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We Took a Day Trip from Chicago to the Grand Canyon | Drop a Pin Ep. 71
We Took a Day Trip from Chicago to the Grand Canyon | Drop a Pin Ep. 71

This 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 t…

2 months, 1 week ago

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What Is Iran Actually Like? A Persian American Answers | Drop A Pin Ep. 70
What Is Iran Actually Like? A Persian American Answers | Drop A Pin Ep. 70

Disclaimer: 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 comedia…

2 months, 2 weeks ago

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How To Plan A Solo Abroad Trip | Drop A Pin Ep. 69
How To Plan A Solo Abroad Trip | Drop A Pin Ep. 69

This 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 …

2 months, 3 weeks ago

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Are All-Inclusive Resorts Actually Worth It? | Drop A Pin Ep. 68 (📍Cancún)
Are All-Inclusive Resorts Actually Worth It? | Drop A Pin Ep. 68 (📍Cancún)

This 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 rec…

3 months ago

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The American Tourist Who Illegally Traveled to North Sentinel Island | Drop A Pin Ep. 67 (📍North Sentinel Island)
The American Tourist Who Illegally Traveled to North Sentinel Island | Drop A Pin Ep. 67 (📍North Sentinel Island)

This 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…

3 months, 1 week ago

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Our Journey Through The Mississippi Delta (📍Rediscovering Memphis Recap) | Drop A Pin Ep. 66
Our Journey Through The Mississippi Delta (📍Rediscovering Memphis Recap) | Drop A Pin Ep. 66

Nick and KB are BACK on the show, this time to break down Rediscovering MEMPHIS! The boys talk about their experiences filming the latest episode of …

3 months, 2 weeks ago

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Donnies Weiredest Jobs In China | Drop A Pin Ep. 64 (📍Shanghai )
Donnies Weiredest Jobs In China | Drop A Pin Ep. 64 (📍Shanghai )

This week we are back with our second CHINASODE! Diving Deep into Donnie’s stories from his time in China and this week we are focusing on the odd jo…

3 months, 3 weeks ago

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

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 tal…

3 months, 4 weeks ago

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

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 do…

4 months ago

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

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 w…

4 months, 1 week ago

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