Watch Sailing & Boating Adventures Around the World – Page 2 of 16

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 382 results
How He Survived a Tropical Storm at Sea
Sailing Zingaro

How He Survived a Tropical Storm at Sea

How to survive a tropical storm at sea: A true sailing survival story. If you’ve ever wanted to sail offshore, you NEED TO WATCH THIS. It may save your life. For deeper training on how to handle the ocean, get your copy of Be The Captain: Johnny was 20 years old and eager for his first Atlantic c...
Can you take a BREAK from the boat?
Sailing Clewless Crew

Can you take a BREAK from the boat?

Can you take a BREAK from the boat when you live aboard a Fountaine Pajot Astrea 42 in the Ionian Sea, Greece? In this episode of Sailing Clewless Crew, we’re back on the move between anchorages, dealing with boat maintenance, marine electrical work, VHF and AIS programming, and the usual never-endi...
Ep 186 On Being Told You Have 12-18 Months To Live | Oyster 485 Talisman
Sailing Talisman

Ep 186 On Being Told You Have 12-18 Months To Live | Oyster 485 Talisman

We’re not the drama channel. But this time was real … and not good. I tell the story in the video, but the short version is that last summer I was diagnosed with a form of tongue/throat cancer. It’s not the rarest form, but it was caught very late in the game, after the tumor had grown to be 2.5cm ...
SOLVING boat issues BALANCED with fun
Sailing Clewless Crew

SOLVING boat issues BALANCED with fun

In this episode of Sailing Clewless Crew, we’re balancing boat issues with a bit of fun aboard our liveaboard catamaran in Greece. From fixing a leaking watermaker, tracing unexpected generator corrosion, and sorting out solar panel installation on the coach roof, to moving through beautiful anchora...
🌴 The Last Paradise Before the Pacific Crossing | San Blas Islands! Ep-227
Leading the Escapade

🌴 The Last Paradise Before the Pacific Crossing | San Blas Islands! Ep-227

After weeks of offshore passages, unexpected challenges, and nonstop movement, we finally wake up in one of the most beautiful cruising destinations in the world: the San Blas Islands of Panama. With only one day to explore before continuing our journey, we move Escapade into crystal-clear shallow ...
This Is Why We Crossed The Pacific
Sailing Big Lost

This Is Why We Crossed The Pacific

After crossing the Pacific Ocean and spending weeks in the Marquesas, we finally arrived at one of the places we've dreamed about for years: the Tuamotus. In this episode, we leave Nuku Hiva behind and make the 500 nautical mile passage to Raroia Atoll. After carefully timing our arrival throu...
Meganisi #1 BEACH & Nidri WATERFALL hike :choosing the RIGHT marine engineer
Sailing Clewless Crew

Meganisi #1 BEACH & Nidri WATERFALL hike :choosing the RIGHT marine engineer

Meganisi #1 beach, Nidri waterfall hike & choosing the right marine engineer takes you on a full week of adventure training, boat admin, and serious mechanical challenges aboard our Fountain Pajot Astrea 42 catamaran in Greece. We kick things off with a brutal 4km waterfall hike up a hill in Ni...
Selling It All To Live On A Sailboat| Episode 3 Season 2
Sailing Banana Pancakes

Selling It All To Live On A Sailboat| Episode 3 Season 2

Join Our Banana Crew Follow the Satterlee boys at www.youtube.com/@UCKZtIu4ylFXnKkBrf161RFg We just bought our dream boat… Now we have to sell everything we own. After months of searching, countless debates, and a lot of prayers, we officially became the owners of a 2021 Leopard 50 catamaran. ...
Ep 185 Final Electrical Upgrades, Launch, and Docking
Sailing Talisman

Ep 185 Final Electrical Upgrades, Launch, and Docking

Finishing up the final electrical upgrades on our list. These include adding a Victron galvanic isolator, replacing the battery crossover switch, and replacing the old battery isolator with a new Victron unit. And following that we LAUNCH! Yay!!!. This is always the big moment of truth. Will she si...
We found  PARADISE on  Kefalonia  and Ithaca
Sailing Clewless Crew

