Watch Sailing & Boating Adventures Around the World – Page 2 of 11

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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BIG FAIL, AMATEURS! Sailing to the NARROWEST PLACE ON EARTH- Ep 196
Sailing Jibsea

BIG FAIL, AMATEURS! Sailing to the NARROWEST PLACE ON EARTH- Ep 196

Join Sailing Jibsea as they navigate their way through the beautiful waters towards the narrowest place on Earth - Glass Window Bridge in Alder. Experience the stunning natural beauty of this remarkable destination with its turquoise waters, pristine beaches, and mesmerizing landscapes.
YOU GOT 2 OPTIONS – Ep 195
Sailing Jibsea

YOU GOT 2 OPTIONS – Ep 195

Explore two unique ways to sail through uncharted islands in the Bahamas. Enjoy crystal-clear waters and hidden gems like Shroud Key and Little Hall's Pond key with Stefan Travis from Sailing Gypsy. Join us for an adventure you won't forget!
BOAT LIFE: GIVING ALL MY TRUST – Ep 194
Sailing Jibsea

BOAT LIFE: GIVING ALL MY TRUST – Ep 194

Join the Sailing Gypsy crew for an unforgettable journey that takes them through serene anchorages, the renowned Thunderball Grotto, and even a hilarious attempt at cutting hair. Don't miss out on their thrilling escapades!
KICKED OUT OF OUR SPECIAL SPOT! – Ep 193
Sailing Jibsea

KICKED OUT OF OUR SPECIAL SPOT! – Ep 193

Sail and Gypsy find themselves in a familiar yet different place at Crab Key Cove in the Exuma Keys. Despite being welcomed initially by nature's beauty, they soon receive an unexpected visit from park wardens regarding their anchorage. Follow them as they navigate these changes while still app...
BOAT PROBLEMS ON REMOTE BOOBY ISLAND – Ep 192
Sailing Jibsea

BOAT PROBLEMS ON REMOTE BOOBY ISLAND – Ep 192

Embark on an adventure with Sailing Gypsy to Booby Island, where they face the trials and joys of self-sufficiency amid stunning surroundings. Catch them as they solve unexpected boat problems while off-grid in this breathtaking haven.
THINGS ALWAYS BREAK AT THE WORST TIME – RAW & UNFILTERED SAIL – Ep 191
Sailing Jibsea

THINGS ALWAYS BREAK AT THE WORST TIME – RAW & UNFILTERED SAIL – Ep 191

Sailing Gypsy ventures into the shallow waters of the Bahamas, facing equipment failures in tricky conditions. Their destination is the secluded and uninhabited Conception Island, a protected sanctuary for animals.
SAILING IN SEARCH OF BLUE HOLES – Ep 190
Sailing Jibsea

SAILING IN SEARCH OF BLUE HOLES – Ep 190

Embark on an exhilarating journey as we sail through the breathtaking Bahama Islands, exploring remote locations such as the Ragged Islands, seeking out crystal-clear Blue Holes while encountering incredible marine life along the way.
THE BEST PLACE TO LIVE OFFGRID – Ep 189
Sailing Jibsea

THE BEST PLACE TO LIVE OFFGRID – Ep 189

Join Sailing Jibsea as they share their journey living off-grid in the stunning Bahamas. Dive into salvaging, snorkeling, and foraging escapades to sustain their lifestyle while navigating unique island challenges.
460 NAUTICAL MILES TO PARADISE! – Ep 188
Sailing Jibsea

460 NAUTICAL MILES TO PARADISE! – Ep 188

Jibsea sets sail from Puerto Rico to the Bahamas on a 3-day offshore journey that covers 460 nautical miles, facing various challenges and relishing delectable provisions along the way. Experience the adventure of crossing open ocean as the duo chase Caribbean blue waters.
Learning what NOT to tinker with on our sailboat – Ep 187
Sailing Jibsea

Learning what NOT to tinker with on our sailboat – Ep 187

Sailing enthusiasts and cruisers alike will find value in this insightful episode that dives deep into sailboat provisioning for extended trips. From strategic grocery shopping and storage strategies to handling unforeseen obstacles on their vessel, follow along as the hosts meticulously prepare the...
BUILDING THE ULTIMATE ISLAND BONFIRE WITH BEACH TREASURES – Ep 186
Sailing Jibsea

BUILDING THE ULTIMATE ISLAND BONFIRE WITH BEACH TREASURES – Ep 186

We're diving into the pristine waters of the British Virgin Islands to scrub the growth on our sailboat hull using a game changing new tool, Our BLU3 Nomad dive system helps get the job done easily and makes it so much more enjoyable. We share good times at Saba Rock and Leverick Bay Marina fo...
SAILING TO EXPLORE UNDERWATER WONDERS of the British Virgins – Ep 185
Sailing Jibsea

SAILING TO EXPLORE UNDERWATER WONDERS of the British Virgins – Ep 185

We're sailing stunning remote islands in the Caribbean and in this episode, we're spending most of our time underwater, showing you what marine life and scenery lies beneath the pristine turquoise waters of the British Virgin Islands. From enjoying the company of friends, buddy boats to h...
ONE SHOT TO GET THIS RIGHT before SAILING to PARADISE – Ep 184
Sailing Jibsea

