Ring of Kerry w Toddler

There will be plenty of places to stop as you meander around the ROK. I'd suggest just taking it as it comes and stopping anywhere that looks interesting to you.
Since you already know about the Skellig Ring Road (and the Chocolate factory) I'd also mention the village of Ballinskelligs just after you turn off the ROK near Waterville. There's the ruins of an old castle and an Abbey there and since the tour buses don't go out there you'll pretty much have it all to yourselves. It's on the beach too which your little one might enjoy...beachcombing, looking for shells, etc. Would be a nice family stop I think.
Wouldn't recommend the Kerry Cliffs in your case - the unguarded drop offs would be a concern.
Portmagee is a cute little village for a stroll and/or lunch, and the Skellig Visitor Center has some exhibits that might distract the toddler. There's a nice little cafe there or, if you prefer, you could pick up picnic fixings in the village and eat at one of their outdoor tables there. Has a nice grassy lawn and pretty views out across the water.
And I think you already know about the jaunting cars at the Gap of Dunloe, right?

These ideas sound perfect. So once we arrive at Skelligs Chocolate Factory, we can drive part of the Skellig Ring Road and not backtrack on the Ring of Kerry? Then, we can get back on the Ring of Kerry further south or east?

Thanks again!

You wouldn't have to backtrack any part of the ROK if you take the spur out along the Skellig Ring Road...assuming that you're driving the loop clockwise around from your base in Killarney. Might want to consult a map to get your bearings.
For a pleasant meander from Portmagee you could drive the length of Valentia Island to Knightstown, then take the short ferry across the little estuary to reconnect to the ROK near Cahersiveen. Very pleasant - hardly any traffic and some pretty scenic vistas if you'd like to stop along the way.

That sounds really nice.
Can I drive the Ring of Kerry Clockwise? I have always heard you need to drive it counter-clockwise to go in same direction as tour buses.

Thanks again.

That used to be the advice - there were some very narrow curves where meeting a tour bus head-on would be guaranteed to recalibrate your startle reflex, but during our last trip a couple of years ago I noticed that the road had been widened to permit easy passing with a minimum of drama. I'd say you could go either way unless you plan to be driving an oversized vehicle yourself.

...and if no one's mentioned it before, you can preview your route using the street view feature on Google Maps if you want to check out road conditions, turnoffs, roundabouts, etc. Comes in real handy sometimes to have seen the route in advance.

We loved driving the Ring of Kerry.. we stopped along the way whenever we hit a little village or cool spot to take pictures. My kids were older ( 11 and 8 ) but be very careful at all the beautiful scenic looks outs... many have no fence or wall and a wandering toddler could get in a lot of trouble. We loved the beach near Derrynane and had a great picnic there

Thanks all again. These ideas sound wonderful and lovely.

Will there be plenty of places to get fuel and / or stop for a bathroom break?

"Will there be plenty of places to get fuel and / or stop for a bathroom break?"
Yes, but do check the map before you set off to get your bearings and have an idea how far it is from one pit stop to another. The village of Waterville is a pretty good halfway point. There's a public park with toilets there as well as numerous cafes and shops along a very pretty beachside promenade. And of course there are public rest rooms in the chocolate factory and at the Skellig Center.

That sounds great. I'll definitely top the car off with fuel before leaving Killarney too.

You might consider taking a private tour with Paul Brown. IMO his van would be great as you could keep your child engaged and experience the beauty of the Ring of Kerry while Paul does the driving and shares stories of the ROK. We went with Paul, just my wife and I, for the entire day and had a great, well informed tour. Paul will adjust the tour for what you are interested in and I know would have great ideas for a family with a young child. Pauls email is brownpaul4321@yahoo.com and his website is www.kenmaretaxitours.com. Don't be put off by the "taxi" tour part, he has a wonderful new van, great seating/viewing, and he is awesome to spend time with. We did a two week driving tour of west Ireland and for me the day with Paul gave me a great opportunity to take a day off of driving and it allowed me to really see the beautiful country while not having to concentrate on the driving. This was a great decision for our trip! dave, Bedford, Indiana

Thank you all for the comments thus far.

Would you recommend driving the Ring of Kerry counter-clockwise? I have heard tour buses go this way too. We would try to get on the road in the morning before 9:00 a.m.

Thanks again.

We drove it clockwise and were fine. We were also on the road shortly before 9

That sounds great. Thanks.

I think clockwise would be less congested.

