Uncle Chaps just got back from the Kentucky Bourbon Trail, exploring the beautiful rolling hills of Kentucky and diving into the history of one of America's most iconic drinks: bourbon! This week on Drop a Pin, we break down his trip, talk about how to plan the ultimate Kentucky Bourbon Trail experience, explore the history of whiskey and bourbon, and discuss what makes Louisville such a great destination. Plus, we get into the best sporting events to bring your wife to and a whole lot more! If you're planning a trip to Kentucky, interested in bourbon history, or just looking for your next travel destination, this episode is for you. 📍 All this and more on this week's episode of Drop a Pin! Timestamps: (00:00:00) - Show Start (00:00:26) - Top 5 (Bourbon) (00:05:47) - Bourbon Trail (00:33:57) - A Word From Our Sponsors (00:38:10) - Bourbon Trail (Cont.) Our Sponsors Cash App - Download Cash App today and make your money work for you. Click here to get started: https://click.cash.app/ui6m/q2t3jrra #CashAppPartner 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. Cash App Visa® Debit Flex Cards issued by Sutton Bank, Member FDIC, and The Bancorp Bank, N.A., pursuant to a license from Visa U.S.A. Inc. See terms and conditions for the Sutton prepaid card (https://cash.app/legal/us/en-us/card-agreement), Sutton debit flex card (https://cash.app/legal/us/en-us/debit-flex-card-agreement-sutton), and Bancorp debit flex card (https://cash.app/legal/us/en-us/debit-flex-card-agreement-bancorp). Cash App Green features, Savings, Direct deposit, Round ups, Overdraft coverage and Discounts provided by Cash App, a Block, Inc. brand. Visit cash.app/legal/podcast for full disclosures. NOBULL - Visit https://www.nobullproject.com and use code DROPAPIN for 35% off your entire FIRST order Stio - Go to https://STIO.COM/DROP for 20% off your order. 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

Our first-ever guest on Drop A Pin is BACK in the studio! Sam Goodwin joins us to share what it was like returning to Syria after being imprisoned there, meeting the president of Syria, coaching hockey in North Korea, and more. From unbelievable international experiences to stories you have to hear to believe, this is an episode you don't want to miss! Timestamps: (00:00:00) - Show Start (00:00:23) - Sam Goodwin Interview (00:35:02) - A Word From Our Sponsors (00:40:58) - Sam Goodwin Interview (Cont.) Our Sponsors NOBULL - Visit https://www.nobullproject.com and use code DROPAPIN for 35% off your entire FIRST order BlueChew - Visit https://BlueChew.com for more details and important safety information. Fora - Become a Fora Advisor today at https://Foratravel.com/wonton Reese’s - Reese’s. The Official Candy Partner of Barstool Sports. Go Get Reese’s Wherever You Shop 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

This week, Donnie takes us inside his wildest stories from living in Shanghai, China! From hanging out with rappers and meeting NBA players to cooking frogs, partying, and experiencing the city's crazy nightlife, Donnie shares some of his most unforgettable adventures abroad. Hear the craziest stories, unexpected encounters, and behind-the-scenes moments from his time in Shanghai on this week's episode! Timestamps: (00:00:00) - Show Start (00:00:40) - Pre Boarding (00:13:00) - Shanghai (00:43:24) - A Word From Our Sponsors (00:49:00) - Shanghai (Cont.) Our Sponsors NOBULL - Visit https://www.nobullproject.com and use code DROPAPIN for 35% off your entire FIRST order BlueChew - Visit https://BlueChew.com for more details and important safety information. DraftKings - GAMBLING PROBLEM? CALL 1-800-GAMBLER or 1-800-MY-RESET, 800-327-5050/visit gamblinghelplinema.org (MA). 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/NH/PR/WY). Void in CAN. On behalf of Boot Hill Casino (KS). Pass-through per wager tax may apply in IL. Event Trading offered by DraftKings Predictions, CFTC-registered: 18+. Trading involves risk of loss. Market availability varies. General: 1 per new DraftKings customer. Trade $5 get $150 in Bonus Dollars (1-year expiry) or bet $5 get $150 in Bonus Bets (7-day expiry and stake removed from payout). Rewards issued in $50 increments every 7 days via click-to-claim for 14 days. Click-to-claims expire 7 days after issuance. Rewards are non-withdrawable. 7 days = 168hrs. Predictions offer void in NY. Terms: dkng.co/offer. Ends 10/11/26 at 11:59 PM ET. Sponsored by DK. Reese’s - Reese’s. The Official Candy Partner of Barstool Sports. Go Get Reese’s Wherever You Shop 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

