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Suggestions for itinerary/places to stay along DINGLE/RING OF KERRY

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Hello,
would love to hear some feedback on my proposed trip to Ireland. I've been there before so i'm just taking a few days to drive Dingle and Ring of Kerry.

Landing in Shannon airport from London (spending first part of trip in England) , pick up a car there on the 17th and make our way to TRALEE which seems to be the beginning of the route around DINGLE. I thought maybe we could stop for tea at ADARE since it's supposed to be a lovely village and has a beautiful castle then do the hour or so drive to Tralee, stay over night there or in area-
LOOKING FOR SOME RECOMMENDS FOR PLACES HERE

On 18th, get up early and spend the entire day driving around Dingle Peninsula. Curious if there are any cute villages along that route we shouldn't miss!

Seems like we might want to spend the night (Sept 18th) somewhere at the end of this long stretch somewhere near CASTLEMAINE or KILLORGLIN which can get us ready for the next morning's start on RING OF KERRY.
Would love recommends for places to stay around the area here.

On 19th, we would follow the coast line around Ring of Kerry
On the route of Ring of Kerry from Killorgin we can stop in Portmagee and take a boat across to SKELLIG MICHAEL which sounds amazing with old monastery on it! It's a half day trip so we would come back spend night (Sept 19) along the Ring and then drive to end in Kenmare...
Would love recommends here as well.

then morning of 20th, we can maybe turn up and drive through the supposedly spectacular scenery to Kilarney, maybe drop the car off there and take train back to Dublin on 20th?

As for places to stay, I'm always looking for places with character/charm. I've stayed in a variety of castles in the past and I would love to stay in one again if there is something close by this region that isn't overly commercialized (i.e. boring hotel rooms and busloads of people)...Would like something more intimate if that's possible. Otherwise totally open to b&b's. Anything with charm and feels like another time is always my preference- doesn't have to be slick/modern/new.

Would love to hear if this itinerary sounds reasonable and if any of you can recommend some places!

thanks in advance!
best,
k

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