Need Help Making A Tough Choice

How long is your trip?

We will have 8 days/7 nights.

Not sure if this helps, but I've hiked the Spinc Loop trail, and it begins (and ends) near the monastic site at Glendalough, so you may be able to cover both these activities in one swoop. The whole hike/site visit took the better part of a day. It was lovely.

Be sure to include the Cobblestone Pub in your Dublin music plans. Will you be driving between destinations, as opposed to train or bus? Allow time for slower speed limits on some narrower, curvy roads.

As you’ve identified many places east, southeast, and southwest, seeing Inishmore and the Cliffs of Moher, iconic as they are, would be places to consider skipping this trip. Our second trip to Ireland, September 2018, had its share of verrrrry rainy days. Hopefully you’ll be bringing rain gear, as your bike rides could be soggy.

Weather can affect more than just bicycling. We went to Inishmore on both of our first two trips to Ireland. Both had boat and ferry delays/cancellations due to rough seas, wind, and rain. Both trips, we spent the night on Inishmore, as planned. On the second trip, rather than going by ferry, we flew on the small Aer Arran plane. They can fly, even when boats can’t go. But the whole second day was spent waiting out a monsoon, and we flew out in late afternoon. However, the airport is west of Galway (a fantastic city), even more out of the way of the rest of your itinerary.

On our first trip (June 2012, a bike tour), after a long delay on our second Inishmore day waiting to see if/when ferries could sail that day, we took the ferry from Inishmore to Doolin on the mainland, and the ferry also made a stop on Inisheer en route. Approaching Doolin, we had a view of the Cliffs of Moher from the water, before getting drenched in a heavy rainstorm once we reached the shore. It would be possible to see the Cliffs on a ferry to/from Inishmore, even if you didn’t get to the Cliffs visitor center (more hiking available there), but this assumes a boat will actually sail.

The Great Western Greenway is even farther north than Galway. I’d stick with your itinerary, except for Inishmore, Cliffs of Moher, Kylemore Abbey, and the potential GWG ride (yes, all a tough choice). This ensures you’ll have at least a night and parts of two days for Dingle and historic sights and scenery its peninsula.

You've got about 14 days worth packed into your trip... but it is difficult to begin to know what to cut.

I would suggest if you are into authentic Irish music, then try and add Roundstone to your itinerary when in County Galway and visit the workshop of Malachy Kearns who makes traditional Bodhráns. It would fit in with a trip to Kylemore Abbey.

Thinking just a bit more, you’ve said your main focus in Dublin will be Pub music. But as you’re flying in and out of Dublin (as opposed to, say, arriving at Cork and departing from Shannon, which we did on our third trip, last year), then music can be found there, and that will work. But we’ve certainly heard lots of Irish trad music in pubs throughout southern and western Ireland, so Dublin wouldn’t necessarily have to be a place for a lot of your time, if just trad music was your goal.