Sailing Into Oblivion Podcast

40 Episodes
Subscribe

By: Jerome Rand, Bleav

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...

✂️ Clip this podcast
Sparrow is Floating Once Again, EP#455
#455
Yesterday at 11:18 PM

We are back on the water and gearing up to set sail in a day or two.  Time to start heading south to find some warmer weather.  First stop Cape Cod and then we will see.  Today I start before the launch and then wrap things up after we splash.  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://gofun...


Tackling the Impossible, EP#454
#454
10/20/2026

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.p...


Work in the Yard Continues, EP#453
#453
10/13/2026

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.a...


Circling the North Atlantic with Dillon, @estrellaoffshore, EP#452
#452
10/07/2026

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.co...


My Story of the Mighty Sparrow, EP#451
#451
10/03/2026

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_=w...


Haul-Out Day Made easy! EP#450
#450
09/28/2026

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...


Florida to Maine with Mazi and Teddy, EP#449
#449
09/25/2026

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/6...


Yard Monkey Day One, EP#448
#448
09/21/2026

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://w...


Back to the Boatyard+Q@A, EP#447
#447
09/14/2026

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/s...


Summer Wrap-up Show, EP#446
#446
09/04/2026

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...


Adventures in Small Boat Sailing with Jacob, EP#445
#445
08/27/2026

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

...


Systems Checks, Rutherford, and Yard Projects, EP#444
#444
08/23/2026

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?r...


Crossing the Gulf of Maine, EP#443
#443
08/17/2026

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/p...


North to Maine, EP#442
#442
08/13/2026

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_=w...


Paper Charts, EP#441
#441
08/05/2026

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...


Morning Ramble Show, EP#440
#440
07/28/2026

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...


Landfall, Cape Cod EP#439
#439
07/21/2026

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.patreon.com/sailingintooblivionpodcast

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

One Time Donations Via Pay...


Offshore Recordings NC-CC Part Two, EP#438
#438
07/18/2026

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.paypal.com/paypalme/JeromeRand https://account.venmo.com/u/sailingintooblivion

Amazon Wishlist: https://www.amazon.com/hz/wishlist/ls/33F...


Offshore NC-CC Part 1, EP#437
#437
07/13/2026

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/ls/33F36RF315G8V?ref_=wl_share

Children's Book: https://a.co/d/1q2Xkev

Sailing Into Oblivion Children's A...


Coast to Coast, Back on Sparrow, EP#436
#436
07/09/2026

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://gofund.me/6df0fb45

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


Pirates on the High Seas, EP#435
#435
06/28/2026

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.paypal.com/paypalme/JeromeRand https://account.venmo.com/u/sailingintooblivion

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


Author Julie Gerstenblatt, The Stargazer of Nantucket EP#434
#434
06/23/2026

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 check out here Instagram: @juliegerstenblatt

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

<...


Weather Forecasting and Routing, EP#433
#433
06/19/2026

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.paypal.com/paypalme/JeromeRand https://account.venmo.com/u/sailingintooblivion

Amazon Wishlist: https://www.amazon.com/hz/wishlist/ls/33F36RF315...


Lord of the Flies, Sailing on Lake Michigan, EP#432
#432
06/11/2026

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 next adventure here: https://gofund.me/6df0fb45

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


Mother Nature with Kelsey, EP#431
#431
06/09/2026

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/sailingintooblivionpodcast

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

One Time Donations Via P...


Sailing on a Gap-Year with Max, EP#430
#430
06/02/2026

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: https://www.patreon.com/sailingintooblivionpodcast

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

O...


Rutherford Returns to the Show from Nova Scotia, EP#429
#429
05/29/2026

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/sailingintooblivionpodcast

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

One Time Donations Via PayPal and Venmo: https://www.paypal.com/paypalme/JeromeRand h...


Sailing with Phoenix Returns for an Update, EP#427
#427
05/26/2026

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

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...


Rutherford and Denker are Underway!, EP#426
#426
05/21/2026

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: https://www.paypal.com/paypalme/JeromeRand https://account.venmo.com/u/sailingintooblivion

Amazon WishList: https://www.amazon.com/hz/wishlist/ls/33...


Fireside at JeromesTown, EP#425
#425
05/19/2026

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 WishList: https://www.amazon.com/hz/wishlist/ls/33F36RF315G8V?ref_=wl_share

Children's Book: https://a.co/d/1q2Xkev<...


Spring is in the Air, Work Update, EP#424
#424
05/13/2026

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/sailingintooblivionpodcast

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

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


Part Two with Colin Denker, EP#423
#423
05/04/2026

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

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


Offshore Recordings FL-NC EP#422
#422
04/28/2026

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/6df0fb45

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


Sailing Adventures with Brendan and Chanell, EP#421
#421
04/22/2026

Today I sit down with Brendan and Chenell who I met while waiting for a weather window in Fort Pierce. These two have had some crazy adventures between the USA, Bahamas, and Panama. Chck out the great videos on their YouTube Channel here: https://www.youtube.com/@LifeOnLaCosmica

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...


Post Light Wind Challenge, EP#420
#420
04/18/2026

And a challenge it certainly was! A good trip though as I have just made landfall in N.C. and that means I made it.  Offshore recordings coming soon.  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...


Light Wind Challenge, EP#419
#419
04/13/2026

We have light winds in the forecast for this next passage from Florida to Cape Fear. It's 400 miles and we have the Gulf Stream but we also have a big wind shift that we will be racing against to make for port. Should be a fun challenge to see if we can keep old Sparrow from needing her engine.  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/6df0f...


Reality of a Refit with Colin Denker, EP#418
#418
04/11/2026

Today I am aboard another Westsail 32 that Colin Denker has been getting ready for the ocean.  We talk about the refit process and much more.  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 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/sai...


Exercise, Sailing to Charlston, and what's next, EP#417
#417
04/05/2026

Today I talk about exercise and sailing, the recent trip on a Morgan 382, and a little bit of the game plan moving forward as spring approaches and we need to get north! Big thanks to Chase for having me on the voyage to Charlston, it was a pleasure cruise!  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: h...


My Cuban Friend, Ernesto EP#416
#416
04/01/2026

Today I sit aboard the Mighty Sparrow with Ernesto, my new Cuban friend, to chat about everything from hard work to cars, to Cuba and beyond. Big thanks to Ernesto for taking time from his busy schedule to share some of his wisdom and experiences.

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...


Glad to be on the Dock, Gale Warning in Effect EP#415
#415
03/29/2026

The wind is howling, rain is driving and I am so glad to be on the dock and not still out at sea!

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...