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

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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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...
We’re Not Supposed to DIY This… But Here We Are | Step 483
Sailing Uma

We’re Not Supposed to DIY This… But Here We Are | Step 483

▸ 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. ▸ BINGE WATCH our story from the beginning: ▸ SUBSCRIBE for weekly Videos: ▸ WEBSITE + MERCH: [ ▸ INSTAGRAM: ▸ MUSIC PLAYLIST:
Sailing Life in Central America🐟⚓E.181
Sailing SV CUBA

Sailing Life in Central America🐟⚓E.181

⛵ In this episode we leave paradise behind and sail back to civilisation to reprovision for our next adventure. We stock up the boat, have fun with exotic fruit, and come face to face with giant monster fish. Join us for a mix of real cruising life, culinary chaos and wild encounters 😅 *Want to su...
RAW & REAL – Sailing REMOTE FIJI – Tourists DON’T SEE THIS!
Sailing Machete

RAW & REAL – Sailing REMOTE FIJI – Tourists DON’T SEE THIS!

This week our family is in remote Fiji! We are seeing all the places that tourists don't get to see. We go into remote villages, have some of the best snorkeling spots all to ourselves, and find a hidden, remote natural rock waterslide in the jungles of Fiji! To God be the glory! #sailingfa...
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...
FULL Sailboat Tour  Bahamas Ready Cruising Catamaran [2002 Leopard 47]
Adventureman Dan

FULL Sailboat Tour Bahamas Ready Cruising Catamaran [2002 Leopard 47]

Welcome onboard "Lani". A beautiful 2002 Leopard 47 cruising catamaran, I had the joy of staying on for several nights while visiting friends Ted and Kim in the Bahamas. In this video we tour the boat and take a look at the layout, systems, and features that make the Leopard 47 such a popu...
Sailing into PARADISE – FIJI – Resorts, Reefs, & Repairs – Sailing Family Vlog (93)
Sailing Machete

Sailing into PARADISE – FIJI – Resorts, Reefs, & Repairs – Sailing Family Vlog (93)

This week our family is in FIJI! We make it to Savusavu, grab some boat parts, and work on some projects. Then we head to PARADISE! Jack gets scuba certified in one of the prettiest places on earth! Thank you for watching and subscribing. You don't know how much we appreciate it! To God be t...
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