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Ireland w/ Greg Fitzsimmons | You Be Trippin' with Ari Shaffir
You Be Trippin' Podcast · Watch on YouTube · Generated with SnapSummary · 2026-10-28

🎙️ Episode Summary: Greg Fitzsimmons’s Ireland Trip

The big story

  • Greg Fitzsimmons recalls a six-month solo backpacking trip through Europe in 1984, shortly after high school. He saved about $3,000 working as a cook and parking cars.
  • He traveled on a tight budget, mostly using hitchhiking, youth hostels, trains, maps, guidebooks, and travelers’ checks—long before smartphones or easy online bookings.
  • Ireland was meant to be a brief stop, but he fell in love with the country and stayed for months. He describes its hospitality, music, pubs, and green countryside as highlights.

Ireland: memorable stops and moments

  • Dublin: Greg arrived there after traveling through London and Wales. He later headed south, choosing a direction and seeing where the road took him.
  • Cork and County Kerry: In Cork, he met Theo, a local student who became a lifelong friend. They hitchhiked together and stayed with Theo’s family.
  • Muckross and the countryside: Greg recounts a chaotic night out in a small town, followed by a very traditional Irish breakfast at a bed-and-breakfast.
  • Kenmare: He rented a basic farm outbuilding, tried to keep warm with peat, and spent his days attempting to write a novel. In the evenings, he visited the local pub and grew fond of Molly, the bartender. He gave her the only copy of his roughly 70-page manuscript.
  • The Aran Islands: He hiked on Inishmore and bought an Aran wool sweater, known for its lanolin-rich wool and water-resistant qualities.
  • Belfast: Greg visited during the Troubles and remembers the tense atmosphere, including armed patrols, checkpoints, and security concerns. He says the experience was unsettling.

Other travel stories

  • Greg says he was hospitalized with an asthma attack shortly after arriving in Ireland. He recalls receiving several days of care without a bill.
  • On the wider trip, he saw Bruce Springsteen at Wembley Stadium on the Born in the U.S.A. tour, then made his way home from Newark Airport by hitchhiking.
  • He describes travel as an adventure that requires effort and flexibility—not simply a holiday: plans change, directions must be asked for, and travelers have to meet people along the way.
  • The conversation also touches on his later travels, including Greece, Denmark, and subsequent visits to Ireland.

Practical travel takeaways 🧭

  • Stay flexible: Pick a direction, allow plans to change, and make the most of wherever you end up.
  • Talk to locals and other travelers: Asking for help can lead to useful recommendations, new connections, and unexpected hospitality.
  • Bring reliable offline navigation: Greg depended on paper maps and budget guidebooks before smartphones and GPS.
  • Protect your valuables and documents: His stories include attempts to steal luggage, and he discusses the importance of keeping backup payment options.
  • Quick hotel hack: Use a trouser hanger with clips to hold a hotel room’s curtains together and block out light.
  • Tip hotel housekeeping: Greg recommends leaving a small daily tip, especially where it can make a meaningful difference.

More from the episode

  • The hosts trade jokes and digress into comedy, pop culture, relationships, and current events.
  • Greg promotes his stand-up special, You Know Me, on YouTube, along with his tour dates and podcasts.
  • In the closing segment, the host reads a postcard from listener Dolan, who writes about traveling in Panama and Mexico and hoping to visit Venezuela. Dolan recommends Oaxaca and mentions Canaima National Park and Angel Falls.
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