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Help needed for Sept Ireland trip!

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Hi,
We are traveling to Ireland in September. We will arrive on the 4th in Shannon and leave from Shannon the morning of the 17th.
We are looking to enjoy the scenery, hiking, pubs, music and the people - historic sites and castles are of interest too. We would rather stick to smaller towns.
Here’s what I have so far for our itinerary:
Day one – Land in Shannon. Drive to Doolin stay at Doll’s B & B
Take the Aran Island and Cliffs of Moher Cruise if the weather cooperates. Wander around Inis Oirr for a while. Dinner and pubs as long as we can last when we get back!

Day 2 – Go to the Burren – do a walking tour. Walk the Cliffs of Moher trail.

Day 3 – Drive to Dingle. There’s a marathon going on there that day – I’m a little leery about going there with the marathon going on but my husband thinks it will be fun. I’m worried it will be too crowded. We’ll be staying at Dingle Esk View. I read about the Courthouse in Dingle that they had good music and was a lot of fun.

Day 4 & 5 - Go to Portmagee. We’ll be hiking the Gap of Dunloe before we get to Portmagee. Wander around the Ring of Kerry – hopefully find another good hike for the next day.

Day 6 & 7 – Staying in Bantry at the Dromloc B & B. Wander the Beara Penninsula, Sheep’s head and Mizen Head.

Ok – that’s all I have planned. From there, we want to go to the Jameson Distillery in Midleton and do the tour and have lunch. From there, go to Cashel. I don’t know if driving from Bantry to Midleton to Cashel is too far in one day? Where should we stay near Cashel?
Next day, travel on. We have 5 more nights after Cashel. We still want to make it up to Connemarra and go to see the Joyce Country Sheepdogs and wander around that area. Then head back to stay somewhere near Shannon for the trip home. I’m not sure where to stay or what to do on the drive to Connemara. Help!

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