Advertise on podcast: Sailing Into Oblivion Podcast

Rating

★★★★★

4.8

from

96 reviews

Description

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.

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Check latest episodes from Sailing Into Oblivion Podcast podcast

Tackling the Impossible, EP#454

2026/10/20

Today I talk about some of the seemingly impossible tasks that we need to get past to and how we get past them. After a crazy week so far int he yard, things are starting to look more possible everyday. Help Support this podcast with the following links, Thanks for listening! Support this Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodcast Starlink Referral Link: https://starlink.com?referral=RC-DF-13132545-72429-94 Help fund my next adventure here: https://gofund.me/6df0fb45 One Time Donations Via PayPal: https://www.paypal.com/paypalme/JeromeRand Venmo:https://venmo.com/u/sailingintooblivion Amazon Wishlist: https://www.amazon.com/hz/wishlist/ls/33F36RF315G8V?ref_=wl_share Children's Book: https://a.co/d/1q2Xkev Sailing Into Oblivion Children's Audio Book: Audible.com Sailing Shirts: https://www.bonfire.com/store/sailing-into-oblivion/ Books: https://a.co/d/eYaP10M Reach out to the Show: https://www.sailingintooblivion.com/podcasts Total Boat 5% discount code: https://www.totalboat.com/?sca_ref=9803393.xY85BaEnxZ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Work in the Yard Continues, EP#453

2026/10/13

Work in the yard continues, this episode is from two weeks leading up to the filling of the yard for the season. Help Support this podcast with the following links, Thanks for listening! Support this Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodcast Starlink Referral Link: https://starlink.com?referral=RC-DF-13132545-72429-94 Help fund my next adventure here: https://gofund.me/6df0fb45 One Time Donations Via PayPal: https://www.paypal.com/paypalme/JeromeRand Venmo:https://venmo.com/u/sailingintooblivion Amazon Wishlist: https://www.amazon.com/hz/wishlist/ls/33F36RF315G8V?ref_=wl_share Children's Book: https://a.co/d/1q2Xkev Sailing Into Oblivion Children's Audio Book: Audible.com Sailing Shirts: https://www.bonfire.com/store/sailing-into-oblivion/ Books: https://a.co/d/eYaP10M Reach out to the Show: https://www.sailingintooblivion.com/podcasts Total Boat 5% discount code: https://www.totalboat.com/?sca_ref=9803393.xY85BaEnxZ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Circling the North Atlantic with Dillon, @estrellaoffshore, EP#452

2026/10/07

Today I sit down with Dillon and talk about his upcoming voyage around the North Atlantic solo and non-stop. Check out his Instagram @esrtellaoffshore for daily updates. Thanks for sharing your time and enthusiasm Dillon, fair winds my friend! Help Support this podcast with the following links, Thanks for listening! Support this Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodcast Starlink Referral Link: https://starlink.com?referral=RC-DF-13132545-72429-94 Help fund my next adventure here: https://gofund.me/6df0fb45 One Time Donations Via PayPal: https://www.paypal.com/paypalme/JeromeRand Venmo:https://venmo.com/u/sailingintooblivion Amazon Wishlist: https://www.amazon.com/hz/wishlist/ls/33F36RF315G8V?ref_=wl_share Children's Book: https://a.co/d/1q2Xkev Sailing Into Oblivion Children's Audio Book: Audible.com Sailing Shirts: https://www.bonfire.com/store/sailing-into-oblivion/ Books: https://a.co/d/eYaP10M Reach out to the Show: https://www.sailingintooblivion.com/podcasts Total Boat 5% discount code: https://www.totalboat.com/?sca_ref=9803393.xY85BaEnxZ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

