Sailing Into Oblivion Podcast

Sailing Into Oblivion Podcast

After my 2012 Thru-hike of the Appalachian Trail, my life was changed forever. The challenge of big adventure had me hooked. I soon set a goal of sailing alone and without stopping around the world. In 2017-18, I did just that! Since then, I have taken my podcast aboard my Westsail32 as well as in my everyday life. The shows are a mix of my own past experiences along with interviews of everyday people that have a seemingly endless number of stories themselves. Support the Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodcast One Time Donations Via PayPal and Venmo: https://www.paypal.com/paypalme/JeromeRand https://account.venmo.com/u/sailingintooblivion Childrens Book: https://a.co/d/1q2Xkev Sailing Merch: https://www.bonfire.com/store/sailing-into-oblivion/ Books: https://a.co/d/eYaP10M Reach out to the Show: https://www.sailingintooblivion.com/podcasts What started as a podcast about sailing has evolved into my way to sit down with people from all walks of life and share our experiences with the listener. I hope you enjoy the podcast and help it grow into the future.

Episodes

August 13, 2026 35 mins

Time to venture north to Maine, quick update about the passage and my time on Cape Cod.  Thanks for listening, offshore recordings coming soon!

Help Support this podcast with the following links, Thanks for listening!

Support this Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodcast

Help fund my next adventure here: https://gofund.me/6df0fb45

One Time Donations Via PayPal and Venmo: https://www.paypal.com/pay...

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Mark as Played

Today I get into some seamanship skills and tools. The recent rescue of a solo sailor in the Pacific is a great case for having some old school tools aboard your vessel.

Help Support this podcast with the following links, Thanks for listening!

Support this Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodcast

Help fund my next adventure here: https://gofund.me/6df0fb45

One Time Donations Via PayPal and Venmo: https...

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Mark as Played
July 28, 2026 60 mins

Just a rambling show with no particular subject today, I talk about the search for the next Marina, boat work and future plans.  Thanks for listening!

Help Support this podcast with the following links, Thanks for listening!

Support this Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodcast

Help fund my next adventure here: https://gofund.me/6df0fb45

One Time Donations Via PayPal and Venmo: https://www.paypal....

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Mark as Played
July 21, 2026 61 mins

We have made landfall!  After 8 days at sea and taking everything mother nature could throw at us, we are safely tied to the dock.  Today I talk about the last few days of the trip and a bit of a breakdown of the Westsail 32 for anyone considering buying one of these boats.  Thanks for listening!

Help Support this podcast with the following links, Thanks for listening!

Support this Podcast on Patreon: https://www.pat...

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Mark as Played

It has been a rollercoaster of weather and emotion out here on this trip.  The second half is way more positive, so hang in there and thanks for listening!

Help Support this podcast with the following links, Thanks for listening!

Support this Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodcast

Help fund my next adventure here: https://gofund.me/6df0fb45

One Time Donations Via PayPal and Venmo: https://www.pa...

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Mark as Played
July 13, 2026 40 mins

Offshore recordings part one...

Help Support this podcast with the following links, Thanks for listening!

Support this Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodcast

Help fund my next adventure here: https://gofund.me/6df0fb45

One Time Donations Via PayPal and Venmo: https://www.paypal.com/paypalme/JeromeRand https://account.venmo.com/u/sailingintooblivion

Amazon Wishlist: https://www.amazon.com/hz/wishlist...

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Mark as Played

We are back from the west coast and gearing up for the sail from North Carolina to Cape Cod. Today we talk about the coaching trip with Oliver, being back on Sparrow and getting ready for our next passage.  Thanks for your support!

Help Support this podcast with the following links, Thanks for listening!

Support this Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodcast

Help fund my next adventure here: https:...

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Mark as Played
June 28, 2026 43 mins

Pirates? A question that so many people have asked me about, today I get into the subject and a story from my own experience during the voyage around the world.

Help Support this podcast with the following links, Thanks for listening!

Support this Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodcast

Help fund my next adventure here: https://gofund.me/6df0fb45

One Time Donations Via PayPal and Venmo: https://www.pa...

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Mark as Played

Today I sat down with Author Julie Gerstenblatt, I am currently diving into her second historical fiction, The Stargazer of Nantucket, and I can hardly put it down! The high sea adventure, characters, and plot have me hooked. It was a pleasure to sit and chat about the great age of sail with Julie, and I hope you will take a peek at both her books and audiobooks. Click here for her website: https://www.juliegerstenblatt.com/

Also c...