If we want to spend a few hours and one meal in Kenmare as a stop, how would this effect our starting direction from Killarney?

Going from Killarney to Kenmare keeps you in the clockwise direction.. is that you mean?

We will be in Killarney four nights, going to Dingle for a full day and driving the Ring of Kerry another full day. We were also thinking of spending a few hours in Kenmare since it is not too far from Killarney. Would it make sense to visit Kenmare during our Ring of Kerry day trip? Or go to Kenmare another day. We still want to explore Killarney National Park as well.
Thanks again

Are you staying over in Dingle? Or just spending the day?

If staying over, I would rive the Ring of Kerry and stop in Kenmore the day you leave Killarney to drive to Dingle. This will get you into Dingle latter part of the day depending on how many stops you make.

If you are driving to Killarney to Dingle for the day and coming back to Killarney for the night then I would drive straight to Dingle to give you the most time in Dingle.

I would then do Kenmore separately while in Killarney.

Does that help at all?

Sorry for the confusion. Below is my tentative itinerary in Killarney (4 nights):
Day 1: Arrive in Shannon 9:00 a.m., Drive to Killarney
Day 2: Drive Day Trip to Dingle
Day 3: Explore Killarney National Park (maybe Kenmare)
Day 4: Drive Ring of Kerry (Visit Skelligs Chocolate, maybe Kenmare, etc....)
Day 5: Depart Killarney early afternoon and drive towards Galway (maybe stop at Cliffs of Moher on way)

Looks like a pretty good itinerary to me.
If you plan to drive the ring clockwise you'll be passing thru Kenmare anyway. Maybe a short stop there for breakfast and a quick look around would be a thought. Also, the village of Sneem, a little further on, is a pleasant stop with numerous little restaurants, cafes, and craft shops to entertain you.
Getting an early start is always highly advised to beat the traffic getting out of town - things really start to get clobbered once the tour buses start queueing up around 9:30, and it tends to stay crowded until 4 PM or so.
Since you have an early arrival at Shannon on day one you should be arriving in Killarney at a reasonable enough hour (and with plenty of daylight left in the day) to explore the attractions in and around the National Park at your leisure.
Based upon your previous comments it looks like your day out on the ROK will take most of a full day - which is a great idea. I would suggest devoting at least part of another of your days to the Gap of Dunloe, however. The little glen is beautiful and would make for a very pretty walk for you and your family, especially when combined with one of the jaunting cars. Suggest an early arrival there too (before 9:30 AM) to beat the tour buses and day trippers from Killarney, which can result in the parking area near Kate's Cottage to fill up quickly.

This sounds great. Thank you all again for all your input!

Just wanted to say, good luck with your trip! We are off to Ireland in just under a week with our two year old.

Good luck to you as well!
What items do you recommended packing for the long plane ride?

To prepare for the flight, I bought several new activities (mostly small, light, and inexpensive) that I am going to wrap up. Ideas: lots of snacks (raisins, applesauce, etc), Melissa & Doug water wow books (paint with water, reusable), coloring books, crayons, suckers (bribe as necessary, help with landing), Kindle Fire and headphones. I had him pick a few Target dollar spot toys that I will wrap up also. Hoping that will all keep him quiet if not entertained.

I just did the Ring of Kerry with a two year old! My friends from Texas came to visit me, and we did everything i do with adults. She was awake for some of it (loved the horse riding in the park in Killarney) and slept in the car seat for alot of it, too.

I think four nights in Killarney is too much. I believe (I'm sure some will disagree) that the smaller towns are better to stay in. I stay in Killarney twice a month so I know it well, but I'd recommend Glenbeigh, Waterville, Sneem as alternatives.

If you feel you need more recommendations that you've already seen, let me know. I live in Waterville and travel around the Ring extensively.....

Susan
Waterville

Inch Beach, in Annascaul, near the town of Dingle has a wide, sandy beach which would be great for a 2 years old to stretch and play. It is one of the few sandy beaches in all of Ireland and there is a small store and restaurant there so you could grab snacks or lunch.

Just to correct the comment above by stmurray(?).

Inch beach is NOT "one of the few sandy beaches in all of Ireland." There are thousands of sandy beaches in Ireland! Probably 100 within 50 miles of Inch. Just because a traveller comes through a beach village at high tide, that's no reason to think it ALWAYS looks like that!! There are 4 within walking distance from where I'm sitting right now (and that's not including Inch, which I can actually SEE from where I'm sitting right now!).

Susan
Sitting at Rossbeigh beach right now.....