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 2013 results
These Waves Hit Harder Than Expected
A smooth sea never made a skilled sailor. Get an exclusive 15% discount on Saily data plans! Use code WYNNS at checkout. Download Saily app or go to ☝Behind the Scenes, Gear Guides & More 🎬 Produced, Filmed and Edited by: Jason & Nikki Wynn ⚓️ Our Explorer Yacht ⚓️ 📷 Photo & Vi...
This Is Not the England We Expected
Fossils, ghost villages, white cliffs and a coastline we never expected... Go to or use code WYNNS at checkout to get 4 extra months of Surfshark VPN! ☝Behind the Scenes, Gear Guides & More 🎬 Produced, Filmed and Edited by: Jason & Nikki Wynn ⚓️ Our Explorer Yacht ⚓️ 📷 Photo & V...
Broken Engine, Big Waves Episode 8
We thought our biggest problem was a broken dinghy… until one of our engines refused to start and a massive wave came crashing through the front door of our boat. After six hours troubleshooting the engine in the Florida heat, Steve finally got us moving again. But our first real day sailing north ...
Mom’s First Adventure Aboard Our Explorer Yacht
Jason's mom finally joins us aboard our explorer yacht in England. 💦Stay Salty! Get your free LMNT Sample Pack with any purchase at The hardest part of this life isn't the weather, the logistics, or the constant maintenance. It's being far away from the people we love. ☝Behind the...
Stranded in a Lightning Storm…Then Our Hair Stood Up Episode 7
Our dinghy died miles from our sailboat as darkness closed in and a massive lightning storm rolled toward us. Then our hair began standing straight up—the terrifying warning that lightning could strike at any moment. What was supposed to be a simple family sailing trip from Miami to Key Largo for k...
Our Last Gulf Sail Before We Cross the Atlantic
In episode 79 of Secondhand Sailors, we update you with some surprise information: We are currently headed towards Europe! Today we let you join us for our last sail in the Gulf before we leave for Europe. #sailing #sailboat #secondhandsailors #SVDaisyMae
First Sail. First Fish | Our First Sail On Our Sailboat & Kamden Caught Dinner! Episode 6
We’re finally setting sail on our new floating home—and our very first fish aboard is a beautiful mahi-mahi! 🎣⛵️ After six exhausting days of moving aboard, organizing, provisioning, and preparing our Leopard 50 catamaran, it’s finally time to leave the dock and begin our next chapter as a full-tim...
One Design Problem Is Limiting Our Entire Boat
Our dinghy problem is bigger than it looks.🤔 Beam Dream is giving you early access to the Labor Day sale: up to 46% off for a limited time. Use the link in the description or Use code WYNNS at checkout! ☝Behind the Scenes, Gear Guides & More 🎬 Produced, Filmed and Edited by: Jason & Nikk...
Will She Fit? | Docking Our 50 ft Cat & Provisioning Our Sailboat Ep.5
We bought a Leopard 50 catamaran, moved our family of six aboard—and immediately discovered our new home wouldn’t even fit at the dock. This is the chaotic reality of becoming a full-time sailing family. After saying goodbye to everything familiar and catching a one-way flight to Florida, it was fi...
The Ultimate Test Sail Checklist-Don’t Buy a Money Pit
In episode 77 of Secondhand Sailors, we walk you through the test sail process of buying a secondhand sailboat. Before buying a used boat, you must perform a proper test sail. Learn how to spot expensive maintenance disasters before closing the deal. Performing a thorough test sail is the most crit...
There’s No Going Back Now Episode 4
We actually did it. We sold almost everything we own, said goodbye to our home, our cabin, our cars, our pets, our friends and the life our kids have always known… and boarded a plane to Florida to begin our new life sailing around the world. This episode is the end of one chapter for our family—an...
Your Boat Could Be Hiding Major Problems- And AI Won’t Find Them
In episode 76 of Secondhand Sailors, we examine the question: Is a professional boat survey really necessary before you buy a sailboat? We break down why skipping this step is a major risk. Buying a used sailboat is a significant investment that requires careful due diligence. Many viewers have ask...
