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. 4 DAYS AGO

    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. After that Kate joins the show to give Chaps some places to check out while he is on his adventure! Timestamps: (00:00:00) - Show Start (00:01:41) - Donnie's Solo Travel Horror Stories (00:20:07) - Chaps Books His Trip (00:41:35) - A Word From Our Sponsors (00:56:08) - Kate Plans Chaps' Excursions Find out why Nutrafol is the best-selling hair growth supplement brand at https://Nutrafol.com promo code PIN. Become a Fora Advisor today at https://Foratravel.com/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 $300 in Bonus Bets if your bet wins. Min. -500 odds req. Token and Bonus Bets are single-use and non-withdrawable. Bet must settle by and Token expires 2/22/26. Bonus Bets expire in 7 days (168 hours). Stake removed from payout. Terms: sportsbook.draftkings.com/promos. Ends 2/15/26 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 15m

  2. 26 JAN

    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 opinion of the popular travel destination. We are joined by Dante, Eddie, Mikey Bets and Miresh Patel who all have varying experiences/beliefs on All Inclusive resorts and Cancun. Timestamps: (00:00:00) - Show Start (00:01:03) - Snowblowing (00:05:06) - All Inclusive Talk (00:11:21) - Chaps Experiences At All Inclusive’s (00:23:19) - Donnies Cancun Trip (00:42:57) - Viva La Cruise (00:47:54) - A word rom our sponsors (00:54:16) - Eddie (01:03:27) - Miresh and Mikey (01:13:34) - Dante Find out why Nutrafol is the best-selling hair growth supplement brand at https://Nutrafol.com promo code PIN. Download Cash App Today: https://click.cash.app/ui6m/q2t3jrra #CashAppPod. Cash App is a financial services platform, not a bank. Banking services provided by Cash App’s bank partner(s). Prepaid debit cards issued by Sutton Bank, Member FDIC. See terms and conditions at https://cash.app/legal/us/en-us/card-agreement. Discounts and promotions provided by Cash App, a Block, Inc. brand. Visit http://cash.app/legal/podcast for full disclosures. 
📍 All Our Links: https://linktr.ee/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 32m

  3. 19 JAN

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

    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 tribe. Disclaimer: This episode discusses the personal experiences of a guest who illegally traveled to North Sentinel Island. Drop A Pin and its hosts do not condone, support, or encourage these actions in any way, nor do we encourage anyone to attempt to visit restricted or protected locations. North Sentinel Island is legally off-limits, and these restrictions exist to protect both the Indigenous Sentinelese people and outside visitors. This conversation is presented solely for educational, journalistic, and storytelling purposes. We believe the guest’s experience is a unique case that raises important questions about travel ethics, curiosity, risk, and responsibility. Listeners should not interpret this episode as an endorsement of illegal or dangerous travel. We strongly encourage responsible, lawful, and ethical travel at all times. Timestamps: (00:00:38) - Pre Boarding (00:05:58) - Interview with Mishka (00:07:01) - How did he get to NSL (00:14:29) - The Coke can and coconut (00:22:09) - Second Trip (00:26:26) - Indian Jail (00:29:42) - Reactions/Blowback (00:34:40) - Regrets (00:47:10) - A Word From Our Sponsors (00:51:17) - North Sentinel Island Discussion (01:02:42) - Pathology Fact Check 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 $300 in Bonus Bets if your bet wins. Min. -500 odds req. Token and Bonus Bets are single-use and non-withdrawable. Token expires 2/1/26. Bonus Bets expire in 7 days (168 hours). Stake removed from payout. Terms: sportsbook.draftkings.com/promos. Ends 1/25/26 at 11:59 PM ET. Sponsored by DK. Get 10% off your first month of BlueChew Gold with code DROP https://BlueChew.com Become a Fora Advisor today at https://Foratravel.com/wonton 
📍 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 16m

  4. 12 JAN

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

    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 make the final cut, and everyones thoughts on the Mississippi delta. Be sure to watch the latest episode of Rediscovering America and also check out our new friend Mohammed on IG @sapphire.esmod ! Timestamps: (00:00:00) - Episode Start (00:06:24) - Memphis (00:17:37) - Drum Shop/Gong Chamber (00:21:59) - Dyers Burgers (00:25:59) - Peabody Hotel (00:39:15) - Earnestine & Hazel's (00:47:19) - Shack Up Inn (01:05:29) - A Word From Our Sponsors (01:10:54) - Rediscovering America Q&A 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 $300 in Bonus Bets if your bet wins. Min. -500 odds req. Token and Bonus Bets are single-use and non-withdrawable. Token expires 2/1/26. Bonus Bets expire in 7 days (168 hours). Stake removed from payout. Terms: sportsbook.draftkings.com/promos. Ends 1/25/26 at 11:59 PM ET. Sponsored by DK. Get 10% off your first month of BlueChew Gold with code DROP https://BlueChew.com 📍 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

  5. 5 JAN

    Donnies Weiredest Jobs In China | Drop A Pin Ep. 64 (📍Shanghai )

    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: (00:00:00) - Episode Start (00:02:16) - Tutor Donnie (00:09:29) - University Professor Donnie (00:24:28) - Donnie Taught on Superbowl Monday (00:30:59) - Whiteface Jobs (00:31:26) - Fertility Clinic (00:33:52) - Donnie's Weirdest Whiteface Jobs (00:37:05) - Donnie Worked With Vice (00:42:54) - Donnie Was A Fake Doctor (00:50:16) - Donnie Was Paid To Drink (00:57:07) - General China Talk 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 $300 in Bonus Bets if your bet wins. Min. -500 odds req. Token and Bonus Bets are single-use and non-withdrawable. Token expires 2/1/26. Bonus Bets expire in 7 days (168 hours). Stake removed from payout. Terms: sportsbook.draftkings.com/promos. Ends 1/25/26 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 11m

  6. 29/12/2025

    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

  7. 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

  8. 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
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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 - 2026
  • Episodes
    69
  • Rating
    Explicit
  • Copyright
    © 2026 Barstool Sports, Inc.
  • Show Website
    Drop A Pin

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