Two leprechauns do the Isle in Style
Okay, here's what we did:

Landed in Shannon.
Drove to Cork City and stayed overnight.
Drove to Cobh.
Drove to Kinsale and stayed two nights.
Drove up to Kenmare and stayed one night.
Drove to Dingle and stayed two nights.
Drove to Doolin and stayed one night.
Drove to Roundstone and stayed one night.
Drove back to Shannon and left.

Here’s what we learned:

Shannon vs. Dublin
NEVER arrive in Dublin.  It's a goddamn nightmare as I'm to understand.  Shannon's a breeze - especially for first time left-side drivers.  I white-knuckled it out of the airport on the way to Cork and since it's all freeways, it's relatively painless.  Get yourself one of those book maps where every specific area is a different page.  Makes it a hell of a lot easier than using one of those fold-up maps. 

Cork City
In a word: SUCKED ASS. It's very much a college town without much personality and it's a BITCH to drive through.  The B&B we stayed in blew and we couldn't wait to get out of there.  If you do decide to stay, try and find a B&B either right on the main drag or try to get a deal at a small hotel.  Anything just outside of the city center pretty much sucked.  Got a good pint at this huge “pick-up” pub on the main drag and the best fried chicken I’ve ever had in my life at this little Kentucky Fried Chicken type place down the street.  Also wandered around absentmindedly searching for this one music pub that specialized in traditional music and stumbled upon it for several pints.  That wasn’t all that bad.

Cobh
Seeing as you’re going in the springtime, I’d suggest spending your first night in Cobh.  It’s a breeze to get to and it’s absolutely beautiful.  Right on the waterfront with boats galore, tons of colorful pubs and restaurants and a gorgeous church up on the hill.  A bitch to park (it’s built into the base of a huge cliff so it’s like driving in San Francisco or something).  You have to park up by the church and walk down some battlements to get to the town.  We just wandered and had lunch then set off for Kinsale.

Kinsale
To get to Kinsale from Cobh you can either take the long way (land) or the short way (water).  Ask anyone to tell you how to get to the Cobh ferry.  Little nerve-wracking for first time lefties getting onto the ferry for the first time, but a well-worth-it shortcut.  From there it’s not far to Kinsale, which I’d also suggest for your first night.  It's atmospheric, right on the water, great food, great pubs, nice people and close to a couple of fun historic walks.  (You can walk from Kinsale along the "Scilly Walk" and up to St. John's Fort, which is fucking HILARIOUS.  We took the high road going there but of course had already had several pints at 2 pm and wound up stopping in a pub at the base of this really steep hill so we could pee and drink - in that order - and complete the walk up to the Fort which ended up being closed and therefore boring so we headed BACK down the hill, hung out in the pub for several drinks and realized that as it was getting awfully dark outside and we had no idea how to get home we'd have to get going.  Ended up firing up the mini-cam and wandering along the "Lower Scilly Walk" through overhanging, moss-drenched trees and along the water and thoroughly enjoying ourselves.  Beautiful views of the harbor.)

B&B Recommendation: The Cottage Inn.  It’s this small, blue building that shows up on many a postcard of Kinsale. It’s a couple small blocks away from the water (we parked in the public parking lot right in front of the grocery store) and run by the people who also operate the gourmet restaurant downstairs.  We had a room on the second floor on the front of the building (I’d request it if I were you – we only got it because it was fucking JANUARY when we were there) that had two double beds with duvets, a fireplace and a view above the window boxes right down to the windy little street.  The restaurant was incredible and even the breakfasts were outstanding.  I think we paid 17 punts each.

Pubs/Food: Down the street is the Admiral – it’s great.  Tons of live music.  The Mad Monk is on the corner and they have great food and an awesome staff that let all of us stay in the pub long after it was closed.  Around the corner is the Seanachi which is huge, has lots of little rooms and fireplaces and great food.  Colm, the owner, is lovely too.  Kinsale’s like the Paris of Ireland when it comes to food.  There’s something for everyone and it usually comes at a high price tag.  But the pub grub is the best I’ve ever had.  If you’re on a budget, stick with that.  We were never disappointed.
 

Kenmare
Megan and I had both stayed in Kenmare before and wanted to return.  Unfortunately, Kenmare’s sort of a tourist town and it shuts down in the off season.  We stayed at a nice B&B though and hung out in a couple of the pubs around town.  But we were virtually alone with a bunch of locals who looked like they REALLY didn’t want us around.  We definitely didn’t feel that in Kenmare.  It’s a little bigger than other towns and a little more moneyed – less of what you think “Ireland” is going to be all about.

B&B Recommendation: The Wander Inn.  It’s on the main street.  A cute red building with its own great restaurant downstairs.  We had warm chicken and mushroom baguettes for lunch and monkfish in a cream sauce for dinner.  Tres excellent.  The bedroom was nice too – more like a hotel.  It had just been rehabbed before we got there, so everything was new and clean and fresh and they had the best goddamn shower and bathroom that we encountered anywhere.

Pubs/Food: The restaurant downstairs – great. The pub downstairs – divey and therefore hilariously great.  There’s a pub just up the hill from the Woolen Mills store on the corner.  Head up the hill past the little shops and restaurants and take a right in front of the bookstore and it’s this pub that’s part of a hotel, I think.  Dark, gloomy and great music some nights.  We watched an Irish soap opera and drank too many Guinness.
 

