Help with itinerary for The Road Less Traveled driving trip

How much time do you have for the trip? What time of year do you intend to go?

May, 12-14 days

Hi there! Looking at your city/town choices, I'd fly in to Dublin and out of Belfast. You could hit all of these places in 14 days with a lot of driving (and if you start in Dublin, head south then work your way north on the Wild Atlantic Way, ending in Belfast.) I have taken many driving trips in Ireland but usually plan them so I am picking up/dropping off at Dublin Airport (it's easiest city for me from either Seattle or Bordeaux.) But have made "circular" drives so that I hit certain areas. You will be covering both the Republic as well as N. Ireland so renting a car in one country then dropping in the other will be very expensive. One idea is to pick up your car outside Dublin, head south then work your way North to Letterkenny (Co. Donegal) to drop off the car then take a short bus ride (35 min) from Letterykenny to Derry, which is in NI. Then either rent another car, take a bus, or train to Pomeroy and Belfast.
Personally I think you can hit all of these towns as long as you organize your drive in a logical fashion.
Enjoy your trip!

I'm going to strongly disagree with the previous poster about flying out of Belfast. That will cost you in airfare, time and the rental car drop fee already mentioned. I think you can do the trip you have planned by flying into and out of Dublin, but if it's convenient for you to use Shannon for one end or the other, by all means do that. Your itinerary is a pretty straightforward clockwise or counterclockwise route that could start at either airport. If you're prone to jet lag and don't feel confident picking up your rental car straight off the plane, then Dublin is the better choice. In fact, you could fly into Dublin and visit both Dublin and Belfast before you pick up the car (in Dublin, not in Belfast). If you're flying out of Dublin, you could take the train to Cork and get your car there and head to Kinsale. The in-country drop fee will be much less than the second-country drop fee.

We love Doolin, but it is very touristy. I'd suggest an overnight on an Aran Island (Inishmor?) as it's less crowded after the last ferry leaves.

You could spend the first day or two in Dublin, get a car and drive to Cookstown/Pomeroy. Then drive to Belfast, and use a car park near the motorway, although you might want to brave a little city driving to save a walk for your folks. Then head west to Donegal, then south to your other destinations. We don't have a Shannon option from Seattle, but I'd usually want to avoid a drop-off fee on principle. You will probably have to cough up a 30euro "recovery fee" for taking an IE car to NI.

There are lots of amazing interior towns. We always go to the pubs, and my wife is really good at finding interesting conversations with the locals, usually while listening to trad.

We've made five trips to IE so far, and always have a car once we leave Dublin and tend to not use the "home base" style.

In 1997, I did a relatively long road route. I started in Dublin, took the bus to Galway and visited the Aran Islands. After my Aran visit ended and I went back to Galway, I picked up a rental car and went to Sligo and Donegal. Then I went to N. Ireland and doubled back to the West in the Republic. Your trip looks excellent.

I did an open jaws ticket, flying into Dublin and flying back from Shannon, an itinerary that worked perfectly for me. Since you'll be in the West, one of the most memorable routes in my five visits to Ireland was the R318 in north County Mayo. It makes sense to to start in Dublin.