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...
Systems Checks, Rutherford, and Yard Projects, EP#444
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
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Crossing the Gulf of Maine, EP#443
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.
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Help fund my next adventure here: https://gofund.me/6df0fb45
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North to Maine, EP#442
Time to venture north to Maine, quick update about the passage and my time on Cape Cod. Thanks for listening, offshore recordings coming soon!
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Support this Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodcast
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Paper Charts, EP#441
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.
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Morning Ramble Show, EP#440
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!
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Landfall, Cape Cod EP#439
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!
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Offshore Recordings NC-CC Part Two, EP#438
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!
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Offshore NC-CC Part 1, EP#437
Offshore recordings part one...
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Sailing Into Oblivion Children's A...
Coast to Coast, Back on Sparrow, EP#436
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!
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Support this Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodcast
Help fund my next adventure here: https://gofund.me/6df0fb45
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Pirates on the High Seas, EP#435
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.
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Author Julie Gerstenblatt, The Stargazer of Nantucket EP#434
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
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!
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Support this Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodcast
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Lord of the Flies, Sailing on Lake Michigan, EP#432
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.
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Support this Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodcast
Help fund my next adventure here: https://gofund.me/6df0fb45
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Mother Nature with Kelsey, EP#431
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.
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Support this Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodcast
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Sailing on a Gap-Year with Max, EP#430
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!
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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
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!!!
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Help fund my next adventure here: https://gofund.me/6df0fb45
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Sailing with Phoenix Returns for an Update, EP#427
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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Help fund my next adventure...
Rutherford and Denker are Underway!, EP#426
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
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Support this Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodcast
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Fireside at JeromesTown, EP#425
JeromesTown is officially open and we are having a fireside chat tonight!
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Support this Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodcast
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Children's Book: https://a.co/d/1q2Xkev<...
Spring is in the Air, Work Update, EP#424
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
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Part Two with Colin Denker, EP#423
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
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Offshore Recordings FL-NC EP#422
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.
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Support this Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodcast
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Sailing Adventures with Brendan and Chanell, EP#421
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
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Support this Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodcast
Help fund my next adventure here: https://gofund.me/6df0fb45
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Post Light Wind Challenge, EP#420
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
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Support this Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodcast
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Light Wind Challenge, EP#419
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!
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Reality of a Refit with Colin Denker, EP#418
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
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Exercise, Sailing to Charlston, and what's next, EP#417
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
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My Cuban Friend, Ernesto EP#416
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.
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Glad to be on the Dock, Gale Warning in Effect EP#415
The wind is howling, rain is driving and I am so glad to be on the dock and not still out at sea!
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Offshore Recordings March 2026, EP#415
On the home stretch, mid trip recordings, thanks for listening.
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Support this Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodcast
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Children's Book: https://a.co/d/1q2Xkev
...
The Westsail has Sold with Marc EP#414
Today I am sitting down with Marc for the third time on the show as we go full circle and talk about the adventures of past aboard his Westsail 32 and the process of passing her on to the new owner. Always a pleasure to have Marc on the show.
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Support this Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodcast
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Holding Fast on the Dock, EP#413
Well, I'm still on the dock and not sad about it one bit! The weather closed in the day I was planning to leave and for once I made the right call to stay safely in port.
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Support this Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodcast
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Amazon...
Knocking Out the Checklist, Pre-departure, EP#412
A big day today getting old Sparrow ready for the open ocean, lots on the list and it is almost done! Ny tomorrow we will know if its a go or no go. Thanks for listening.
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Support this Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodcast
Help fund my next adventure here: https://gofund.me/6df0fb45
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Time for a Quick Trip in the Atlantic! EP#411
Time to go Sailing!!! Just got back on Sparrow and the weather look good enough for a nice little rip into the Atlantic! Thanks for listening, more to come and hopefully from the offshore world.
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Support this Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodcast
Help fund my next adventure here: https://gofund.me/6df0fb45
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Fireside Podcast from JeromesTown EP#410
Stuck for another night, let's have a fireside chat!
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Support this Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodcast
Help fund my next adventure here: https://gofund.me/6df0fb45
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Children's Book: https://a.co/d/1q2Xkev
Sailing...
Self-Steering Systems, EP#409
Today I get into some info and stories about Windvanes and Autopilots, so many to choose from and the pros and cons to all! Thanks for listening!
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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
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Solo Show Updates, EP#408
Today I sit solo as the winter is starting to let up a bit and soon, I will be heading back to Sparrow for some sailing!
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Support this Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodcast
Help fund my next adventure here: https://gofund.me/6df0fb45
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Chartering a Yacht with Ian Pedersen, EP#407
Today I sit down with Ian Pedersen who is the Senior Marketing Manager for The Moorings yacht charters, and has been in the yacht charter industry for 15 years. He is a passionate ambassador of the sailing lifestyle, and has sailing experience worldwide, from The Bahamas to St. Martin, Croatia, Thailand, and of course, the British Virgin Islands.
Moorings Website: http://www.moorings.com/
BVI Destination Page: https://www.moorings.com/destinations/caribbean/british-virgin-islands-yacht-charters
Information on Sailing Qualifications: https://www.moorings.com/yacht-charter/resumes-requirements
Help Support this podcast with the following links, Tha...
Living Life and Facing Fear with Shane Pollard, EP#406
Today I sit with author Shane Pollard, an old friend from the BVI days that has since published a book and been grabbing life by the horns. We get deep on this show about fear and how to overcome it; I hope you enjoy and check out his new book here https://a.co/d/0hTV2bdc
Shane's Website: Shane Pollard – Content Production Company. Creative Communication Design.
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Support this Podcast on Patreon: https://www.patreon.com/sailingintooblivionpodcast
Help fund...
The Engine Lives! EP#405
It's been a mission to get everything squared away on old Sparrow. Boats hate to be left unused and after nearly 2 months in the marina we are getting this old Westsail ready for sailing in March.
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
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