Watch Sailing & Boating Adventures Around the World tagged “Caribbean sailing” – Page 2 of 28

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We Know We’re Sailing Fast When Our Dog’s Ears Are Flapping Like Crazy – Ep. 271
Sailing Zephyr

We Know We’re Sailing Fast When Our Dog’s Ears Are Flapping Like Crazy – Ep. 271

In today’s episode, we’re taking the boat out for an epic sail from our slip in the Bahamas (lucky us, right?) to Guana Cay! We’re excited to check out what all the fuss is about at Grabbers and Nippers on a Sunday Funday. It’s a day full of sailin...
CHASING BUBBLES around the Virgin Islands! ⛵️ Let’s Bring Her Back WITH A BANG!  🎉  l ep.61
Spear It Animal

CHASING BUBBLES around the Virgin Islands! ⛵️ Let’s Bring Her Back WITH A BANG! 🎉 l ep.61

Get your free LMNT Sample Pack with any purchase at http://DrinkLMNT.com/SIA. Also try the new LMNT Sparkling — a bold, 16-ounce can of sparkling electrolyte water. Join the Next Chasing Bubbles Regatta HERE (APRIL 9th, 2025)- https://www.chasingbubbles...
Let’s Get This Boat on a Lean: Epic Sailing Through the Bahamas! – Ep. 270
Sailing Zephyr

Let’s Get This Boat on a Lean: Epic Sailing Through the Bahamas! – Ep. 270

We’ve finally arrived in the Bahamas, and it’s as incredible as we remembered! The blue water is calling, and we couldn’t be more excited to explore. We find some secluded anchorages and untouched beaches, enjoying perfect sailing conditions with ple...
Wing-on-Wing Sailing and a Bridge Fail on Our Way to Florida – Ep. 269
Sailing Zephyr

Wing-on-Wing Sailing and a Bridge Fail on Our Way to Florida – Ep. 269

Join us as we leave the boatyard behind in North Carolina and make our way down the Intracoastal Waterway (ICW) to Charleston, SC. After dealing with a frustrating bridge delay, we finally head out into the Atlantic Ocean, aiming for Fernandina Beach, Flor...
BAD TIMING IN ANTIGUA – Ep 227
Sailing Jibsea

BAD TIMING IN ANTIGUA – Ep 227

Join us as we sail to Falmouth Harbour, Antigua, a hotspot for luxurious super yachts and boat enthusiasts. We take you on a scenic hike where we encounter local wildlife, share stunning views of the island and explore the UNESCO heritage site, Nelson’s...
Emergency Haul Out: Fixing Our Boat’s Shaft Seal & Coupling to Stop Us Sinking – Ep. 268
Sailing Zephyr

Emergency Haul Out: Fixing Our Boat’s Shaft Seal & Coupling to Stop Us Sinking – Ep. 268

In this week´s video, we are at the Zimmermans Boatyard in NC for an emergency haul-out! Our mission? To replace Zephyr´s coupling and shaft seal as quickly as possible to stop our saltwater leak that held us back on our journey south. We are joined by t...
SHE’S A THRILL TO SAIL! – Ep 226
Sailing Jibsea

SHE’S A THRILL TO SAIL! – Ep 226

We embark on a sail from the half French, half Dutch island of of Saint Martin/Sint Maarten to Antigua, covering 100 nautical miles across the Caribbean. We face a winch malfunction shortly after picking up anchor. See how we solve this issue on the go. We...
Engine Flooding Disaster on Zephyr: The Worst Problem We’ve Faced Yet! – Ep. 267
Sailing Zephyr

Engine Flooding Disaster on Zephyr: The Worst Problem We’ve Faced Yet! – Ep. 267

This episode is jam-packed! Not only do we leave beautiful New Bern, where we spent the hurricane season, but we also run into the worst problem we’ve ever had on Zephyr. As you can probably guess from the thumbnail, we take on saltwater in the engine co...
TEAK & THROTTLE: Custom Yacht Interior & Tohatsu 2 Stroke vs 4 Stroke – Ep 225
Sailing Jibsea

TEAK & THROTTLE: Custom Yacht Interior & Tohatsu 2 Stroke vs 4 Stroke – Ep 225

We're in St. Martin/Sint Maarten in the Caribbean while cruising on our custom aluminum sailboat and working on the teak restoration and varnishing. After restoring the cockpit, we're tackling the wooden interior of our tiny home with final touches. We al...
Life on a monohull 📐🌬️🤗 #sailing #monohull #belowdeck
Sailing Jibsea
24 HRS OF BOAT LIFE: Day in the Life & Tropical Escape – Ep 222
Sailing Jibsea

24 HRS OF BOAT LIFE: Day in the Life & Tropical Escape – Ep 222

Ever wondered what it’s like to live on the open water, exploring hidden islands, and embracing a minimalist, off-the-grid lifestyle? In this video, we take you on a journey through 24 hours aboard our custom aluminum sailboat, showcasing life in a tiny ...
NIGHTMARE SAIL ON NEW ALUMINUM BOAT: Huge Waves, Storms & Nowhere to go – Ep 220
Sailing Jibsea

NIGHTMARE SAIL ON NEW ALUMINUM BOAT: Huge Waves, Storms & Nowhere to go – Ep 220

Join us on an unforgettable sailing adventure across the Atlantic Ocean as we face huge waves, rough weather, and the challenges of short-handed sailing on our custom aluminum sailboat. After spending the past six months outfitting our boat to be fully off...
New OUTBOARD MOTOR Setup, TEST & Review | Simple Boat Life – Ep. 264
Sailing Zephyr