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Mark as Played

Today we are talking weather Forecasting and Passage Planning. These days we have all the info at our fingertips but sometimes that can lead to analysis paralysis!

Help Support this podcast with the following links, Thanks for listening!

Support this Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodcast

Help fund my next adventure here: https://gofund.me/6df0fb45

One Time Donations Via PayPal and Venmo: https://www...

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Mark as Played

When the going gets tough, the tough get going! We are back on Lake Michigan and the world seems dead set on tossing everything from weather to swarms of flies right into our path. But we forge forth and ever onward around this great lake! Thanks for listening.

Help Support this podcast with the following links, Thanks for listening!

Support this Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodcast

Help fund my ne...

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Mark as Played
June 9, 2026 67 mins

Today I am sitting down with Kelsey, a student of Mother Nature and someone that loves the natural world even more than me!  We talk about all the little miracles that you can find in nature and more, thanks for listening and big thanks to Kelsey for sharing her time and passion for Mother Nature.

Help Support this podcast with the following links, Thanks for listening!

Support this Podcast on Patreon: https://www.patreon.com/...

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Mark as Played

Today I sit down with Max, a fellow instructor here in Northen Michigan who will soon be setting sail on an epic adventure that includes the Med, an Atlantic crossing and the Caribbean! I can't wait to hear all about the adventure when we do our follow up show next year.  Safe sailing my friend ns thanks for sharing!

Help Support this podcast with the following links, Thanks for listening!

Support this Podcast on Patreon: http...

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Mark as Played

Matt Rutherford returns for an update from Nova Scotia as he waits out some weather and gets some rest, check out the Ocean Research site here for tracing and ways to help the non profit; https://www.oceanresearchproject.org/ also follow him on the OceanResearch Instagram!!!

Help Support this podcast with the following links, Thanks for listening!

Support this Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodc...

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Mark as Played

Oliver Returnes to the Show, we are getting an update on the boat and all things having to do with the upcoming adventure. Alway a pleasure to have @sailingwithPhoenix back on the Pod, thanks for listening! For more content from Oliver check out his YouTube and all social media @sailingwith phoenix.

Congrats to Ollie for making the crossing to Hawaii, check out his Instagram: @olliebergquist

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Mark as Played

Quick show update on Rutherford and Denker, check out there tracking pages here:

https://www.predictwind.com/tracking/Chimera

https://www.predictwind.com/tracking/Hoppipolla

Help Support this podcast with the following links, Thanks for listening!

Support this Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodcast

Help fund my next adventure here: https://gofund.me/6df0fb45

One Time Donations Via PayPal and Venmo: h...

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Mark as Played
May 19, 2026 58 mins

JeromesTown is officially open and we are having a fireside chat tonight!

Help Support this podcast with the following links, Thanks for listening!

Support this Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodcast

Help fund my next adventure here: https://gofund.me/6df0fb45

One Time Donations Via PayPal and Venmo: https://www.paypal.com/paypalme/JeromeRand https://account.venmo.com/u/sailingintooblivion

Amazon Wis...

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Mark as Played

Spring is in the air and the boats are coming out and getting ready for the sailing season.  We have some new tech for the show and just wanted to do a quick update!

Thanks for listening and check out Colin's YouTube channel here: https://www.youtube.com/@colin.denker

Help Support this podcast with the following links, Thanks for listening!

Support this Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodcas...

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Mark as Played
May 4, 2026 93 mins

Today I have the second part of my visit with Colin Denker aboard his Westsail 32, this time w get into the dreams and destinations that our boats may take us to.

Thanks for listening and check out Colin's YouTube channel here: https://www.youtube.com/@colin.denker

Help Support this podcast with the following links, Thanks for listening!

Support this Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodcast

Help f...

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Mark as Played
April 28, 2026 52 mins

Today we have the recordings I made while sailing from Florida to North Carolina. It was a light wind battle for sure but a nice time out at sea and thanks to the engine working, low stress.  Thanks for listening.

Help Support this podcast with the following links, Thanks for listening!

Support this Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodcast

Help fund my next adventure here: https://gofund.me/6df0fb...

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Mark as Played

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