Drop A Pin

Barstool Sports
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  • PLACES & TRAVEL
  • UPDATED WEEKLY

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.

  1. 6 DAYS AGO

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

    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 Timestamps: (00:00:00) - Donnie and Chaps 2026 Travel Plans (00:15:41) - Donnie Tried DMT (00:33:50) - Joey Avery and Chris O'Connor Join (00:36:17) - Joey Averys 2026 Travel Plans (00:41:16) - Chris O'Connors 2026 Travel Plans (00:51:31) - Megan Makin Money Joins The Show (00:54:10) - MMM's 2026 Travel Plans (01:04:23) - Chief Joins The Show (01:25:29) - Mikey Bets Joins The Show Follow Drop A Pin! IG: https://www.instagram.com/thedropapinshow/?hl=en X: https://x.com/DropAPinShow Tik Tok: https://www.tiktok.com/@thedropapinshow Follow The Wonton Don! IG: thewontondon TikTok: thewontondon X: @donniedoesworld FB: https://www.facebook.com/DonnieDoes/ Follow Uncle Chaps! IG: @unclechaps TikTok: @unclechaps X: @UncleChaps

    1h 40m

  2. 22/12/2025

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

    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 over their highs and lows, tell stories that didn't make the final cut, and explain what lead to that unpleasant surprise appearance from White Sox Dave. Tune in to learn more about how Rediscovering Minnesota came to be and stay tuned for Rediscovering Missouri coming early January! Then for this week's Gettin Cultured Mook joins us to go over his first time traveling abroad to Europe! Timestamps: (00:00:00) - Preboarding (00:02:28) - Accordion Museum (00:09:23) - Meat Raffle (00:14:12) - Jucy Lucy (Cut Scene) (00:20:07) - The Mall of America (00:26:11) - White Sox Dave (World's Largest Twine Ball) (00:37:14) - The Boys Souvenirs (00:42:16) - Driving a Tank (00:54:01) - Chaps' Quiz (01:05:20) - A Word From Our Sponsors (01:06:12) - Gettin’ Cultured with Mook Gambling problem? Call 1-800-GAMBLER (MI/NJ/PA/WV). Help is available for problem gambling, call (888) 789-7777 or visit ccpg.org (CT).  21+. Physically present in MI/NJ/PA/WV only. Void in CT/ONT. Eligibility restrictions apply. 1 per new customer. Opt-in req. Min. $5 in wagers req. Max. 500 Casino Spins for featured game. Spins issued as 50 Spins/day upon login for 10 days. Spins are non-withdrawable and expire 24 hours after issuance. $0.20 per Spin. Game availability may vary. Terms: casino.draftkings.com/promos. Ends 1/4/26 at 11:59 PM ET. Sponsored by DK. 
📍 Listen Now: Apple Podcasts https://podcasts.apple.com/us/podcast/drop-a-pin/id1773703211 Spotify https://open.spotify.com/show/31NNzfeA0tEfKE9LpqycFN?si=5dc8e774513e4458 Youtube https://www.youtube.com/@DropAPinShow Follow Drop A Pin! IG: https://www.instagram.com/thedropapinshow/?hl=en X: https://x.com/DropAPinShow Tik Tok: https://www.tiktok.com/@thedropapinshow Follow The Wonton Don! IG: thewontondon TikTok: thewontondon X: @donniedoesworld FB: https://www.facebook.com/DonnieDoes/ Follow Uncle Chaps! IG: @unclechaps TikTok: @unclechaps X: @UncleChaps

