Watch Sailing & Boating Adventures Around the World – Page 2 of 18
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 415 results
The Soggy Dollar Bar on Jost Van Dyke, in the British Virgin Islands. Voted best in the Caribbean!
"Discover the Iconic Soggy Dollar Bar on Jost Van Dyke, British Virgin Islands" Voted as the #1 beach bar in the caribbean by USA Today! Join us on a tropical adventure to the world-famous Soggy Dollar Bar, located on the stunning shores of Jost Van Dyke in the British Virgin Islands. Kno...
TEAK, TENDERS & THEFT in the TROPICS – Ep 224
Join us as we set sail from the beautiful British Virgin Islands island hopping the half French, half Dutch island of St. Martin/Sint Maarten during the winter aboard our custom aluminum sailboat. In this video, we take you through the practical side of cruising, including essential DIY boat mainten...
CRUISING ALUMINUM SAILBOAT: GOING WITH THE FLOW
Join us on sailing adventure as we explore the stunning U.S. Virgin Islands (USVI) aboard our aluminum sailboat and sail to the British Virgin Islands (BVI) . In this episode, we were hoisting the sails in whichever direction where the wind takes us even if it means backwards or double the mileage. ...
24 HRS OF BOAT LIFE: Day in the Life & Tropical Escape – Ep 222
Ever wondered what it’s like to live on the open water, exploring hidden islands, and embracing a minimalist, off-the-grid lifestyle? In this video, we take you on a journey through 24 hours aboard our custom aluminum sailboat, showcasing life in a tiny floating home in the stunning Caribbean. We&...
BOAT LIFE AFTER ROUGH PASSAGE: Assessing the Damage…Is this Lifestyle Worth It? – Ep 221
After a challenging and intense journey across the open Atlantic Ocean we’ve finally made it to the British Virgin Islands in the Caribbean. Join us on this new exciting chapter of full-time cruising as we arrive in paradise to live life on anchor. We walk you through our recent anchor and chain i...
Exploring the British Virgin Islands by boat. Why this trip should be on your BUCKET LIST!!!
Set sail with us for an unforgettable week in the British Virgin Islands! 🌊🏝️ From the stunning rock formations of The Baths to the vibrant underwater world at The Indians and Norman Island’s caves, every stop on this journey is a dream come true. Explore the charm of Cooper Island, the lively vibe ...
Sailing the BVI. Setting sail for Cooper Island
Our BVI sailing adventure kicks off with an exciting Day 1! We set sail from Nanny Cay, enjoy the beauty of the open water, and arrive at the picturesque Cooper Island. After settling in, we wrap up the day with a delicious dinner at the Cooper Island Beach Club, surrounded by stunning views and isl...
Best BVI beach bar! Nigel’s boom boom beach bar. Things to do on Tortola!
Discover the ultimate beach bar experience on Tortola at Nigel’s Boom Boom Beach! 🌴🍹 Located on the pristine sands of Smuggler’s Cove, this hidden gem is all about good vibes, refreshing drinks, and breathtaking views. Whether you’re sipping Nigel’s famous rum punch or enjoying the laid-back island ...
Sailing the BVI. Soggy Dollar Bar on Jost Van Dyke
Day 5 in the British Virgin Islands: Jost Van Dyke & White Bay Adventure Join us for another breathtaking day in the British Virgin Islands! On Day 5, we visit the iconic Jost Van Dyke and dive into the vibrant beauty of White Bay. Famous for its crystal-clear waters and powdery sand, White Bay ...
Sailing the BVI. Seeking shelter (& RUM) at Foxy’s
Join us on Day 4 of our sailing adventure as we navigate from Leverick Bay to Great Harbour on Jost Van Dyke, all while braving some rainy weather. Despite the drizzle, the beauty of the islands never fades, and we make the most of the day. Watch the full journey unfold as we sail through the Caribb...
Sailing the BVI. The Baths National Park on Virgin Gorda
Join us as we head out on an adventure in an open air pickupas we explore the island of Virgin Gorda, one of the most stunning islands in the British Virgin Islands! In this video, we take you to the famous Baths, a unique and breathtaking natural wonder known for its massive granite boulders, cryst...
