Watch Sailing & Boating Adventures Around the World – Page 4 of 30

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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...
We Didn’t Think We’d Make It
Finding Our Isla Sailing

We Didn’t Think We’d Make It

After weeks of rough weather, Christmas winds, storms, and learning how to sail in real time… we finally make it to Saint Martin. But getting there was far from easy. In this episode, we leave Martinique and continue battling our way north through the Caribbean. Along the way we experience incredi...
How We Sailed 14,500 Miles on $2,604 | Resupply Mission | Port Denarau Fiji
WE|Sail

How We Sailed 14,500 Miles on $2,604 | Resupply Mission | Port Denarau Fiji

Welcome back to another episode of WE|Sail. EPISODE 342 After nearly a month exploring the remote Yasawa Islands—anchored in secluded spots, living off-grid, limited access to supplies—we're pulling into Port Denarau Marina on Fiji's main island, Viti Levu. This is our first fuel stop in...
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 ...
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 ...
Sailing Blind | Season 1, Episode 8
Finding Our Isla Sailing

Sailing Blind | Season 1, Episode 8

In this episode, we leave Le Marin and continue sailing north toward beautiful Saint-Pierre. What started as one of our most peaceful and enjoyable sails yet quickly changed when we suddenly lost critical electronics onboard Isla. Our charts, depth readings, wind instruments, and navigation system...
Leaving the Yasawas After a Month | Sailing Back to Fiji’s Main Island
WE|Sail

Leaving the Yasawas After a Month | Sailing Back to Fiji’s Main Island

Welcome back to another episode of WE|Sail. EPISODE 341 After nearly a month exploring the Yasawa Islands in Fiji, it's time to move on. We're running low on provisions, we've explored the majority of the island group here, and it's time to sail back to Viti Levu—Fiji's mai...
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...
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...
2 Days and counting  #sailboatrefit #cromox #anchoright
Sailing Roam

2 Days and counting #sailboatrefit #cromox #anchoright

So many jobs, so little time remaining. Tomorrow we're being lifted on the trailer to put the rudders back in, so tonight is it. The last critical pieces must be done tonight. We'll sleep when we're dead! There is a ton of stuff under the boat that must be moved to make room for the t...
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 Found a HIDDEN Cave in Fiji | Swimming to the Secret Chamber
WE|Sail

We Found a HIDDEN Cave in Fiji | Swimming to the Secret Chamber

Welcome back to another episode of WE|Sail. EPISODE 340 We explored one of Fiji's most stunning natural attractions—the Sawa-i-lau freshwater caves in the northern Yasawa Islands. But the main cave isn't the whole story. There's a secret chamber hidden behind an underwater passage th...
5 Days and Counting  #sailboatrefit
Sailing Roam

5 Days and Counting #sailboatrefit

One of the remaining critical projects is wiring the wiindlass controls. What should have been a 1/2 days effort took the entire day, half the night, and still didn't quite work. Some projects are more frustrating than others.
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 ...
6 days and counting  #sailboatrefit
Sailing Roam

6 days and counting #sailboatrefit

We got a lot accomplished today, and it's a good thing because we're only 6 days from splashing! Shawn commissioned the Victron gear which means we have AC power! That means our appliances work! We also started to pretty up the boat before she goes back in, and after an entire day of work,...
We Fixed One Thing… And Broke Another | Boat Life in Martinique
Finding Our Isla Sailing

We Fixed One Thing… And Broke Another | Boat Life in Martinique

Welcome back to Finding Our Isla. In this episode, we continue settling into life in Le Marin while waiting out strong winds and tackling a long list of boat repairs and projects. From fixing our steering cable and unclogging the toilet… to provisioning the boat, homeschooling, laundry days, and ex...
7 Days and Counting  #sailboatrefit
Sailing Roam

7 Days and Counting #sailboatrefit

We're running out of time, but today the helm controls are in and programmed. Does that mean we're ready to go? Not quite yet...
This Is What Having a Dog on a Boat Is REALLY Like 🐾 #boatdogs #boatlife #luxuryyachtlife
UNANCHORED LIFE

This Is What Having a Dog on a Boat Is REALLY Like 🐾 #boatdogs #boatlife #luxuryyachtlife

Life on a boat is amazing… until you add a dog. 🐾 In this clip, we show what boat life with a dog is really like as Gypsy takes on the ultimate challenge—getting on and off the dinghy and then getting cleaned up back on board. From sandy paws to full-on dinghy drama, this is the unfiltered reality o...
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...
9 Days and Counting…  #sailboatrefit
Sailing Roam

9 Days and Counting… #sailboatrefit

We have 9 days left on the hard, and today we're putting the steering back in place. Mistakes were made...
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