4-5 nights per stop for 21 days

To see The Burren and the Connemara region, you could base yourself in Westport or Clifden.
To see Killarney National Park and Ring of Kerry, you could base yourself in Agrahdoe or Kenmare. We recommend Killeen House.
To see Dingle Peninsula, base yourself in Dingle. We stayed at and loved The Pax house B&B.
I can’t speak of the north as I have not been there yet.

If your dates are flexible I'd suggest scheduling your trip for after the Labor Day holiday in the US when all of the kids will be back in school - you'll see a noticeable decrease in the crowds if you do.
Like you we prefer to find a place to use as a base for several nights and explore from there. We find it much more relaxing to minimize the pack/unpack and move along cycles when we travel. Here are some places we've particularly enjoyed on previous visits to Ireland:
The seaside village of Kinsale is beautiful - lots to see and do in and around the town, and it's handy for day trips (Cobh for example). The level walk from the town to Charles Fort is quite nice, and it's even nicer if you stop at Bulman's Pub in the village of Summercove along the way for a pub lunch and a pint of Murphy's while sitting next to the fire. Should probably stop there on your return else you may never make it to the Fort. It can get crowded during the day during the peak season, but not so much after Labor Day.
Kenmare is central for day trips exploring the southern part of the Ring of Kerry, the National Park and the town of Killarney. It's also a good jumping off point for the beautiful and underrated Beara Peninsula, which features some terrific hiking, beautiful seascapes, and some old deserted famine villages to explore.
Dingle is always a good choice, although we've found that staying near Castlemaine or Kilorglin makes for an easy day trip to Dingle and Slea Head Drive while also being close to the attractions along the northern part of the ROK - the Gap of Dunloe, Valencia Island, Portmagee for the trip out to the Skelligs, the Skellig Ring Road and the Kerry Cliffs.
Connemara is our favorite part of Ireland, and we usually base ourselves in or near the village of Clifden which is central for day trips around the Sky Road, the Connemara Loop drive, down to Rossaveal for the ferry over to the Aran Islands and, for an off the beaten track adventure, the nearby village of Cleggan and a short ferry ride over to the island of Inishbofin ... another one of Ireland's better kept secrets.
On our most recent trip we enjoyed staying in Dunfanaghy in Donegal - some really spectacular seascapes along the coastal drive there.
Last trip we stayed in Derry, which is beautiful, but if we had it to do over again I think we'd stay outside the town in or near Portrush and visit the city as a day trip. Portrush is also central for exploring the Causeway Coast (Giant's Causeway, Dunluce Castle, etc) as well as the Ulster-American Folk Park near Omagh which we enjoyed very much.
The Glens of Antrim is a beautiful area along the coast just north of Belfast. Wish we had devoted several days to it in fact. Reminded us of the drive along Highway 1 in California. Fact is we plan to return to the area on our next trip to do just that and plan to base ourselves in the village of Glenarm.
Safe travels.

Agree with Robert......Inishbofin is a hidden gem!!!!! Loved it! We rented bikes and had a grand time!

I was very happy to see these answers. Thank you, so much, for taking the time and effort to provide me with great information and details. As I progress in my planning, I'll have more questions!

Hi Kay.

I'd suggest staying north of Belfast in Carrickfergus to explore the northeast. Portrush or Portstewart to explore the north. Somewhere close to Gwedore in Donegal to explore the northwest. Galway city to explore the west. Tralee, Co Kerry to explore the south west. Cork city to explore the south and Dublin to explore the east.

You are within driving distance of everywhere if you stay in these locations.

Best,
Mike.

Great central locations for day trips, Mike. Thank you!

Great ideas. We loved Castlemaine for Dingle very much as well. One other idea is if it fits the plan consider a weekly house rental during your stay. A full weeks rental is often less expensive than a 3-5 night B&B stay.....and you don't have to use all the nights. We rented a wonderful old blacksmith shop in Tinahely for a week, used 4 nights and not only saved money but we're able to really spread out and relax. That just one example but we often work in these weekly rentals regardless of days used and get the fun of having "our" own house ...often beach front with the quiet, room and beauty for less than hotels and B&B`s for half the nights. So fun after a day of exploring to come home to your own home, wander the grounds, pet the sheep, take in the insane scenery and be able to fully relax ! Anyway just an idea to consider.

ewewoolknit...your response is exactly why I asked the question. I hope you will respond to my private message!

Hi Kay, our first trip over was 7 days each in Scotland and Ireland, from which we learned that 1-2 nights in a place didn't really do it for us either! Now we do 5 places for 3 nights each, and a night near the airport before flying home. We have a 3rd trip to Ireland planned for the Spring, but based on our previous ones, I'd recommend the following as possible bases.
Trim is a short drive from Dublin, so a great start if you're flying into DUB. It's near the Hill of Tara, Newgrange/Knowth/Dowth and other megalithic sites, the High Crosses at Monasterboice, Drogheda,etc, and Trim itself has the "Braveheart Castle" and a great pub {Brogan's]. Highfield House is a marvelous B&B in Trim.
A "don't miss" on our list would be Europe's highest seacliffs at Slieve League on the south coast of Donegal. Be sure to view from above [and below if the sea isn't too rough. You can catch the tour-by-fishing-boat from Teelin]. Nearby is Studio Donegal tweed in Kilcar, home of handwoven woolens, and if you go on a weekday they will even take you upstairs to watch the giant old-timey looms in action. Glenveagh National Park is in the north central part of Donegal. We haven't been farther north than Milford but hope to get to Malin Head next time. We have stayed at Glencolmbkille on both trips but Slieve League and the rest are all easily reachable from Ardara, Killybegs, Donegal Town, and even Letterkenny. The further west you are in Donegal the more wild and untamed it seems, so if that sort of thing appeals to you...
We found Westport, home of Matt Molloy's Pub, a great northern base for Connemara-- if you venture up to Achill Island, it's worth it to drive all the way to the end of the R319 at Keem. And of course you can head south from Westport to Croagh Patrick and into Connemara. The Westport-Clifden-Galway triangle encloses some of the most beautiful scenery in Ireland, IMO, and any of them would make a great base, leaning toward Westport or Galway if you're into trad music and the pub experience! We have only passed thru Clifton so can't address the nightlife there. Speaking for us both, we think the hours we've spent in some lively [friendly crowds and live trad music] Irish pubs are among the best-spent hours in our lives. So, while we definitely aren't drawn to cities large or small, we do appreciate them for those pub opportunities. It's such a great way to connect with people!
We have rented a car on both of our trips and have had the predictable hairy moments on those narrow Irish roads. But no doubts about it being the best way to see the country. Just remember to add another 50% [at least] to the times Google gives you between places as, unless you are much "braver" than I, you will only rarely be able to drive the speed limit.
We are looking forward to our days in the southwest of Ireland, but not having done it before, I can't offer any thoughts. Hope this is somewhat helpful, and happy trails ! J R

Thank you so much, robledge!

In Northern Ireland, I quite liked Portrush. Very cute coastal town and it was an easy drive from Giant's Causeway and then over to Donegal. Derry is a great small city, so even if you aren't city people, it really doesn't feel like one especially if you stay inside the walls.

In the Republic, Dingle is fantastic.