Watch Sailing & Boating Adventures Around the World

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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We Almost Quit Sailing
Finding Our Isla Sailing

We Almost Quit Sailing

What was supposed to be a manageable overnight sail from the USVIs to St. Martin turned into one of the hardest passages we’ve experienced as a sailing family. The forecast said one thing. The ocean gave us something completely different. We found ourselves beating directly into the wind and waves...
Our First Overnight Sail as a Family
Finding Our Isla Sailing

Our First Overnight Sail as a Family

Our first overnight sailing passage took us from St. Martin to the U.S. Virgin Islands aboard our Lagoon 450 catamaran—and honestly, it wasn't what we expected. As a family of six living aboard full-time, sailing through the night with our kids was one of the biggest milestones of our journey....
Sailing to the Caribbean’s Most Remote Islands! Ep-226
Leading the Escapade

Sailing to the Caribbean’s Most Remote Islands! Ep-226

After a whirlwind week in Cartagena, it's time to continue our journey west. Before leaving Colombia, we make the most of our time ashore celebrating our friends' wedding and exploring one of the Caribbean's most vibrant cities. From island beach clubs and sunset catamaran cruises to...
Overnight Passage to Sardinia – Sailing Paradise – Sailing Helios S03E11
Sailing Helios

Overnight Passage to Sardinia – Sailing Paradise – Sailing Helios S03E11

In this episode, we visit the beautiful beachside town of San Vito Lo Capo, a favourite stop on Sicily’s western coast, and set out on our overnight passage to Sardinia. After a day and night in a rolling sea, we arrive and drop anchor at Spiaggia del Riso, near Villasimius — a quiet and welcome la...
BEHIND THE SCENES: THE SAILING STRUGGLES WE USUALLY CUT! Ep-175
Leading the Escapade

BEHIND THE SCENES: THE SAILING STRUGGLES WE USUALLY CUT! Ep-175

Sailing from Puerto Rico to the Dominican Republic doesn’t go as planned. Delayed by missing boat parts, sick at sea, no wind, storms, and no fuel. In this episode, we finally leave Puerto Rico after waiting weeks for a crucial boat part to arrive—but our passage to the Dominican Republic turns int...
We sail from Escudo De Veraguas to Linton Bay ep77   HD 1080p
Motherload sailing

We sail from Escudo De Veraguas to Linton Bay ep77 HD 1080p

We set off from Escudo de Veraguas just as a sudden squall turns our peaceful anchorage into chaos, forcing us to quickly head out on the next leg of the journey. Join us as we sail 115 nautical miles overnight, passing massive ships lining up for the Panama Canal, and catching both lunch and dinner...
We Found the Ultimate Floating Bar Experience in St. Martin! 🏝️🍹 Ep-149
Leading the Escapade

We Found the Ultimate Floating Bar Experience in St. Martin! 🏝️🍹 Ep-149

#sailingadventure #stmartin #boatlife 🌊 After an overnight sail from the BVIs, we’re back in beautiful St. Martin! Kicking off with an indoor shower on our boat (thanks to our new pump!), we hit the beach for some well-deserved relaxation. Next, we move to another stunning anchorage, where we joi...
Midnight Voyage: Tunisia to Malta
Sailing Gargoyle

Midnight Voyage: Tunisia to Malta

Hey crew! It has been three months and we have loved Tunisia, but we are out of here. We finally have a thirty-six-hour weather window, and we are going to make the dash to Malta. Malta, location for many iconic shows such as Popeye, Gladiator, World War Z and yes, Game of Thrones. Come join the cre...
Our Longest Passage Yet | Pacific Baja | Sailing Avocet
Sailing Avocet

Our Longest Passage Yet | Pacific Baja | Sailing Avocet

After a very tedious check in process we were cleared to explore the rest of Mexico, so we untied from the dock and sailed south on our longest passage yet! From Ensenada to Bahia Santa Maria with a fun celebration in between 🎉 But with every high, there is a low... and that is for the NEXT video 😉...
Answering All YOUR Questions! Why did we sell? Pregnancy? What’s next? – S4EP16
Taylor’s Travels

Answering All YOUR Questions! Why did we sell? Pregnancy? What’s next? – S4EP16

In this episode we address a lot of questions/concerns/assumptions that so many of YOU commented on the last video. Although this is not my normal adventurous style of video - we wanted to make a dedicated video to chat with you all and clear the air, hopefully allowing you some insight into our liv...
The End of an Era. I Sold My Sailboat – S4EP15
Taylor’s Travels

The End of an Era. I Sold My Sailboat – S4EP15

This episode was an emotional one to make to say the least. We haul out Gypsy Moon at Spice Island Marine in Grenada one last time to get her ready for the potential buyers to survey and inspect. All went well and Gypsy Moon has now found her new owners! This process happened so fast and was a lot t...
Adios California, Hola Mexico! | Sailing Avocet
Sailing Avocet

Adios California, Hola Mexico! | Sailing Avocet

After months of planning, delays, and other misadventures we FINALLY sailed over the border from California to Mexico! Our first stop was Ensenada where we checked into the country, which was easier said than done. We had some serious issues with our TIP but luckily everything was ironed out. Intere...
Did We Just Find Our Next Boat?! – S4EP14
Taylor’s Travels

