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 Invited a Family to Live on Our Boat for a Month
Gone with the Wynns

We Invited a Family to Live on Our Boat for a Month

Two of us became six. Here's how that actually went. Head to to get a FREE AG1 Flavor Sampler and a FREE bottle of Vitamin D3+K2 in your Welcome Kit with your first AG1 subscription order ☝Behind the Scenes, Gear Guides & More 🎬 Produced, Filmed and Edited by: Jason & Nikki Wynn ⚓...
From Sea to Streets: Sailing into Cartagena & Touring the Walled City
Sailing Big Lost

From Sea to Streets: Sailing into Cartagena & Touring the Walled City

We’re a family sailing full-time, exploring the Caribbean and Central America aboard our sailing catamaran Big Lost. New episodes every Tuesday at 10:30 AM ET. After three days at sea in light winds, dodging debris from the Magdalena River, we finally make landfall in Cartagena, Colombia! 🇨🇴 It was...
Sailing Maine’s Stunning Coast & Islands!
BoatFools Sailing

Sailing Maine’s Stunning Coast & Islands!

#boatfoolssailing #SailingMaine #Gunkholing #sailinglife #Morgan382 #CruisingSailboat #coastalcruising 5 Days Gunkholing The Maine Coast! 5 Sailboats, 85 NM, and the Sturgeon Moon! Join Green Mountain Josh and me as we take our Morgan 382 on an unforgettable 4-night, 5-day gunkholing cruise from...
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...
NEW CREW Explores Yelapa, Jalisco | Mainland Mexico | Sailing Avocet
Sailing Avocet

NEW CREW Explores Yelapa, Jalisco | Mainland Mexico | Sailing Avocet

Join the Sailing Avocet crew on a mesmerizing journey to Yelapa, Jalisco, where they immerse themselves in the charming village's culture, hike to breathtaking waterfalls, and encounter both triumphs and hilarities along the way. Embark on this unforgettable sailing adventure that showcases the...
Diving with a Thousand Sharks in the Middle of the Pacific Ocean | Episode 226
WE|Sail

Diving with a Thousand Sharks in the Middle of the Pacific Ocean | Episode 226

We have spent the last month diving nearly everyday here in Fakarava, and have loved every single minute of it, but we have come to the end of our time here and our final dive with the groupers and sharks. This was one of the most epic dives as we see the congregation of groupers along with 700 shar...
Diving with Delos in the Middle of the Pacific Ocean | Episode 225
WE|Sail

Diving with Delos in the Middle of the Pacific Ocean | Episode 225

This episode is one not to miss, especially if you like scuba diving! We return to the famed South Pass of Fakarava for a phenomenon that literally blew our minds last year, so we had to make sure that we returned again to dive and witness one of the most unbelievable events under the sea. We are ...
Parlay Revival or WE|Sail – Who Sailed it Best? | Episode 224
WE|Sail

Parlay Revival or WE|Sail – Who Sailed it Best? | Episode 224

On this episode, we set sail against Parlay Revival and finally see who has the faster catamaran. With two identical spinnaker sails from our friends at @PrecisionSailLoftVictoria we test the hull speeds of their 465 Lagoon and our 44 Fountaine Pajot followed by an epic birthday bash for Warren as ...
WE Take The Crew of Parlay Revival Diving with Sharks | Episode 223
WE|Sail

WE Take The Crew of Parlay Revival Diving with Sharks | Episode 223

This week on WE|Sail, we are very excited to join back up with the crew of Parlay Revival after they sail into Fakarava. We welcome them to Fakarava and take them on their first scuba dive on the famed south pass. But first, we show them the only little local bar and catch up with the crew of Parla...
Island Adventures in Fakarava with Kite Surfing, Beach Bliss & Pizza Parties | Episode 222
WE|Sail

Island Adventures in Fakarava with Kite Surfing, Beach Bliss & Pizza Parties | Episode 222

This week on WE|Sail, we take a little break from diving and head to another anchorage in Fakarava, where we learn for the very first time how to fly. We attempt to kite surf with a local school and get waterboarded instead. After we have friends over for a pizza party and then take the day off t...
Full Moon Fun in Fakarava, French Polynesia | Episode 221
WE|Sail

Full Moon Fun in Fakarava, French Polynesia | Episode 221

This week we are excited about having a new Highfield dinghy tender delivered to us just before welcoming friends on board to sail and play with us for a few weeks. We set sail back down to the famed Fakarava South Pass for adventures above and below the surface, enjoying a few days lounging beach s...
A South Pacific Playground | Episode 220
WE|Sail

A South Pacific Playground | Episode 220

This week's episode finds us sailing from the island atoll of Tahanea and into the beautiful famed South Pass of Fakarava for its famous shark diving. We have four friends with us who we get to show around this place that we know quite well from the year before. We show them some of our favorit...
A Whole Lot of First Times in the South Pacific | Episode 219
WE|Sail