My Story of the Mighty Sparrow, EP#451

2026/10/03

A Tribute to the Mighty Sparrow, the passing of a true legend. Help Support this podcast with the following links, Thanks for listening! Support this Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodcast Starlink Referral Link: https://starlink.com?referral=RC-DF-13132545-72429-94 Help fund my next adventure here: https://gofund.me/6df0fb45 One Time Donations Via PayPal: https://www.paypal.com/paypalme/JeromeRand Venmo:https://venmo.com/u/sailingintooblivion Amazon Wishlist: https://www.amazon.com/hz/wishlist/ls/33F36RF315G8V?ref_=wl_share Children's Book: https://a.co/d/1q2Xkev Sailing Into Oblivion Children's Audio Book: Audible.com Sailing Shirts: https://www.bonfire.com/store/sailing-into-oblivion/ Books: https://a.co/d/eYaP10M Reach out to the Show: https://www.sailingintooblivion.com/podcasts Total Boat 5% discount code: https://www.totalboat.com/?sca_ref=9803393.xY85BaEnxZ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Haul-Out Day Made easy! EP#450

2026/09/28

Today we get into a few top tips for the haul-out season for all you boat owners that dread the end of the season's most stressful day. Just a few things that I think will make life a little easier for all parties involved in getting your boat safely from the water to dry land Colin's Westsail 32 listing: https://www.facebook.com/share/19jXG6oUaZ/ Help Support this podcast with the following links, Thanks for listening! Support this Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodcast Starlink Referral Link: https://starlink.com?referral=RC-DF-13132545-72429-94 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/ls/33F36RF315G8V?ref_=wl_share Children's Book: https://a.co/d/1q2Xkev Sailing Into Oblivion Children's Audio Book: Audible.com Sailing Shirts: https://www.bonfire.com/store/sailing-into-oblivion/ Books: https://a.co/d/eYaP10M Reach out to the Show: https://www.sailingintooblivion.com/podcasts Total Boat 5% discount code: https://www.totalboat.com/?sca_ref=9803393.xY85BaEnxZ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Florida to Maine with Mazi and Teddy, EP#449

2026/09/25

Today I sit down with @washupsailing aka Mazi and Teddy, to talk about how they made the leap to living on a boat and cruising from Florida to Maine! Check out the YouTube Channel and Instagram @washupsailing! Big thanks for sharing you're time and experiences! Fair winds you two, thanks so much! Help Support this podcast with the following links, Thanks for listening! Support this Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodcast Starlink Referral Link: https://starlink.com?referral=RC-DF-13132545-72429-94 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/ls/33F36RF315G8V?ref_=wl_share Children's Book: https://a.co/d/1q2Xkev Sailing Into Oblivion Children's Audio Book: Audible.com Sailing Shirts: https://www.bonfire.com/store/sailing-into-oblivion/ Books: https://a.co/d/eYaP10M Reach out to the Show: https://www.sailingintooblivion.com/podcasts Total Boat 5% discount code: https://www.totalboat.com/?sca_ref=9803393.xY85BaEnxZ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Yard Monkey Day One, EP#448

2026/09/21

Day one of being back at work and working for the Boatyard! Great to be filthy, tired and ready for many days to come working with the team here at Knight Marine Services, the biggest little boatyard in Maine! Help Support this podcast with the following links, Thanks for listening! Support this Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodcast Starlink Referral Link: https://starlink.com?referral=RC-DF-13132545-72429-94 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/ls/33F36RF315G8V?ref_=wl_share Children's Book: https://a.co/d/1q2Xkev Sailing Into Oblivion Children's Audio Book: Audible.com Sailing Shirts: https://www.bonfire.com/store/sailing-into-oblivion/ Books: https://a.co/d/eYaP10M Reach out to the Show: https://www.sailingintooblivion.com/podcasts Total Boat 5% discount code: https://www.totalboat.com/?sca_ref=9803393.xY85BaEnxZ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Back to the Boatyard+Q@A, EP#447

