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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Sailor, Captain, Instructor and Entrepreneur. She’s done it all!
Sail Stillwater

Sailor, Captain, Instructor and Entrepreneur. She’s done it all!

USCG Master Captain Amanda Haley joins Sail Stillwater to break down Caribbean navigation, charter captain licensing, inter-island channel crossings beyond Tortola, and seamanship throughout St. Vincent and the Grenadines.
The Charter Captain everyone wants, in the BVI
Sail Stillwater

The Charter Captain everyone wants, in the BVI

Join us for an inspiring conversation with Captain Jason Geyser, one of the most requested yacht charter captains in the British Virgin Islands (BVI). In this episode, Jason shares his journey into the world of luxury yacht charters, his lifelong passion for sailing, and the hospitality-first minds...
Caribbean Freedom, Baby… ALMOST – Eps 74
Salty Days Adventures

Caribbean Freedom, Baby… ALMOST – Eps 74

Hey Legends, We’ve finally made it to Tortola in the British Virgin Islands… and this is the moment we first lay eyes on our new floating home. After selling everything and hitting reset on life, we’ve been housesitting, dreaming, and chasing our way back to the water. A failed boat search in Phuk...
Best BVI beach bar! Nigel’s boom boom beach bar. Things to do on Tortola!
Sail Stillwater

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 British Virgin Islands
Sail Stillwater

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...
Sailing from BVI to Guatemala (FULL DOCUMENTARY)
Sailing Big Lost

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)
Sailing Big Lost

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
Sailing Big Lost

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.
Sailing lessons ASA 101 & 103: The Good, The Bad, The Ugly
Sailing Big Lost

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?
Sailing Big Lost

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.
Catamaran Paradise: Our Journey to Buy a Boat in the Virgin Islands
Sailing Big Lost

Catamaran Paradise: Our Journey to Buy a Boat in the Virgin Islands

Sailing Big Lost reaches the Virgin Islands after a grueling week of travel, unwinding at Coral World Ocean Park on St. Thomas before boarding a ferry to Road Town, Tortola to survey a custom Robertson and Caine 62 catamaran on the hard.
Ep 160 Cursed Projects Part II | Tortola and Scrub Island, BVI
Sailing Talisman

Ep 160 Cursed Projects Part II | Tortola and Scrub Island, BVI

In this episode we make the hop from Sint Maarten to the British Virgin Islands without fully completing the projects we were working on. And, of course more crop up. And things go from mere nuisance to much bigger problems when our mainsail starts jamming so brutally that it actually breaks the a...
Catamaran bareboat charter (how much does it cost)
Sail Stillwater

Catamaran bareboat charter (how much does it cost)

Whenever we are planning a trip the first question we get from people is wanting to know how much a trip like this costs. So we put this together hoping it would help/encourage more people give it a try! Bareboating a catamaran is a wonderful way to vacation and the price you pay isnt all that much ...
TROUBLE WITH CUSTOMS! SAILING the BVI’s – Ep. 20
The Ocean Bandits

TROUBLE WITH CUSTOMS! SAILING the BVI’s – Ep. 20

Join us as we explore the BVI’s! Hit the SUBSCRIBE button! We do our best to film, edit, and post in REAL TIME Buy us a Beer🍻 For Bonus content, early access to ad-free episodes, and updates within our community: ▸ ↓ BINGE WATCH ↓ ▸ Watch our story from Episode 1 : FOLLOW US: ▸ Website:...
Moorings Bareboat Charter to Cane Garden Bay | Boating Journey
Boating Journey

Moorings Bareboat Charter to Cane Garden Bay | Boating Journey

In episode 144 we leave Saba Rock and head to Monkey Point for some snorkeling and then to Cane Garden Bay in our bareboat Moorings 433 Power Catamaran. Check out the first leg of the trip here: Be sure to subscribe to our channel and our blog at www.boatingjourney.com for more adventures! Next...
Exploring the Ruins on St John | Boating Journey
Boating Journey

Exploring the Ruins on St John | Boating Journey

In episode 113, we explore the sugar mill ruins and plantations on St John, USVI with a private guide named Tony. This was a great way to see the ruins up close without being in a large tour group. What we didn't expect was a mode of transportation! It was also cool to see how close we actually...
Freediving: Wreck of the RMS Rhone in BVI – Sailing Sweet Ruca
Sailing Sweet Ruca

Freediving: Wreck of the RMS Rhone in BVI – Sailing Sweet Ruca

Just before the Covid-19 lockdown in BVI we had the unique chance to be the only people at the wreck of the RMS Rhone. Normally there are dozens of dive and charter boats here with hundreds of people in the water. We got to experience it like no other. Check it out as Kate and Curtis from team Saili...
Sailing Interview with Greg Fisher, 20 questions
Sailing Views

Sailing Interview with Greg Fisher, 20 questions

Greg, talks about coaching , sailing ,Pan Am's etc. Due to my hectic schedule the past 2 weeks I had tp pull the earlier unedited version down. And repost this one.
20 questions Elizabeth Kratzig
Sailing Views

20 questions Elizabeth Kratzig

Elizabeth Kratzig talks with me about sailing. Match racing and other things. You will notice some editing in this video as I thought we lost some things, Turns out we didn't. But I threw a double dose in anyway. Sorry for the sound quality. I just rebuilt my computer and am having tons o...
20 questions with Dawn Riley
Sailing Views

20 questions with Dawn Riley

Dawn talks answers my questions about Women's sailing, Americas Cup, Maiden, Might Mary, OaKcliff, and more. Even turns me down when I try to sell her some sails.
20 questions With Chris Watters
Sailing Views

20 questions With Chris Watters

Chris answers all the usual questions, talks about his favorite program, sailing in the Islands and Canada, Coaching and more.
THE FAILED LIVE INTERVIEW,  Eduardo Cordero.
Sailing Views

THE FAILED LIVE INTERVIEW, Eduardo Cordero.

8x World Champ, Eduardo Cordero and I rehash the past. We thought we were Live... But I` kinda messed up. Ok I really messed it up! Needless to say. This is the result. At least I Did record it. So you have something to watch. It just wasnt Live like I hoped.... I need help with t...
Lagoon 450 Review – Sailing Croatia with 10 Women
Igor Stropnik

Lagoon 450 Review – Sailing Croatia with 10 Women

Sailing Croatia on Lagoon 450 from Dubrovnik to Split with 10 Women. SUBSCRIBE to my channel: My Outdoor YouTube Channel
The BVIs: Still Worth It After Hurricanes Irma & Maria? Absolutely!!! [🎥14🇻🇬]
The Sailing Family

The BVIs: Still Worth It After Hurricanes Irma & Maria? Absolutely!!! [🎥14🇻🇬]

We were told by many people to avoid the BVIs after two Category 5 Hurricanes leveled the BVIs just a year before - but we had so many lasting memories from our previous cruise that we had to share this special place with our boys. Despite visible signs of devastation on land, much of the BVIs remai...
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