Drop A Pin

Barstool Sports
  • 4.9 (37)
  • 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. 2d ago

    We Got High and Took A Deep Dive On The Aztec Empire | Drop A Pin Ep.88

    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 specific subject. Today Donnie is teaching White Sox Dave, Annika Christy and Megan Makin’ Money all about the conquest of the Aztec Empire! Originally Filmed: September 18 2025 Timestamps: (00:00:00) - Show Start (00:00:35) - Pre Boarding (00:26:44) - High School: The Aztecs Start your transformation journey with EsteNove: transparent excellence, proven outcomes, and accessible premium care. Tap to plan your journey! Visit https://nobullproject.com and use code DROPAPIN for 35% off your entire FIRST order. Enjoy the refreshing citrus kick of Mountain Dew: an American Original. Grab a Dew. Tasting Great Since 48. 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

    58 min

  2. Jun 8

    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 making content at parks all over the world! He is here to tell us everything we need to know about traveling to Disney’s various theme parks and cruises! Timestamps: (00:00:00) - Show Start (00:00:42) - Weekly Top 10 (00:04:21) - Pre Boarding (00:26:44) - A Word From Our Sponsors (00:31:38) - Interview with Papa Best Find Your Wins with New Amsterdam Vodka Visit https://BlueChew.com for more details and important safety information, and we thank BlueChew for sponsoring the podcast. Enjoy the refreshing citrus kick of Mountain Dew: an  American Original. Grab a Dew. Tasting Great Since 48.   Embrace Debate — shop now at https://Walmart.com or in stores nationwide. 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 35m

  3. Jun 1

    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 through some of his favorite destinations. Timestamps: (00:00:00) - Show Start (00:00:45) - Chaps Asks A Trivia Question (00:05:10) - Pre Boarding (00:13:24) - A Word From Our Sponsors (00:16:16) - Ryen Russillo Interview Go to http://shadyrays.com and use code PIN for 50% off 2+ pairs of polarized sunglasses. GAMBLING PROBLEM? CALL 1-800-GAMBLER or 1-800-MY-RESET, 800-327-5050/visit gamblinghelplinema.org (MA). Call 877-8-HOPENY/text HOPENY (467369) (NY). Call 888-789-7777/visit ccpg.org (CT), mdgamblinghelp.org (MD), 800-981-0023 (PR). Wagering offered by DK Sportsbook: 21+. Present in most states. (18+ DC/KY/NH/PR/WY). Void in ONT. On behalf of Boothill Casino (KS). Pass-thru of per wager tax may apply in IL.Event Trading offered by DraftKings Predictions, CFTC-registered: 18+. Trading involves risk of loss. Market availability varies. Predictions offer void in NY. General: 1 per new DraftKings customer. $5+ deposit req. Trade $5, get $200 Prediction Dollars (1-year expiry) issued as $50 increments every 7 days via click-to-claim for 21 days; or bet $5, get $200 Bonus Bets instantly (7-day expiry and stake removed from payout). 7 days = 168hrs. Rewards are non-withdrawable. Terms: dkng.co/offer. Ends 6/28/26 at 11:59 PM ET. Sponsored by DK. Enjoy the refreshing citrus kick of Mountain Dew: an  American Original. Grab a Dew. Tasting Great Since 48.   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 38m

  4. May 25

    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 Zealand and so much more! Pre Order Sam’s new Book Brut Here Out September 22: https://a.co/d/07KnHkO2 Timestamps: (00:00:00) - Show Start (00:02:24) - A Word From Our Sponsors (00:06:18) - Weekly Top 10 (00:12:18) - Pre Boarding (00:24:57) - Sam Tallent Interview (00:36:05) - Writing His Book In Paris (00:55:00) - Touring In Australia and New Zealand Go to http://shadyrays.com and use code PIN for 50% off 2+ pairs of polarized sunglasses. Get Reese's at https://www.hersheyland.com/reeses  Enjoy the refreshing citrus kick of Mountain Dew: an  American Original. Grab a Dew. Tasting Great Since 48.   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 44m

