Watch Sailing & Boating Adventures Around the World – Page 2 of 31

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 25-48 of 743 results
We Found Guadeloupe’s Most Beautiful Beach! | Grand Anse by Sailboat E393
Wildly Intrepid Sailing

We Found Guadeloupe’s Most Beautiful Beach! | Grand Anse by Sailboat E393

Anse Leroux, Guadeloupe is perfect, with crystal-clear water, a close by beach and fantastic snorkeling just a short ride from the boat. From there, we take a long dinghy ride to the colorful village of Deshaies, where we wander the charming streets and discover an amazing local bakery serving deli...
Been to the BVI? Sail these islands next!
Sail Stillwater

Been to the BVI? Sail these islands next!

If you have sailed the British Virgin Islands and are looking for a new challenge or just new scenery, look into sailing Antigua or the Abacos Bahamas. In this video, we're comparing Antigua and The Abacos in the Bahamas as two of the best alternatives to a BVI sailing charter. Whether you�...
Goodbye Saba… A 3-Day Caribbean Sailing Adventure to Guadeloupe E392
Wildly Intrepid Sailing

Goodbye Saba… A 3-Day Caribbean Sailing Adventure to Guadeloupe E392

Leaving Saba was one of the hardest departures yet. It quickly became one of our favorite islands in the Caribbean, but the weather had other plans. With stronger winds on the way, it was time to keep heading south. Our original plan was to spend a few days exploring St. Kitts and Nevis, but the an...
SSL776 ~ First Overnight Test after Refit.. How did She perform?
Captain Rick Moore

SSL776 ~ First Overnight Test after Refit.. How did She perform?

After almost a year on the hard, Sophisticated Lady is back where she belongs — offshore, under full sail, heading somewhere extraordinary. We pulled anchor from the stunning Rosario Islands of Colombia at dawn and pointed the bow toward one of the most legendary sailing destinations on the planet:...
Our FINAL Day on Saba | The Caribbean’s Most Incredible Island? E391
Wildly Intrepid Sailing

Our FINAL Day on Saba | The Caribbean’s Most Incredible Island? E391

Saba completely stole our hearts, and saying goodbye wasn't easy. 🌋❤️ Before setting sail, we squeezed every last adventure out of what has become our favorite island in the Caribbean. Our final day starts with one last spectacular hike from The Bottom to Windwardside via the beautiful Crispee...
Sailing to Saba: The Caribbean’s Hidden Jurassic Island E390
Wildly Intrepid Sailing

Sailing to Saba: The Caribbean’s Hidden Jurassic Island E390

Saba completely blew us away. 🤯 After waiting for the perfect weather window, we finally sailed to one of the least-visited islands in the Caribbean—and it instantly became one of our favorites. Towering straight out of the sea, Saba looks more like something from Jurassic World than the Caribbean...
We Hiked a Volcano with a 2 & 4 Year Old! | Mount Scenery, Saba E389
Wildly Intrepid Sailing

We Hiked a Volcano with a 2 & 4 Year Old! | Mount Scenery, Saba E389

After finally finding the perfect weather window, we arrive in spectacular Saba and check in by sailboat to one of the most unique islands in the Caribbean. Our adventure begins with a ride along the legendary "Road That Couldn't Be Built"—an engineering marvel carved into impossibly...
ANSE DE COLUMBIER IN ST. BARTS – A MUST SEE SAILING ANCHORAGE.
Sailing PILAR - Blue Dot Voyages

ANSE DE COLUMBIER IN ST. BARTS – A MUST SEE SAILING ANCHORAGE.

Discover the serene beauty of Anse De Columbier, a perfect spot for your next boating mooring ball pickup. This marine park offers peaceful waters, scenic hiking trails, and picturesque beaches for sailors of all levels. Subscribe for more sailing destination guides and cruising tips. LINKS: SUB...
Our First Overnight Sail as a Family
Finding Our Isla Sailing

Our First Overnight Sail as a Family

Our first overnight sailing passage took us from St. Martin to the U.S. Virgin Islands aboard our Lagoon 450 catamaran—and honestly, it wasn't what we expected. As a family of six living aboard full-time, sailing through the night with our kids was one of the biggest milestones of our journey....
Sailing to a Volcano: The Caribbean’s Island in the Clouds E388
Wildly Intrepid Sailing

Sailing to a Volcano: The Caribbean’s Island in the Clouds E388

After a much longer stay in Saint Martin than we ever planned, the day has finally arrived—we're setting sail for Saba! 🌊⛵️ Known as the Island in the Clouds, Saba rises dramatically from the sea as a towering volcanic peak, creating one of the most breathtaking landscapes in the Caribbean. We...
WE SAW JEFF BEZO’S $500M MEGA YACHT IN ST KITTS ( AND KILLER BEES IN NEVIS ! )
Sailing PILAR - Blue Dot Voyages

WE SAW JEFF BEZO’S $500M MEGA YACHT IN ST KITTS ( AND KILLER BEES IN NEVIS ! )