Chaps and Donnie kick off a brand-new segment taking a deep dive into Jacksonville! We sit down with folks around the office and special guests to talk about their hometowns—covering local history, food, music, and more! Later in the episode, Ronny Doitche stops by to give us his ultimate travel tips fresh off his trip to Oktoberfest! Timestamps: (00:00:00) - Show Start (00:00:36) - Hometown Series: Jacksonville (00:33:35) - A Word From Our Sponsors (00:36:54) - Hometown Series: Jacksonville (Cont.) (01:05:31) - Travel Tips: Ronny Doitche Our Sponsors Reese’s - Reese’s. The Official Candy Partner of Barstool Sports. Go Get Reese’s Wherever You Shop Quince - Download the Quince app for app-exclusive offers, or go to https://Quince.com/WONTON. 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

This week on Drop A Pin, our friend Giulio Gallarotti joins the show to talk about his travels through Alaska and Rwanda, plus his upcoming adventure to Bolivia. We also dive into some wild topics, including Khat, the search for Noah’s Ark, a new map created by the UN, and plenty more. All that and more on this week’s episode of Drop A Pin! Timestamps: (00:00:00) - Show Start (00:00:25) - A Word From Donnie (00:03:21) - Top 10 (Landlocked Countries) (00:08:12) - Giulio Gallarotti Interview (00:35:44) - A Word From Our Sponsors (00:39:41) - Giulio Gallarotti Interview (Cont.) Our Sponsors Shady Rays - Go to http://shadyrays.com and use code PIN for 50% off 2+ pairs of polarized sunglasses. Cash App - 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. Cash App Visa® Debit Flex Cards issued by Sutton Bank, Member FDIC, and The Bancorp Bank, N.A., pursuant to a license from Visa U.S.A. Inc. See terms and conditions for the Sutton prepaid card, Sutton debit flex card, and Bancorp debit flex card. Cash App Green features, Savings, Direct deposit, Round ups, Overdraft coverage and Discounts provided by Cash App, a Block, Inc. brand. Visit cash.app/legal/podcast for full disclosures. Reese’s - Reese’s. The Official Candy Partner of Barstool Sports. Go Get Reese’s Wherever You Shop 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

This week, our good friend Sydnie Wells joins us on Drop a Pin! Sydnie tells us all about her travels to Patagonia and South America, including her experiences hunting across the region. We also get into her adventures traveling through Europe, the benefits of hunting and eating wild game in the age of “clean eating,” dealing with invasive animals, and plenty of stories from the road. Plus, Sydnie gets some tips on traveling abroad, and we cover a whole lot more on this episode of Drop a Pin! Timestamps: (00:00:00) - Show Start (00:00:19) - Top 5 (Immigrants) (00:08:00) - Pre Boarding (00:16:21) - Sydnie Wells Interview (00:37:27) - A Word From Our Sponsors (00:42:55) - Sydnie Wells Interview (Cont.) Our Sponsors NOBULL - Visit https://www.nobullproject.com and use code DROPAPIN for 35% off your entire FIRST order BlueChew - Visit https://BlueChew.com for more details and important safety information. DraftKings - GAMBLING PROBLEM? CALL 1-800-GAMBLER or 1-800-MY-RESET, (800) 327-5050 or visit gamblinghelplinema.org (MA). Please Gamble Responsibly. 888-789-7777/visit ccpg.org (CT), or visit www.mdgamblinghelp.org (MD), 1-800-981-0023 (PR). Wagering offered by DK Sportsbook: 21+. Present in most states. (18+ DC/NH/PR/WY). Void in CAN. On behalf of Boot Hill 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. General: 1 per new DraftKings customer. Trade $5 get $150 Prediction Dollars (1-year expiry) or bet $5 get $10 in Bonus Bets (7-day expiry and stake removed from payout). Rewards issued in $50 increments every 7 days via click-to-claim for 14 days. Click-to-claims expire 7 days after issuance. Rewards are non-withdrawable. 7 days = 168hrs. Predictions offer void in NY. Terms: dkng.co/offer. Ends 10/18/26 at 11:59 PM ET. Sponsored by DK. Shady Rays - Go to http://shadyrays.com and use code PIN for 50% off 2+ pairs of polarized sunglasses. Fora - Become a Fora Advisor today at https://Foratravel.com/wonton 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

