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How best to spend two nights in Kenmare / Killarney, Ireland?

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I'm planning a pretty aggressive tour of Southern Ireland at the end of the September (in two weeks!). And I need a little help trying to plan out one leg of the tour -- our two-night stay in Kenmare. Here's what the trip looks like so far:

THURS: Arrive in Dublin in the evening (night in Dublin)
FRI: Tour Dublin (night in Dublin)
SAT: Tour Dublin (night in Dublin)
SUN: Drive to Cork, stopping at Powerscourt and Cashel along the way (night in Cork)
MON: Drive to Blarney Castle first thing in the morning and then drive to Killarney to hike the Gap of Dunloe (night in Kenmare)
TUES: Bike ride the Ring of Kerry or Beara Peninsula (night in Kenmare)
WED: Drive to Galway, stopping at Adare and Cliffs of Moher along the way (night in Galway)
THURS: Tour Galway/Clare (night in Galway)
FRI: Drive to back to Dublin (night in Dublin)
SAT: Fly home early

As you can see, we're trying to do a lot in 9 days. The trickiest parts are SUNDAY, MONDAY and TUESDAY.

We're using Cork as a stop-over on our way to County Kerry so that we can easily kiss the Blarney Stone MONDAY morning (I know-I know) and then drive to Killarney in time for a quick lunch and a hike through the Gap of Dunloe. Of course, that doesn't give us time to do the full proper hike to Lord Brandon's Cottage and boat ride to Ross Castle (I think the last boat leaves Brandon's at 2PM). Our plan is to get to Kate's at 1PM from Blarney Castle, hike to Lord Brandon's, walk back down and drive to our hotel in Kenmare, arriving a little after dark.

On TUESDAY, we'd have a leisurely day biking around either the Ring of Kerry or Beara from our hotel in Kenmare.

But I'm wondering if it's best to stay in Killarney, instead of Kenmare. Maybe on MONDAY, we'll simply drive through Beara on the way to Killarney and then have a proper tour of the Gap of Dunloe on TUESDAY from Killarney.

Any advice? Is 1 or 2PM too late to start a hike of the Gap of Dunloe? Is the drive from Kate's Cottage to Kenmare dangerous in the dark? Would you recommend staying in Killarney for this sort of thing?

Thanks in advance!

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