updated: first Ireland/Europe trip; help with itinerary

Flying into Dublin and out of Shannon (or the reverse) would help make the most of your limited time. Though the cost would be greater you'll save a day by not having to return to Dublin for your flight home.
Assuming that you plan to rent a car: you could pick it up in Dublin (the airport would be my suggestion) or you could take the train to Galway to begin your excursion into the west of Ireland, pick up the car there, drive down to Dingle, and then return the vehicle to Shannon Airport as you depart. You won't need, nor would you want, a car in Dublin - pick it up as you're departing the city.
With less than 10 full days at your disposal I wouldn't recommend trying to pack in much more than the rough itinerary you've already mapped out.
Pick up a good guidebook (or 3) and flesh out your itinerary from there.

Thanks Robert.

I've started to read the RS Ireland Guidebook so far. Flying out of SNN sounds fine; last time I checked there were still a few award seats available coinciding with our dates.

How many days/nights in Dublin would you recommend?

Mike

If this is your first trip to Ireland you could literally spend all of your time in Dublin and not run out of things to do, so how much time to spend there will be completely subjective - better to study some guidebooks to see what appeals to you in the area, knowing that you can easily (and relatively cheaply) book day trips outside the city to Glendalough, the Wicklow Mtns., Powerscourt, Tara, Newgrange, the Boyne Valley...the list really does go on and on, and that's before you consider a possible side trip via the train to Belfast - a fascinating city in its own right and worth a visit, if not on this trip then sometime in the future.
The west of Ireland is everyone's favorite, and for good reason. History, scenery, great hiking...pretty much everything that you mention as being your interests are there.
My only advice would be to resist the temptation to try to cram in too much in too little time. If there's a country that's best savored at a leisurely pace it's Ireland.

Might add that we had good luck with this website for finding terrific hikes around the country: http://www.irishtrails.ie/
Do bring some waterproof boots if you plan to strike out into the countryside - it does get boggy in places.

Thanks for the insights!

Thanks all, phenomenal resource you have here. I am starting to flesh out at least the bookends of our itinerary. Open to suggestions.

Arrive DUB
Night 1: Dun Laoghaire
2: Dun Laoghaire
3:?
4:?
5:?
6:?
7:?
8: Ashford Castle/falconry
9: Ennis
Depart SNN airport at 12:45pm

2 or 3 nights at Dun Laoghaire to start? Plan to do Trinity College, Jail, National Museums, Castle. Then head to Dingle. Where to stop on the way? Cashel? How many nights in Dingle? Can Galway be squeezed in?

Thanks.

Mike

What about night 3 in Kilkenny? You can visit Cashel from there

Night 4 and 5 in Dingle... can do either or both of Ring of Kerry/Slea Head drive. We did both and they are different

Night 6 and 7 in Galway.. can do the Cliffs of Moher on the way to Galway from Dingle.

It will be busy but I think doable

Thanks for input Sharon. Do you think 2 nights is enough in Dublin? That would leave us part of arrival day Friday, full day Saturday, and part of Sunday until we drove to next spot. If we do 3 nights in Dublin I feel like we might need to nix one of the other proposed stops.

Mike

Dun Laoghaire is a pretty little town, but it's about 30 minutes via the DART line from central Dublin and all of the attractions you list. Therefore, I'd suggest staying in a more central Dublin location to simplify the logistics of your stay in the city.
Two nights (and most of two days) would probably be enough to see what you really want to see and then be on your way - I wouldn't short-change the west of Ireland for time spent in Dublin.
I also wouldn't spend any time in Kilkenny - just doesn't compare to Kerry, Dingle, or Connemara (IMO). Cashel would be a convenient stop on your drive across. Rather than spending time in Killarney town you might consider staying in Kenmare at the other end of the ROK - less traffic and easier access to the Ring drive, plus you wouldn't have to deal so much with the tour buses departing on their daily runs from Killarney. Easier access to the Beara peninsula (charming place) too. For a slightly off the beaten path excursion from the ROK take the Skellig Ring Road out near Valencia Island. As of the summer of '14 the tour buses still didn't go out there which makes for a much more mellow experience than the ROK.
While driving the ROK we highly suggest stopping at the Gap of Dunloe - one of the prettiest little glens in Ireland. The walk from the parking area at Kate Kearney's Cottage to the head of the glen and back is about 7 miles of level walking (round trip). Suggest arriving as early as possible in the AM. The tour buses and jaunting cars start operating around 9:30. If you're there earlier you'll have the place, and the experience, all to yourself.

