Watch Sailing & Boating Adventures Around the World tagged “Sailing away”
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.
Welcome back to another episode of WE|Sail!
We're BACK in the Bahamas!
Fresh off the boat show in Annapolis, we're diving straight into hosting our Patreon charter with 10 incredible people from all over the world. What happens when strangers meet on a ...
The Sunfish is the best-selling sailboat of all time — over half a million built — and for good reason. It’s simple, portable, affordable, nearly indestructible, and one of the purest ways to learn and love sailing. Today, I’m diving into why the S...
Welcome back to another episode of WE|Sail!
Erica's finally on her way back to VA! After months of recovery, we're easing back into boat life one step at a time, and what better place to start than the Annapolis Boat Show.
This year's show felt extra sp...
Today we’re taking a deep dive into one of the best budget bluewater sailboats on the market: a 1984 Tayana 37 listed for $59,900. Yes… a real, offshore-ready, world-capable cruiser for under $60K — and you could quite literally buy it today and sail...
Welcome back to another episode of WE|Sail!
This weeks episode is a little different. The story we've never told. After seven years of documenting our sailing adventures around the world, we're finally sharing the story that started it all- how WE became...
Could you really live on a sailboat for just $20,000? In this episode, we’re building the perfect budget cruiser — the legendary Catalina 30 — and transforming it into a self-sufficient liveaboard for under twenty grand.
We’re adding 800 watts of ...
Could you really live on a sailboat for just $20,000? In this episode, we’re building the perfect budget cruiser — the legendary Catalina 30 — and transforming it into a self-sufficient liveaboard for under twenty grand.
We’re adding 800 watts of ...
https://youtu.be/eBBfMDkHfBk?si=PLWkZ4ej6x4PSUUR
How I bought a 35 foot sailboat for $9k
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Sail Smarter!
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Ahoy WE|Sailors!!!!
This week we are skipping out on an episode and making sure everyone spends some time with family for the holiday. This is a time to give gratitude and we have so much to our family, friends and sailing community who have supported us ...
Welcome back to another episode of WE|Sail!
Get some merch from our new collection:
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So you’ve worked your whole life, ready to retire and sail off into the sunset — but your spouse just isn’t interested in sailing. You’re not alone. In this episode of Lady K Sailing, we talk about why one partner often resists the sailing lifestyl...
Welcome back to another episode of WE|Sail!
We're back! Sorry for the two-week hiatus – charters and boat shows took over our lives, but we promise it's still all about the sailing.
In this episode, we're five days into our catamaran delivery from Tah...
Sailing looks calm, romantic, and free — until it isn’t.
In this video, we explore the real-life disasters and accidents that show just how fast things can go wrong at sea — from the 1979 Fastnet Race tragedy to the Cheeki Rafiki and Sydney to Hobart...
The Valiant 40 sailboat is one of the most iconic offshore cruisers ever built. Designed by Bob Perry in the 1970s, this legendary 40-foot yacht combined speed, comfort, and safety in a way no production cruiser had before.
In this video, we take a deep d...
Welcome back to another episode of WE|Sail!
We had done about a week of good hard work to prep the boat for this long sail north to Hawai'i and now it was go time!!
It had been a good week and we had been able to tackle just about every known issue wit...
Looking for a proven bluewater catamaran that won’t break the bank? Meet the Prout 34 Catamaran, a legendary British cruising multihull designed for serious passagemaking. In this video, we take a closer look at the history, design, layout, and sailing p...
Thinking about buying a Westsail 32 Shipmaster? In this video, we take a deep dive into one of the most iconic bluewater cruising sailboats ever built. The Westsail 32 earned its reputation as a rugged, heavy-displacement cutter that’s carried sailors sa...
Welcome back to another episode of WE|Sail!
Warren barely has time to unpack his bags in Fiji before he's off on his next adventure – his very first boat delivery! This week, he's heading to French Polynesia to take on a delivery of a used Catana 55 fr...
Thinking about buying a 30 foot sailboat? The Catalina 30 is one of the most popular and best-selling cruising sailboats of all time — and for good reason. In this video, we dive into why the Catalina 30 is considered the best 30 foot sailboat to buy and...
Get 'em while they're signed: https://bethecaptain.com
The Captain’s Collector’s Edition books are finally shipping! 4,000 copies signed and stacked, ready to make their way around the world. This is just the beginning of a huge adventure. Thank you f...
Welcome back to another episode of WE|Sail!
This episode Erica and I are FINALLY back together! Unfortunately not sailing or even back on the boat, but together in Colorado!
I pack up the boat, take a long flight and its all worth it to wrap my arms aro...
This is the story of sailor Jay Caunter, a man who set out aboard his Sabre 34 sailboat Venture in search of freedom and the call of the sea. Sadly, Jay was lost at sea, leaving behind both mystery and memory. In this video, we honor his journey, explore h...
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