  5. May 17

    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 to get hair transplants at the Este Nove Clinic in Turkey Watch the first 3 Episodes of Baldstool OUT NOW on The Wonton Don Youtube page and be on the lookout for Episode 4 this Wednesday! Timestamps: (00:00:00) - Show Start (00:00:35) - Weekly Top 10 (00:03:38) - Pre Boarding (00:29:09) - A Word From Our Sponsors (00:33:14) - Mook and White Sox Dave Join The Show (01:15:41) - Mintzy and Mikey Bets Join The Show When you buy two months of BlueChew Gold, you get the third for FREE with promo code DROP https://bluechew.com Visit https://nobullproject.com and use code DROPAPIN for 35% off your entire FIRST order.  Enjoy the refreshing citrus kick of Mountain Dew: an  American Original. Grab a Dew. Tasting Great Since 48.   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 44m

  6. May 11

    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 about Greece, and her observations while traveling abroad. Timestamps: (00:00:00) - Show Start (00:01:01) - New Segment (00:04:47) - Pre Boarding (00:33:34) - A Word From Our Sponsors (00:37:07) - Kelly Keegs Interview (01:24:26) - Greece Discussion When you buy two months of BlueChew Gold, you get the third for FREE with promo code DROP https://bluechew.com Visit https://nobullproject.com and use code DROPAPIN for 35% off your entire FIRST order. Enjoy the refreshing citrus kick of Mountain Dew: an American Original. Grab a Dew. Tasting Great Since 48. 📍 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 31m

  7. May 4

    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 from his experiences in the beautiful country. If you’re going to Medellin hit up Chaps’ Tour Guide CJ: +57 311 6444581 Timestamps: (00:00:00) - Show Start (00:00:54) - New Segment (00:04:43) - Pre Boarding (00:27:12) - A Word From Our Sponsors (00:31:25) - Medellin (00:41:44) - Hostel Life (00:53:53) - Pablo Escobar Go to http://shadyrays.com and use code PIN for 50% off 2+ pairs of polarized sunglasses. Exclusive $25-off Carver Mat at https://on.auraframes.com/WONTON. Promo Code WONTON When you buy two months of BlueChew Gold, you get the third for FREE with promo code DROP https://bluechew.com 📍 Listen Now: Apple Podcasts https://podcasts.apple.com/us/podcast... Spotify https://open.spotify.com/show/31NNzfe... Youtube / @dropapinshow Follow Drop A Pin! IG: https://www.instagram.com/thedropapin... X: https://x.com/DropAPinShow Tik Tok: / thedropapinshow Follow The Wonton Don! IG: thewontondon TikTok: thewontondon X: @donniedoesworld FB: / donniedoes Follow Uncle Chaps! IG: @unclechaps TikTok: @unclechaps X: @UncleChaps

    1h 41m

  8. Apr 27

    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 Iraq and is also a travel youtuber in his own right and is here to talk to us about his trip to Turkmenistan which he says is the weirdest country on earth! Follow Doug Barnard: https://www.youtube.com/@doug_barnard instagram.com/doug_barnard tiktok.com/@doug_barnard dougbarnardtravel.com/trips Timestamps: (00:00:00) - Show Start (00:01:00) - New Segment (00:09:42) - Pre Boarding (00:37:58) - A Word From Our Sponsors (00:42:19) - Doug Interview Exclusive $25-off Carver Mat at https://on.auraframes.com/WONTON. Promo Code WONTON When you buy two months of BlueChew Gold, you get the third for FREE with promo code DROP https://bluechew.com Gambling Problem? Call 1-800-GAMBLER. 18+ (21+ in certain states) to open, own, or access an advance deposit wagering account and resident of a state where DK Horse or DK Racing is available. Eligibility restrictions apply. Void where prohibited. Opt-in req. Min. $5 wager. Only the first straight single horse win wager on the Kentucky Derby placed after opt-in is eligible. Wager must win to qualify for an equal share of $1,000,000. Reward issued in cash within 7 days of race completion via a click to claim, which expires 30 days (720 hours) after receipt. Unclaimed rewards will be forfeited. Ends at the closing of the betting pool for the Kentucky Derby on 5/2/26. Terms: www.dkhorse.com/bet/offers/details; www.racing.draftkings.com/promos Sponsored by DraftKings. Enjoy the refreshing citrus kick of Mountain Dew: an American Original. Grab a Dew. Tasting Great Since 48. \ 📍 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 33m
See All (88)

Hosts & Guests

4.9
out of 5
37 Ratings

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
    88
  • Rating
    Explicit
  • Copyright
    © 2026 Barstool Sports, Inc.
  • Show Website
    Drop A Pin

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