Robert - appreciate your thoughtful reply. I considered DL for lodging after reading it was a quiet and peaceful alternative to staying downtown. We would be open to staying downtown for the convenience. How does this outline look?

Night 1: Dublin
2: Dublin
3: Cashel? Push straight through to West coast?
4: Dingle
5: Dingle
6: Dingle/Galway?
7: Galway
8: Ashford
9: Ennis

Looks good to me.
Know that you really can't go wrong no matter how you organize this, so I wouldn't agonize over the schedule a whole lot. It's all Ireland, which means it will all be great. That said, splitting time between Kerry and Dingle would be my suggestion...maybe a couple of nights each on your way up towards Galway. The connecting day between Killarney/Kenmare up to Dingle will be short one - essentially an extra day for touring - so you could easily stop by the Gap of Dunloe or the Skelling Ring...or both. Dingle is terrific, but more than two nights there would be overkill (IMO).
Connemara is our favorite area in all of Ireland. A leisurely day trip from Galway north towards Clifden, the Sky Road west of there, down thru the National Park (nice hikes), the Abbey, etc on down to Cong and Ashford Castle would make for a very pleasant excursion for you.
Watch the old John Wayne/Maureen O'hara film "The Quiet Man" before you go. It was filmed in and around the village of Cong, which still looks like the movie set it was back in 1953.

mike, looks like you have a direction here, it sounds great. My comment is that when we were in Dingle we paid for a half day tour with a local guide who drove us, with numerous stops, around Slea Head Drive. If you are doing the ROK it may seem redundant, but the pleasure of a driver who knows the area intimately and the ability to ride along and enjoy the sights and narration was great. We stopped at Ventry to read the Ogham stones, the Beehive Huts, Dunbeg Promontory Fort, Coumeenoole Beach, Ballyferriter and the excellent West Kerry Museum there, then on to the Gallarus Oratory, which we had to ourselves. I got about ten minutes all alone in there, wow. There is Kilmalkedar Church out there as well. Of our three weeks in Europe that trip, our most memorable day.

There's a good T.I. in Dingle where you could arrange something, or plan ahead-there are several good local guides. We used Denis Ryan, he was incredibly knowledgeable and fun to hang out with. Here are links for Denis, and as I say there are others you can read up on:

http://www.dingletours.com/

https://www.tripadvisor.com/Attraction_Review-g211861-d1393516-Reviews-Dingle_Tours-Dingle_Dingle_Peninsula_County_Kerry.html

I enjoyed the Middleton Distillery tour (Jameson). It was on a tour after the Rock of Cashel and on the way to Cork. Since it was a tour, I can't tell you if it fits into your itinerary.

Robert: Connemara sounds great and we would love to incorporate if possible. By the way, awesome pics on your blog from your last trip!

Dave: Appreciate input. Not sure if we will have time for both Slea Head and ROK drives. My research to date has recommended doing Slea Head if time precludes both. Would you agree?

Chani: I enjoyed a bottle of Midleton Very Rare over the holidays a few years back; indeed, a quite special dram. This might be too ambitious to squeeze in on this visit. Perhaps we can accommodate on a future trip.

We had 3 nights in Dublin and we did not see everything that was on our list. I honestly want to go back and just stay in Dublin. We love cities and all that they offer though. The first day for us was a write off though between getting our luggage, check in at the hotel and being exhausted from the red eye light.... so, we really had 2 days in Dublin.
We also LOVED the West Coast... as someone mentioned, it is all Ireland and will just be great no matter here you go :)

Definitely do the Slea Head drive. Have done it numerous times and never stops to amaze. Last trip took us five hours as we just couldn't pass up stopping frequently, went down to the beach, climbed over rocks, etc. For Dublin, don't miss the gaol but book tickets ahead. Whatever you do, Ireland will make you want to return.

Slea Head over ROK. Gap of Dunloe and Killarney national park.

Don't miss Glendalough and the Wicklow mountains either.