We found PARADISE on Kefalonia and Ithaca

We Found PARADISE on Kefalonia and Ithaca in this episode as we enjoy a couple of peaceful days in Sami, Kefalonia before sailing across to Ithaca in search of a beautiful bay to relax in for a few days. Along the way we handle provisions, fill up with water, do laundry, explore stunning Greek ancho...
Life After Landfall | Exploring the Marquesas Following Our Pacific Crossing
Sailing Big Lost

Life After Landfall | Exploring the Marquesas Following Our Pacific Crossing

After crossing more than 3,000 miles of Pacific Ocean, we finally had a chance to slow down and enjoy life in the Marquesas Islands. But life after landfall isn't just tropical anchorages and waterfalls. There were still boat projects to finish, new places to explore, and old friends to reunite...
LAND at Last – Arriving in COLOMBIA After a WILD Passage | Day 15
Leading the Escapade

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
Leading the Escapade

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...
Ep 184 Offshore Passage and Liveaboard Prep
Sailing Talisman

Ep 184 Offshore Passage and Liveaboard Prep

What does it take to prep for extended passagemaking and the liveaboard lifestyle? A lot of hard work, that’s what! And plenty of time spent sourcing all the parts we either broke or need to upgrade. In this episode we focus on electrical system repairs and upgrades, installation of a new Gen3 Star...
The Raw Reality of Offshore Sailing – Torn Sail, No Fuel & Wild Weather | Day 12
Leading the Escapade

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...
Crossing the Pacific Changed Our Family
Sailing Big Lost

Crossing the Pacific Changed Our Family

After months of preparation and 24 days at sea since leaving Panama, we finally crossed the Pacific Ocean and arrived in Nuku Hiva in the Marquesas Islands of French Polynesia. This crossing pushed our family physically and mentally in ways difficult to explain. Interrupted sleep, endless sail chang...
The Last Glimpse of Land Before South America | Day 11
Leading the Escapade

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 ...
Sailing STUNNING Meganisi
Sailing Clewless Crew

Sailing STUNNING Meganisi

Join us aboard our 42ft catamaran as we sail the stunning Greek Ionian Islands, cruising from Nidri to Vlycho Bay and Meganisi, where we discover paradise in crystal-clear water and beautiful hidden anchorages. In this episode, we tackle boat life, island hopping, and a close look at our solar panel...
We Fixed the Sail… But Now the Rigging Might Fail | Day 8
Leading the Escapade

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...
Our Sail Tore in 40 Knots…10 Minutes Into the Crossing | Day 7 Continued…
Leading the Escapade

Our Sail Tore in 40 Knots…10 Minutes Into the Crossing | Day 7 Continued…

We use Airalo to stay connected when we land in new countries — super easy eSIMs with no physical SIM needed. Try it here: Code: LEADING Day 7 continued of our sail from the USA to Colombia… and this is not how we imagined it going. After days of waiting in the Bahamas for the right weather wind...
Somehow… This Became Normal | Pacific Crossing
Sailing Big Lost

Somehow… This Became Normal | Pacific Crossing

Two weeks into our Pacific crossing and something unexpected started happening… Life out here began to feel normal. The watches, the meals, the routines, the exhaustion, the quiet moments in between — somewhere along the way the Pacific stopped feeling so unfamiliar. In this episode we share what da...
We Sailed to a FORBIDDEN ISLAND | Sailing Truth Show
Sailing Zingaro

We Sailed to a FORBIDDEN ISLAND | Sailing Truth Show

Most boats never make it to Mai'O. You can't just sail in... the island decides who comes ashore. Years ago, my girlfriend and I were anchored in Moorea when we met a man whose friend was from Mai'O. He asked if we could bring his friend home. We said yes — and what happened next was...
We Flew to Florida to Buy Our Dream Boat…Then Everything Went Wrong| Season 2 Episode 1
Sailing Banana Pancakes

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
Leading the Escapade

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...
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