Watch Sailing & Boating Adventures Around the World – Page 5 of 42
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.
Gone with the Wynns embarks on an incredible sailing adventure to the Island of No Return (Kona, Philippines) in search of history and hidden gems. Uncover a fascinating past filled with resilience, hope, and a remarkable local community's journey from stigma to vibrancy!
This week we share last part of the recommended I-65 route from Bahamas to Puerto Rico.
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Discover why Gone with the Wynns chose not to register their boat in the US upon pickup. Learn about their decision to opt for foreign registration instead, and what that means for them on the open water.
Embark on a sailing adventure with Sailing Sisu as they navigate the preferred I-65 route from the Bahamas to Puerto Rico. Compare the thorny path with the more favored I-65 path, experiencing different wind conditions and sea states along the way.
Join us as we explore the fascinating world of the cashew business in the Philippines, where entrepreneur Raul has revolutionized the industry by establishing a fair trade processing facility that benefits both local gatherers and international markets. Uncover the secrets behind his successful oper...
Sailing Sweet Ruka leaves the fjords of Chile and sets sail for French Polynesia via the South Pacific Ocean, facing treacherous currents and upgrading the yacht.
Jason and Nikki of Gone with the Wynns find themselves in a whirlwind adventure when they decide to embark on a 70 km bicycle journey across challenging terrain to renew their visas before expiry. This exciting tale takes readers through their struggles, hilarious moments, unexpected encounters, and...
Join the Gone with the Wynns on their captivating sailing voyage, where they tackle their first offshore passage, showcasing an electrifying blend of skill and resilience amidst unpredictable winds, shifting currents, and hidden coral reefs. Immerse yourself in the untold stories behind their transf...
Grab a tube of elbow grease (or just some butter for your popcorn) and join us for a week of problem solving, jury rigging, chandlery hopping and casting off the lines.
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If you're curious, and want to learn more about WIN or Ocean Adventure I've listed their websites below. If you find yourself in Subic Bay Philippines we highly recommend you stop by and see it for yourself:
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Full Tour of our New HH44 Catamaran. Let our sponsor BetterHelp connect you to a therapist who can support you, all from the comfort of your own home. Visit and enjoy a special discount on your first month.
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Things got better after I exited the Thorny Path. In fact, hurricane Cindy stole the Trade Winds when she passed further north and I was forced to motor sail the last three days. This gave me time to fix some broken stuff.
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Our first BIG ocean passage is done! From China to the Philippines. Secure your privacy with Surfshark! Enter coupon code WYNNS for an extra 3 months free at
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My first solo sail and I had to select the worst and most toughest route we have sailed up to now. The Thorny Path. It sure broke a lot of things on the boat!
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We’ve just been handed our brand new HH44 Catamaran and we only have 3 days before we must sail the boat out of the country. → Get a year supply of vitamin D3+K2 & 5 travel packs FREE with your first purchase:
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NOT RECOMMENDED!!!! The Thorny Path goes basically through South Bahamas, south of Great Inagua, south of Turks & Caicos. It is an acceleration zone for the Trade Winds. A biljard table for the big Atlantic swells bouncing off Puerto Rico, T&C, Haiti, Great Inagua. A super confused sea state...
It’s been 2 years since we put down a deposit for our HH44 Catamaran. Now the big acceptance day is finally here, and we don’t have even a moment to soak it all in.
We have exactly 4 days to move into a brand-new boat, prepare for our first big passage, provision up and sail out of China. 🫨 It’s a...
I managed to sail to Great Inagua where I am waiting for Hurricane Bret to fizzle out and Hurricane Cindy to make up her mind before I tackle the Thorny Path....
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I heard that Storm Three was upgraded to Hurricane Brett and that I am heading straight for it. Why? Watch the video to find out where is the method in my madness.
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Sea Trials on our new HH44 CURIOSITY! Get Surfshark VPN at - Enter promo code WYNNS and get up to 6 extra months FREE.
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I receive confirmation that a hurricane has formed and it is on its way towards me....
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China is not all what we expected and trust me, as a couple of Americans, we certainly had some reservations about trekking through the country without a real plan.
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ĺIn this video, I share my experience of sailing solo from the Bahamas to Puerto Rico, a journey of over 700 nautical miles that took me nine days to complete. I show you the challenges and rewards of single-handed sailing, the beauty and diversity of the Caribbean islands, and the tips and tricks I...
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