Watch Sailing & Boating Adventures Around the World – Page 3 of 43
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 49-72 of 1014 results
WORST WEEK EVER! Injury, Storm Damage & Boat Chaos 😱⛵ E386
People often see the beautiful beaches, sunsets, and tropical anchorages... but this is the side of cruising life nobody talks about. What started as a simple solar panel upgrade quickly turned into the worst week we've had in a long time. ⚠️ Kai falls and splits his forehead open ⚠️ Everyone...
DON’T MISS These St. Martin & Sint Marteen Highlights! ✈️ Carnival & Giant Planes E385
If you're visiting Saint Martin / Sint Maarten, these are experiences you won't want to miss! We hop on a local bus to the Dutch side and head to the world-famous Maho Beach, where massive jets fly just overhead before landing at Princess Juliana Airport. Seeing these giant planes pass on...
From Paradise to France! Overnight Sail, Tuna Feast & St. Martin’s French Lifestyle E384
After exploring beautiful St. John in the US Virgin Islands, it's time to check out of Cruz Bay and set sail for a long overnight passage to the island of Saint Martin! The crossing keeps us busy as the fishing lines come alive and we land multiple tuna along the way. After arriving in Marigot...
We Didn’t Expect St John to Be THIS Beautiful E383
This week aboard SV Wildly Intrepid we continue exploring the stunning island of Saint John! We sail from beautiful Waterlemon Bay to the world famous Trunk Bay with its crystal clear turquoise water and perfect white sand beach. A tropical rain shower clears the crowds and leaves us almost alone i...
We Found the PRETTIEST Island in the Caribbean E382
This week aboard SV Wildly Intrepid we explore what might be the most beautiful island we’ve visited all season… 🌴🇻🇮 Sailing the US Virgin Islands with our buddy boat, we explore St John Island and hike the incredible trail from Francis Bay while discovering the crystal clear waters of Francis Bay ...
Boat Life in the Remote Bahamas Hits Different | Day 6-7
Still tucked away in the Ragged Islands, we’re waiting on the right weather window to make our next big move south to Colombia… but life out here doesn’t exactly slow down. While we wait, it’s time to get a few jobs ticked off. We break out the sewing machine onboard and get to work repairing our...
Why St. John Feels Nothing Like St. Thomas E381
🌴 Island hopping through the USVI brought us from the busy streets of Charlotte Amalie on St. Thomas to the wild beauty of St. John… and what an adventure it turned into. We wandered the steep chaotic roads of Charlotte Amalie (definitely not the most pedestrian-friendly place 😅), got rescued with ...
This 46-Foot Yacht Is Shockingly Cheap… Here’s the Catch
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We Didn’t Expect THIS in the US Virgin Islands… E380
Our sail from Puerto Rico to the US Virgin Islands started off absolutely perfect… warm winds, beautiful seas, and another unforgettable Caribbean passage aboard SV Wildly Intrepid. But once we arrived in St. Thomas, things got interesting fast. We explored the abandoned tunnels of Fort Segarra on ...
From Chaos to Paradise: Sailing Vieques → Culebra → Puerto Rico E379
What started as a simple sail turned into a full-on emergency… As we left Vieques, a hose clamp suddenly snapped—dumping all our engine coolant in seconds. With no engine and two little ones onboard, we had no choice but to drop anchor fast and figure things out. From there, we sail on to Culebra—...
PRIVATE Island bliss…Then we Invited a Rock Legend Aboard | Guana Island BVI #trawlerlife
Sailing through the British Virgin Islands, we moored off the ultra-exclusive Guana Island—a private island paradise with one of the most beautiful beaches in the Caribbean. What starts as a peaceful day of boat life quickly turns surreal when we meet rock legend Billy Squier… and end up inviting hi...
We Found the BRIGHTEST Bioluminescent Bay on Earth! Vieques (Family Sailing Caribbean) E378
Not every stop is planned… and sometimes those are the best ones. We dropped anchor in Puerto Patillas, Puerto Rico and were blown away. A peaceful anchorage, a waterfront park with a playground (perfect for homeschooling days), live music, and even iguanas roaming around—it quickly became one of t...
