Dublin and Western Ireland in February with young teen - help

Driving in Ireland for the first time immediately after getting off a redeye flight is generally not a good idea. A better option for you might be to take the train to Killarney (about 3.5 hrs.) on your arrival day, settle into your hotel or B&B and then, after a good night's rest, pick up your car there for your explorations around the ROK and Dingle. You could turn it in there too and just reverse the train journey to Dublin to keep it simple.
There's plenty to keep you busy in the immediate area - I'd resist the urge to spend a day or two going well out of your way just to see the Cliffs and Galway.
Keep in mind that you'll be dealing with short (and probably wet) days while you're in Killarney, so you'd be well advised to get an early start every day to maximize the available daylight.
And of course pack your waterproofs - if you're dressed for the weather you can still enjoy the outdoors in Ireland on all but the worst of days.
Know too that you can enjoy the pubs with you son until 9 PM, when minors under the age of 15 must vacate ... not that it's strictly enforced anyway.

I should have mentioned that the car rental price to pick up and drop off from Dublin airport is 1/2 or 1/3 the price to pick it up in Galway and drop it back off in Dublin. Plus I wanted to use the Conns Hertz outfit and they don't have a Galway or a Killarney location. They do have a Cork location. I guess we could bus or train to Cork for the night then rent in the AM but that means we can't stop at Cashel and /or Killkenny en route like we wanted. How easy is it to rent a car in Killarney or Doolin on arrival, versus Dublin? I'm open to ideas for trustworthy rental companies in Killarney or Galway, but it does seem that pickup/dropoff same location make more sense.

Dublin airport will have a larger selection of cars, and thus better likelihood that you'll actually get that automatic that you've booked. It'll be slimmer pickings anywhere else, so starting in Dublin is probably the way to go. Unless you're pretty sure you'll get enough sleep on the redeye flight to be alert on your arrival day I'd really encourage you to just pack it in for the night and get a good night's sleep before hitting the road. One thing that will help is that the first part of your drive to Cashel will be on modern motorways - the fun in Ireland doesn't really begin until you venture off the motorway. The N roads are two lane affairs similar to what you're used to in the US. No problem there as long as you exercise the usual cautions behind the wheel. The smaller R and L roads are more challenging until you get the hang of it - only wide enough for one car to pass in places, requiring one of the opposing drivers to pull over in order to let the other pass. Not that big a deal but it will get your heart pumping the first few times it happens.
I wouldn't bother diverting to Cork - you just don't have the time.

Do you think it makes more sense to head south to Cashel and Kilkenny first on the way out of Dublin versus over to the Galway area and then south? Also - do I really need an automatic car? I drove stick for many years so am fine with that (and kind of miss it, although it's been 20 years ...), it's mostly having the steering wheel on the right side of the car that worries me (even more than driving on the left), and having the stick to my left not right. Is it that much safer driving automatic?

Sounds like if I reverse the order it might work - spend night 1 in Dublin near-ish the airport, and then rent a car the next morning at the airport and drive down to Kilkenny castle (my son likes South Park so that one is a must), then stay over in Cashel, then the next day drive down to Killarney for 2 nights as a base, then head north and spend 2 nights up near the cliffs, and head back to Dublin via Galway the last day. A little better? Still seems crowded but avoids the "driving after a redeye" risks.

It's a judgement call for you regarding whether to go with the manual rather than the automatic. With everything else that you'll have going on, ie different sight picture driving on the left for the first time, navigating turns and roundabouts from the "wrong" side of the road, looking for traffic in unfamiliar places and generally trying to fight the muscle memory you've learned all your life while driving in the US, I generally suggest that trying to shift with your left hand is probably an additional fun factor that you don't need, especially with the likelihood of having to do all this in the rain. Your call though. I will say that the learning curve really isn't that bad, especially starting out on the motorways.
My only thought is that you're trying to pack in an awful lot of geography in a very limited amount of time, hence the suggestion to slow down, skip Galway this trip and concentrate on the area in and around Killarney. If you have your heart set on including the Cliffs then your proposed itinerary is as good as any ... if you don't mind spending an awful lot of time driving with the possibility of getting skunked upon your arrival at the cliffs due to rain, fog, etc.