    1h 28m

  3. 15/12/2025

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

    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 travel hacks and recommendations. Then we are trying out a new segment: Pinball! Pinball is where we talk about interesting topics or stories that aren’t big enough for an entire episode. Chaps talks about the largest city with the least amount of advertising: Sao Polo and Donnie shares the story of Karl Bushby the man who is trying to walk across the entire globe! Timestamps: (00:00:17) Preboarding (00:00:48) Fred Smoot Interview (00:02:43) Monaco (00:08:46) Fred's Travel Hacks (00:15:45) New Orleans (00:16:39) Fred Likes to Travel By Himself (00:28:09) Fred Smoot's Dream Destinations (00:37:10) Mississippi (00:42:30) Fred’s Favorite Nightlife city (00:52:00) Fred’s A History Buff (00:53:16) A Word From Our Sponsors (00:57:57) Pinball (01:09:33) Donnie’s Pinball Get 10% off your first month of BlueChew Gold with code DROP https://bluechew.com Exclusive $35 off Carver Mat at https://on.auraframes.com/WONTON. Promo Code WONTON Get Huel today with this exclusive offer for New Customers of 15% OFF with code WONTON at https://huel.com/wonton (Minimum $75 purchase) 
📍 Listen Now: Apple Podcasts https://podcasts.apple.com/us/podcast/drop-a-pin/id1773703211 Spotify https://open.spotify.com/show/31NNzfeA0tEfKE9LpqycFN?si=5dc8e774513e4458 Youtube https://www.youtube.com/@DropAPinShow Follow Drop A Pin! IG: https://www.instagram.com/thedropapinshow/?hl=en X: https://x.com/DropAPinShow Tik Tok: https://www.tiktok.com/@thedropapinshow Follow The Wonton Don! IG: thewontondon TikTok: thewontondon X: @donniedoesworld FB: https://www.facebook.com/DonnieDoes/ Follow Uncle Chaps! IG: @unclechaps TikTok: @unclechaps X: @UncleChaps

    1h 24m

  4. 08/12/2025

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

    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. Then for this weeks Gettin’ Cultured Uncle Chap’s Mom joins us to talk to the boys about her experiences living in Sicily while raising Uncle Chaps! Timestamps: 00:00:00 — Dante Interview 00:05:44 — Favorite Italian Foods 00:22:34 — Dante Is an Italian Citizen 00:30:13 — The Most Underrated Part of Italy 00:39:59 — Dante’s Travel Experiences 00:46:23 — Eating Horse Meat 00:51:36 — The Mafia 01:04:50 — Dante’s Personal Recommendations 01:17:59 — A Word From Our Sponsors 01:22:18 — Gettin' Cultured With Chaps' Mpm Get 10% off your first month of BlueChew Gold with code DROP https://bluechew.com Exclusive $35 off Carver Mat at https://on.auraframes.com/WONTON. Promo Code WONTON GAMBLING PROBLEM? CALL 1-800-GAMBLER, (800) 327-5050 or visit gamblinghelplinema.org (MA). Call 877-8-HOPENY/text HOPENY (467369) (NY). Please Gamble Responsibly. 888-789-7777/visit ccpg.org (CT), or visit www.mdgamblinghelp.org (MD).  21+ and present in most states. (18+ DC/KY/NH/WY). Void in ONT/OR/NH. Eligibility restrictions apply. On behalf of Boot Hill Casino & Resort (KS). Pass-thru of per wager tax may apply in IL. 1 per new customer. Must register new account to receive reward Token. Must select Token BEFORE placing min. $5 bet to receive $200 in Bonus Bets if your bet wins. Min. -500 odds req. Token and Bonus Bets are single-use and non-withdrawable. Token expires 1/11/26. Bonus Bets expire in 7 days (168 hours). Stake removed from payout. Terms: sportsbook.draftkings.com/promos. Ends 1/4/26 at 11:59 PM ET. Sponsored by DK. 
📍 Listen Now: Apple Podcasts https://podcasts.apple.com/us/podcast/drop-a-pin/id1773703211 Spotify https://open.spotify.com/show/31NNzfeA0tEfKE9LpqycFN?si=5dc8e774513e4458 Youtube https://www.youtube.com/@DropAPinShow Follow Drop A Pin! IG: https://www.instagram.com/thedropapinshow/?hl=en X: https://x.com/DropAPinShow Tik Tok: https://www.tiktok.com/@thedropapinshow Follow The Wonton Don! IG: thewontondon TikTok: thewontondon X: @donniedoesworld FB: https://www.facebook.com/DonnieDoes/ Follow Uncle Chaps! IG: @unclechaps TikTok: @unclechaps X: @UncleChaps

