Drop A Pin

🌎 Ari Shaffir Joins Donnie & Chaps for a No-Frills Travel Deep Dive

✈️ Hostel Life: Ari shares unfiltered stories from dirt-cheap stays, including bunking with strangers, wild hostel parties, and unexpected friendships.
💸 Budget Travel Hacks: How Ari stretches a dollar on the road—sleeping in airports, hitchhiking, and eating like a local.
🏝️ Off-the-Grid Adventures: From hidden villages to under-the-radar countries, Ari talks about the best (and worst) places he's wandered into.
🤢 Sketchy Situations: A few close calls—dodging scams, weird food experiences, and the occasional "should I be here?" moments.
📚 Gettin’ Cultured w/ Nick Turani

🤔 Chaps & Donnie challenge Nick with travel trivia and odd cultural facts.
🏆 Can Nick guess the customs, taboos, or weird laws from different countries?
😂 As always, chaos ensues.

Presented by Barstool Sports, Drop A Pin takes you on a weekly 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 across the globe, exploring the world from the iconic to the obscure. Sometimes they dive into serious topics, and other times, it's just about having a laugh as they uncover the weird, wild, and unexpected. 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 drop pins and share the unique experiences behind each one.

Uncle Chaps

The Wonton Don

Ari Shaffir's Nomad Phase Is Upon Us! | Drop A Pin Ep. 23

🎙️ Drop A Pin: Frank “The Tank” Fleming’s Producer, Matthew Piper Jenks Takes Flight + Embracing the Florentine Spirit ✈️🇮🇹
🚨 This week’s episode is a must-listen for travel enthusiasts and Italy aficionados! @DonnieDoesWorld & @UncleChaps welcome the one and only Matthew Piper Jenks—producer to Frank “The Tank” Fleming—who shares his incredible experiences living in Florence. From intense Calcio Storico matches to the captivating Palio di Siena, Jenks and Donnie swap stories of adrenaline-fueled spectacle and genuine cultural immersion. You’ll hear how one warm-hearted Florentine family welcomed Jenks like their own son, creating memories he’ll never forget.

Timestamps:
Interview With Jenks - 00:00:44
Florence Discussion - 1:33:16
Gettin' Cultured with Mark Titus - 2:12:42

🎤 Matthew Piper Jenks: The Man Behind the Legend of Frank The Tank & His Life in Florence
🔹 Calcio Storico: Jenks and Donnie break down the historic—and sometimes downright brutal—sporting event and why it’s a must-see for anyone visiting Florence. ⚽
🔹 Palio di Siena: Hear about the centuries-old horse race that captivates an entire city, and learn what makes this tradition a true bucket-list experience. 🏇
🔹 Florence Family Ties: Jenks reveals a heartfelt story of how a local Florentine family embraced him, giving a fresh perspective on Italian hospitality. ❤️

🎙️ THEN… Mark Titus Joins for “Gettin' Cultured” for advice on Fatherhood & Travel ✈️👨‍👧
Mark Titus slides into the airplane seat for a candid chat about his upcoming journey into fatherhood and his burning desire to keep traveling.
🔹 Parenting on the Road: How to prepare for family trips without losing your mind—or your passport. 🍼🌍
🔹 Advice from a Veteran Father: As a seasoned father Chaps share his top tips and travel hacks for traveling with a child.

🔥 This episode has it all—Italian sports, heartfelt stories, culture-shock anecdotes, and fresh perspectives on balancing fatherhood with a passion for travel.

💬 Let us know—what’s your favorite Italian tradition or destination? Share in the comments below!

Download the Gametime app today and use code DROP for $20 off your first purchase

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Go to https://www.heydude.com today and find your perfect pair 
Download the Gametime app today and use code DROP for $20 off your first purchase

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). 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 5/18/25 at 11:59 PM ET. Sponsored by DK.