Cliffs of Moher: You might want to use the Search field, above, to see the comments on the cliffs. Many feel the Cliffs of Kerry (geographically sound since you plan to be on the ROK) are a better time investment than Moher. We saw both (Moher from the tour boat out of Doolin), and found Kerry to be the more enjoyable experience. Given the available time, I'd do the Kerry cliffs while on the ROK and save Moher for the return trip that you'll surely want to make.

While on the ROK, you and your teen may both enjoy the sheep dog demonstration at Kissane Sheep Farm, between Killarney and Kenmare. An entertaining and interesting hour or so in a beautiful setting. If interested, be sure to check their highly variable calendar to be sure of the day/time. http://www.kissanesheepfarm.com/

Galway: we arrived around 9:00 a.m., walked the tourist area, saw the Spanish Arch (underwhelming, to us, at least), had a nice lunch (The Pie Maker), and were back in the car early afternoon. If you're going to be nearby, then a half-day should be sufficient unless you want to sample the nightlife, dinner and music.

Car in the cities: we struggled with navigation in both Dublin (picked up rental car the night before checking out of B&B) and Cork (just passing through en route to Kilkenny). However, we did not have GPS and were relying on a road atlas and our wits. Bad decision. Bring or get GPS in the car. Driving in the countryside is fun. There are challenging roads, but other drivers are patient and courteous, the signage is generally good, and the tour bus driver coming toward you in what appears to be an impossibly narrow stretch will probably be giving you helpful hand-signals from his seat high above you. As others have recommended on the Ireland Forum, buy all the insurance, especially the windshield/tire damage coverage.

I am kind of the opposite of others here. I prefer driving after landing in Dublin. I have done it many times and I feel better after doing that. That is just me though. I always get an automatic. The one easy thing to always remember when driving is the driver is always in the center of the road. If you are driving and not in the center, you are on the wrong side of the road. One thing to keep in mind for the Ring of Kerry is the weather. We were planning on doing it last January and one of my colleagues from Ireland recommended against it due to the weather. It is foggy in that area a lot in the winter and he said all you see is fog. We ended up doing other stuff on that trip and were glad we did. You may want to have a backup just in case. Just something to keep in mind. Driving in Cork and Galway is easy. Dublin is easy as well, just a little more congested.

We're definitely renting a car at the Dublin airport and the only question is whether to go straight from the red-eye or wait a day, and then whether to head south or west first. With a teen child who typically conks out for hours the first day after a redeye (and struggles with jetlag), I'm strongly inclined to head to Galway day 1 so he can sleep for a few hours, then hunker down in and around Galway the first day and wander the cliffs the second day, then head to Kerry for at least two days before heading up to the Rock of Cashel and Kilkenny en route to Dublin for 1-2 days. The alternatives are to hang in Dublin day 1 (to get a feel for whether we love it and want to spend more time in Dublin on the back end) and head to Kilkenny day 2 en route to Kerry. Then in case we fall in love with Kerry (and we might) I will book cancellable hotels around Galway so we can skip the Cliffs of Moher entirely if we decide to hunker down around Dingle and Kerry.

I usually book hotels with no intent to change plans mid-trip, but with Ireland I'm getting the feel that it would be better to keep things a little more open than usual. I often book airbnb but those aren't really cancellable especially last minute. I'm leaning toward booking places with loose cancellation policies so we can rejigger a little as needed.

(and I'm now convinced to get an automatic car rental, to remove that extra variable. I would always rent stick shift in Europe and enjoy it but for safety's sake, think automatic makes the most sense.)

Thanks for all the great advice.

Final itinerary worked out to this -

Day 1 (Sunday) - Rent car drive to Cork via Kilkenny Castle and Rock of Cashel (total drive time around 3.5 hours - 1.5h to Kilkenny, 1 more hour to Rock, 1 to Cork)

Day 2 (Monday) - Drive Cork to Killarney (1.5 hours), then Ring of Kerry and/or Dingle
Day 3 (Tuesday) - Explore Killarney / Kerry area

Day 4 (Wednesday) - Drive to Doolin (under 3 hours), as early in day as possible, see caves
Day 5 (Thursday) - Cliffs of Moher and perhaps Burren

Day 6 (Friday) - drive to Galway (1.5 hours) for lunch, then Dublin (under 2.5 more hours) in afternoon, return rental car to airport and check into hotel, dinner in Dublin
Day 7 (Saturday) - explore Dublin and go to Gaol

Day 8 (Sunday) - airport and leave

What decided this was that we found a great Doolin B&B and want to stay there 2 days toward the end of the trip. The rest has to flow from there.

