Watch Sailing & Boating Adventures Around the World – Page 4 of 71

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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...
Turning Our Powerboat Back Into a Sailboat | Step 487
Sailing Uma

Turning Our Powerboat Back Into a Sailboat | Step 487

▸ After 2years since Umas has been a powerboat, it is finally time to convert her back into a sailboat again! ▸BTW You can find out more info about John mast here: contact: [email protected] ▸ JOIN THE UMA NATION: The Uma Nation is what makes this YT channel possible. Join from $2/month to see o...
We Found the PRETTIEST Island in the Caribbean E382
Wildly Intrepid Sailing

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
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...
Boat Life in the Remote Bahamas Hits Different | Day 6-7
Leading the Escapade

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...
ZERO BOAT LIFE DRAMA | Sunshine & Sharks | E184 | Sailing SV CUBA
Sailing SV CUBA

ZERO BOAT LIFE DRAMA | Sunshine & Sharks | E184 | Sailing SV CUBA

No boat drama…Unexpected wildlife encounters, this is the kind of boat life we dream about. #sailing #BoatLife #LifeStyle *Want to support us?" Patreon: Buy Salsa a Coffee☕🧡: Amazon Wish List: PayPal:
Sailing Greece’s Most Underrated Coastline on a Lagoon 42
Sailing Bluefish

Sailing Greece’s Most Underrated Coastline on a Lagoon 42

We leave Pylos and begin making our way along the Messinian coast of Greece, with short sails, quiet anchorages, old stone walls, and a few lessons learned along the way. From Methoni Castle to Koroni Fortress, this stretch becomes one of those reminders that learning does not always need a classro...
The Ragged Islands Are Pure Paradise! | Day 4-5
Leading the Escapade

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 ...
We Cut our Mast in Half | Step 486
Sailing Uma

We Cut our Mast in Half | Step 486

▸ About this video: It's finally time to work on our rigging... But first, we had to cut our mast in half! ▸ You can find out more info about John mast here: contact: [email protected] ▸ JOIN THE UMA NATION: The Uma Nation is what makes this YT channel possible. Join from $2/month to see ou...
42′ Manta Catamaran   FULL SAILBOAT TOUR
Adventureman Dan

42′ Manta Catamaran FULL SAILBOAT TOUR

Welcome to this FULL tour of a beautiful 2003 forty-two foot long Manta Catamaran named "Now & Zen. Owned by Ralph & Leslie, who I stayed with onboard for two weeks. This boat is a PERFECT sailing dream and full time home upon the sea. _________________________________________________...
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 ...
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.
We Sailed to Fiji’s Most Remote Island Paradise
Sailing Machete

We Sailed to Fiji’s Most Remote Island Paradise

This week our family is in remote Fiji! We are seeing true PARADISE. Off-the-beaten-track, no tourists, all-to-ourselves-type-of-place with blue water, tropical islands, pristine beaches, and village life. Let me pinch myself. I don't know how we will ever leave. To God be the glory! #sa...
The Last Jobs Before We Step the Mast | Step 485
Sailing Uma

The Last Jobs Before We Step the Mast | Step 485

▸ If you’ve been thinking about starting therapy.head over to to get 10% off your first month #ad ▸ JOIN THE UMA NATION: The Uma Nation is what makes this YT channel possible. Join from $2/month to see our videos early and ad-free. Thanks to our top patrons for keeping this channel going 💙: S...
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 ...
Our ‘New’ Sailboat Is Already Fighting Back | Morgan 384
BoatFools Sailing

Our ‘New’ Sailboat Is Already Fighting Back | Morgan 384

#sailing #boatfoolssailing #morgan384 #boatwork #boatprojects #sailboat Our ‘New’ Sailboat Is Already Fighting Back | Morgan 384 Canadian Ken and I are back aboard our “new-to-us” Morgan 384 as we race to get her ready for charter season in Maine… but like every old sailboat, she has a few opinio...
S1E47. This Sailboat’s Wiring Scares Me 😅 (Bilge Pump Install + Boat Work)
Sailing UV ( UltraViolet )

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...
The MOST Beautiful PARADISE We’ve Ever Found
Sailing Machete

The MOST Beautiful PARADISE We’ve Ever Found

This week our family is in remote Fiji! We are seeing true PARADISE. Off-the-beaten-track, no tourists, all-to-ourselves-type-of-place with blue water, tropical islands and pristine beaches. Let me pinch myself. I don't know how we will ever leave. To God be the glory! #sailingfamily #fa...
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—...
The Most Overbuilt Furler We’ve Ever Seen  | Step 484
Sailing Uma

The Most Overbuilt Furler We’ve Ever Seen | Step 484

▸ if you want to take a bit of control back, you can head to and use code SAILINGUMA to get 60% off an annual plan. Thanks to our top patrons for keeping this channel going 💙: Special shout out to these legends: Maje Brennan. John Seymour · Rod Collin · Robert H. Kraus · John Knox · greene02 ·...
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...
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