A Whole Lot of First Times in the South Pacific | Episode 219

It’s time to hop to the next island! We sail from Makemo to Tahanea with our friends aboard. We set sail for our friends very first overnight and open ocean sail to the next Tuamotu island. We sail out of the pass, catch a marlin, and go on our first night dive! So much fun getting to experience al...
From Turmoil to Tranquility: Rekindling Spirits After the Storm at Anchor | Episode 218
WE|Sail

From Turmoil to Tranquility: Rekindling Spirits After the Storm at Anchor | Episode 218

After avoiding a near disaster in the anchorage from a storm, Warren is back safely aboard VA and now in a scramble to get our outboard motor running again before we welcome our friends for the next two weeks. WE are grateful that this was the worst of the whole situation after trying to recovery...
Fleet Week SUCKS?! | Berkeley & Horseshoe Cove | Sailing Avocet
Sailing Avocet

Fleet Week SUCKS?! | Berkeley & Horseshoe Cove | Sailing Avocet

After three weeks of anchoring around the San Francisco Bay we decided to flex our reciprocal yacht club privileges and visit the Neely family’s old stomping – or sailing – grounds in Berkeley to replenish our tanks, and pick up some day crew for the San Francisco Fleet Week festivities. Our time in...
Why Choose the Intracoastal Waterway? | Sailing Wisdom [S5 Ep 48]
Rigging Doctor

Why Choose the Intracoastal Waterway? | Sailing Wisdom [S5 Ep 48]

▸ OUR SHIRTS: ↓BINGE WATCH↓ BINGE WATCH FROM THE BEGINNING: ▸ OUR BOAT (1968 Morgan 45): ▸ MERCHANDISE: ▸ INSTAGRAM: ▸ FACEBOOK: ▸ WEBSITE: ▸ PAINTING COMMISIONS: [email protected] ▸ ART FROM OUR VOYAGE: ▸ MAIN CAMERA: ▸ SECONDARY CAMERA: ▸ UNDERWATER CAMERA: ▸ STABILIZED CAM...
YOUNG CRUISERS FLOTILLA – SAILING CROATIA! EP-69
Leading the Escapade

YOUNG CRUISERS FLOTILLA – SAILING CROATIA! EP-69

Sailing Croatia, Exploring Vodice, yacht racing , our own private flotilla fleet and a beach potluck with our boat buddies!
AN ACTION PACKED 1 YEAR SAILIVERSARY!! EP-68
Leading the Escapade

AN ACTION PACKED 1 YEAR SAILIVERSARY!! EP-68

We play tourist for the day and visit a Croatian hotspot, KRKA National Park, before exploring Croatia's oldest town, Šibenik. We then sail back out of the KRKA
SAILING TO CROATIA’S BLUE GROTTO! EP-65
Leading the Escapade

SAILING TO CROATIA’S BLUE GROTTO! EP-65

We Sail on our friends beautiful Outremer catamaran and enjoy the firework's right from the boat, we check out The incredible Blue Cave on Bisevo Island.
It’s Getting HOT in Here!! We Better Get WET 🙃 (Calico Skies Sailing, Ep 161)
Calico Skies Sailing

It’s Getting HOT in Here!! We Better Get WET 🙃 (Calico Skies Sailing, Ep 161)

This episode opens with Calico Skies underway, motor sailing of the Baja California Peninsula’s eastern shores, in the Sea of Cortez located on Mexico’s western coast. We left a little fishing village are set out for a spot called Los Gatos, which is famous for its beautiful red rock formations. Whi...
BOAT LIFE – DIVING WITH OUR NEW SMACO TANK, HIKING THE KOTOR FORT & STRAY KITTEN RESCUE’S! EP-57
Leading the Escapade

BOAT LIFE – DIVING WITH OUR NEW SMACO TANK, HIKING THE KOTOR FORT & STRAY KITTEN RESCUE’S! EP-57

Exploring Montenegro, Diving with our new SMACO dive tank, Spearfishing, Hiking the Kotor Fortress, Strolling through Kotor Old town and a tiny stray kitten!
Traditional Tattoos & Good-Byes to the Crew | Episode 169
WE|Sail

Traditional Tattoos & Good-Byes to the Crew | Episode 169

On this week’s episode we sail into the last Marquesas island before making our way to the Tuamotus. We arrive in Nuku Hiva and drop anchor around the most boats we have seen in months! We also say a sad goodbye to our crew who have lives to get back to outside of the sailing world! Afterwards we ce...
Sailing from Island to Island Around the Marquesas | Episode 168
WE|Sail

Sailing from Island to Island Around the Marquesas | Episode 168

Our Sailing Adventures bring us to island hoping around some of the world's most remote islands in the South Pacific. We sail the dramatic coastlines of the Marquesas Island chain only to find each anchorage more beautiful than the next. Join us on our sailing adventures throughout the Pacifi...
WE Sail into the Marquesas Best Anchorage | Episode 167
WE|Sail

WE Sail into the Marquesas Best Anchorage | Episode 167

After arrival to the Marquesas we thought we sailed into the prettiest anchorage in the Marquesas, until we arrived to the Baie of Virgins in Fatu Hiva. We are blown away at the beauty this remote little anchorage out in the middle of the South Pacific has to offer! Join us on our sailing adventu...
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