New OUTBOARD MOTOR Setup, TEST & Review | Simple Boat Life – Ep. 264

We BUY a NEW Outboard motor for our dingy. It's been 6 years since we bought a new outboard and we are really nervous about our decision. IT´s been almost a year trying to decide what to buy and the day has finally arrived. Join us as we take you through ...
Teak Restoration on a SAILBOAT Part 2 | Sailing Zephyr – Ep. 263
Sailing Zephyr

Teak Restoration on a SAILBOAT Part 2 | Sailing Zephyr – Ep. 263

We get right back into the teak work on our Beneteau sailboat. Last week we did the long hours of sanding all the teak toe rails till they were nice and smooth. Then we went through the process of using wood filler to fill in all the gaps in the teak. Thi...
RESTORING TEAK on a SAILBOAT | Sailing Zephyr – Ep. 262
Sailing Zephyr

RESTORING TEAK on a SAILBOAT | Sailing Zephyr – Ep. 262

There are many parts of a sailboat that require ongoing maintenance, but few are generally as laborious as working on teak. Whether it's decks, toe rails, seats or interior wood. Teak requires constant maintenance. The debate around Stain vs Varnish contin...
Simple LIVING on a SAILBOAT | Sailing Zephyr – Ep. 261
Sailing Zephyr

Simple LIVING on a SAILBOAT | Sailing Zephyr – Ep. 261

Living aboard a sailboat can get complicated very fast. We have spent enough time sailing the world to witness it first hand to us and other sailors. So sometimes it makes sense to just simplify your day to day life on a sailboat so that stress doesn't get...
No BullS#!T……Just THANK YOU! | Sailing Zephyr – Ep. 260
Sailing Zephyr

No BullS#!T……Just THANK YOU! | Sailing Zephyr – Ep. 260

Thank You!...and the boat works continue. We have been very fortunate to have the lifestyle we've had for the last 6 years and the people that make that possible...Thank You! The journey, the exploration and everything in-between is because of you! We a...
Not Doing this will COST You THOUSANDS of $$$$$$ | Sailing Zephyr – Ep. 259
Sailing Zephyr

Not Doing this will COST You THOUSANDS of $$$$$$ | Sailing Zephyr – Ep. 259

Most things you do on your boat will have only minor impacts to your sailboat performance and your wallet. But sometimes there are certain things, that if ignored, could end up costing you thousands of dollars in repairs and render your sailboat useless. ...
We Visit the ABANDONED BENETEAU Sailboat Factory & REPLACE our WATER TANK | Sailing Zephyr – Ep.258
Sailing Zephyr

We Visit the ABANDONED BENETEAU Sailboat Factory & REPLACE our WATER TANK | Sailing Zephyr – Ep.258

It's rare if not unheard of for someone to ever have the chance to visit the factory where their sailboat was made. It's even more rare if that factory has been abandoned. Well, we get that chance and it's an emotional experience. We also finally replace ...
How LONG does it Take to ABANDON SHIP? | Sailing Zephyr – Ep. 257
Sailing Zephyr

How LONG does it Take to ABANDON SHIP? | Sailing Zephyr – Ep. 257

Abandon Ship, we are sinking, the boat is going down! All words that bring complete fear, loss, sadness and the reality that Mother Nature needs to be respected. We sail the world with the full understanding that we are susceptible to the risk of losing t...
Our Biggest Non-Sailing Investment Yet! | Surprise Purchase Revealed! – Ep.255
Sailing Zephyr

Our Biggest Non-Sailing Investment Yet! | Surprise Purchase Revealed! – Ep.255

Sleep on a sailboat can mean the difference between good and bad decisions, decreased safety and just overall quality of life. There are few things we value this important on our sailboat, so we take it pretty seriously when it's time to make improvements....
Intracoastal Waterway (ICW)…Is it worth the HOURS on our Sailboat ENGINE? |Sailing Zephyr – Ep.254
Sailing Zephyr

Intracoastal Waterway (ICW)…Is it worth the HOURS on our Sailboat ENGINE? |Sailing Zephyr – Ep.254

With the most dangerous part of the hurricane season looming over us, we are desperate to get north as fast as possible. We have been traveling up the ICW for the better part of a week now and we still have hundreds of miles to sail before we reach our des...
Braving Hurricane Ernesto’s Aftermath: Tough Decisions Ahead & Our Dog’s First Catch! – Ep. 251
Sailing Zephyr

Braving Hurricane Ernesto’s Aftermath: Tough Decisions Ahead & Our Dog’s First Catch! – Ep. 251

In this episode of Sailing Zephyr, we face a tough decision: should we brave the leftover swells and winds from Hurricane Ernesto to continue our journey, or make a quick dash to Florida and wait for a better weather window? 🌊 As we weigh our options,...
Visiting the most Dutch place outside Holland   |   Ep122
Sailing Fair Isle

Visiting the most Dutch place outside Holland | Ep122

Caracou is a surprising island with one of the best anchorage areas in the Caribbean, a great place to escape from the hurricane belt. 👟 Embrace your daily life adventure with Vessi! Visit https://vessi.com/fairisle for an automatic 15% off your first ...
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