Did We Just Find Our Next Boat?! – S4EP14

In this episode we fly to France with @OddLifeCrafting to attend the International Multihull Show in La Grande Motte. We are going aboard a lot of different catamarans and trimarans to really get a good look up close, in person look at all the details so we can get a sense of our like/dislikes of ea...
We Have Some BIG NEWS! – S4EP13
Taylor’s Travels

We Have Some BIG NEWS! – S4EP13

Check out the BRNKL System here: In this episode we share some big news - we are SELLING Gypsy Moon. It's been an emotional roller coaster to come to this decision, but it is the only way we can move forward to something new. We also take you through the full install of our BRNKL Security syst...
Spend 36 Hours at Sea with Us! – S4EP12
Taylor’s Travels

Spend 36 Hours at Sea with Us! – S4EP12

Blu3 Nomad portable diving system: In this episode we set sail on a 36 hour passage to St.Martin! We had an amazing sails with beautiful conditions, but our autopilot fails on route leaving us to hand steer for 24 hours. Upon arrival we have to navigate through a busy, narrow and shallow bridge to...
BOAT-LIFE: SHE MADE ME SAIL HERE?! EP-107
Leading the Escapade

BOAT-LIFE: SHE MADE ME SAIL HERE?! EP-107

SAILING FROM THE AEOLIAN ISLANDS TO THE FAMED AMALFI COAST IN ITALY, ROCKING OUR VALLON SUNGLASSES ON OUR PASSAGE, BIG SWELL AS WE REACH LAND, HORRIBLE ROLLING ANCHORAGES, A FREE MARINA & AN IMPROMPTU SCOOTER ADVENTURE ALONG THE AMALFI COAST! Check out VALLON EYEWEAR here: LOVE OUR CONTENT?? ...
Goodbye’s Never Get Any Easier😢 – S4EP11
Taylor’s Travels

Goodbye’s Never Get Any Easier😢 – S4EP11

In this episode we explore Martinique by sea and by land - we rent a car to be able to drive around and see more of the island for Cass' last day. The sad day comes to drop her off at the airport and say goodbye after an amazing time spent together. She is the best crew and best friend I could ...
Her FIRST OVERNIGHT Sail – S4EP10
Taylor’s Travels

Her FIRST OVERNIGHT Sail – S4EP10

In this episode we set sail from Bequia to the french island of Martinique! As this would be Cass' first overnight sail we take time to prep everything like food and filling up with water before setting off. We were blessed with amazing conditions for this sail, that is until the wind picked up...
UNLEASHING LIMITLESS POWER ON OUR SAILBOAT – BLUETTI AC200MAX POWER STATION! EP-98
Leading the Escapade

UNLEASHING LIMITLESS POWER ON OUR SAILBOAT – BLUETTI AC200MAX POWER STATION! EP-98

We harness boundless power aboard our sailboat with the remarkable BLUETTI POWER AC200MAX portable station! This nifty device is an absolute game changer! If you watch our channel you know we like to keep things real around here and would only reccomend products we use and love! YOU CAN CHECK IT O...
SAILING NORTH AFRICA – IS THIS TUNISIA?! EP-95
Leading the Escapade

SAILING NORTH AFRICA – IS THIS TUNISIA?! EP-95

SAILING FROM MALTA TO TUNISIA ON THE NORTH AFRICAN COAST, THE LARGEST SWELL WE'VE EXPERIENCED, DIARIES OF AN OVERNIGHT PASSAGE, BOARDED BY POLICE, BRIBERY & SICK STREET KITTENS...IS THIS TUNISIA? LOVE OUR CONTENT?? Here are the many ways you can support us! ❤️️ Support our creations &...
OUR LONGEST PASSAGE & BIGGEST CATCH YET! EP-77
Leading the Escapade

OUR LONGEST PASSAGE & BIGGEST CATCH YET! EP-77

OUR LONGEST PASSAGE YET, SAILING FROM VENICE TO THE TREMETI ISLANDS IN ITALY, OUR BIGGEST CATCH YET, THE MOST EXPENSIVE FISH IN THE WORLD, NIGHT WATCH, DOWN-WIND SAILING, DOLPHINS AND DODGING FISHING BOATS! A SUCCESSFUL 2 DAY/2 NIGHT PASSAGE! Want to see what it’s like to sail through the night, w...
It’s Not Always Sunshine & Rainbow Sailing | Episode 186
WE|Sail

It’s Not Always Sunshine & Rainbow Sailing | Episode 186

It's time for us to up anchor and sail away to another island. We have spent 4 beautiful months in the stunning island of Mo'orea exploring, hiking, diving, and snorkeling, but it is time for us to explore new islands. We set sail for our first overnight passage since arriving to Tahiti ...
Sailing North! | Sailing Avocet
Sailing Avocet

Sailing North! | Sailing Avocet

Ventura California filled our hearts up to a capacity I didn’t know existed which is why it made sailing away SO hard. We spent 4 years doing DIY boat projects preparing for this grand adventure and the time finally came - a bittersweet moment full of excitement and tears. Ventura is the first place...
FIRST OVERNIGHT SAIL…AN EPIC FAIL!!! EP-56
Leading the Escapade

FIRST OVERNIGHT SAIL…AN EPIC FAIL!!! EP-56

This week we attempt round two of our passage from Albania Montenegro but the weather had other plans for us!
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