ONE SHOT TO GET THIS RIGHT before SAILING to PARADISE – Ep 184

Join us as we do another DIY project on our sailboat while anchored in St. Martin in the French Caribbean. It's a long awaited addition to our headsail. Installing our own decal before sailing offshore and overnight to the British Virgin Islands. NEW VIDEOS EVERY SUNDAY! Please subscribe and ...
Hoping for a $12 MIRACLE FIX for our LEAKY BOAT – Ep 183
Sailing Jibsea

Hoping for a $12 MIRACLE FIX for our LEAKY BOAT – Ep 183

Repairing our leaky inflatable PVC dinghy in St. Martin when patches won't do. Trying an automotive tube sealant NEW VIDEOS EVERY SUNDAY! Please subscribe and share our videos - every bit of support is much appreciated, keeps our journey going and the content coming! OUR ACTION CAMERA - Ins...
REPLACING ANCHOR CHAIN – DON’T make the same SILLY MISTAKE we did! – Ep 182
Sailing Jibsea

REPLACING ANCHOR CHAIN – DON’T make the same SILLY MISTAKE we did! – Ep 182

We are continuing with some boat maintenance projects while anchored in St. Martin, a French Caribbean Island. After sailing thousands of nautical miles and anchoring 99% of the time while living offered cruising full time for the past three years, it's time to replace our 300’ of galvanized an...
BALLIN’ ON A BUDGET – BOAT MODIFICATIONS to SET THE MOOD – Ep181
Sailing Jibsea

BALLIN’ ON A BUDGET – BOAT MODIFICATIONS to SET THE MOOD – Ep181

Travis doing what he does best! Tinkering and chipping away at boat projects making small budget-friendly modifications to our floating home and sailboat so that we can live offgrid more comfortably. We take you through modifications in the steelwork on our bimini, inside our cockpit, touching up o...
GENIUS DIY OFFSHORE SAILING & TINY HOME CREATION – Ep 180
Sailing Jibsea

GENIUS DIY OFFSHORE SAILING & TINY HOME CREATION – Ep 180

Join is as we anchorage bounce and settle into Saint Martin in the Caribbean islands. We spearfish with fellow cruisers and friends, snorkel to explore underwater marine life before knocking out a long awaited DIY in our sailboat saloon. A multi-functional poece of equipment that will change comfor...
Why We’ll NEVER forget SAILING to MADEIRA – Ep 167
Sailing Jibsea

Why We’ll NEVER forget SAILING to MADEIRA – Ep 167

Sign up for a 14-day free trial and enjoy all the amazing features MyHeritage has to offer. If you decide to continue your subscription, you’ll get a 50% discount. Join Steph and Travis, Canadian sailors as they explore the perfect island in the middle of the Atlantic Ocean for adventure and explo...
SUMMER SAILING | Pros & Cons of OFF-SEASON CRUISING on Australia’s North Queensland Coast
The Sailing Adventures of Brilliant II

SUMMER SAILING | Pros & Cons of OFF-SEASON CRUISING on Australia’s North Queensland Coast

If you could continue to cruise a particular destination "out of season", when the vast majority of seasonal sailors have 'gone with the wind', would you? We have - and that is exactly what the videos in our La Niña Summer Sailing Series have been about. In this final episode of...
HIGHS & LOWS of SAILING in GIBRALTAR – Ep 164
Sailing Jibsea

HIGHS & LOWS of SAILING in GIBRALTAR – Ep 164

We’re embarking on an unforgettable adventure in Gibraltar! Join us as we arrive in this stunning destination by sailboat, experiencing the excitement of walking across a live runway from Spain to Gibraltar. But our journey doesn't stop there. We encounter heavy weather conditions that wreak ...
OFFSHORE SAILING + WHY WE’RE LEAVING – Ep 163
Sailing Jibsea

OFFSHORE SAILING + WHY WE’RE LEAVING – Ep 163

Join us offshore as we sail our Hunter Passage from Ibiza to Gibraltar as we leave the Mediterranean. We re-rig our second reef before departing on a 4 day passage out at sea. NEW VIDEOS EVERY FRIDAY! Please subscribe and share our videos - every bit of support is much appreciated, keeps our journe...
HOW WE GET OUR KICKS SAILING IBIZA – Ep 162
Sailing Jibsea

HOW WE GET OUR KICKS SAILING IBIZA – Ep 162

We're a Canadian couple who aren't your typical full time travelling cruisers who live on their sailboat while sailing the Mediterranean. We enjoy a good adrenaline rush and getting our kicks both above and underwater while exploring the beautiful island of Ibiza. We're testing oursel...
Cruising Checklist: the GOOD, the BAD & THE S#ITT¥! – Ep 161
Sailing Jibsea

Cruising Checklist: the GOOD, the BAD & THE S#ITT¥! – Ep 161

Ever thought of living full time on a sailboat while cruising the most beautiful places in the world? We'e been living on our sailboat for three years and are showing our landlubber Canadian friend what it's REALLY like onboard as a full time cruiser in the Mediterranean. We show him the ...
RESCUE MISSION: NOT the ANCHOR you want  – Ep 160
Sailing Jibsea

RESCUE MISSION: NOT the ANCHOR you want – Ep 160

We continue cruising the Balearic Islands in the Mediterranean while dealing with vital equipment failure - our water maker. We're sailing from Mallorca to Menorca and encounter a strange package drifting out at sea. While waiting for a replacement part in transit, we encounter a sailboat dragg...
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