Ukuleles, Ancient Ruins, and the “Real” Hollywood: My Wild Rover Adventure

Note: Wild Rover Tours arranged a special tour for our group attending a conference in Dublin. Also, sheep herding part of the tour is discontinued and will be replaced by a new experience at the beginning of March 2026.

There is a specific kind of magic that happens when you leave the Dublin city limits and the concrete gives way to the “forty shades of green” everyone talks about. I recently spent a day exploring the heart of the Irish countryside with Wild Rover Tours, and it was easily the highlight of my trip. If you’re looking for a day that balances years of history with modern-day farming—and a bit of musical comedy—this is the way to do it.

🪕 The Legend of Dave and the Ukulele

Our journey began at 8:45a in Dublin, I was severly jetlagged so I’ve been up since 4:30a. So I had an early breakfast at 7a and was ready for our departure. Please don’t keep others waiting when you do a tour.

We pulled out of the Clayton Hotel with our guide, Dave, who gave the introductions and set the pace for our day in the Wicklow Mountains. It would take us about 1.5 hours to reach the mountains. We made a quick stop for a snack just before we hit the highways and headed into the country.

Dave isn’t just a guide; he’s a storyteller, a historian, and a bit of a musician. As we wound our way through the mountain passes, Dave pulled out his ukulele for a few “trad” sessions. It made the story so much better, and Dave can really sing too, so it made for an unforgettable experience. It turned a long drive into a rolling party on the huge bus.

🐑 Cullen’s Sheep Farm: Four Generations of Tradition

The most authentic part of the day was visiting Cullen’s Sheep Farm. This isn’t a staged tourist attraction; it’s a working, four-generation family farm that sits right in the heart of the rugged mountain slopes. There’s one ram for 40 female sheep, and they have about 7 rams.

Watching the Border Collies work was a masterclass in focus. At a mere whistle from the farmer, the dogs would “eye” the flock and move it with incredible precision. 

The area is perfect for sheep farming, which is governed by the seasons, the climate, and the mountains, said Richard, the farmer.

But the moment most had been waiting for was the hands-on experience. We were able to hold the sheep (I didn’t)—they are apparently much sturdier and “oilier” (from the natural lanolin in their wool!) than you’d expect, I’m told :-).

 

⛪ Walking with Monks in Glendalough

Next was Glendalough, the 6th-century monastic city founded by St. Kevin. This place is hauntingly beautiful. We walked through the only surviving monastic gateway in Ireland and stood beneath the iconic Round Tower.

 

One of the coolest parts was seeing St. Kevin’s Cross. Unlike most Celtic crosses, this one is “unpierced” (no hole in the center). Local legend calls it the “Wishing Cross.” They say if you can wrap your arms around the massive granite trunk and touch your fingertips on the other side, your wish will come true.

The Mysteries of St. Kevin’s Cross

Our tour guide Dave, gives the history of the Cross.

🎬 The “Original” Hollywood & The Wicklow Gap

As we departed Glendalough, we climbed into the Wicklow Mountains, the views at the Wicklow Gap were breathtaking—rugged, moody, and perfectly Irish. We got lucky, kind of. There as no rain once we got to the Wicklow Gap, but we couldn’t see the gap due to the low lying fog :-).

We didn’t stop as we drove through the tiny village of Hollywood.

While everyone knows the California version, Dave told us the story of Matthew Guirke, a local blacksmith who fled the Famine in 1850. He eventually settled in California and named his homestead after his native village. Looking up at the Wicklow “Hollywood” sign on the hill, you realize that the glitz and glam of L.A. actually has its roots in this quiet, green corner of Ireland. Our sightings were sporadic as we drove along the curving road.

🏰 Kilkenny: The Medieval Mile & The “Smit-icks” Experience

We finished the day in Kilkenny, Ireland’s medieval capital. Our bus dropped us off at the Castle at one of end of town and our tour guide let us loose on the town to have lunch, walk the Medieval Mile—a stretch of history connecting the massive Kilkenny Castle to the cathedral, then meet back at the Castle where he’d give us a mini walking tour, and we would end up at the Smithwick’s Experience.

 

I started to wander aimlessly, running into some of the other people on the tour. I love to have bubble tea when I travel, so I used Google Maps to find a place called Namo Plus. They didn’t have my signature mango green tea with aloe vera, but they did have a mango lemonade tea, so I had that. It was O.K.; tasted a bit different.

I then continued my walk up a side street and ended up at St. Mary’s Cathedral.

After my visit, I made my way back to the Castle, as that was our meeting point. Then we made our way back down the main street to the Smithwick’s Experience.

Located on the site of a 13th-century abbey where monks first brewed ale, it’s a total sensory experience. I loved the “milling the malt” section—you can actually plunge your hands into the barley and smell the hops. We had what seemed like a private tour that ended with beer of course.

Pro Tip: In Kilkenny, don’t pronounce the ‘w’! Ask for a “Smit-icks” and you’ll blend right in with the locals at the brewery taproom.

🎒 What’s in My Bag? (The Essential Packing List)

If you’re heading out with Wild Rover, don’t let the Irish weather catch you off guard. Here is what you should bring:

• Rain Jacket: Non-negotiable for the mountains.
• Umbrella: Good for all travels. Get a portable one. Some hotels will have one you can use or one you can rent.
• Comfortable Walking Boots: Essential for those Kilkenny cobbles.
• Layers (Sweater/Fleece): The wind at the Wicklow Gap can be biting!
• Portable Power Bank: You’ll need it for all the sheepdog videos; the bus I was on did have a USB charger though.
• A Bit of Cash (Euros): Handy for small farm souvenirs or a quick pint. They do take credit cards, to a very limited extent, American Express, so have a MasterCard or Visa ready. You can use an ATM to get cash as you get a much better rate.

I didn’t have a rain jacket as it was too bulky for my backpack, but I did have an umbrella. Luckily, it only rained when we were in the bus :-).

Frequently Asked Questions

Final Thoughts

If you want a tour that feels like a friend is showing you around their backyard, book with Wild Rover Tours. Between the sheepdogs, the ancient crosses, and Dave’s ukulele, it’s a day that perfectly encapsulates why people fall in love with Ireland.

 

Book Your Wild Rover Adventure Here

 

Have you ever visited the Wicklow Mountains, or did you make a wish at St. Kevin’s Cross? Let’s chat in the comments!