Obviously for many people who have been through it, you have too many one night stays -- but that is a personal choice and I note that you are trying to fit in as much as you can in a short stay. My thoughts are in blue. 

Day 1 - Arrive Shannon from Boston on Aer Lingus around 7:00 a.m.  After collecting rental car from Dan Dooley (paid extra for automatic transmission--one less thing to worry about while learning to drive on the left), drive to Doolin and, weather permitting, take ferry to Inisheer.  Explore the island a bit, ward off jet lag in a pub or two, take the Cliffs of Moher boat tour on the way back to the mainland.  (If the weather is bad, we'll skip Inisheer and check out the Cliffs from the mainland and maybe drive through the Burren).  Spend night in Ballyvaughan.

That is a great deal to pull off with jet lag.  You do indeed need to stay active that day and be awake until the evening hous, but that is a lot stuff to do after an all night flight.  I would stay in Doolin, be within a two minute stroll to great food and traditional music, close to the Cliffs, and not drive to Ballyvaughan, which would be in the opposite direction of Dingle, your destination the next day.

Day 2 - Assuming we didn't drive through the Burren on Day 1, we'll do so by leaving the Ballyvaughan area on the R480.  Catch the R67 and continue through Kilkee to the Shannon River ferry.  From there, drive through Tralee to Dingle, taking the Connor Pass route if the weather is good.  Time permitting, explore the Slea Head drive and/or Dingle Town.  Spend night in Dingle town.

That is good.  Take the Tarbert Ferry to save some driving time.

Day 3 - If we didn't get to Slea Head on Day 2, we'll do so in the morning, otherwise explore Dingle town in the morning.  Drive from Dingle to Kenmare for a brief stop there.  Drive from Kenmare to Kinsale (on the "scenic" route (N71/R600) if the weather is good).  Spend night in Kinsale.  (Note: we've made the strategic decision to skip the Ring of Kerry in favor of the Slea Head drive.)

Driving from Dingle to Kenmare to Kinsale in one day is not easy or even realistic, when you factor in any stops for scenery, food, etc.  The roads, especially on the west coast, can be beautiful but tough to make up ground -- think about covering 35 miles in an hour, not 60 like in the states.  This route would be over 200 miles, which in Ireland equates to most of the day behind the wheel. Dingle to Kenmare would be fine.  I would take Kinsale off the list for this trip, as it would take too long to get there and is not on your way to Cashel or Kilkenny the next day.

Day 4 - Drive from Kinsale to Cashel to explore the Rock of Cashel (intentionally skipping Blarney Castle).  Drive from Cashel to Kilkenny, explore the town and spend the night there.

Drive from Kenmare to Cashel, see the Rock of Cashel, and continue on to Kilkenny.  Long day, but at least you have a chance of walking around Kilkenny that evening -- you need to see this city if you are staying there.

Day 5 - Drive from Kilkenny to Dublin Airport to drop off rental car.  Taxi into town to explore (Trinity College, etc.).  Spend night in Dublin at the Roxford Lodge Hotel (only non-B&B on trip).

Fine. Forget a taxi if your budget is an issue.  Take the bus from the airport and then do the Hop-On-Hop-Off Tour available in Dublin, seeing Trinity College and so much more. Well worth it for a quick glimpse of the key places there.

Day 6 - Explore Dublin further in the morning before heading to airport for 2:15 flight to Boston.

Be careful not to stray too far from the airport.  Getting through customs in Dublin is not quick, and now since you clear on the Ireland end of things it can take a long slot standing in line. You must be there quite a long time before your flight to make sure you get on the airplane.

Hope this helps.  I think you are running around a bit too much, but the first time I was there I did the same thing -- heck, most of us did.   That is why we try to share some of our experiences.

Best wishes,

Bert

Thanks to both of you for the advice.  Let me make sure I've got some of the details right.

First night, stay in Doolin instead of Ballyvaughan.  My wife definitely wants to go to Inisheer weather permitting on Day 1, so I suppose that means sacrificing the Burren in favor of getting to Dingle earlier on Day 2.  I think I'm OK with that since we'll get some sense of the topography from the Cliffs and Inisheer.

I had considered an overnight in Kenmare, but opted for Kinsale because of its reputation as the "gastronomic capital of Ireland".  We're kind of foodies, so that was appealing to us.  I know Michele's a big fan of Kilkenny, but what if we skipped Kilkenny in favor of overnights in Kenmare AND Kinsale? We could then check out the Rock of Cashel on the way to Dublin from Kinsale on Day 5.  Just a thought I'd like your feedback on.

Many thanks!

Could not agree more with Michele regarding Kinsale.  If going there is on your way to a destination, certainly worth seeing.  But do not feel you need to go there to find good quality food in Ireland, as the "gastronomic capital of Ireland" tag is a public relations ploy to a degree.  There are good places to eat there, but not really better than many other areas -- and you will pay higher prices to dine out in Kinsale at many establishments.

The strides made in food the last 20 years is amazing, and Kenmare or Kilkenny will provide just as solid of options for fine dining as Kinsale. Given the choice of staying in Kenmare or Kinsale, I would select Kenmare.  It is a lovely village in one of the most beautiful areas in the western part of the country. And for eating options, I would put Kenmare's Lime Tree and Packie's on par or above anything you can find in Ireland. The Lime Tree's creme brulee with short bread cookies is a must, and at Packie's you can't do much better than the crab cakes they make.  For good pub food, Coachmans on Henry Street has always been tremendous.

Wow. Got off on a food rant there for a moment! Think I am ready to get back to Ireland.

Bert

Just wondering what B&Bs you have booked?  Perhaps I have stayed at one of them.

In Doolin I always stay at Susan Daly's place, which is literally a 100 yard stroll to Gus O'Connor's Pub, one of the best traditional music pubs in Ireland.

Have no experience at Tower View.  Many nice places to stay in Dingle.

In Kenmare stayed a few places, but we have enjoyed Shelburne Lodge a great deal.

Rosquil House is terrific!  A short walk into town, which is always nice.

No experience with the Roxford Lodge.

You are off to a great start!

Bert

Wanted to note that the Shelburne is a bit pricey compared to some other places (probably 50 euros each per night), but is quite nice.  To stay right in town and a better rate, we liked Virginia's Guesthouse also.  Probably about 30 -32 euros each there.

Tossing another bug in the oinment here...since Inis Oirr is your goal, have you considered staying on Inis Oirr? South Aran is my favorite there and if you are a foodie, like me, you will love their restaurant.

The only consideration would be Ferry times, as they are on a reduced schedule usually only two trips a day until the first of May.

In Dingle, my favorites are Blooming Wildflower Cottage & Quayside B&B. Again, knowing you are foodie, I would suggest staying outside of Dingle at the Shores.

In Kenmare, my choice would be between Virginia's, due to its city centre location and Arthur's Lodge, a splurge but well worth it considering this is a 10th anniversary trip!