    1h 50m

  5. 01/12/2025

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

    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 treacherous mountains of British Columbia then Corey Rutledge and Tyler Spaid, two of the producers behind Peakin' join us in studio to give us their sides of the story of the making of Peakin' Season 2. Check Out Peakin’ here: Pilot - https://youtu.be/TYxvsJjdkQw?si=3k1nzOHchcOl3G0L Episode 1 - https://youtu.be/XFKCblJLCB4?si=R9uE6kioLgbBk7TO Episode 2 - https://www.youtube.com/watch?v=VkfSd_gnz9U Timestamps: 00:00:14 - Pre Boarding 00:10:27 - How Season 2 Came Together 00:17:20 - Vancouver 00:24:23 - The H!ghest Donnie's Been On Camera 00:27:09 - Don and Biz Peaks and Valleys 00:34:33 - Episode 3 Preview 00:44:16 - What's Next for Peakin' 00:48:52 - Chaps Teaches Biz About Duels 00:51:58 - Closing Thoughts 01:05:34 - a word from our sponsors 01:09:39 - Gettin' Cultured with Corey and Tyler 01:17:21 - Corey and Tylers Peaks and Valleys 01:20:14 - What's next for Peakin Season 3 01:22:49 - Pros of Cons of filming with Biz Gambling problem? Call 1-800-GAMBLER (MI/NJ/PA/WV). Help is available for problem gambling, call (888) 789-7777 or visit ccpg.org (CT). 21+. Physically present in MI/NJ/PA/WV only. Void in CT/ONT. Eligibility restrictions apply. 1 per new customer. Opt-in req. Min. $5 in wagers req. Max. 500 Casino Spins for featured game. Spins issued as 50 Spins/day upon login for 10 days. Spins are non-withdrawable and expire 24 hours after issuance. $0.20 per Spin. Game availability may vary. Terms: casino.draftkings.com/promos. Ends 1/4/26 at 11:59 PM ET. Sponsored by DK. Exclusive $35 off Carver Mat at https://on.auraframes.com/WONTON. Promo Code WONTON Get Huel today with this exclusive offer for New Customers of 15% OFF with code WONTON at https://huel.com/wonton (Minimum $75 purchase) 📍 Listen Now: Apple Podcasts https://podcasts.apple.com/us/podcast/drop-a-pin/id1773703211 Spotify https://open.spotify.com/show/31NNzfeA0tEfKE9LpqycFN?si=5dc8e774513e4458 Youtube https://www.youtube.com/@DropAPinShow Follow Drop A Pin! IG: https://www.instagram.com/thedropapinshow/?hl=en X: https://x.com/DropAPinShow Tik Tok: https://www.tiktok.com/@thedropapinshow Follow The Wonton Don! IG: thewontondon TikTok: thewontondon X: @donniedoesworld FB: https://www.facebook.com/DonnieDoes/ Follow Uncle Chaps! IG: @unclechaps TikTok: @unclechaps X: @UncleChaps

    1h 28m

  6. 24/11/2025

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

    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 about the world of competitive birdwatching and some of their wild stories from their time living in a van while making the movie. Then we are joined by White Sox Dave and Chief to go through some of our favorite bird facts from around the internet! Timestamps: (00:00:34) - Pre Boarding (00:08:36) - Black Friday/Peakin' Announcement (00:09:10) - Interview Starts (00:17:17) - Their goals while making the doc (00:32:31) - Oklahoma (00:45:00) - Cougars (01:14:19) - Dream Birdwatching Locations (01:16:14) - A word from our sponsors (01:17:42) - Gettin' Cultured with White Sox Dave and Chief GAMBLING PROBLEM? CALL 1-800-GAMBLER, (800) 327-5050 or visit gamblinghelplinema.org (MA). Call 877-8-HOPENY/text HOPENY (467369) (NY). Please Gamble Responsibly. 888-789-7777/visit ccpg.org (CT), or visit www.mdgamblinghelp.org (MD). 21+ and present in most states. (18+ DC/KY/NH/WY). Void in ONT/OR/NH. Eligibility restrictions apply. On behalf of Boot Hill Casino & Resort (KS). Pass-thru of per wager tax may apply in IL. 1 per new customer. Must register new account to receive reward Token. Must select Token BEFORE placing min. $5 bet to receive $200 in Bonus Bets if your bet wins. Min. -500 odds req. Token and Bonus Bets are single-use and non-withdrawable. Token expires 1/11/26. Bonus Bets expire in 7 days (168 hours). Stake removed from payout. Terms: sportsbook.draftkings.com/promos. Ends 1/4/26 at 11:59 PM ET. Sponsored by DK. 📍 Listen Now: Apple Podcasts https://podcasts.apple.com/us/podcast/drop-a-pin/id1773703211 Spotify https://open.spotify.com/show/31NNzfeA0tEfKE9LpqycFN?si=5dc8e774513e4458 Youtube https://www.youtube.com/@DropAPinShow Follow Drop A Pin! IG: https://www.instagram.com/thedropapinshow/?hl=en X: https://x.com/DropAPinShow Tik Tok: https://www.tiktok.com/@thedropapinshow Follow The Wonton Don! IG: thewontondon TikTok: thewontondon X: @donniedoesworld FB: https://www.facebook.com/DonnieDoes/ Follow Uncle Chaps! IG: @unclechaps TikTok: @unclechaps X: @UncleChaps