Way too much driving and moving around for me, but to each his own.
I’m not sure where you are getting your drive times, but they seem a tad unrealistic to me. If you are using google, the general consensus is to add 30% to the times.
We spent 7 nights in Ireland this past August, and stayed 3 nights in Dingle and 3 nights in Aghradoe ( near Killarney) and 1 night near airport to catch an early am flight.
If you are set on Doolin, I would skip the south on this trip and just do western area like The Burren and Connemara.
Remember, weather and shorter days will be a factor.
Ring of Kerry takes all day! We left at 8:30am and did not return to our hotel in Aghradoe till 5:30. And we only made 4 stops. You are not going to be able to drive from Cork and do the ring in one day!
I drove as a solo ( had two kids in backseat), but def get an automatic and gps.

Your drive times are based on not stopping along the way, but there will be occasions where you see something interesting en route that's worth pulling in for and not just spotting through the windscreen as you rush past. It would be a shame to miss so many places because you're in a hurry to drive to the next destination as quickly as possible.

Your drive times are WAY off. Agree ad MINIMUM of 30% to the times - and that's drive time and doesn't include stops for bathroom, food or sights you see. At best you can cram all that in and spend almost all the time in the car and whiz past many wonders and great spots to stop....linger and actually experience Ireland.

There are spectacular B&B 's all over the Kerry area.....and the Cliffs of Kerry are exponentially better than the Cliffs of Moher. With the limited time - you have to decide if you want to experience Ireland or fly around to get a few pictures and experience little. We did that our first trip and we ended up seeing some stuff but exhausted, with only a unsatisfying superficial trip. Less is much more. Next trip we slowed down....concentrated on an area......still saw a ton but saw and experienced Ireland....Not the inside of our car and had a lifetime of memories.

I could list literally hundreds of examples from our trips but here's one. While driving on the ROK we did the fantastic Skellig Ring offshoot and stopped above St. Finans Bay to look at horses and the view. While there the farmer happened by, we got to talking and we helped feed his animals and were then invited for tea, scones and biscuits at his home. We heard stories of the area, had some of the best food we've ever had and made a friend we still keep in contact with. If we had been racing to drive the ROK "and/or Dingle" ("and" is Impossible in one day btw unless you drive like NASCAR) we would have missed out on a memory light years better than Moher or Doolin. Especially since you can get better right there in Kerry.

If you are committed to the beautiful but tourist overrun Cliffs of Moher and Doolin...stay there...skip the ROK and do Connemara and the Burden or a day trip to the Aran islands. Please learn from our mistakes....don't race around....it is not worth it....and totally counterproductive.

I should clarify that if this was summer weather, my approach would be entirely different - we would probably hang in Dingle and do more outdoorsy things. Since I have a 13 year old and it will be February, and have no idea what we'll/he'll like in Ireland, or weather will be like, this really is a bit of an overview, knowing that we can always skip things, add things, and slow down and change plans as needed. We just want an outline of where we expect (or need) to be when for lodging, and the rest will be improvisation. Thus far we have mostly done urban trips on foot - and we do tend to cover a lot of ground, us Americans generally get a week's vacation at a time so the idea is to explore. I am reading these forums like mad while still knowing that I tend to go for breadth until I know where to focus on depth another time.

New final-itinerary (clarifying - if we want to skip anything or add anything, we just know where we are sleeping that night and the rest will be improvised...) -

Day 1 (Sunday) - Arrive 7 a.m., explore Dublin (on foot)

Day 2 (Monday) - Rent car, drive to Cork by way of Kilkenny Castle and/or Rock of Cashel

Days 3-4 (Tuesday/Wednesday) - Drive to Kerry, stay 2 days, explore ROK and/or Dingle as time/weather allows

Days 5-6 (Thursday/Friday) - Drive to Doolin, stay 2 days, explore Cliffs of Moher, Burren, caves as time/weather allow

Day 7 (Saturday) - Drive back to Dublin (by way of Galway if time permits), return car rental at airport

Day 8 (Sunday) - Leave for airport by 8 a.m.

I don't think we would do the full Ring of Kerry, unless we wanted to skip Dingle or dip our toes in the water there. I assume everything goes by the wayside once you're in a place and get a better feel for things.