Drop A Pin
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About This Podcast
Drop A Pin takes you on a weekly travel adventure with Barstool's foreign correspondent, The Wonton Don, and Barstool personality, Uncle Chaps. Each episode, the fellas will Drop A Pin on a different spot around the globe and dive deep, learning everything about that location from the iconic to the obscure. Sometimes they delve into serious topics, and other times, it's just about having a laugh as they uncover the weird, wild, and unexpected. When possible, they'll have guests on to share personal anecdotes from whichever place they've dropped a pin that week. Whether you’re looking for travel tips, hilarious stories, or a fresh take on global destinations, Drop A Pin delivers the perfect blend of humor and insight as they get to the bottom of what makes every place in the world unique.
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Recent Episodes
A Real Disney Adult Walks Us Through The Ins And Outs Of Disney Travel (📍Disney) | Drop A Pin Ep. 86
This week on Drop A Pin we are talking to Papa Best, former Baldstoolie and Barstool Idol participant. Aside from his appearances in the Barstool Universe Papa is a theme park and cruise influencer…
Nobody Does Solo Travel Like Ryen Russillo | Drop A Pin Ep. 86
This week on Drop A Pin we are joined by the king of travelogues, Ryen Russilo! Ryen talks about his appreciation of solo travel and how he makes his Russillo on the road Travelogues. Ryen walks us…
Sam Tallent Got Caught In A Paris Riot While Writing His New Book (📍Sam Tallent) | Drop A Pin Ep. 85
This week on Drop A Pin we have Sam Tallent live from Donnie’s Hoon Deck! Sam talks about how Chaps helped write his new novel Brut, writing in Paris during riots, touring in Australia and New…
The Behind The Scenes Chaos Of Getting A Hair Transplant In Turkey (📍Baldstool Recap) | Drop A Pin Ep. 84
This week on Drop A Pin we are recapping Baldstool Season 2 with Mook, White Sox Dave, Mikey Bets and the one and only Ben Mintz. The boys tell the their experienced going with a group of 30+ people…
How A Mid Flight Break Up Got Kelly Keegs a Job at Barstool (📍Greece) | Drop A Pin Ep. 83
This week on Drop A Pin Kelly Keegs jons us to talk about her favorite travel destination, Greece! Kelly talks about how a mid flight break up landed her her job at barstool, her favorite things…
Medellín Is The Greatest Comeback Story in the World (📍Medellin) | Drop A Pin Ep. 82
This week on Drop A Pin we are recapping Uncle Chaps’ most recent solo adventure to Medellín! Chaps breaks down his first time staying in a hostel, his thoughts on Colombia, and Donnie compares notes…
Is Turkmenistan the Weirdest Country on Earth? Feat. Doug Barnard | Drop A Pin Ep. 81
This week on Drop A Pin we are joined by Doug Barnard, a fellow travel youtuber who helped Donnie when planning his trip to Iraq and the most recent season of Baldstool. Doug leads group tours to…
Doitche Explains Everything New Hampshire and Oktoberfest (📍New Hampshire) | Drop A Pin Ep. 80
This week on Drop A Pin we are joined by one of Barstools newest hires - Ronnie Doitch! Doitch has always been around in the Barstool world but now he is all in and is here to tell us his stories…
What It’s Actually Like in the World’s Newest Country ft. Giulio (📍South Sudan) | Drop A Pin Ep. 79
This week on Drop A Pin we are joined by our good friend Giulio Gallerotti to catch up with him on his most recent adventures to India and the the newest country, South Sudan. Follow Giulio on IG…
Rone’s Big Fat Ethiopian Wedding (📍Ethiopia) | Drop A Pin Ep. 78
This week on Drop A Pin we are joined by Rone from Son Of A Boy Dad and Rone Dot Com. Rone is here to talk about being a new father and traveling with kids and then he breaks down his wild trip to…
Finding the Last Cannibals Was Easier Than Leaving Dubai feat. Seal On Tour | Drop A Pin Ep. 77
This week on Drop A Pin we are joined by travel YouTuber Seal on Tour to talk to Donnie about some of his craziest adventures, more specifically his trip to West Papua with the goal of meeting a…
Stop Being an Idiot With Your Airline Miles - The Point Guy Shows Us How | Drop A Pin Ep. 76
This week on Drop A Pin we have Nicky Kelvin from The Points Guy to teach us everything there is to know about credit card points and how to maximize your points to book the best…
Want To Party With New York’s Hasidic Jews? Joey Avery Has A Guy For That | Drop A Pin Ep. 75
This week on Drop A Pin Joey Avery joins to talk about how he got his start doing comedy in Cape Town, how he ended up spending the holiday of Purim with New York’s Hasidic Jewish community and tells…
Budapest Made Me Fall In Love With Solo Travel and Goulash (📍Budapest) | Drop A Pin Ep. 74
This week on Drop A Pin Chaps is back from his trip to budapest on his first ever solo international trip. Timestamps: (00:00:00) - Show Start (00:00:30) - Pre Boarding (00:16:12) - Chaps Trip to…
So You Found a Dead Body in China… Now What? (📍Inner Mongolia) | Drop A Pin Ep. 73
This week on Drop A Pin we have on Jake, one of Donnie's friends from his China days. Jake joins us to tell the story about how he and a group of friends found a dead body while out in Inner…
Two Massholes Recap Hair Transplant Trip to Turkey with 30 Americans (📍 Turkiye) | Drop A Pin Ep. 72
This Week on Drop A Pin we are coming to you from a hotel room in Istanbul with one of the baldstoolies, Jeremy Phelps, who you will see in Baldstool Season 2. Jeremy is from Boston so he is here to…
We Took a Day Trip from Chicago to the Grand Canyon | Drop a Pin Ep. 71
This week on Drop A Pin we are recapping our trip featured in our new series Daytripping. We break down our trip to the American Southwest and then talk about what Chap's learned about the Grand…
What Is Iran Actually Like? A Persian American Answers | Drop A Pin Ep. 70
Disclaimer: This Episode Was Recorded on January 30th 2026 This week on Drop A Pin we are joined by friend of the program Chris Bader a local comedian and his father to talk about his birthplace…
How To Plan A Solo Abroad Trip | Drop A Pin Ep. 69
This week on Drop A Pin we are sending Uncle Chaps on his first ever solo abroad content trip! Donnie walks us through how he personally has planned his trips and we pick a location for Chaps to go.…
Are All-Inclusive Resorts Actually Worth It? | Drop A Pin Ep. 68 (📍Cancún)
This week on Drop A Pin we are diving into one of the most divisive topics in the travel work: All Inclusive resorts. Donnie talks about his most recent trip to Cancun that reinforced his negative…
Frequently Asked Questions
Drop A Pin has published 87 episodes since October 2024, covering topics in Places & Travel, Society & Culture.
Drop A Pin is currently highly active with new episodes weekly. Average episode length is 1h 40m.
Sign up on Grep.FM to access contact details for Drop A Pin, including email and social media links.
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