Watch Sailing & Boating Adventures Around the World
Explore sailing, boating, and water sports through our curated video archive. From epic sea voyages to serene diving escapes, discover unforgettable adventures from top YouTube creators. Start your journey. Dream big. Sail far.
Showing 1-24 of 44 results
He’s Built 400 Boats. The Cheap Used Sailboats He’d Buy in 2026
A 40-year boatbuilder and former charter-fleet operator breaks down which cheap, used cruising sailboats are actually worth buying, and which ones will eat your savings and your dream. If you are shopping for a first bluewater boat on a budget, watch this before you wire a deposit. Kyle Jachney has...
High Seas Adventure in the North Atlantic 2022, Westsail 32 Mighty Sparrow
The high seas adventure of 2022 was difficult and did not go according to plan, but I was able to learn some valuable lessons and also truly see what I was made of when the world gets out of control. The ocean is a great teacher of so many lessons, and I am grateful to everyone that helped get me o...
EP#367 Colin Denker Returns to the Show
Today I sat down with Colin Denker to check in as he is aboard his Westsail 32 in the Carolinas. Always great to chat about his trips, plans and work that needs to be done aboard his new boat. Thanks for sharing your time Colin! Check Colin's most recent Video on YouTube about sailing to Haw...
2 Hour Westsail Relaxing Sailing View
Support this Podcast on Patreon: One Time Donations Via PayPal and Venmo: Amazon WishList: Children's Book: Sailing Into Oblivion Children's Audio Book: Audible.com Sailing Merch: Books: Reach out to the Show:
Open Ocean Cabin Tour Westsail 32 Mighty Sparrow
This is how the boat looks down below when I am offshore sailing.Support this Podcast on Patreon: One Time Donations Via PayPal and Venmo: Amazon WishList: Children's Book: Sailing Into Oblivion Children's Audio Book: Audible.com Sailing Merch: Books: Reach out to the Show:
Choosing the Right Sail Plan at Sea
This is a few examples of sail planning when dealing with squalls, changing winds and the ocean itself. Every boat is different so always know your own vessel. Support this channel on Patreon: One Time Donations Via PayPal and Venmo: Children's Book: Sailing Into Oblivion Children's Au...
Podcast EP#241 Gunnar Christensen GGR2026
Today we are joined by Gunnar Christensen who has recently signed up for the GGR 2026 Solo around the world race. Over the next two years, Gunnar will be fundraising, finding and outfitting the boat, and getting in some good practice before heading over to France for the start. We will be checking ...
7 Day Offshore Training Session aboard Westsail 32
The goal was to get some experience with offshore sailing aboard this Westsail 32. I joined the owners and we embarked on a 600 mile passage around the Little Bahama Bank. With head seas and head winds the first few days, I filmed very little but after the passing of the low pressure system, the sa...
Podcast Interview with fellow Westsailor James Hodge
Today we are trying something new, still some improvements to be made on my audio but getting closer to the goal of quality A/V virtual podcasts. James and I chat about boat projects, why a Westsail, Transporting boats and much more. Big thanks to James for sharing his time and experiences. Suppo...
Sailing Liberty- How to Afford Cruising Life /Boat Delivery Westsail 32 Rigging/How to Cook Panini
Panini/Bacon Press: E-commerce link-Coffee Cups and T-Shirt Store: Drop shipping direct to you! Shipboard plan for adventure & financing cash flow with our online business, we are learning how to make a living on social media & affiliate marketing - Sailing Liberty Wish List: SUPPOR...
Sailing Liberty- Unfiltered and Raw, Real Life Aboard Our 41 ft Sailboat / fixing AC and Electric
Sailing Liberty Wish List: For Sailing Liberty Coffee Club: SUPPORT US ON PAYPAL: [email protected] Music: Tarantino Country Rock by Infraction Drifter (Spaghetti western)
Grey Day Sailing View
Passing by Georges bank mid May. Typical overcast and foggy weather but blowing good. Support the Sailing Into Oblivion Channel on Patreon: Merch Store: Donations Via Paypal and Venmo:
Post Knockdown Wrap-up
After nearly 36 hours without sleep, being knocked down and damaged, and going through some serious waves; the world around Sparrow and I began to calm. This clip is a short wrap-up, thoughts and feelings after such a crazy event at sea.
Back after 25 Tough Days at Sea
Just a quick update now that I have reached land for repairs to old Sparrow. We suffered a violent knockdown and lots of heavy weather during our trip from Maine. The good news is that I have lots of video from the voyage for bunch more videos. For now I just want to clean up the boat and get som...
Stepping the Mast on my Westsail32 Mighty Sparrow
Rain or shine, the mast had to go up! This is a quick high speed video and narration of the process of putting the mast back on the boat.
Westsail 32 in my favorite offshore conditions
A little sailing on a flat sea a few hundred miles from land. These are the conditions I enjoy the most and are very rare to find offshore. Become a Patron,
Westsail 32 Hove-To preparing for the coming Heavy Weather
This is a quick video and narration of the hours before Tropical Storm Wanda overtook Sparrow and I mid Atlantic. We are Hove to, small sails and just wanting to keep things under control for the long night ahead. Become a Patron; Shirts Available now;
Changing Sails on a Westsail32
Just a quick video about changing sails out at sea. Winds are getting light, and I need more sail, so a bigger sail, the drifter, needs to be rigged and hoisted. Support the Content on Patreon;
Preparing the Mast for Removal Tomorrow
Just a quick overview of the prep that I am doing to get ready to take down the mast on Mighty Sparrow.
Top Three Myths About Solo Sailing
Today I talk about the Myths that are sometimes thought of when it comes to solo sailing. Support this Channel on Patreon: One Time Donations Via PayPal and Venmo: Children's Book: Sailing Into Oblivion Children's Audio Book: Audible.com Sailing Merch: Books: Reach out to the ...
EP#119 Finding Sparrow
Today I tell the story about how I became the owner of my Westsail 32 Mighty Sparrow. A big thanks to all the Patreon Supporters! If you want to help support the show click the link!
EP#111 Choosing a Marina, Sailjunky, and plans for the fall
Today I just had to get a solo podcast in and was inspired by an article in Sailjunky about Marina experiences. We also hit on some of the options for Sparrow and I coming up this fall. Mostly its just me rambling! Support the show on Patreon;
Sailing Into Oblivion Part Four, the Vast Pacific
Today we get into the last of the untouched oceans, the Pacific. After being at sea for almost 5 months I had cleared New Zealand and made my way into the largest expanse of open water in the world. Over 4,000 miles to Cape Horn and the escape from the Southern Ocean. Support the Channel on Patreo...