If you didn’t know that the vice president and managing director of Trump International Hotel & Tower Chicago was also an expert on Ireland, Colm O’Callaghan’s name and dashing accent give him away.

O’Callaghan was born in Killarney and has impressive ties to the scenic, charming town in southwest Ireland’s County Kerry: his family owns The Failte, a popular Killarney pub and restaurant (where his mother still greets customers), and both his father and his brother have served as mayor.

O’Callaghan still visits Killarney with his family once a year. One of his favorite times to go is early fall, especially September. “The weather is still quite mild,” he says. “Most of the tourists have gone home and locals have more time for you.” It’s also a great time to find deals on hotels and airfare.

Here’s more from O’Callaghan on visiting Ireland now.

How do you get to Killarney?

I always pass through Dublin, and it’s an easy trip with many direct flights from O'Hare International Airport. The seven-and-a-half-hour flight takes off in the evening and lands in Dublin first thing in the morning. From there, I love to take the train from Dublin’s Heuston Station into Killarney—about a four-hour ride. I recommend it to everybody, as it is a lazy way to sit back and watch the countryside roll by as people go about their daily lives. You also pass through towns with old train stations that were built approximately 60-100 or so years ago, and so you see the personality of that era.

What do you do in Dublin?

Dublin surprises people. It’s such a diverse and energetic city with its pubs and restaurants, interesting streets, nightlife, and all the history. We always spend a day on the way in or out, and usually stay at the Merrion Hotel, which is located a short walk from St. Stephen’s Green, shopping on Grafton Street and a flurry of restaurants. My son’s favorite Indian restaurant in the world, called Jaipur, is in Dublin, so as a rule we always go there for dinner one night.

And what about Killarney?

Killarney is another world entirely. It’s a small town with its own character and accent. The locals seem to have more time to relax and engage with you, which gives you greater insight into the culture. It’s also very close to the countryside, only 16 miles from the coast, and surrounded by the picturesque lakes and mountains of Killarney National Park. That allows for some great outdoor activities, like miles and miles of cycling, mountain climbing, fishing, and boating. Killarney is also a great home base for day trips. You can travel around the Ring of Kerry and visit Waterville, a charming coastal village with an interesting connection to Charlie Chaplin. I especially love visiting Dingle, another town about a 45-minute drive away and home of Fungie, the lone dolphin. We eat at Doyle’s Seafood Restaurant or stop at Dick Mack’s Pub, which has a shoe store on one side, the pub on the right, and an old snug, where women and priests used to have their drinks.

Where do you stay in Killarney?

I like the family-owned Killarney Park Hotel right in the center of town. There are also two beautiful luxury resorts outside of town that overlook the Lakes of Killarney: the Aghadoe Heights Hotel and the Europe Hotel, which has an interesting story and a great spa.

Why September?

All-Ireland Finals for Gaelic football take place over the third weekend of September. It’s immensely popular in the country—as much so as hurling and on par with American football here in the States. The finals are played in Croke Parke in Dublin and the city just explodes with the colors of the teams, the pubs are busy, people are singing songs, and there’s just a vibrant energy in the air everywhere.

What’s next when you visit again?

At the top of my list is a visit to Doonbeg and Trump International Golf Links & Hotel Ireland, a fabulous resort right on the coast in West Clair. The property was rated the No. 1 resort in Europe by Condé Nast Traveler. I’ve also become a runner in recent years and am running the Chicago Marathon this fall. Next year, I’m thinking about running the Dublin Marathon in October, when the weather is cooler and ideal for running.

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