Control Body Odor ANYWHERE with @shop.mando and get $5 off off your Starter Pack (that’s over 40% off) with promo code WONTON at https://shopmando.com! #mandopod 

Go to https://www.heydude.com today and find your perfect pair 

🎧 Listen Now:
📍 Apple Podcasts | Spotify | YouTube
📲 Follow & Subscribe: @BarstoolSports | @TheDropAPinPod
Follow The Wonton Don!
IG: thewontondon
TikTok: thewontondon
twitter: @donniedoesworld
FB: https://www.facebook.com/DonnieDoes/ 
Barstool: https://www.barstoolsports.com/bio/62720/donnie-does
Follow Uncle Chaps!
IG: @unclechaps
TikTok: @unclechaps
Twitter: @UncleChaps
Barstool: https://www.barstoolsports.com/bio/13906103/chaps

Finding Yourself in Florence feat. Jenks | Drop A Pin Ep. 27

🚨 This week’s episode is an absolute can’t-miss for all you travel junkies! @DonnieDoesWorld & @UncleChaps dive into their unforgettable adventures in Thailand—from Donnie’s early content creation days to the wild stories to crazy festival experiences
Donnie & Chaps: Life & Laughs in Thailand
• From the Streets of Bangkok to the Islands: Hear about the nightlife, hidden gems, and local delicacies that left Donnie & Chaps wanting more! 🌃🌴
• Donnie’s First-Ever Content Series: Get the backstory on how Donnie took the leap into vlogging, the challenges he faced, and how Thailand played a massive role in his journey. 🎬💥
• Tyler, a new Barstool producer, reveals how he got busted smoking weed in Thailand—and the hectic bribe he had to pay to dodge trouble with the cops. 🚨💰
• Lessons Learned: From facing local laws head-on to making it out unscathed, Tyler shares the adrenaline-packed story and how it changed his perspective on traveling. 😬🌏
Gettin’ Cultured with Steven Cheah
• Why Do Different Countries Drive on Different Sides of the Road?: Steven stops by to break down the fascinating history, cultural quirks, and sometimes dangerous realities behind left-side vs. right-side driving. 🚦🤔
• Travel Adjustments & Tips: Whether you’re a first-timer or seasoned globetrotter, learn how to adapt when hitting the roads in countries with traffic flowing in “the other lane.” 🛣️✅
🔥 This episode is loaded with Thai memories, production secrets, and global insights. It’s a must-watch for anyone craving a little wanderlust!

Let us know—what’s your top tip for staying out of trouble abroad? Drop it in the comments!

Listen Now:
📍 Apple Podcasts | Spotify | YouTube
Follow & Subscribe:
@BarstoolSports | @TheDropAPinShow
#DropAPin #ThailandTravel #PeakinSeries #DonnieDoes #UncleChaps #StevenCheah #BarstoolSports #DrivingAbroad #CultureShock
Follow The Wonton Don!
IG: thewontondon
TikTok: thewontondon
twitter: @donniedoesworld
FB: https://www.facebook.com/DonnieDoes/ 
Barstool: https://www.barstoolsports.com/bio/62720/donnie-does

Thai'd Up in Bangkok | Drop A Pin Ep. 26

This week’s episode of Drop A Pin is loaded with wild travel stories and big laughs! @DonnieDoesWorld & @UncleChaps bring you the legendary Sam—the dedicated Barstool fan who joined Donnie on his now-infamous #Baldstool adventure. Buckle up for on-set plane seat antics, epic tales from India, and a touch of global intrigue. 🪑✈️

Timestamps:
00:53 Interview with Sam
2:04:04 Gettin' Cultured with Big T

🎤 Sam’s Wild Ride: From Baldstool to India

🔹 Baldstool Beginnings: Hear how Sam ended up shaving it all and following Donnie on an around-the-world escapade—truly a life-changing leap.
🔹 Highs in India: From navigating bustling streets to witnessing iconic landmarks, Sam and Donnie share their most memorable moments on the subcontinent. 🌏
🔹 Hezbollah Encounters in Lebanon: Get the inside scoop on Sam’s unexpected run-ins with Hezbollah—an adventure straight out of a spy thriller. 🤯
🎙️ THEN… Big T Takes the Mic on Being a LARGE Traveler 🏋️‍♂️💺
@BarstoolBigT joins to chat about the ups and downs of globe-trotting when you’re bigger than most airplane seats. 
🔹 Cramped Airline Struggles: Which carriers get a thumbs-up, and which leave you with bruised elbows? ✈️
🔹 Fit to Travel: How Big T handles seatbelt extenders, tight hotel rooms, and travel hacks every large traveler needs in their back pocket. 🤯
🔹 Surprisingly Comfy Destinations: Discover the places that truly welcomed a 6’5”+, 300-pound traveler—and the ones that definitely did not. 🏨
🔹 Sharing the Journey: Donnie, Chaps, and Big T compare stories of destinations that blew their minds, proving you never know what you’ll love until you explore. 🌐🔥
🔥 This episode offers comedy, culture, and a real look into how travel can surprise you around every corner (sometimes involving unexpected groups like Hezbollah).

