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.
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Should You Quit Your Job and Go Sailing?
What if you stopped waiting for retirement, quit your job, bought a sailboat, and actually went sailing? For a lot of sailors, that idea sits in the back of their mind for years. Buy a cruising sailboat, head for the Bahamas or Caribbean, live aboard, work remotely if you have to, and trade the mor...
What Does $300,000 Buy You in a Sailboat?
Is this your dream sailboat? Today we tour a 2020 Beneteau Oceanis 46.1 currently for sale for $299,000 and take a close look at what nearly $300,000 buys you in a modern cruising sailboat. The Beneteau Oceanis 46.1 is 47 feet 11 inches long with a 14-foot 9-inch beam and combines a massive cruisin...
The 3 Worst Sailboats of All Time
What are the worst sailing sailboats ever built? In this Practical Sailor episode, we examine three unusual production sailboats that sacrificed pure sailing performance for speed, comfort, portability, or powerboat capability: the MacGregor 26X and 26M, the Hunter Edge 27, and the Island Packet SP ...
Are we making a MISTAKE?
After spending our first season sailing the Caribbean as a family, we returned home to Idaho... and suddenly, going back to boat life didn't feel quite as simple as we thought it would. Being home meant family, friends, mountains, camping, birthdays, Yellowstone, and everything we had left beh...
Shipwrecks, Volcano Ruins & a HUGE Family Surprise! | Martinique E401
We’re exploring St. Pierre, Martinique, a Caribbean town with an incredible—and tragic—history. Once known as the “Paris of the Caribbean,” St. Pierre was devastated by the eruption of Mount Pelée in 1902. We wander through the ruins left behind, explore the remains of the old theatre, and visit t...
Is Sailing Really Dying? I Checked the Numbers
If you’re new to sailing, you might be asking yourself: Is sailing dying? Is sailing hard? Is sailing fun? Is sailing expensive? What should I know before buying my first sailboat? Maybe you’re learning how to sail, sailboat shopping, looking for an affordable used sailboat, or wondering whether bec...
Dominica Didn’t Let Us Leave Easily… E400
Our time in Dominica comes to a pretty rough ending! We grab a mooring in Roseau and head ashore to explore downtown, only to realize we’ve LOST our cellphone as we head back home. 😩 Not exactly how we planned to spend our last days on one of our favorite Caribbean islands! Back at the boat, thing...
The Coolest Boat You’ve Never Heard Of
Mr. Trash Wheel might be the coolest boat you’ve never heard of. This bizarre floating machine in Baltimore’s Inner Harbor uses river current, solar power, a giant water wheel and a conveyor belt to collect trash before it reaches the Chesapeake Bay and Atlantic Ocean. And yes, the giant googly eyes...
Hot Take – Slow Sailboats Aren’t Safer
Thinking about buying a sailboat? Whether you’re shopping for your first sailboat, a liveaboard sailboat, a bluewater cruising boat, or the perfect sailboat for the Bahamas and Caribbean, there’s one thing buyers often underestimate: speed. Cruising sailors are constantly told that heavy, slow sailb...
WORTH NO SLEEP? Dominica’s hidden gem E399
Sometimes the best cruising stops are the ones you never planned! ⛵🌴 We sail out of Portsmouth, Dominica, hoping to make a quick hop around the coast and drop anchor just around the corner. But our anchoring plans don’t exactly go as expected… That little failure leads us to Coulibistrie, an unexp...
Don’t Buy A Sailboat Until You See This | Pacific Seacraft 37 | $59,900 | TOUR
@boatfools #pacificSeacraft #sailboat #sailing #bluewatersailing #sailboattour Don't Buy A Sailboat Until You See This! | Pacific Seacraft 37 | $59,900 | TOUR Is the Pacific Seacraft 37 the Goldilocks boat—not too big, not too small, but just right? And at $59,900 she could be the best deal ...