2026/09/14

Sumer is over and all my plans have changed; I'm heading back to the boatyard to work the haul-out season before setting sail south. Plus to questions from listeners. Help Support this podcast with the following links, Thanks for listening! Support this Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodcast Starlink Referral Link: https://starlink.com?referral=RC-DF-13132545-72429-94 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/ls/33F36RF315G8V?ref_=wl_share Children's Book: https://a.co/d/1q2Xkev Sailing Into Oblivion Children's Audio Book: Audible.com Sailing Shirts: https://www.bonfire.com/store/sailing-into-oblivion/ Books: https://a.co/d/eYaP10M Reach out to the Show: https://www.sailingintooblivion.com/podcasts Total Boat 5% discount code: https://www.totalboat.com/?sca_ref=9803393.xY85BaEnxZ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Summer Wrap-up Show, EP#446

2026/09/04

End of summer is here, and we talk about all things from teaching sailing to Starlink review. Thanks for listening! Help Support this podcast with the following links, Thanks for listening! Support this Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodcast Starlink Referral Link: https://starlink.com?referral=RC-DF-13132545-72429-94 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/ls/33F36RF315G8V?ref_=wl_share Children's Book: https://a.co/d/1q2Xkev Sailing Into Oblivion Children's Audio Book: Audible.com Sailing Shirts: https://www.bonfire.com/store/sailing-into-oblivion/ Books: https://a.co/d/eYaP10M Reach out to the Show: https://www.sailingintooblivion.com/podcasts Total Boat 5% discount code: https://www.totalboat.com/?sca_ref=9803393.xY85BaEnxZ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Adventures in Small Boat Sailing with Jacob, EP#445

2026/08/27

Today, Jacob and I sit down after a week of sailing on the lovely Walloon Lake here in Northern Michigan. It's been an adventure with ups and downs, good times and storms. Big thanks to Jacob for returning to the show and sharing his experiences. Thanks for listening! Help Support this podcast with the following links, Thanks for listening! Support this Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodcast Starlink Referral Link: https://starlink.com?referral=RC-DF-13132545-72429-94 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/ls/33F36RF315G8V?ref_=wl_share Children's Book: https://a.co/d/1q2Xkev Sailing Into Oblivion Children's Audio Book: Audible.com Sailing Shirts: https://www.bonfire.com/store/sailing-into-oblivion/ Books: https://a.co/d/eYaP10M Reach out to the Show: https://www.sailingintooblivion.com/podcasts Total Boat 5% discount code: https://www.totalboat.com/?sca_ref=9803393.xY85BaEnxZ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Systems Checks, Rutherford, and Yard Projects, EP#444

2026/08/23

Today I talk about the yard work, Rutherford's trip being derailed, and systems checks before setting sail. Thanks for listening and thanks for the 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://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/ls/33F36RF315G8V?ref_=wl_share Children's Book: https://a.co/d/1q2Xkev Sailing Into Oblivion Children's Audio Book: Audible.com Sailing Shirts: https://www.bonfire.com/store/sailing-into-oblivion/ Books: https://a.co/d/eYaP10M Reach out to the Show: https://www.sailingintooblivion.com/podcasts Total Boat 5% discount code: https://www.totalboat.com/?sca_ref=9803393.xY85BaEnxZ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Crossing the Gulf of Maine, EP#443

2026/08/17

Made it to Maine in just over two days, this is a recap of the trip with the offshore recording added to the end(the audio had a buzz to it, sorry about that). Now it's time to haul Sparrow out and get to work! 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.com/paypalme/JeromeRand https://account.venmo.com/u/sailingintooblivion Amazon Wishlist: https://www.amazon.com/hz/wishlist/ls/33F36RF315G8V?ref_=wl_share Children's Book: https://a.co/d/1q2Xkev Sailing Into Oblivion Children's Audio Book: Audible.com Sailing Shirts: https://www.bonfire.com/store/sailing-into-oblivion/ Books: https://a.co/d/eYaP10M Reach out to the Show: https://www.sailingintooblivion.com/podcasts Total Boat 5% discount code: https://www.totalboat.com/?sca_ref=9803393.xY85BaEnxZ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

