Watch Sailing & Boating Adventures Around the World – Page 4 of 21
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 73-96 of 495 results
Sailing to the Caribbean’s Most Remote Islands! Ep-226
After a whirlwind week in Cartagena, it's time to continue our journey west. Before leaving Colombia, we make the most of our time ashore celebrating our friends' wedding and exploring one of the Caribbean's most vibrant cities. From island beach clubs and sunset catamaran cruises to...
Our Fight for Justice After the Stabbing
We are pausing our regular Sunday episode schedule because something serious has happened. This video is a compilation of our evidence from a recent stabbing incident, which we've submitted as part of the legal process. We've navigated the Mexican justice system and are now awaiting a cour...
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...
kefalonia BLEW us away – LITERALLY!
Kefalonia Blew Us Away Literally! In this episode, we’re sailing through stormy conditions, dealing with a seriously stressful anchorage, and making a tricky escape from the rocks before the weather gets worse. If you’re into catamaran sailing, Mediterranean cruising, liveaboard life, and real-world...
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...
LAND at Last – Arriving in COLOMBIA After a WILD Passage | Day 15
The final stretch to Colombia… and after everything this passage threw at us, the wind completely disappears. After battling storms, big seas, a shredded headsail, and days offshore, we spend the entire night drifting slowly toward Cartagena at just 2–3 knots. If we’d had enough fuel, we could have...
Wet, Exhausted & Hanging On – 50 Knot Caribbean Storm | Day 13 & 14
Day 13 & 14 of our offshore passage from the USA to Colombia… After days at sea, the weather forecast suddenly shifts for the worse. What was meant to be manageable conditions turns into a long-lasting storm stretching across the entire Caribbean Sea — leaving us with nowhere to run and no way...
The Raw Reality of Offshore Sailing – Torn Sail, No Fuel & Wild Weather | Day 12
Day 12 of our sail from the USA to South America… and this is where the crossing starts to get rough. After finally reaching stronger winds out in the Caribbean Sea, the conditions quickly deteriorate and our headsail completely shreds offshore. With over 30 knots of wind, building swell, and no fu...
The Last Glimpse of Land Before South America | Day 11
Day 11 of our sail from the USA to South America… and today feels like a real turning point. The last glimpse of land disappears behind us as we head further offshore with nothing but ocean ahead. After barely any wind and carefully watching our fuel levels, we finally start to feel the conditions ...
We Found the PRETTIEST Island in the Caribbean E382
This week aboard SV Wildly Intrepid we explore what might be the most beautiful island we’ve visited all season… 🌴🇻🇮 Sailing the US Virgin Islands with our buddy boat, we explore St John Island and hike the incredible trail from Francis Bay while discovering the crystal clear waters of Francis Bay ...
We Fixed the Sail… But Now the Rigging Might Fail | Day 8
We Fixed the Sail… But Now the Rigging Might Fail | Day 8 We fixed the sail and set off again… but now we’re worried the rigging might fail. After tearing our sail on our first attempt to leave the Bahamas, we finally get it repaired and feel ready to try again. We haul anchor, hoist the sails, an...
Boat Life in the Remote Bahamas Hits Different | Day 6-7
Still tucked away in the Ragged Islands, we’re waiting on the right weather window to make our next big move south to Colombia… but life out here doesn’t exactly slow down. While we wait, it’s time to get a few jobs ticked off. We break out the sewing machine onboard and get to work repairing our...
The Ragged Islands Are Pure Paradise! | Day 4-5
We finally get a moment to breathe… After a wild crossing from Miami and getting hit with way more wind than expected, we wake up in the remote Ragged Islands in the Bahamas — and honestly, it feels like paradise. With the next weather window not quite ready for our push down to Colombia, we slow ...
Why St. John Feels Nothing Like St. Thomas E381
🌴 Island hopping through the USVI brought us from the busy streets of Charlotte Amalie on St. Thomas to the wild beauty of St. John… and what an adventure it turned into. We wandered the steep chaotic roads of Charlotte Amalie (definitely not the most pedestrian-friendly place 😅), got rescued with ...
We Flew to Florida to Buy Our Dream Boat…Then Everything Went Wrong| Season 2 Episode 1
Welcome back to Banana Pancakes 🍌🥞 Or if you’re new here… welcome to our beautiful little shit show. After waiting THREE years, we finally flew to Florida to survey what could become our future floating home — a 2021 Leopard 50 catamaran. This is the exact boat we first stepped on during spring bre...
Survival Mode at Sea + Monster Fish Caught | Day 2-3
Day 2 & 3 of our sail from the United States to Colombia did not go to plan. What was meant to be a comfortable beam reach in 18–22 knots quickly turns into something very different. Instead of cruising south, we find ourselves stuck in gale-force winds, beating upwind for nearly two straight d...
Crossing the Gulf Stream & Fishing for Dinner | Day 1
After leaving the Gulf Stream behind, we finally arrive on the Bahama Bank — and the ocean greets us with something completely unexpected. Glass-off conditions. The water turns into a mirror as far as we can see, leaving us with no wind and a long day and night of motoring across the shallow turqu...
We Didn’t Expect THIS in the US Virgin Islands… E380
Our sail from Puerto Rico to the US Virgin Islands started off absolutely perfect… warm winds, beautiful seas, and another unforgettable Caribbean passage aboard SV Wildly Intrepid. But once we arrived in St. Thomas, things got interesting fast. We explored the abandoned tunnels of Fort Segarra on ...
S1E47. This Sailboat’s Wiring Scares Me 😅 (Bilge Pump Install + Boat Work)
Welcome back to Sailing UV ⛵🐾 The greatest sailing show on Earth… according to Violet anyway 😅 If you’re new here — I’m Jonathan, and alongside my giant dog Violet, we’re restoring this old sailboat for a future circumnavigation. Every week gets us one step closer to finally setting sail. And this...
I’ve been doing a bad job…
The boat finally goes back in the water after months of being on the hard. I also talk about why I haven't been uploading content recently and where things stand as I get closer to finishing the refit. We’re getting there. Slowly but surely. And huge thanks to Taylor for the drone footage - ...
Stocking Our Boat Like We’ll Never See Land Again! Ep-213
If we’re going to cross the Pacific… we need to be ready for weeks without seeing land 🌊 In this episode, we take provisioning seriously (maybe a little too seriously 😅). We start by building a master shopping list for everything we think we’ll need to survive the crossing—then head out to stock up...
From Chaos to Paradise: Sailing Vieques → Culebra → Puerto Rico E379
What started as a simple sail turned into a full-on emergency… As we left Vieques, a hose clamp suddenly snapped—dumping all our engine coolant in seconds. With no engine and two little ones onboard, we had no choice but to drop anchor fast and figure things out. From there, we sail on to Culebra—...
Anchored in Perfect Weather, Then We Hid in Syvota
We anchored in perfect weather on the island of Ithaca, then made a quick escape to Syvota to hide away from the incoming weather and enjoy a few peaceful days on the pontoon in Greece. But that changed when we had to tackle the joker valve on the toilet and get it fixed. This sailing Greece episod...