    1h 56m

  7. 17/11/2025

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

    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 talk to us about North Korea! Giulio also just put out a new incredible video “The Lama’s Prophecy” Check it out now on his youtube page! Timestamps: (00:00:25) Show Start (00:00:47) Giulio's New Video (00:03:54) Giulio's Trip to Rwanda (00:05:36) Rwanda's Comedy Scene (00:11:56) Dave Chappelle (00:13:59) How Often Do Comedians Change Their Sets (00:17:25) Kigali (00:21:25) Bisoke Crater (00:23:58) Travel Youtuber Inside Baseball (00:25:38) Tanzania (00:30:17) Cheap Safaris (00:33:44) Swimming with Hippos (00:34:53) Malaria Medication (00:38:10) Space (00:40:24) Kilimanjaro (00:43:12) Zanzibar (00:43:49) Comoros (00:50:22) Flying Fox Bat (00:53:40) Travel Hack for Cheap Flights (00:59:36) A Word From Our Sponsors (01:03:23) Gettin' Cultured with Giulio Head to https://BlueChew.com for details and safety info. Get your first month of BlueChew FREE Just use promo code DROP at checkout and pay five bucks for shipping Over 2 million butts love TUSHY. Get 10% off Tushy with the code PIN at https://hellotushy.com/PIN! #tushypod Try Huel with 15% OFF for New Customers today using my code WONTON at https://huel.com/wonton. Fuel your best performance with Huel today! 📍 Listen Now: Apple Podcasts https://podcasts.apple.com/us/podcast/drop-a-pin/id1773703211 Spotify https://open.spotify.com/show/31NNzfeA0tEfKE9LpqycFN?si=5dc8e774513e4458 Youtube https://www.youtube.com/@DropAPinShow Follow Drop A Pin! IG: https://www.instagram.com/thedropapinshow/?hl=en X: https://x.com/DropAPinShow Tik Tok: https://www.tiktok.com/@thedropapinshow Follow The Wonton Don! IG: thewontondon TikTok: thewontondon X: @donniedoesworld FB: https://www.facebook.com/DonnieDoes/ Follow Uncle Chaps! IG: @unclechaps TikTok: @unclechaps X: @UncleChaps

    1h 25m

  8. 10/11/2025

    How Donnie Survived His Awkward First Weeks in China (Guangzhou 📍)| Drop A Pin Ep. 57

    This week on Drop A Pin we are finally diving into Donnie's earliest Chinese Adventures. Before he had ever picked up a camera he spent a year living in Guangzhou and in this episode we are taking a deep dive into Donnies lost year in china from teaching preschoolers, parting with scousers, to camping in the great wall Donnie tells us some never before heard stories from far east! Then stick around for a very special Gettin' Cultured with our good friend Henry from 3 Little Pigs in Chicago who happens to be from Guangzhou for a special segment we are calling Ask a Chinese Person! Timestamps: (00:00:24) Show Start (00:09:26) Teaching in China (00:26:27) Donnie was hired as a rapper (00:42:23) Camping on the Great Wall (01:17:02) A Word from our sponsors (01:19:51) Ask A Chinese Person (01:21:14) Steven Cheah asks a question (01:36:06) Nicky Smokes asks a question (01:45:51) White Sox Dave asks a question Head to https://BlueChew.com for details and safety info. Get your first month of BlueChew FREE Just use promo code DROP at checkout and pay five bucks for shipping Today, get Huel for FIFTEEN PERCENT OFF with this exclusive offer for New Customers only with code wonton at https://huel.com/wonton (Minimum $75 purchase).

    1h 60m
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Hosts & Guests

About

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.

Information

  • Channel
    Barstool Sports
  • Creator
    Barstool Sports
  • Years Active
    2024 - 2025
  • Episodes
    64
  • Rating
    Explicit
  • Copyright
    © 2026 Barstool Sports, Inc.
  • Show Website
    Drop A Pin

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