Watch Sailing & Boating Adventures Around the World – Page 4 of 21

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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...
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...
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...
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 ...
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 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...
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 ...
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...
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—...
Anchored in Perfect Weather, Then We Hid in Syvota
Sailing Clewless Crew

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...
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...
We TORE Up Our DECK to Install SYNTHETIC TEAK… Ep-212
Leading the Escapade

We TORE Up Our DECK to Install SYNTHETIC TEAK… Ep-212

We just completed one of the biggest transformations we’ve ever taken on… a full synthetic teak deck refit. What started as a simple idea quickly turned into a full-on project—removing deck hardware, stripping everything back, prepping the surface, and completely rebuilding the deck. For this job,...
This Is Where the Galápagos Changed for Us
Sailing Big Lost

This Is Where the Galápagos Changed for Us

We had already experienced parts of the Galápagos… but this is where it started to feel different. After leaving San Cristobal, we made our way to Isabela Island — the largest island in the Galápagos. What we found here wasn’t just incredible wildlife, but an experience that felt completely differen...
S1E46. Nothing Goes As Planned… But We Fixed a MAJOR Boat Leak!
Sailing UV ( UltraViolet )

S1E46. Nothing Goes As Planned… But We Fixed a MAJOR Boat Leak!

This week on Sailing UV… nothing goes according to plan 😅 We bounce between projects, start things we don’t finish (classic), and somehow still manage to make serious progress on the boat. From installing speakers 🎶 to tracking down and fixing a stubborn leak at the base of the mizzen mast… it’s on...
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...
ESCAPING Preveza: Our First Night at Anchor
Sailing Clewless Crew

ESCAPING Preveza: Our First Night at Anchor

We finally escaped Preveza town quay and reached our first anchorage — and it felt like cruising heaven after all the noise, hassle, and dock chaos. A few nights at anchor were pure bliss: no lines to adjust, no quay drama, just peace, floating, and the kind of silence that reminds you why you came...
We Shouldn’t Have Sailed to the Bahamas… But We Did Anyway | Sailing Sunday Vlog 306
Sailing Sunday

We Shouldn’t Have Sailed to the Bahamas… But We Did Anyway | Sailing Sunday Vlog 306

We shouldn’t have left when we did… but we sailed anyway. In this episode of Sailing Sunday, we sail to the Bahamas on a 3-day ocean passage after rushing across the USA to get back to our boat. With almost no sleep, we left the dock and crossed toward the Bahamas, dealing with rough seas, bad timi...
S1E45. Living on a Boat After 3 Weeks With NO Days Off… Here’s Reality
Sailing UV ( UltraViolet )

S1E45. Living on a Boat After 3 Weeks With NO Days Off… Here’s Reality

Welcome back to Sailing UV ⛵🔥 (aka… the greatest sailing show on Earth) If you're new here — I’m Jonathan, that’s Violet 🐶 (115 lbs of chaos), and we’re restoring this boat while working full-time and trying to build a life that actually makes sense. This week is a little more real life than ...
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