💬 Tell us—what’s the most unexpected place you’ve found yourself while traveling? Drop your stories in the comments!

Download the Gametime app today and use code DROP for $20 off your first purchase

Go to https://www.heydude.com today and find your perfect pair 

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 CT/MI/NJ/PA/WV only. Void in ONT. Eligibility restrictions apply. 
1 per new customer. Opt-in req. Min. net loss of $5 on eligible games to earn 100% of net losses back (“Lossback”) for 24 hours following opt-in. Max. $1,000 issued in Casino Credits for select games that are non-withdrawable, single-use, have no cash value, and expire in 7 days (168 hours). Terms: casino.draftkings.com/promos. Ends 4/27/25 at 11:59 PM ET. Sponsored by DK. 

🎧 Listen Now:

📍 Apple Podcasts | Spotify | YouTube
📲 Follow & Subscribe: @BarstoolSports | @DropAPinPod


#DropAPin #Baldstool #IndiaTrip #Hezbollah #Lebanon #BarstoolSports #SamTakesOnTheWorld #BigT #TravelPodcast #ComedyTravel #DonnieDoes #UncleChaps #Adventure #MustListen #GlobalAdventures

Follow The Wonton Don!
IG: thewontondon
TikTok: thewontondon
twitter: @donniedoesworld
FB: https://www.facebook.com/DonnieDoes/ 
Barstool: https://www.barstoolsports.com/bio/62720/donnie-does

Follow Uncle Chaps!
IG: @unclechaps
TikTok: @unclechaps
Twitter: @UncleChaps
Barstool: https://www.barstoolsports.com/bio/unclechaps

Hezbollah Detained Barstool Fan TWICE | Drop A Pin Ep. 25

In this episode of Drop A Pin, Donnie Does and Uncle Chaps are joined by comedian, world traveler, and globetrotting storyteller Giulio Gallarotti (@notjulio) to talk about the wild trip: vacationing in Iraq and Afghanistan. Yes, you read that right.

Chaps reflects on his time in Iraq through the lens of combat as a Marine, while Donnie and Giulio hilariously recount their civilian travels to the very same regions—not as soldiers, but as tourists. From ancient ruins to modern-day chaos, they compare what it's like to visit these countries with wildly different perspectives. 🌍✈️💥

Topics include:

Giulio’s bold decision to vacation in Afghanistan 🇦🇫

Touring Baghdad vs. surviving Fallujah 🇮🇶

How travel changes your worldview—even in warzones

Cultural gems, local hospitality, and surreal moments in conflict regions

Comedy, courage, and how far curiosity will take you

If you’ve ever wondered what it’s like to visit places most people only see in headlines, this episode will open your eyes—and probably make you laugh. It’s a wild, thoughtful, and unexpectedly inspiring ride.

🔔 Don’t forget to like, comment, and subscribe for more insane travel stories and global weirdness every week!

#DropAPin #GiulioGallarotti #TravelPodcast #IraqTravel #AfghanistanTrip #DonnieDoes #UncleChaps #CombatVsVacation #WarzoneTourism #MilitaryVsCivilian #TravelComedy #WorldExplorer #CrazyTravelStories #ChapsInIraq #GiulioInAfghanistan #GlobalAdventures

📍 Watch now on YouTube + Listen wherever you get your podcasts!

Try your first month of BlueChew FREE when you use promo code DROP -- just pay $5 shipping.  https://BlueChew.com

Go to https://www.heydude.com today and find your perfect pair
 
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 CT/MI/NJ/PA/WV only. Void in ONT. Eligibility restrictions apply. 
1 per new customer. Opt-in req. Min. net loss of $5 on eligible games to earn 100% of net losses back (“Lossback”) for 24 hours following opt-in. Max. $1,000 issued in Casino Credits for select games that are non-withdrawable, single-use, have no cash value, and expire in 7 days (168 hours). Terms: casino.draftkings.com/promos. Ends 4/27/25 at 11:59 PM ET. Sponsored by DK.

Iraq War Vet and Iraqi Tourist Squash Their Beef | Drop A Pin Ep. 24

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Ari Shaffir's Nomad Phase Is Upon Us! | Drop A Pin Ep. 23

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