Sailing the British Virgin Islands
Join us as we start our BVI bareboat charter adventure with an overnight stay at Nanny Cay marina on Tortola. This charter we will be on Limin, a 45' Fountaine Pajot catamaran from Navigare Yachting. In this video we introduce you to our amazing crew, explore the marina and share a glimpse of...
Growing Up Living On A Sailboat (Sailing the US Virgin Islands) Episode 26
This video is of our sailing family. My 3 BOYS have long hair. They are BOYS NOT GIRLS. Sailing Adventures in the Virgin Islands | Family, Repairs, and Stunning Beaches Join us as we navigate the ups and downs of life on the water in the Virgin Islands! This week, our genoa sail tears, leaving us...
Sailing charter almost ruined by tropical storm…
In the days leading up to our recent bareboat sailing charter in the British Virgin Islands, the weather forecast predicted severe conditions, including a low-level hurricane. We flew into St. Thomas and took a ferry to Tortola a few days before our charter was set to begin. Fortunately, the weather...
RACE CHAOS: Man Overboard in the Heat of Competition!! EP-146
Sailing the British Virgin Islands in Leg 2 and Leg 3 of the Chasing Bubbles Regatta was an unforgettable adventure! From broaching and nearly shredding our sail in a sudden squall to Jason falling overboard, this week had it all. We capped off the chaos with an epic after-party at Willy T's an...
SAILORS GONE WILD: EPIC RAFT PARTY & REGATTA KICKOFF! EP-145
Sailing the British Virgin Islands! We kick off the week with an unforgettable Young Cruisers Raft Party, hosted by our mates from @SpearItAnimal , before diving into the first-ever @ChasingBubbles Regatta! From the Skippers Meeting at Virgin Gorda to the exhilarating race to Scrub Island, this jou...
We invited complete STRANGERS to join our BOAT crew! CASTAWAYS…
Call us crazy, but we recently invited some complete strangers on our upcoming bareboat charter trip! In this video we fly to Ft. Myers beach, Florida to meet up with some Castaways who will be joining our boat crew in November as we island hop throughout the British Virgin Islands on a 45' Fou...
Sailing from BVI to Guatemala (FULL DOCUMENTARY)
Sailing Big Lost navigates a 1,400-nautical-mile passage from Nanny Cay in the British Virgin Islands to Rio Dulce, Guatemala, battling mechanical repairs, squalls, and relentless wing-on-wing helming across the Caribbean.
Unlocking the Secrets of the Deep with PADI (Open Water Course)
Conor, Finn, and 10-year-old Maddie earn their PADI Open Water Diver certifications with Blue Water Divers in the British Virgin Islands, tackling regulator drills, CESA ascents, and reef dives off Norman Island.
Setting Sail: Our First Adventure Aboard the New Catamaran
After earning their ASA certifications, Conor and Kelly Malone board their newly acquired Leopard 62 catamaran, The Big Dog, for a week-long shakedown cruise across the British Virgin Islands with Captain Terry and Ruth.
Ep 163 Back in the Amazing BVIs Again | Full Moon Party Trellis Bay, Foxy’s New Year’s Eve Party
Following our leaving for the USVI’s after being disappointed by the BVI’s ridiculous 30-day tourist visa rules, we return knowing that the officious behavior is simply the gatekeeping, and we know from long experience that these challenges are rarely, if ever, representative of the greater populati...
Sailing lessons ASA 101 & 103: The Good, The Bad, The Ugly
After purchasing a cruising catamaran, Connor and Connie of Sailing Big Lost head to Nanny Cay in the British Virgin Islands to master basic keelboat and coastal cruising skills through intensive ASA 101 and 103 courses aboard a Beneteau 38.
Is The Survey And Sea Trial Worth It On Your New Boat?
Join the Malone family in Tortola, BVI, as they undertake an in-water marine survey, rigging inspection, and heavy-wind sea trial aboard Big Dog, a 2002 Robertson & Caine 62 catamaran.