We Shouldn’t Have Sailed to the Bahamas… But We Did Anyway | Sailing Sunday Vlog 306
We shouldn’t have left when we did… but we sailed anyway. In this episode of Sailing Sunday, we sail to the Bahamas on a 3-day ocean passage after rushing across the USA to get back to our boat. With almost no sleep, we left the dock and crossed toward the Bahamas, dealing with rough seas, bad timi...
Do Lagoon 450s REALLY Break in Half?
If you’re researching the Lagoon 450 bulkhead issue, wondering about Lagoon 450 structural problems, or asking “do Lagoon 450s break in half?” — this video breaks down everything you need to know. We cover forward bulkhead deformation on Lagoon catamarans, how common the issue actually is, which yea...
3 Fails in 3 Days… Puerto Rico Didn’t Go As Planned E377
Not every sailing day goes to plan… and this one REALLY didn’t 😅 We kick things off with a beautiful, calm sail past Cabo Rojo Lighthouse—one of the most stunning coastlines in Puerto Rico. But from there… things start to unravel. We anchor in La Parguera hoping to experience the famous biolumines...
Everyone Hates This Sailboat… So Why Do People Love It?
Hunter 380 review, Hunter sailboat review, B&R rig explanation, Hunter Marine sailboats, is a Hunter sailboat good, Hunter 380 specs, Hunter 380 problems, coastal cruising sailboat, best sailboat for beginners, easy to sail sailboat, Chesapeake Bay sailing, Bahamas cruising sailboat The Hunter ...
Why Would Anyone Want a Trimaran?
Why would anyone choose a trimaran over a monohull? In this video, we compare the Dragonfly 36 trimaran vs a Beneteau Oceanis 40.1 to answer one of sailing’s biggest questions: are trimarans better than monohulls? We break down trimaran vs monohull pros and cons, including speed, stability, comfort,...
We Survived the MONA PASSAGE (47hrs Nonstop Sail to Puerto Rico) E376
After months of life in Luperón, Dominican Republic, it was finally time to move on… and take on one of the Caribbean’s most notorious crossings — the Mona Passage. We set sail for Puerto Rico on a 47-hour, 245 nautical mile passage, pushing through a double overnight sail with little sleep and sea...
Why Are Whales Sinking Sailboats?
Why are whales sinking sailboats? Over the last few years, reports of orcas attacking sailboats have exploded across the sailing world, particularly off the coasts of Spain, Portugal, and the Strait of Gibraltar. Sailors have reported killer whales targeting rudders, disabling steering, and in some ...
This Was Our Toughest Hike (Isabel de Torres) + Our Final Luperón Days
This one tested us 😅 We took on the steep and slippery climb up Isabel de Torres in Puerto Plata—and it was no joke. Muddy trails, sketchy footing, and a serious leg burn… but the view at the top made every step worth it. Sitting above the city with a mini botanical garden and that iconic statue, i...
Why Most People Quit Living on a Sailboat
Living on a sailboat sounds amazing… until reality sets in. In this video, we talk honestly about why most people quit living on a sailboat. Not the romantic Instagram version. The real, day-to-day challenges that catch people off guard and slowly wear them down. If you’re thinking about: • living o...
The Cheapest Modern Sailboats You Can Actually Live On
Can you live on a sailboat if you’re not a sailor? Yes. And it doesn’t have to be expensive, old, or uncomfortable. In this video, we’re talking about the cheapest modern sailboats you can actually live on. Not performance boats. Not ocean-crossing yachts. Just modern, affordable, floating homes tha...
Free Sailboat Living The Only Way It Actually Works
Can you really live on a sailboat for free? Not the Instagram fantasy version — the real, practical version. In this video, we break down how people actually live on sailboats for little to no monthly cost, using real systems that work in the real world. This isn’t about hacks or shortcuts. It’s ab...