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...
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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...
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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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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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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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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Fireside Podcast from JeromesTown EP#410
Stuck for another night, let's have a fireside chat!
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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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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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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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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.
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Land and Sea Adventures with Sondra EP#404
Today I sit with Sondra who has for the last two years been section hiking the Appalachian Trail. She is also gearing up to set sail later this week on a trip that will take her all the way to Guatemala for the hurricane season. Sondra is truly living a life of many adventures, and it makes me want to get back out there and go after some of the same. Thanks for listening!
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The Adventures of Lutra with Bryan and Katie EP#403
Today I stit down with fellow Westsailors Katie and Bryan who have been cruising their way down the West Coast to Baja. Always a pleasure to chat with other Westsail 32 owners that are following their dreams. Thank for listening and check out the YouTube channel here: https://www.youtube.com/@TheAdventuresOfLutra
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Small Boat Adventures and the Raid Erie Event with Eric Miller EP#402
Today I sat down with Eric Miller, the founder of Raid Erie to talk about his sailing event, small boat adventures and everything in-between. Check out the links for more information on how to join in on the fun this summer:
https://www.raiderie.net/
https://www.facebook.com/groups/raiderie
https://www.erieexpeditionchallenge.org/
https://www.facebook.com/groups/erieexpeditionchallenge
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Walking with the Silverbacks, EP#401
Today we talk about a trip my cousin Micheal took to Rwanda to visit the Silverbacks. An amazing experience to say the least. Thanks for listening!
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Back on Sparrow Post Bahamas Trip, EP#400
It's 3 am and time for a podcast, yes, the sleep schedule is still off from the last voyage and I'm taking advantage of the quiet time for a little ranting and raving plus some details from this last trip.
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<...Aboard the New Boat with Oliver @SailingwithPhoenix, EP#399
Today I am on the West Coast and helping with the maiden voyage, only 32 miles, and the start of the biggest coaching adventure I could ask for. Oliver has set his sights on a solo non-stop, and I am going to help get him ready for the adventure ahead. Tonight, we just chat and have fun, but this will be a multi part series spanning the next 9 months. Thanks for listening
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Appalachian Trail Series, Maine EP#398
The last state on the AT was a big one, sorry for the delay on this one and thanks to those who reminded me that I needed to get it done!
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Holiday Update EP#397
Just a quick update show and a glimpse of the coming trips! Thanks for listening.
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Skin and the Sun with my Dermatologist, Lisa Bowersox EP#396
Today I sit down with my dermatologist, Lisa Bowersox to chat about skin, sun, and how to protect against aging or even worse, cancer. Big thanks to Lisa for sharing her weather of knowledge and her time! Thanks for listening.
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Music and the Mind with Matt Jones, EP#395
Today Matt Jones returns to the show to chat about the positive effects of music. He is passionate to say the least about the sweet sounds of music, and I am finding more and more that if I am looking to fill the air with sound, music is the way to go. Check out his Podcast that streams on all platforms: "Ya'll Need Music Podcast" Thanks for listening!
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Heavy Weather Preparations, EP#394
Today I talk through my process for getting ready for sailing in heavy weather. After being in a sassy little gale a few weeks ago and being asked about this topic, I wanted to share my system for getting ready for a blow, thanks for listening!
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EP#393 From the Sea, to a Plane, to a Car
Well we are back on the road and heading to the coast for some presentations. Just an update on things past, present and future. Thanks for listening.
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EP#392 Dry Land is not a Myth!
We made it! Despite the weather, the gulf stream, the engine issues, the cruise ships and the waiting; we made it! Back on the dock and getting ready to jump on a plane for the great white north. Thanks for joining me on this voyage and all the support!
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EP#391 Welcome to Squall Country
A battle through a dark night! Thanks for listening
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EP#390 Low Input Mode Achieved
After 10 days at sea we have reached the mind state I always chase out here, low input-high enjoyment. Thanks for listening
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EP#389 A Quiet Day at Sea
Update from day 8
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EP#388 Becalmed and then Sailing
Back for another update, day 5, Nov 19th Thanks for listening
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EP#387 The Gale
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Children's...
EP#386 Going for it!
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EP#385 Day 1 Escape From the Cape
November 14th update from the sea, thanks for listening.
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EP#384 Getting Ready for the High Seas Once Again!
We are back on Sparrow and prepping to get back out there for the 1200-mile passage south. I was leaving today but decided to push back a day and be more prepared and in a better position with the coming weather. Thanks for listening!
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EP#383 Waylaid by the Weather
Well, the fall weather is proving to be a big challenge for getting Sparrow to her winter home in Florida. As sailors we have to have patience and also be ready to set sail at a moment's notice. Just an update on the situation.
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EP#382 Sailing with a 14-month-old, the Vanabond Tales
Today I sit down with Eddie, Kelli and Nora, also known as the VanabondTales. They are currently sailing another season in the Med but with the new addition or Nora, things have had to change but the sailing will continue. Check out the YouTube channel here: https://www.youtube.com/@TheVanabondTales and the blog here: https://thevanabondtales.com/
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EP#381 Maine-Cape Cod, Part 2
Part 2, landfall on the Cape!
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EP#380 Maine-Cape Cod, Day 1
Day one offshore recordings!
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EP#379 Last Night on Land! Sparrow is going back to Sea
Just a quick show about my time in the yard, keeping my head screwed on, and the upcoming voyage. Thanks for listening!
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