Podcasts · Society & Culture

Drop A Pin

Barstool Sports

107 episodes · Explicit

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.

Episodes page 1 of 3

  1. Kentucky Bourbon Trail Tour Guide: Where to Stay, Drink & Eat | Drop A Pin Ep. 107

    · 1 h 09 min · Explicit

    Uncle Chaps just got back from the Kentucky Bourbon Trail, exploring the beautiful rolling hills of Kentucky and diving into the history of one of America's most iconic drinks: bourbon! This week on Drop a Pin, we…

  2. Syria Put Him in Prison… Then Invited Him Back 7 Years Later Feat. Sam Goodwin | Drop A Pin Ep. 106

    · 1 h 24 min · Explicit

    Our first-ever guest on Drop A Pin is BACK in the studio! Sam Goodwin joins us to share what it was like returning to Syria after being imprisoned there, meeting the president of Syria, coaching hockey in North Korea,…

  3. Shanghai Used to Be Disney World for Adults | Drop A Pin Ep. 105

    · 1 h 38 min · Explicit

    This week, Donnie takes us inside his wildest stories from living in Shanghai, China! From hanging out with rappers and meeting NBA players to cooking frogs, partying, and experiencing the city's crazy nightlife,…

  4. From Jacksonville to the Panhandle: The Ultimate North Florida Deep Dive | Drop A Pin Ep. 104

    · 1 h 20 min · Explicit

    Chaps and Donnie kick off a brand-new segment taking a deep dive into Jacksonville! We sit down with folks around the office and special guests to talk about their hometowns—covering local history, food, music, and…

  5. Alaska Is Where You Go to Disappear Feat. Giulio Gallarotti | Drop A Pin Ep. 103

    · 1 h 19 min · Explicit

    This week on Drop A Pin, our friend Giulio Gallarotti joins the show to talk about his travels through Alaska and Rwanda, plus his upcoming adventure to Bolivia. We also dive into some wild topics, including Khat, the…

  6. Sydnie Wells’ Epic Big Game Adventures in the Mountains of Patagonia | Drop A Pin Ep. 102

    · 1 h 19 min · Explicit

    This week, our good friend Sydnie Wells joins us on Drop a Pin! Sydnie tells us all about her travels to Patagonia and South America, including her experiences hunting across the region. We also get into her adventures…

  7. We Recorded a Podcast Hiking OUT the Grand Canyon | Drop A Pin Ep. 101

    · 1 h 44 min · Explicit

    Biz joins the show to tell the wild story of his Havasupai adventure with Wonton — and everything that went down along the way. Stick around for The Come Down Podcast, the FIRST-EVER mobile podcast, and what it’s like…

  8. Donnie’s Wife Reveals What It’s Really Like Traveling the World with Him | Drop A Pin Ep. 100

    · 1 h 24 min · Explicit

    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…

  9. Timm Woods Might Be The Most Cultured Dungeon Master In All The Lands | Drop A Pin Ep. 99

    · 1 h 10 min · Explicit

    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,…

  10. Moving To Argentina With Only 5 Grand Changed Gareth Leonard’s Life | Drop A Pin Ep. 98

    · 1 h 29 min · Explicit

    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…

  11. We Went To Greenland And Here’s Why You Should Too (📍Greenland) | Drop A Pin Ep. 97

    · 1 h 25 min · Explicit

    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…

  12. Top 5 Bucket List Destinations For The Fellas | Drop A Pin Ep. 96

    · 1 h 47 min · Explicit

    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…

  13. The Reality Of Living in Venice Italy: Everything You Need To Know (📍Venice) | Drop A Pin Ep. 95

    · 1 h 32 min · Explicit

    This week on Drop A Pin the boys are flying solo and we are recapping Donnie’s year living in Venice! We go through Donnie's experiences and insights from his year living in Venice and talk about the history and…

  14. Ginger Mongolian Throat Singer Wows The Fellas (📍Mongolia) | Drop A Pin Ep. 94

    · 1 h 29 min · Explicit

    This week on Drop A Pin we have on Kuja the Mongolian throat singer to talk all about how he got into throat singing and learn all about Mongolian culture! Timestamps: (00:00:00) - Show Start (00:00:14) - Top 5…

  15. Donnie’s Cousin Was Kidnapped in Yemen (While Pregnant) (📍Yemen) | Drop A Pin Ep. 93

    · 1 h 21 min · Explicit

    This week on Drop A Pin we are talking to Donnies Cousin, Jennifer Steil. Jennifer is an award winning author and journalist who started her career working at Playgirl magazine then ended up being a journalist living…