We’ll Never Look at Honey the Same Again
We thought honey was simple. We were very wrong. 🐝 Go to or use code WYNNS at checkout to get 4 extra months of Surfshark VPN! ☝Behind the Scenes, Gear Guides & More 🎬 Produced, Filmed and Edited by: Jason & Nikki Wynn ⚓️ Our Explorer Yacht ⚓️ 📷 Photo & Video Gear 📷 📱Socials ...
We Invited a Family to Live on Our Boat for a Month
Two of us became six. Here's how that actually went. Head to to get a FREE AG1 Flavor Sampler and a FREE bottle of Vitamin D3+K2 in your Welcome Kit with your first AG1 subscription order ☝Behind the Scenes, Gear Guides & More 🎬 Produced, Filmed and Edited by: Jason & Nikki Wynn ⚓...
Her FIRST SOLO PROJECT! She Spent $0 & No One Got Hurt-Renee’s Sailboat Galley UPGRADE
In Episode 73 of Secondhand Sailors, we maximize our sailboat galley storage with these practical DIY modifications. Learn how we custom fit our cabinetry for provisioning for longer trips. Optimizing space on a small vessel requires creativity and the right tools. In our case, it involves repurpos...
Inside Our 50ft Aluminum Explorer Yacht
Tour of our new Explorer Yacht. Stay Salty! Get your free LMNT Sample Pack with any purchase at ☝Behind the Scenes, Gear Guides & More 🎬 Produced, Filmed and Edited by: Jason & Nikki Wynn ⚓️ Our Explorer Yacht ⚓️ 📷 Photo & Video Gear 📷 📱Socials INSTAGRAM: FACEBOOK: 📧J...
DIY Lithium Battery Upgrade Under $600 | Sailboat Power System Overhaul
In episode 72 of Secondhand Sailors, we upgrade our 37 foot sailboat's battery bank from lead acid to lithium. See how we safely perform a lithium battery conversion on Daisy Mae.This guide covers the full process of removing old lead acid banks and installing a modern lithium battery setup on...
Crossing the World’s Busiest Ocean Highway
The first true test of our new-to-us explorer yacht. 🌊 Beam Dream changed our sleep! Get up to 48% off sitewide right now with our exclusive code: WYNNS ☝Behind the Scenes, Gear Guides & More 🎬 Produced, Filmed and Edited by: Jason & Nikki Wynn ⚓️ Our Explorer Yacht ⚓️ 📷 Photo &...
We Expected a Sail | We Got an EPIC Dock Party Instead
In episode 71 of Secondhand Sailors, Turner & Renee try sailing on the 4th of July weekend. Our relaxing sailing trip turned into a major sailing breakdown when the engine failed. Watch how we handled a broken boat engine at sea. This video documents the reality of unexpected boat engine troub...
A Different Kind of Boat Life
Our first miles on the North Sea and a new chapter ahead.🌊 Get an exclusive 15% discount on Saily data plans! Use code WYNNS at checkout. Download Saily app or go to ☝Behind the Scenes, Gear Guides & More 🎬 Produced, Filmed and Edited by: Jason & Nikki Wynn ⚓️ Our Explorer Yacht ⚓️ ...
The Last Thing Standing Between Us and Open Water
The one test that had to work before we could finally leave the dock. 🦈 Go to or use code WYNNS at checkout to get 4 extra months of Surfshark VPN! 🎬 Produced, Filmed and Edited by: Jason & Nikki Wynn More Gyro Specs: 🧰 Anchor, Chain, Tools and all the other gear 🛠️ ⚓️ Our Explorer Yacht ...
NO SAILING TODAY! Tropical Storm Arthur Arrives
In episode 69 of Secondhand Sailors, Turner and Renee remain in their sailboat while TS Arthur hits Gulfport. They can't go sailing but they did give you a bird's eye view into what it's like to experience a tropical storm on a sailboat. #sailing #sailinglife #secondhandsailors #SVD...
This Cost a Fortune… We Removed It Anyway
We've discovered a surprising number of things that made us stop and ask, "Why on earth was this installed?" Plus, we finally splash! We are back on the water! ☝Behind the Scenes, Gear Guides & More 🎬 Produced, Filmed and Edited by: Jason & Nikki Wynn ⚓️ Our Explorer Yac...