Podcast
Drop A Pin
Hosted by Barstool Sports · EN
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.
42episodes
Episodes
Newest firstAll episodes
Stop Being an Idiot With Your Airline Miles - The Point Guy Shows Us How | Drop A Pin Ep. 76
Mar 2301:18:54Tap to summarizeThis 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) - Show Start (00:00:34) - Pre Boarding (00:06:21) - The Points Guy Interview Starts (00:20:53) - A Word From Our Sponsors (00:28:54) - The Best Credit Cards for Points (00:38:09) - Airline Lounges (01:09:58) - Chaps Booked A Trip (01:17:38) - Dream Drop A Pin Trip Visit https://nobullproject.com and use code DROPAPIN for 35% off your entire FIRST order. Start building your credit the easy way. Go to https://Super.com/credit right now to see how Super+ can help you boost your credit score. GAMBLING PROBLEM? CALL 1-800-GAMBLER or 1-800-522-4700, (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. $5+ first-time bet req. Max. $200 issued as non-withdrawable Bonus Bets that expire in 7 days (168 hours). Stake removed from payout. Terms: sportsbook.draftkings.com/promos. Ends 4/6/26 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
Transcribe →Want To Party With New York’s Hasidic Jews? Joey Avery Has A Guy For That | Drop A Pin Ep. 75
Mar 1601:39:46Tap to summarizeThis 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 some of his other travel stories. Check out Joey Avery Live in San Francisco Out Now: https://www.youtube.com/watch?v=t4xlXat3ck4 Timestamps: (00:00:00) - Show Start (00:00:40) - Pre Boarding (00:14:18) - Starting Comedy in Cape Town (00:43:06) - A Word From Our Sponsors (00:46:19) - Celebrating Purim With Hassidic Jews (01:05:53) - Another Word From Our Sponsors (01:09:36) - Cuba 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 Start building your credit the easy way. Go to https://Super.com/credit right now to see how Super+ can help you boost your credit score. GAMBLING PROBLEM? CALL 1-800-GAMBLER or 1-800-522-4700, (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. $5+ first-time bet req. Max. $200 issued as non-withdrawable Bonus Bets that expire in 7 days (168 hours). Stake removed from payout. Terms: sportsbook.draftkings.com/promos. Ends 4/6/26 at 11:59 PM ET. Sponsored by DK. Follow Drop A Pin! IG: TheDropAPinShow X: DropAPinShow Tik Tok: 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
Transcribe →Budapest Made Me Fall In Love With Solo Travel and Goulash (📍Budapest) | Drop A Pin Ep. 74
Mar 901:53:34Tap to summarizeThis 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) - Traveling by Yourself (01:07:33) - A Word From Our Sponsors (01:11:25) - Gettin Cultured Get 10% off your first month of BlueChew Gold with code DROP https://BlueChew.com Get $10 off your first month’s subscription and free shipping when you go to https://Nutrafol.com and enter the promo code PIN Visit https://nobullproject.com and use code DROPAPIN for 35% off your entire FIRST order. 📍 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
Transcribe →So You Found a Dead Body in China… Now What? (📍Inner Mongolia) | Drop A Pin Ep. 73
Mar 201:24:06Tap to summarizeThis 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 Chaps do a deep dive on Inner Mongolia in this weeks Gettin' Cultured segment. Timestamps: (00:00:00) - Show Start (00:00:30) - Pre Boarding (00:04:34) - Jake Joins The Show (00:23:00) - Finding A Dead Body (00:48:54) - DJ Spenny (00:55:08) - A Word From Our Sponsors (00:57:38) - Gettin' Cultured on Inner Mongolia Get $10 off your first month’s subscription and free shipping when you go to https://Nutrafol.com and enter the promo code PIN Visit https://NOBULLproject.com and use code DROPAPIN for 35% off your entire FIRST order. 📍 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
Transcribe →Two Massholes Recap Hair Transplant Trip to Turkey with 30 Americans (📍 Turkiye) | Drop A Pin Ep. 72
Feb 2301:20:34Tap to summarizeThis 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 thoughts on Istanbul and Cappadocia, and to overall give a sense of what's to come in Baldstool Season 2. Timestamps: (00:00:00) - Show Start (00:15:17) - Cappadocia (00:30:19) - A Word From Our Sponsors (00:38:03) - Istanbul Facts (00:54:14) - Baldstool Season 2 Visit https://nobullproject.com and use code DROPAPIN for 35% off your entire FIRST order. Get $10 off your first month’s subscription and free shipping when you go to https://Nutrafol.com and enter the promo code PIN 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
Transcribe →We Took a Day Trip from Chicago to the Grand Canyon | Drop a Pin Ep. 71
Feb 1601:33:44Tap to summarizeThis 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 in seminary and how prostitution helped shape the American West! Find out why Nutrafol is the best-selling hair growth supplement brand at https://Nutrafol.com promo code PIN. Get 10% off your first month of BlueChew Gold with code DROP https://BlueChew.com Timestamps: 00:00:51 -Recapping Daytripping 01:02:29 - A Word From Our Sponsors 01:05:03 - More Grand Canyon Talk 📍 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
Transcribe →What Is Iran Actually Like? A Persian American Answers | Drop A Pin Ep. 70
Feb 901:25:45Tap to summarizeDisclaimer: 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 their personal experiences and thoughts on the current situation going on in the country and how they have seen the country change over the course of their lifetimes. Timestamps: (00:00:35) - Preboarding (00:01:37) - Donnie's Going to the Super Bowl (00:04:39) - Chris and Bijan join the show (01:11:35) - Gettin' Cultured Visit https://nobullproject.com and use code DROPAPIN for 35% off your entire FIRST order. Find out why Nutrafol is the best-selling hair growth supplement brand at https://Nutrafol.com promo code PIN. 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
Transcribe →How To Plan A Solo Abroad Trip | Drop A Pin Ep. 69
Feb 201:14:31Tap to summarizeThis 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
Transcribe →Are All-Inclusive Resorts Actually Worth It? | Drop A Pin Ep. 68 (📍Cancún)
Jan 2601:32:28Tap to summarizeThis 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
Transcribe →The American Tourist Who Illegally Traveled to North Sentinel Island | Drop A Pin Ep. 67 (📍North Sentinel Island)
Jan 1901:16:29Tap to summarizeThis 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
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