  16. The True Story Of The Viral Indian Norwegian Living In The Slums Of Mumbai (📍Mumbai) | Drop A Pin Ep. 91

    · 1 h 24 min · Explicit

    This week on Drop A Pin we are talking to Lasse Lund, the viral Norwegian Indian living in the slums. We got ahold of Lasse to hear his story of being a Norwegian STUCKED IN INDIA. Timestamps: (00:00:00) - Show Start…

  17. Everything You Didn’t See from Our America 250 Trip (ft. Nick & KB)(📍Philadelphia) | Drop A Pin Ep. 90

    · 1 h 36 min · Explicit

    This week on Drop A Pin we are joined by Nick and KB and they are here to recap the most recent season of Rediscovering America. Timestamps: (00:00:00) - Show Start (00:05:28) - A Word From Our Sponsors (00:09:22) -…

  18. Amsterdam Might Be the World's Greatest City (📍Amsterdam) | Drop A Pin Ep. 89

    · 1 h 45 min · Explicit

    This week on Drop A Pin the boys are flying solo and we are talking about one of the most infamous travel destinations: Amsterdam. Chap’s just got back from a family trip and is here to tell all about his experiences…

  19. Donnie and PFT’s Wild Trip to Qatar for Soccer’s Biggest Tournament (📍Qatar) | Drop A Pin Ep. 88

    · 1 h 44 min · Explicit

    This week on Drop A Pin we are joined by PFT Commenter to recap his 72 Hours in Qatar with Donnie. The boys reminisce on their time going to the Middle East to see the soccer on the worlds largest stage and tell…

  20. We Got High and Took A Deep Dive On The Aztec Empire | Drop A Pin Ep. 87

    · 58 min · Explicit

    This week on Drop A Pin we are back with another HIGH SCHOOL episode where Donnie and Chaps gather a class of their peers from around the barstool office to indulge in some of the devils lettuce and learn about a…

  21. A Real Disney Adult Walks Us Through The Ins And Outs Of Disney Travel (📍Disney) | Drop A Pin Ep. 86

    · 1 h 35 min · Explicit

    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 making content at…

  22. Nobody Does Solo Travel Like Ryen Russillo | Drop A Pin Ep. 86

    · 1 h 38 min · Explicit

    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 through some of his…

  23. Sam Tallent Got Caught In A Paris Riot While Writing His New Book (📍Sam Tallent) | Drop A Pin Ep. 85

    · 1 h 44 min · Explicit

    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 Zealand and so much more!…

  24. The Behind The Scenes Chaos Of Getting A Hair Transplant In Turkey (📍Baldstool Recap) | Drop A Pin Ep. 84

    · 1 h 44 min · Explicit

    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 to get hair…

  25. How A Mid Flight Break Up Got Kelly Keegs a Job at Barstool (📍Greece) | Drop A Pin Ep. 83

    · 1 h 31 min · Explicit

    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 about Greece, and her…

  26. Medellín Is The Greatest Comeback Story in the World (📍Medellin) | Drop A Pin Ep. 82

    · 1 h 41 min · Explicit

    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 from his…

  27. Is Turkmenistan the Weirdest Country on Earth? Feat. Doug Barnard | Drop A Pin Ep. 81

    · 1 h 33 min · Explicit

    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 Iraq and is also a…

  28. Doitche Explains Everything New Hampshire and Oktoberfest (📍New Hampshire) | Drop A Pin Ep. 80

    · 1 h 42 min · Explicit

    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 from his career as a…

  29. What It’s Actually Like in the World’s Newest Country ft. Giulio (📍South Sudan) | Drop A Pin Ep. 79

    · 1 h 03 min · Explicit

    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 @notjulio Check out…

  30. Rone’s Big Fat Ethiopian Wedding (📍Ethiopia) | Drop A Pin Ep. 78

    · 1 h 48 min · Explicit

    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 Ethiopia for a…

  31. Finding the Last Cannibals Was Easier Than Leaving Dubai feat. Seal On Tour | Drop A Pin Ep. 77

    · 1 h 26 min · Explicit

    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 Cannibal. He also goes…

  32. Stop Being an Idiot With Your Airline Miles - The Point Guy Shows Us How | Drop A Pin Ep. 76

    · 1 h 19 min · Explicit

    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 vacations. Timestamps: (00:00:00) -…