Why is a December sailing trip to St. Kitts and Nevis worth the effort? We captured the island rhythm firsthand before the January/February tourist rush. If you are plotting a Caribbean sailing trip, this dual-island nation offers a unique pace that feels distinct from the rest of the region. We sp...
Caribbean Festival, Wasp Attack & Boat Repairs! ⛵ E387
Wildly Intrepid Sailing

Caribbean Festival, Wasp Attack & Boat Repairs! ⛵ E387

Life in Saint Martin is looking much brighter this week! 🌴⛵ After a rough stretch of boat problems and setbacks, we're finally enjoying island life again. Coral is having the time of her life jumping off the sailboat into the crystal-clear Caribbean waters, and we experience the vibrant atmosp...
WORST WEEK EVER! Injury, Storm Damage & Boat Chaos 😱⛵ E386
Wildly Intrepid Sailing

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...
WE SAILED ST. BARTS – 16 BEACHES & EXCLUSIVE SPOTS YOU HAVE TO SEE!
Sailing PILAR - Blue Dot Voyages

WE SAILED ST. BARTS – 16 BEACHES & EXCLUSIVE SPOTS YOU HAVE TO SEE!

People often ask us “what is your favorite place you have sailed?” We have sailed from Maine to Florida and every Caribbean Island and hands down, our favorite was St. Barts. (also known as St. Barths, Saint Barthelemy). This “Riviera of the Caribbean” is known for it’s red roofed homes, volcanic...
🌴 The Last Paradise Before the Pacific Crossing | San Blas Islands! Ep-227
Leading the Escapade

🌴 The Last Paradise Before the Pacific Crossing | San Blas Islands! Ep-227

After weeks of offshore passages, unexpected challenges, and nonstop movement, we finally wake up in one of the most beautiful cruising destinations in the world: the San Blas Islands of Panama. With only one day to explore before continuing our journey, we move Escapade into crystal-clear shallow ...
DON’T MISS These St. Martin & Sint Marteen Highlights! ✈️ Carnival & Giant Planes E385
Wildly Intrepid Sailing

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...
We Thought the Lagoon Was Safe… We Were Wrong
Finding Our Isla Sailing

We Thought the Lagoon Was Safe… We Were Wrong

After months of upgrades, projects, and settling into life aboard our Lagoon 450 catamaran, Isla is finally starting to feel like home. In this episode, we install our Seawater Pro watermaker, spend time enjoying life in the lagoon, navigate unexpected health challenges, make Isla official with her...
We Finally Fixed the Worst-Looking Part of Our Boat Ep. 277
Sailing Zephyr

We Finally Fixed the Worst-Looking Part of Our Boat Ep. 277

After months of projects, upgrades, and hard work, Zephyr 2.0 is finally starting to become the boat we’ve always dreamed of. This episode takes us to the Bahamas where James tackles one of the biggest transformation projects yet. Out goes the tired old lazy bag and in comes a beautiful new custom ...
From Paradise to France! Overnight Sail, Tuna Feast & St. Martin’s French Lifestyle E384
Wildly Intrepid Sailing

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...
The Pros and Cons of Sailing in Anguilla
Sailing PILAR - Blue Dot Voyages

The Pros and Cons of Sailing in Anguilla

Anguilla should be on all sailor's lists to visit, if only for a short stay. Pristine beaches and beautiful coastlines make it worthwhile. Learn how to sail Anguilla while keeping the costs down in this video. Why did we go to Anguilla ? Anguilla is not a popular destination for sailors, b...
We Somehow Made It To The Bahamas…Then The Boat Work Started – Ep.276
Sailing Zephyr

We Somehow Made It To The Bahamas…Then The Boat Work Started – Ep.276

In our last episode we splashed the boat and moved her to a new marina… and now somehow we’re already in the Bahamas?! Things moved fast after that. My dad flew out to help James bring our new catamaran all the way from a freezing North Carolina down to the Bahamas. Unfortunately the cameras didn’t...
Guess How Much We Spent On Our Catamaran!
Finding Our Isla Sailing

Guess How Much We Spent On Our Catamaran!

After weeks of battling Christmas winds, rough anchorages, and learning how to sail our Lagoon 450, we finally arrived in Saint Martin — the cruiser "Promised Land." And then we spent $12,870.66. 😳 In this episode, we're transforming Isla from a bare-bones boat into a true home for ...
My Son Had To Retrieve His Spear… While Sharks Circled 😳🦈
Finding Our Isla Sailing

My Son Had To Retrieve His Spear… While Sharks Circled 😳🦈

One of those moments that reminds you we’re visitors in their world. 🦈 Krew speared a fish, but it became lodged in the rocks. Within seconds, two sharks showed up and started circling. We left the water immediately and came back later to retrieve the spear. The sharks were still there. The missi...
We Didn’t Expect St John to Be THIS Beautiful E383
Wildly Intrepid Sailing

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...
WeBoating
Logo
Shopping cart