Four days around Dingle and Kenmare

My wife and I did that itinerary, though in reverse, as part of a longer driving tour about a year ago. The timing seems fine; we spent 3 nights in Dingle, but you can certainly see the area in 2. (BTW, we stayed at the Towerview B&B and loved it; also loved the Dingle Pub.) We spent 2-3 hours in Killarney NP, which was about right unless you want to hike (but there is hiking everywhere), and 2 nights in Kenmare. One very memorable thing we did was deviate from the ROK to cut south across the peninsula, since we did not want to go through Killarney again; we went south c. 3km past Glenbeigh through, eventually, Ballaghbeama Gap. The driving was hair-raising at times (narrow twisty roads, with improbably high speed limits), but the country was gorgeous, and it sure was not crowded.

The southwest corner of Ireland is very picturesque, and the area has really good B&B's. You should be able to get some good pictures.

We went in May, and it was before the tourist season started. We found the place to be very quiet. We expected pubs, but satellite television has changed the lifestyle of the Irish. Pubs now are more sports bars with about a dozen guys hanging around for happy hour watching big screen television.

When in Dingle, stop by the little music shop (?) or little shop that sold some musical instruments...Find out if they know of any little local concerts. We lucked out (2009) when we overheard conversation about a fundraiser for Malawi in the large church---many well-known Irish artists, as well as a smaller concert in a smaller church. It was great. We loved our our few days there.

Thanks for all of the great trips. Good to know I am on the right track. Just found a great bike rental shop for the Dingle peninsula! Looking forward to some Murphy’s and trad music as well.

If you're an avid photographer, consider some short potential side-trips from this area: Skellig Michael (access is from Portmagee, on the ROK), and Great Blasket Island (access is from near Dingle). These two islands were some of the best, and most jaw-droppingly photogenic, highlights of our trip to Ireland. You will be very, very close to both, give them some consideration.

When in September (early/mid/late) is your trip? - that could easily make a major difference for many places (including these).

(ah, yes - @uwe04 below is correct, I had incorrectly swapped the access points - now corrected).

Just the other way round access Skelligs from Portmagee and Blaskets from near Dingle

Looks good to me and you aren't trying to do too much. Problem with both the Skelligs and Blasket Islands is they are weather dependent and if you only have one day , you may not get there...

Also Kenmare isn't a good base for a trip to the Skelligs. You realluy need to base yourself around Portmagee.

Plan another trip back to ireland to concentrate on these islands - build in plenty of time to allow for weather conditions too!

Since you mentioned trad music, you'll find that in September, since tourism is winding down a bit, a lot of pubs' music offerings are only certain days of the week. It will be hard to NOT find good trad in Dingle on any night. Cork is trying hard to become a music center (check https://www.theleesessions.com/). Kenmare will probably have something at one of the half-dozen pubs claiming to have trad. You may find some of the pub offerings are "Irish music" rather than "trad".
For me, at least, "trad" is mostly amateurs sitting in a booth or in a corner with lots of breaks for gossip among themselves and sips of beer, playing reels/jigs etc. "Irish music" tends to be more professional (or at least amplified) with lots of "favorite" sing-alongs, like Galway Girl, Whiskey in the Jar, etc. We always prefer sessions, but the sing-alongs can be fun once in a while. Unlike David's experience, the pubs we've explored are not sports bars (except maybe during the Football playoffs), and everyone was intent on the music. Temple Bar in Dublin is largely as David stated.

Problem with both the Skelligs and Blasket Islands is they are weather
dependent and if you only have one day , you may not get there...

Yep - but that's true any time you hope to go, even if you have a longer trip in midsummer.

Also Kenmare isn't a good base for a trip to the Skelligs. You realluy
need to base yourself around Portmagee.

I do agree with @wasleys about both points above - Portmagee is the jumping-off point for the Skelligs, and due to the logistics (the operator will make a last-minute go/no-go decision on weather or not the boat goes each day, based on weather and sea conditions), so being close-by is strongly recommended, rather than facing a long drive to get there (you may not get much advance notice, but need to be able to be there on time).

And for sure, both islands require fair weather, so with limited time, you are going to need some luck to pull it off. But the OP is going to be right there, and if they get lucky with the weather on either day (or both) the islands are so worthwhile I think it would be a shame to not set things up so as to be able to do it IF the weather cooperates...just be aware that it is a roll of the dice, and you would need some luck (so be prepared to pivot to an alternative plan for the day).

And about that luck...OP needs to look carefully at a calendar: I believe trips to the Skelligs end at some point in early/mid September (depends on the operator, but is also regulated by government agency). Hence my question above about exactly when in September this trip is. Going the first week of September? Weather (and regulatory limits) would give a much better chance at either island than if the trip was the last week of the month (at least the Skelligs would probably be "closed for the season" even if you get a lovely day).

It's a wonderful area with so much great stuff. Lucky to have an excuse to go there.

We are going September 20-29, so the islands may have to wait for another trip. Being a photographer, I can appreciate a nice rainy day. We have some flexibility day to day to adjust based on weather but one goal is to bike the Dingle peninsula so a rain cancellation then would be a disappointment.

I did find a fellow photographers google map of all of the locations he photographed in a three week Ireland trip and the highest concentration of shots were by far right along this stretch of coast.