  33. Want To Party With New York’s Hasidic Jews? Joey Avery Has A Guy For That | Drop A Pin Ep. 75

    · 1 h 40 min · Explicit

    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 Donnie and Chaps…

  34. Budapest Made Me Fall In Love With Solo Travel and Goulash (📍Budapest) | Drop A Pin Ep. 74

    · 1 h 54 min · Explicit

    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 Budapest (00:31:35) -…

  35. So You Found a Dead Body in China… Now What? (📍Inner Mongolia) | Drop A Pin Ep. 73

    · 1 h 24 min · Explicit

    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 Mongolia. Then Donnie and…

  36. Two Massholes Recap Hair Transplant Trip to Turkey with 30 Americans (📍 Turkiye) | Drop A Pin Ep. 72

    · 1 h 21 min · Explicit

    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 give us his…

  37. We Took a Day Trip from Chicago to the Grand Canyon | Drop a Pin Ep. 71

    · 1 h 34 min · Explicit

    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 Canyon during his time…

  38. What Is Iran Actually Like? A Persian American Answers | Drop A Pin Ep. 70

    · 1 h 26 min · Explicit

    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 Iran. We talk about…

  39. How To Plan A Solo Abroad Trip | Drop A Pin Ep. 69

    · 1 h 15 min · Explicit

    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. After that Kate…

  40. Are All-Inclusive Resorts Actually Worth It? | Drop A Pin Ep. 68 (📍Cancún)

    · 1 h 32 min · Explicit

    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 opinion of the…

  41. The American Tourist Who Illegally Traveled to North Sentinel Island | Drop A Pin Ep. 67 (📍North Sentinel Island)

    · 1 h 16 min · Explicit

    This week on Drop A Pin we spoke with Mykhailo Polyakov, the American Tourist who was arrested for illegally traveling to North Sentinel Island in an attempt to capture on camera the isolated indigenous Sentinelese…

  42. Our Journey Through The Mississippi Delta (📍Rediscovering Memphis Recap) | Drop A Pin Ep. 66

    · 1 h 28 min · Explicit

    Nick and KB are BACK on the show, this time to break down Rediscovering MEMPHIS! The boys talk about their experiences filming the latest episode of Rediscovering America. We talk the blues, conversations that didn't…

  43. Donnies Weiredest Jobs In China | Drop A Pin Ep. 65 (📍Shanghai )

    · 1 h 11 min · Explicit

    This week we are back with our second CHINASODE! Diving Deep into Donnie’s stories from his time in China and this week we are focusing on the odd jobs he picked up for content and to keep the lights on. Timestamps:…

  44. Exploring The Top Travel Destinations For 2026 feat. Joey Avery and Chris O'Connor | Drop A Pin Ep. 64

    · 1 h 40 min · Explicit

    It's the last Drop A Pin of 2025! To ring in the new year we invited people from the office along with comedians Chris O'Connor and Joey Avery to talk about the locations they want to travel to the most in the new year…

  45. Rediscovering America Recap with Nick and KB | Drop A Pin Ep. 63 (📍Minnesota)

    · 1 h 28 min · Explicit

    This week on Drop A Pin we are joined by the Rediscovering America Crew to talk about their most recent expedition to Minnesota. Nick and KB break down their favorite moments from this most recent trip. The boys go…

  46. Fred Smoot Has Been To Every Continent And Has Some Bold Takes | Drop A Pin Ep. 62

    · 1 h 24 min · Explicit

    This week on The Drop A Pin Show we have sat down with ex NFL cornerback and host of the Pro Football Football Show: Fred Smoot! Smoot blew us away with his stories from traveling to every content* and some of his…

  47. Exploring The Most Conquered Island In Europe With Dante and Chaps' Mom (📍Sicily) | Drop A Pin Ep. 61

    · 1 h 50 min · Explicit

    This week we are dropping a pin in the island of Sicily! First we have one of Barstools most Italian employees Dante the Don on to talk about his experiences in Europe and give some recommendations and hidden gems.…

  48. Biz and Donnie Break Down The Highs and Lows of Filming Peakin' in Canada | Drop A Pin Ep 60

    · 1 h 28 min · Explicit

    This week Donnies hiking buddy Paul Bissonnette and he's here to break down the highs and lows of their time spent hiking in Canada while filming Peakin Season 2. They talk about how they managed to make it through the…

  49. Inside The World of Competitive Bird Watching feat. Creators of Viral Documentary "Listers" | Drop A Pin Ep 59

    · 1 h 56 min · Explicit

    This week on Drop A Pin we are joined by Quinn and Owen Reiser, the creators of the viral bird watching documentary "Listers", which is available for free on Youtube. The brothers sat down with Donnie to tell him all…

  50. We Didn't Even Know This African Country Existed - Until Giulio Went There (📍Comoros ) | Drop A Pin Ep. 58

    · 1 h 25 min · Explicit

    This week on Drop A Pin we are joined by one of our best friends, Giulio Gallarotti, to tell us all about his most recent adventures in Rwanda and Tanzania. Then Giulio sticks around for this weeks Gettin’ Cultured to…

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