Biz joins the show to tell the wild story of his Havasupai adventure with Wonton — and everything that went down along the way. Stick around for The Come Down Podcast, the FIRST-EVER mobile podcast, and what it’s like taking a podcast on the road. Timestamps: (00:00:00) - Show Start (00:00:14) - Biz Interview (00:58:55) - A Word From Our Sponsors (01:03:13) - The Come Down Podcast Our Sponsors NOBULL - Visit https://www.nobullproject.com and use code DROPAPIN for 35% off your entire FIRST order DraftKings - GAMBLING PROBLEM? CALL 1-800-GAMBLER or 1-800-MY-RESET, 800-327-5050/visit gamblinghelplinema.org (MA). 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/NH/PR/WY). Void in CAN. On behalf of Boot Hill 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. NEW: 1 per new DraftKings customer. $5+ deposit req. Trade $5 get $200 Prediction Dollars (1-year expiry); or bet $5 get $200 in Bonus Bets (7-day expiry and stake removed from payout). Rewards issued in $50 increments every 7 days via click-to-claim for 21 days. Click-to-claims expire 7 days after issuance. Rewards are non-withdrawable. 7 days = 168hrs. Ends 9/20/26 at 11:59 PM ET. BOOST: Opt-in req. 1 Profit Boost issued per customer per day (10% for trades, 50% for bets), valid only for NFL/CFB football transactions on the platform for which it's been issued. Bet/Trade restrictions apply and vary when offered (e.g. market, bet/trade type, min./max. transaction, bet odds/market pricing req. etc.). Boosts are single-use and must be applied BEFORE placing bet/trade. Boost only applies to profit from qualifying bet/trade and expires at the end of the final football game of the select game slate when offered. Trade market must settle to receive boost. Predictions offer void in NY. Terms: dkng.co/offer. Sponsored by DK. Shady Rays - Go to http://shadyrays.com and use code PIN for 50% off 2+ pairs of polarized sunglasses. Reese’s - Reese’s. The Official Candy Partner of Barstool Sports. Go Get Reese’s Wherever You Shop 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

On the 100th episode of Drop A Pin, Donnie’s wife joins the podcast to share what it’s really like traveling the world with Barstool Sports’ own “Foreign Correspondent,” Donnie Does. From their very first vacation together in the Philippines, where Donnie contracted E. coli, to helping him film multiple videos throughout China—and dealing with all the unexpected drama that comes with international travel—she gives a behind-the-scenes look at life on the road with one of Barstool’s most traveled personalities. She also breaks down the pros and cons of having Donnie as a travel partner, what it’s like being married to someone constantly exploring new countries, and the wild experiences that come with traveling the world together. A huge shoutout to all the Pinheads who have supported Drop A Pin Podcast and helped us reach 100 episodes. We couldn’t have done it without you. Here’s to 100 more! In this episode: • What it’s really like traveling the world with Donnie Does • Their disastrous first trip together to the Philippines • Donnie getting E. coli while traveling • Behind the scenes filming videos in China • The drama that comes with international travel • The pros and cons of Donnie as a travel partner • Celebrating 100 episodes of Drop A Pin Timestamps: (00:00:00) - Show Start (00:00:27) - Top 5 countries (NFL Edition) (00:03:33) - The Wonton Wifey Interview (00:27:03) - A Word From Our Sponsors (00:31:35) - The Wonton Wifey Interview (Cont.) Our Sponsors NOBULL - Visit https://www.nobullproject.com and use code DROPAPIN for 35% off your entire FIRST order DraftKings - GAMBLING PROBLEM? CALL 1-800-GAMBLER or 1-800-MY-RESET, 800-327-5050/visit gamblinghelplinema.org (MA). 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/NH/PR/WY). Void in CAN. On behalf of Boot Hill 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. NEW: 1 per new DraftKings customer. $5+ deposit req. Trade $5 get $200 Prediction Dollars (1-year expiry); or bet $5 get $200 in Bonus Bets (7-day expiry and stake removed from payout). Rewards issued in $50 increments every 7 days via click-to-claim for 21 days. Click-to-claims expire 7 days after issuance. Rewards are non-withdrawable. 7 days = 168hrs. Ends 9/20/26 at 11:59 PM ET. BOOST: Opt-in req. 1 Profit Boost issued per customer per day (10% for trades, 50% for bets), valid only for NFL/CFB football transactions on the platform for which it's been issued. Bet/Trade restrictions apply and vary when offered (e.g. market, bet/trade type, min./max. transaction, bet odds/market pricing req. etc.). Boosts are single-use and must be applied BEFORE placing bet/trade. Boost only applies to profit from qualifying bet/trade and expires at the end of the final football game of the select game slate when offered. Trade market must settle to receive boost. Predictions offer void in NY. Terms: dkng.co/offer. Sponsored by DK. Shady Rays - Go to http://shadyrays.com and use code PIN for 50% off 2+ pairs of polarized sunglasses. Reese’s - Reese’s. The Official Candy Partner of Barstool Sports. Go Get Reese’s Wherever You Shop 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