Watch Sailing & Boating Adventures Around the World – Page 2 of 14
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 326 results
Installing Windlass Foot Switches — Sort Of
Today’s episode is all about cursed boat projects. I’m back in Waikiki and tackling a foot switch install for my broken windlass remote. Along the way, I get hot, frustrated, sentimental, and somehow wired things backwards, but hey, it still works (sort of). This is real-life boat work: messy, slow...
Sailing Into Trouble: The Day Our Anchorage Was a Crime Scene | Sailing Sitka Ep 179
Jay and Kenna lift the hook and set sail from Green Island toward the stunning Holadaze Cayes, one of the most picture-perfect anchorages in all of the San Blas Islands. But just when we thought we’d found paradise, we suddenly found ourselves—and Sitka—in the middle of an active criminal investigat...
Chasing Shelter: This is Saillife in the Canary Islands
Help to make these videos possible here When you’re cruising, anchoring isn’t just a detail—it’s what shapes your days, your nights, and sometimes your sanity. In this episode, we leave what we thought was the perfect anchorage in La Graciosa and head for shelter on the east coast of Lanzarote, tr...
TROUBLE IN PARADISE – Dinghy DISASTER in the REMOTE BAHAMAS! Ep-184
Get a FREE Wise card or your first transfer fee-free (up to $1,000 AUD) when you sign up with our link: 👉 Stuck in the remote Exumas with outboard engine trouble, we discover our dinghy is leaking oil—and we don’t have the right boat part to fix it. With limited options, we jury-rig a solution to ...
Dropping Anchor in a Lightening Storm⚡️ | Sailing Sunday VLOG 291
This week’s video is a raw, unfiltered look at what sailing really looks like when a storm rolls in out of nowhere — and you’re trying to make it to safe harbour with a baby onboard. It's the kind of moment that reminds us why preparation matters… and also why sailing with a baby adds a whole ...
We haven’t stepped foot on land in a week! (and heres why) | Sailing Sitka Ep 178
Jay and Kenna have been off the grid, not setting foot on land for over a week while sailing through the San Blas Islands. While anchored at Green Island, they took it slow to ride out some intense winds. With no working outboard and a less-than-reliable paddleboard, getting to shore has felt more l...
Like Sailing Through a Giant Swimming Pool – Bahamas Magic! Ep-183
Sailing the Bahamas in the clearest, bluest water we've ever seen—like a swimming pool! We explore sinkholes, swing off the boat, and soak it all in. This episode is packed with classic Bahamas magic—turquoise water, underwater adventures, and a few unexpected moments (including one accidental...
What it takes to keep this dream alive | Sailing Sitka Ep 177
Jay and Kenna have arrived at a new destination—Green Island, a stunning atoll tucked within the San Blas Islands. While this lifestyle often feels like a dream and looks like something straight off a postcard, it takes real balance to maintain it. Could you keep up? Subscribe, watch the journey, an...
Sailing & Small Town Charm | Boat Life in the Bahamas VLOG 290
This week’s episode is a simple one — just a real, honest look at life onboard right now. From slow mornings with coffee in the cockpit to climbing the iconic Elbow Reef Lighthouse and setting sail again (while dodging some pretty sketchy squalls), it turned into one of those days that makes us step...
SPORTY SAIL to Newfoundland with MASSIVE ENDING – Ep 244
Join us on this epic offshore sailing journey as we leave the calm beauty of Bras d'Or Lake, Cape Breton Island, and sail straight across the powerful Cabot Strait to St. John’s, Newfoundland! In this episode, we sail in big offshore waves, witness humpback whales breaching and approach the b...
OFFICIALLY Back in The Bahamas! | Sailing Sunday Vlog 289
We’ve officially made it to the Bahamas! After months on land adjusting to life as new parents we’re finally back on board sailing to the Bahanas. We checked into Marsh Harbour here in the Abaco, Bahamas to clear customs and immigration to start our first cruising days as a family of four. From chec...
