Watch Sailing & Boating Adventures Around the World – Page 6 of 51

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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Why St. John Feels Nothing Like St. Thomas E381
Wildly Intrepid Sailing

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 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...
This 1984 Swan 42 Proves Classic Yachts Still Dominate | $90K Reality Check
BoatFools Sailing

This 1984 Swan 42 Proves Classic Yachts Still Dominate | $90K Reality Check

#boatfoolssailing #sailing #nautorswan #sailboattour #bluewatersailing #swan42 This 1984 Swan 42 Proves Classic Yachts Still Dominate | $90K Reality Check | Ron Holland Offshore Legend for $90K | TOUR Welcome aboard, BoatFools Nation! ⚓ Today Canadian Ken and I step aboard a true offshore thoroug...
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...
Crossing the Gulf Stream & Fishing for Dinner | Day 1
Leading the Escapade

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...
A 50 Knot Squall Hit Before We Even Left | Day 0
Leading the Escapade

A 50 Knot Squall Hit Before We Even Left | Day 0

A 52-knot squall, a new crew member, and a recalcitrant anemometer—Day 0 for SV Escapade was anything but a calm departure from Miami's Key Biscayne. Following Janaye McDonald and Jason Marshall as they begin their journey to Colombia.
Preparing Our Sailboat to Leave Civilisation Behind! Ep-214
Leading the Escapade

Preparing Our Sailboat to Leave Civilisation Behind! Ep-214

We’ve officially entered full Pacific prep mode 🌊 In this episode, we spend the day hunting down everything we need to get Escapade ready for another ocean crossing and life in remote destinations far from civilisation. From safety gear and spare parts to haul out supplies, off-grid essentials, to...
Eventually, Life in the Pacific Felt Normal
Sailing Big Lost

Eventually, Life in the Pacific Felt Normal

Eventually, life in the Pacific started to feel normal. After more than a week at sea crossing the Pacific Ocean, the routines of offshore life slowly began to settle in. Night watches, sail changes, repairs, fishing, cooking, exhaustion, and family life all became part of our everyday rhythm somew...
We Didn’t Expect THIS in the US Virgin Islands… E380
Wildly Intrepid Sailing

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 ...
Ever Been Seasick? Here’s how to fight it… | Sailing Truth Show
Sailing Zingaro

Ever Been Seasick? Here’s how to fight it… | Sailing Truth Show

Since you’re leaning into the "Sailing Truth Show" angle, the description needs to feel less like a "vlog" and more like a masterclass. You want to hook the casual viewer who is afraid of getting sick, while establishing yourself as the authority who has written the book on the s...
Sailing the North Atlantic. Bermuda to New England! 822 miles
Sail Stillwater

Sailing the North Atlantic. Bermuda to New England! 822 miles

Join Brian and a crew of three other experienced sailors aboard an Amel Super Maramu 2000 as they prepare for an 800-mile offshore passage from Bermuda to New Hampshire. But the Atlantic has other plans. Strong weather systems force the crew to stay docked in Bermuda while they wait for a safe weat...
This 12-Minute Video Will Save You $50,000 on a Sailboat
Sailing Zingaro

This 12-Minute Video Will Save You $50,000 on a Sailboat

I charge $500 for a 90-min boat consultation. Today, for free, I'm giving you the forensic audit process I’ve developed over 24 years on the water, from nuclear submarines to offshore sailboats. Why this matters: * The Forensic Audit: How to list every system and calculate its true remaining ...
I’ve been doing a bad job…
Sailing With Phoenix | Oliver

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
Leading the Escapade

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...
This Is It. We’re Crossing the Pacific
Sailing Big Lost

This Is It. We’re Crossing the Pacific

We’re finally doing it. After months of preparation, we’re leaving the Galápagos and setting sail across the Pacific Ocean — 3,000 nautical miles to the Marquesas. This is the moment everything has been building toward. What started as a dream is now reality. With no turning back, we begin one of t...
From Chaos to Paradise: Sailing Vieques → Culebra → Puerto Rico E379
Wildly Intrepid Sailing

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—...
We’re Back…..|Pre-Season 2
Sailing Banana Pancakes

We’re Back…..|Pre-Season 2

🌴 WE SOLD EVERYTHING… AND WE’RE DOING IT AGAIN | Sailing Around the World as a Family of 6 Welcome to Banana Pancakes… or if you’re new here—welcome to the chaos. After sailing the Caribbean for a year, selling our boat, and trying “normal life” again… we realized something: We’re not meant for n...
41 Hours Offshore: Sailing from Sicily to Greece
Sailing Bluefish

41 Hours Offshore: Sailing from Sicily to Greece

We finally leave Sicily and sail east toward Greece. After our winter months, waiting, fixing, preparing, and slowly getting Bluefish ready again, it is time to cross the Ionian Sea. This passage takes us from Sicily toward Kefalonia — 41 hours offshore, sailing through changing light, weather, nigh...
We Found the BRIGHTEST Bioluminescent Bay on Earth! Vieques (Family Sailing Caribbean) E378
Wildly Intrepid Sailing

We Found the BRIGHTEST Bioluminescent Bay on Earth! Vieques (Family Sailing Caribbean) E378

Not every stop is planned… and sometimes those are the best ones. We dropped anchor in Puerto Patillas, Puerto Rico and were blown away. A peaceful anchorage, a waterfront park with a playground (perfect for homeschooling days), live music, and even iguanas roaming around—it quickly became one of t...
This Could’ve Brought Our Mast Down… So We Fixed It! Ep-211
Leading the Escapade

This Could’ve Brought Our Mast Down… So We Fixed It! Ep-211

We finally took on one of the biggest and most important upgrades you can do on a sailboat… replacing all of our standing rigging. With our rigging over 14 years old and a Pacific crossing ahead of us, this wasn’t something we were willing to risk pushing any further. Even with regular inspections,...
3 Fails in 3 Days… Puerto Rico Didn’t Go As Planned E377
Wildly Intrepid Sailing

3 Fails in 3 Days… Puerto Rico Didn’t Go As Planned E377

Not every sailing day goes to plan… and this one REALLY didn’t 😅 We kick things off with a beautiful, calm sail past Cabo Rojo Lighthouse—one of the most stunning coastlines in Puerto Rico. But from there… things start to unravel. We anchor in La Parguera hoping to experience the famous biolumines...
I Answered 50 of Your Questions
Sailing With Phoenix | Oliver

I Answered 50 of Your Questions

Installed nothing. Fixed nothing. Just sat down and answered your questions as honestly as possible. In September 2026 I will begin a 30,000 mile solo nonstop circumnavigation of the planet aboard my 1998 Pacific Seacraft 40, "Phoenix do Mar", meaning Phoenix of the Sea in Portuguese. Dep...
Arriving in Miami by Sailboat! (At Night 🤯) Ep-210
Leading the Escapade

Arriving in Miami by Sailboat! (At Night 🤯) Ep-210

This week on Escapade the clock starts working against us! We kick things off by upgrading our guest cabin with a brand new custom mattress from Ship Shape Bedding. After templating the space, it’s time for the big moment—unpacking and fitting it onboard… and safe to say, it completely transforms t...
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