in early July based on the kids school and our jobs.
I am just starting to plan, and have read quite a few posts and looked over travel books. We really like hiking, picnicking, some historical sights, and just generally exploring new places. It is too expensive for us to fly to Shannon (live in Canada and with 5 people the extra $300/ticket adds up, also we would like to see Dublin) so I have come up with the following:

Dublin 3 nights
Kilkenny 1 night (would like to see Glendalough, Wicklow on the way), then Cashel on the way to..
Kenmare 4 nights (Killarney Nat Park, Ring of Kerry)
Dingle 2 nights (Slea Head drive, Connor Pass)
Somewhere near Ennis/Galway for 3 nights (for Cliffs of Moher, Doolin, Galway City for a day, maybe Connemara, Loop Head peninsula, the Burren...)
Dublin 1 night before we fly home.

I am not sure where to base after Dingle, I have read Ennis, Doolin, Lahinch, or Galway recommended. We would like a scenic town where we can walk to dinner and a pub for music, and is accessible to the sights for day trips.
I haven't worked out details of where exactly we will visit each day, but wanted to get the bases sorted out. Wonder if this itinerary sounds too exhausting? I chose the Kilkenny 1 night so we could break up the journey to the south after Dublin and find time to see the Wicklow mountains.
Thank you in advance for any comments or suggestions.

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