Drop A Pin

Sep 07, 2026 — On the 100th episode of Drop A Pin, Donnie’s wife joins the podcast to share what it’s really like traveling the world with Barstool Sports’ own “Foreign Correspondent,” Donnie Does. From their very first vacation together in the Philippines, where...

Aug 31, 2026 — This week on Drop A Pin we are coming to you from Camp Barstool and are ABSOLUTELY delighted to be joined by the one and only, legendary dungeon master Timm Woods! Timm talks about his experiences teaching abroad, traveling in Vang Vieng, and his...

Aug 24, 2026 — This week on Drop A Pin Donnie and Chaps are joined by Gareth Leonard the travel YouTube behind Travel Deeper. He talks to us about how he started his Travel YouTube channel and his experiences moving to Argentina with just $5000 in his pocket!...

Aug 17, 2026 — This week on Drop A Pin Uncle Chaps and White Sox Dave recap their recent trip to Greenland for Uncle Chaps Series No Objectives Out September 17th! Visit https://www.nobullproject.com and use code DROPAPIN for 35% off your entire FIRST order Visit...

Aug 10, 2026 — This week on Drop A Pin Donnie and Chaps are breaking down their about their all time dream travel destinations and we are joined by Miresh and our new friend Ric Gazarian (@globalgaz) to discuss more. Ric has visited 190 countries and is chasing 193...