North to Maine, EP#442

2026/08/13

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/paypalme/JeromeRand https://account.venmo.com/u/sailingintooblivion Amazon Wishlist: https://www.amazon.com/hz/wishlist/ls/33F36RF315G8V?ref_=wl_share Children's Book: https://a.co/d/1q2Xkev Sailing Into Oblivion Children's Audio Book: Audible.com Sailing Shirts: https://www.bonfire.com/store/sailing-into-oblivion/ Books: https://a.co/d/eYaP10M Reach out to the Show: https://www.sailingintooblivion.com/podcasts Total Boat 5% discount code: https://www.totalboat.com/?sca_ref=9803393.xY85BaEnxZ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Paper Charts, EP#441

2026/08/05

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://www.paypal.com/paypalme/JeromeRand https://account.venmo.com/u/sailingintooblivion Amazon Wishlist: https://www.amazon.com/hz/wishlist/ls/33F36RF315G8V?ref_=wl_share Children's Book: https://a.co/d/1q2Xkev Sailing Into Oblivion Children's Audio Book: Audible.com Sailing Shirts: https://www.bonfire.com/store/sailing-into-oblivion/ Books: https://a.co/d/eYaP10M Reach out to the Show: https://www.sailingintooblivion.com/podcasts Total Boat 5% discount code: https://www.totalboat.com/?sca_ref=9803393.xY85BaEnxZ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Morning Ramble Show, EP#440

2026/07/28

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.com/paypalme/JeromeRand https://account.venmo.com/u/sailingintooblivion Amazon Wishlist: https://www.amazon.com/hz/wishlist/ls/33F36RF315G8V?ref_=wl_share Children's Book: https://a.co/d/1q2Xkev Sailing Into Oblivion Children's Audio Book: Audible.com Sailing Shirts: https://www.bonfire.com/store/sailing-into-oblivion/ Books: https://a.co/d/eYaP10M Reach out to the Show: https://www.sailingintooblivion.com/podcasts Total Boat 5% discount code: https://www.totalboat.com/?sca_ref=9803393.xY85BaEnxZ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Podcast reviews

Read Sailing Into Oblivion Podcast podcast reviews

4.8 out of 5

96 reviews

★★★★★

Pete McGill 2025/12/19

Inspirational!

Jerome is an inspiration, great stories, tone, and point of view. Better without the slurping ;)

★★★★★

MadMax691 2025/09/01

Love it!

Absolutely love listening to Jerome! A wonderful mix of reflections and humor and both physical and mental advice, with a ‘boatload’ of great ramblin...

★★★★★

Rat stinker 2025/03/26

Good pod

Jerome is an honest, genuine guy and has some great stories, thoughts and guests on the show

★★★★★

passagesfromtheheart 2024/03/22

Inspiration Adventure = Jerome Rand!

Good thing that this pod comes out weekly (sometimes 2x a week!) as I can’t go too long without a good dose of the ol’ Jerome and his Sailing Into Obl...

★★★★★

IA sailor 2024/01/16

What kind of boat?

love listening to your podcast lots of knowledge and great stories, my question would be I live in Iowa close to a decent size lake and recently got i...

★★★★★

O'Treasaigh 2023/10/16

Consistently interesting

I had the good fortune to spend a weatherbound week in Ocean City with Jerome as my slip-neighbor, and in the year and a half since, I’ve been hooked ...

★★★★★

S/V JG 2023/06/01

A natural raconteur. Wow.

Ever wondered what it’d be like to be stuck on a boat in the doldrums with only Owen Wilson as company? Wow. All joking aside, this is a terrific re...

★★★★★

KalamazooKev 2023/05/18

Great storytelling energy!

I have never sailed & I love your podcast! Wonderful energy & great story telling! I enjoy your genuine passion for your craft & sailing skillset.

★★★★★

AssociateVP 2022/08/03

Impressive

Jerome has a ton of experience and enjoys sharing it in the most unpretentious way. His storytelling is infectious. He always sounds like he’s having ...

★★★★★

No Boat guy 2022/01/22

Awesome!

I’m completely caught up with your podcasts. Love listening to your adventures and your attitude and honesty. Your interviews are great too and I love...

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