Spearfishing, SHALLOW Cuts & BULL SHARK Encounter – SAILING the Jumentos Cays! Ep-182
Go to or use code LEADING at checkout to get 4 extra months of Surfshark VPN! We're sailing deep in the remote southern Bahamas — starting off with a dive and spearfishing session at Jamaica Cay in the Jumentos Cays. Then it's time to move north to Flamingo Cay… but not without a little ...![Our New Plan REVEALED! Did you guess right? [Ep. 191]](https://i.ytimg.com/vi_webp/W0yzlerzyvg/mqdefault.webp)
Our New Plan REVEALED! Did you guess right? [Ep. 191]
We reveal the next destination of our journey! But first we must finish this amazing passage from Rongelap to Majuro in the Marshall Islands! Don't miss out on some more sailing fun :) #sailing #marshallislands #travelvlog Don’t forget to subscribe to follow our journey across the Pacific and...
Sailing North: Navigating New Waters to an ICONIC Island – Ep 241
Sail with us from through New England as we leave Martha’s Vineyard behind and head for the fog-shrouded shores of Nantucket aboard our rugged aluminum sailboat. Navigating in dense fog and unfamiliar waters, we arrive in one of the most iconic destinations of a New England summer, Nantucket Island....
Off-Grid GIRLS Doing the DIRTY WORK – Sailing Wild Bahamas E-146
Our girl sailing crew dive for conch and experience the raw, real side of off-grid life in the Bahamas. Living on a sailboat isn’t always glamorous—but it's always an adventure! The girls get covered in conch 💩 and take an off grid shower. *Want to support us? Patreon: Buy Salsa a Coffee☕🧡: ...
Missed last week’s sailing adventure? Catch up before tomorrow’s full episode drops! ⛵️✨ #travel
We sailed deep into the remote Ragged Islands—where boat life gets seriously off-grid 🌴 From catching hogfish and cooking beach dinners to fixing the boat with whatever we had onboard, this trip had it all. 🏝 Wild beaches 🐟 Spearfishing success 🛠 Boat fixes (of course) 🔥 Bonfire nights 🐾 Cats gone ...
This Was NOT Part of the Plan…INJURED while Anchoring | VLOG 286
👇 Drop a comment: This week we're cruising down the ICW with Oakley and Jackson onboard, weaving through narrow channels and shifting sandbanks. Just when we thought we were in the clear, storms rolled in—and to top it off, I managed to injure myself while anchoring. Classic. ⛵️ KEEP UP WITH...
BUILDING MORE USABLE LIVING SPACE on our SAILBOAT before Sailing to the Arctic! – Ep 238
Join us as we tackle one of our biggest DIY boat projects yet: sewing and installing a full canvas enclosure on our custom aluminum sailboat! In this episode, we walk you through the entire process — from choosing the right marine-grade materials to patterning, sewing, and installing our cockpit enc...
The ONE Question That Changes Everything About Buying a Boat
Want a signed copy of my book? Limited time: Buying your first sailboat? There’s ONE question you must ask before you spend a dime—or you’ll end up with a floating disaster that doesn’t match your life at all. In this video, I break down the six real-world sailing archetypes—and exactly what kin...
Better off Naked?! Rash ending to final days of Boat Life in Paradise – Ep 236
Get an exclusive 15% discount on Saily data plans! Use code JIBSEA at checkout. Download Saily app or go to Sailing the British Virgin Islands as our last stop in the Caribbean before we set sail for the high latitudes for our next big adventure on our new to us custom aluminum sailboat. In this ...
Upgrading My Sailboat for Summer: Solar, Teak & Adventures in Greece
Support on Patreon: After months of lockdown on the Greek island of Evia, I finally upgraded my sailboat’s solar power, repaired the teak, fixed the outboard, and patched up the dinghy — all to get ready for the next big adventure. In this video, I take you behind the scenes as I prepare for summer...
Wild BAJA Sailing Life | GALES, Dolphins, & SHARKS! – Ep. 97
Welcome back! It's been a little while, but we're back with another fun episode from our adventures around the Loreto area in the Gulf of California. In this episode, we continue our trip with our friend Chelsea aboard. As we leave Isla Danzante, we are greeted by some robust winds that ha...
Installing Starlink & Diesel Heat on Our Sailboat + Carbon Fiber Vacuum Bagging (w/ Ducks!)
From Racer to Home: Installing Starlink, Diesel Heat & Vacuum Bagging Magic! Plus Meet the Ducks! Welcome back aboard SV Another Adventure, where we’re turning a retired racing trimaran into our dream cruising/liveaboard sailboat—and this episode’s got a little bit of everything! 📡 We kick thi...