Drop A Pin

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
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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.

Uncle Chaps

The Wonton Don

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

Ladies and gentlemen, this is your captain speaking, fasten those seatbelts and strap in, we'll get you to those margaritas ASAP. Hello, bonjour Ciao bella madame, monsieur. Salam, salam Welcome back to Drop a Pen, a very special New Year's episode because we are looking into the future, looking int

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

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 📍 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

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Follow The Wonton Don!
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X: @donniedoesworld
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IG: @unclechaps
TikTok: @unclechaps
X: @UncleChaps

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

One time you were on a six foot boulder and then. Oh yeah, you hated that. We need we need you to get down and you just kind of like froze you're like I can't do it like I am afraid of falling from a height that would severely injure me. I'm not afraid of heights I'll go to the top of a tower, but I

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

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Follow The Wonton Don!
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X: @donniedoesworld
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Follow Uncle Chaps!
IG: @unclechaps
TikTok: @unclechaps
X: @UncleChaps

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

So you were saying you've maybe been to all of the continents, but I'm assuming you have not been to In some books it's not called a continent. It's a desert. People don't like to look at Antarctica as a desert. So therefore I can't call that a country. Hey, how are you? Welcome back to Drop a Pin. 

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

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 📍 Listen Now:
Apple Podcasts https://podcasts.apple.com/us/podcast/drop-a-pin/id1773703211
Spotify https://open.spotify.com/show/31NNzfeA0tEfKE9LpqycFN?si=5dc8e774513e4458
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Follow Drop A Pin!
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X: https://x.com/DropAPinShow
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X: @donniedoesworld
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Follow Uncle Chaps!
IG: @unclechaps
TikTok: @unclechaps
X: @UncleChaps

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

You see what's happening with all the AI shit this week? Like it's crashing. Everyone's jumping ship and they're realizing it's all they're all just propping each other up. And cities and states are getting tired of that bullshit. Like all the water that they're using. It's such a f dude, it's It's 

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

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📍 Listen Now:
Apple Podcasts https://podcasts.apple.com/us/podcast/drop-a-pin/id1773703211
Spotify https://open.spotify.com/show/31NNzfeA0tEfKE9LpqycFN?si=5dc8e774513e4458
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Follow The Wonton Don!
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TikTok: thewontondon
X: @donniedoesworld
FB: https://www.facebook.com/DonnieDoes/ 

Follow Uncle Chaps!
IG: @unclechaps
TikTok: @unclechaps
X: @UncleChaps

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

And I don't know what I had to redeem myself for. I think it's because on our first hike I was the only one that had a map and like I let us off the trail a couple of times. No, I think it's never too far too. Water. We ran out of water. Hey, who are you? Welcome back to Drop a Pin. Today we're doin

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

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