Dingle
Now, Dingle is where everyone goes when its summer in Ireland. NO ONE GOES THERE IN THE WINTER.  NO ONE.  EVER.

It was deader than a doornail when we were there. All but a couple of restaurants are closed and the ones that are open are pretty dim.  The pubs are open but fairly empty.  We stayed in this fairly lame B&B that had its own restaurant (which wasn’t open until April) across from a pub where we spent 95% of our time.  When we arrived at the B&B, there was something, shall we say LEFT BEHIND by the previous guests due to the faulty toilet.  Not only would they not give us a different room, but the plumber wasn’t going to show up for four hours or something.  We had a nice early dinner in the hotel up the street.  Great apple crumble, lemme tell you.  And then we walked around so I could get cold medicine (bad one) and then had a couple pints at the famous music pub down by the water (can’t remember the name right now). The “music” consisted of some drunk sitting at the bar singing to the bartender, equally drunk and plucking on a banjo.  We left immediately.  We retired to the pub where I drank Club Orange and lamented my weak Irish genes.

The next day we attempted to bribe a local farmer to lend us his horses for a ride along the beach to no avail.  So we settled for a drive around the Beara Penninsula and a trip to the Gallarus Oratory.  Remember when I said it was dead?  Well, that was before we took a drive in the fog on a single laned mountain with crashing waves below.  Gallarus just freaked us out.  Beach was pretty, though.  We ate at some pub around the corner from the other one.  Sandwiches. Discovered the Irish cure-all for colds that night: Hot Whiskey.  Never felt better.  Of course, until the following day when my liver woke me up by poking me in the eyeball and shouting “YOU DRUNKEN EEJIT.”

B&B Recommendation: Not where we stayed, that’s for sure.  There’s a nicer one up the street that my parents and I stayed in when we last visited.  It’s got a Gaelic name – An Soapa I think.  Very nice.

Pubs/Food: The hotel was nice.  Good soup.  The pub across, An Droichad Beag, I think, the street was great.  Low-ceilinged with good music and a nice fire.  Megan even almost got lucky with a sixty year old fisherman.  Um.
 

Doolin
If Dingle was dead than Doolin was painful.  Let it be said that Doolin is strictly a summer town and there’s a reason for that: THERE ARE TWO PUBS, EIGHTY YARDS APART, TWO RESTAURANTS, FIFTY YARDS APART AND NOT A SINGLE STREET LAMP TO LIGHT YOUR WAY.

That didn’t stop us from getting completely hammered of course.

The B&B was purpose-built and absolutely terrible.  Nice owners.  Tons of guests, including an American couple dressed in furs and gold jewelry that we kept trying to avoid by pretending not to speak English.  They were hideous.  And, seeing as there was only one choice for dinner (the famous lobster place was closed) – namely the pub across the street – we kept running into them.  We just nodded our heads and spoke gibberish to each other.  Dinner was good (how can you fuck up mushroom soup anyway?) but I wasn’t feeling well and getting cranky and there was a sum total of three people in the pub, all of whom knew each other and had no interest in talking to us.  There wasn’t a radio or a TV in site and Megan and I had long grown tired of talking to each other.  It was bitch time.  We got the hell out of there and began the long (and not entirely unterrifying) walk toward the other pub which was, according to the B&B owner, “just a skip away”.  Riiiiiiight.  After entertaining images of American Werewolves in Ireland we nearly BOLTED into the first pub we came upon.  Good choice, too.  Stayed there until 3 am.  Not pretty.  But met hilarious people (including Paddy the Hippie and a German guitarist) and sang folk songs all night.

B&B Recommendation: Our place is perfect if you like pink frills and over-solicitious owners.  If not, I can’t help ya.  It was pitch black when we were there and I couldn’t tell you thing one about the “town” which vaguely resembled A BUILDING.

Pubs/Food:  Obviously the place we ended up.  Small and dark and fun.  Great food too.  I even accidentally left my notebook behind (with my journal) and went by the next day and they had kept it for me behind the counter.  Love them.
 

Roundstone
We chose Roundstone as our last stop because they filmed “The Matchmaker” there and we loved that movie. 

The drive to Roundstone was an enormous challenge.  Truly.  We went through Galway and stopped (Megan was an absolute GENIUS behind the wheel) to shop around and get some lunch.  Can’t remember the place we ate.  Sort of like an Irish Dennys.  Lots of shops and pubs but very collegey.  We got completely lost on the way to Roundstone and missed our turn TWICE winding up at opposite ends of the Connemara each time.  And there was NO ONE around.  Very fun.  Finally wound up in Roundstone around 6 pm after calling the owner and apologizing for being late.

I have a feeling that Roundstone’s much more fun in the warmer months.  The people were lovely, the town’s adorable and it’s all right on the water.  There’s tons of pubs and a couple hotels – none of which were open.  There were like TWO open – one whose exterior they used to shoot Matchmaker.  We stayed in a B&B that was really crappy but the owner was really nice.  AND it was the genealogy researchers office in the movie.  At least, the exterior was.  Also, there was a music/craft center down the lane so we stopped there on our last day and picked up tons of crap we didn’t need, including a tin whistle and bodhran for me, which to this day I have not learned to play.
 
 

And that was about it.

I can dig up my journal and get you the exact names of B&B’s and pubs.  I think I did most of my trip research on goireland.com and travel-ireland.com.  I found all the B&B’s online at townandcountryhomes.com I think.  Not sure.  I’ll find out for ya.

Hope this is helpful, dude!  Have fun!