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Itinerary/Day Trips from Kinsale and Dingle

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After falling in love with Ireland on a self-drive tour 10 years ago, my husband and I are taking our 4 adult children and 2 grandchildren in late September! We are all very excited but planning a trip for the family of 8 is a bit more challenging! We are hiring a private driver/guide to minimize the stress (have a couple type A personalities that are short on patience at times). With the children (ages 7 and an infant 3 months) we felt like we needed to base ourselves in a couple spots. We chose Kinsale And Dingle because we loved both of them, and because our daughter-in-law has family in Fermoy or Mallow, plus interested in Waterford area. Of course we will be heading southwest as well!
Here's what is booked so far:
-Flying into Dublin...1st night at Ariel House in Ballsbridge...plan on touring Dublin a bit that day and half next day.
-Leave after lunch and head to Kinsale... Renting a house in Kinsale for 3 nights.
-Next is Dingle for 3 nights at the Dingle Skellig.
-then heading to Malahide for our last night, flying out of Dublin next day. (Should have flown out of Shannon, but too late for that now).
The accommodations fit our needs and are all walking distance to center of town/pubs/restaurants...

Looking for suggestions for good day trips from those locations, and for stops along the way on traveling days. Should we do Cashel Or Wicklows on way from Dublin to Kinsale? My husband and I did not see the Wicklows on our previous trip. Is the Beara Penn a reasonable day trip from Kinsale? Should we do Ring of Kerry on way from Kinsale to Dingle? Killarney day trip from Dingle? Cliffs of Moher realistic? And lastly, it has been suggested that the trip from Dingle back to Dublin is long and maybe we should cut Dingle to 2 nights and spend a night elsewhere to shorten the drive. Your thoughts or suggestions about where...Bunratty? Traditional Music Night there?

We don't want to spend every minute touring, we are not strong museum/history buffs but do enjoy some of that, the 25-33 year olds will want to get in their pub time (well, we all want to do that), love the scenery, good food, meeting the locals, and playing a round of golf. With varied interests among the group and with the baby, we may go in different directions at times. We know we will barely scratch the surface, but everyone will get a good taste of the Emerald Isle and we will, hopefully, have a wonderful week together! Your thoughts are most appreciated!

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