The Boating Industry Has a Trust Problem
If you own a sailboat, sooner or later you’re going to need a marine mechanic, boatyard, marina, sailmaker, rigger, marine electrician, surveyor, or somebody to handle sailboat repair and maintenance. But how do you know who you can trust? Whether you’re researching how to fix a sailboat, sailboat...
Eastern Caribbean Was NOT What We Expected
This was NOT the Caribbean we expected. Sailing south through the Eastern Caribbean brought us to Guadeloupe—and what we found completely surprised us. After leaving St. Kitts and Nevis and making a quick stop in Montserrat, we sailed Isla into Deshaies, Guadeloupe, ready to get off the boat and e...
STOP! You Don’t Need to Sail Around the World!
Are you looking for the best sailboat to sail around the world? Wondering what makes a good bluewater sailboat, whether you need a full keel, heavy displacement, a skeg-hung rudder, or one of those legendary offshore cruising boats everyone recommends? Here’s the problem: you might be shopping for ...
HUGE Sailboat for Young Couple! Beneteau 440 and the Sailblazers
Check out the @Sailblazers Meet Sail Blazers, a young sailing couple doing something most people only dream about. Kendall and Finn are just 21 years old, sailing the Bahamas aboard their Beneteau Oceanis 440 and building their own sailing YouTube channel along the way. In this interview, we tal...
We Got LOST in the Pirates of the Caribbean Indian River! E398
We set out to explore Dominica’s famous Indian River… but somehow managed to lose the trail! What followed turned into one of those adventures that makes Dominica so incredible. We wandered through thick jungle, crossed the river and found ourselves surrounded by huge twisted roots that looked str...
Why You Need to Come to Annapolis This Year
BUY TICKETS HERE PLEASE 😊 Are you thinking about coming to the 2026 Annapolis Sailboat Show? Do you want to see the newest sailboat models, find the best cruising boat for a couple, buy a liveaboard sailboat, or finally start working toward your sailing dream? Join me at the Annapolis Sailboat Sho...
Don’t Live on a Sailboat Until You Hear This
Are you thinking about living on a sailboat? How much does it cost to live on a sailboat? Is living aboard cheaper than owning a house? How does a sailboat toilet work? Where does the waste go? How do liveaboards get electricity, fresh water, internet, groceries, showers and laundry? What happens wh...
ROUGH Sail to Dominica But it’s WORTH IT E397
We say goodbye to Guadeloupe and set sail for Dominica, but it definitely isn't the smooth Caribbean sail we were hoping for! The day starts with a bad feeling in my gut before we head out into a rough, lumpy sea for the crossing to Dominica. 🌧️⛵ It isn't our most comfortable passage, but...
Their First Sailboat Is an Island Packet 40
Would you buy an Island Packet 40 before you even knew how to sail? M and Nick did exactly that. With zero sailing experience, they skipped the typical starter boat and jumped straight into owning a serious 40-foot bluewater cruising sailboat. In this episode of Small Channel Sunday, we talk about ...
Why Most People Never Live Their Sailing Dream
Why do most people never live their sailing dream? It isn’t because sailing is impossible—it’s because they keep waiting for more money, more experience, the perfect sailboat, or the perfect time. Whether you’re interested in sailing for beginners, buying your first used sailboat, learning to sail, ...
Why Are Used Sailboats So Cheap in 2026?
Why are used sailboats so cheap in 2026? The used sailboat market has changed dramatically since the pandemic buying boom. Boats are sitting longer, asking prices are dropping, and many buyers are making offers thousands of dollars below list price. In this Lady K Sailing episode, we explore whether...
Hidden Hot Springs & Sailing life of a family in Guadeloupe E396
Sailing Guadeloupe with the family ⛵ Another beautiful stretch of Caribbean cruising! We start out anchored in Malendure, where it’s time to tackle one of the less glamorous parts of boat life — the grocery run! With the boat stocked up, we jump into the clear Caribbean water for another incredible...