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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Off the Dock, ADVENTURE AWAITS!   Sailing British Columbia – Ep53 S3
Breaking Waves

Off the Dock, ADVENTURE AWAITS! Sailing British Columbia – Ep53 S3

This week the Breaking Waves crew soaks up boat life in Tofino, and load up the boat with provisions for an extended sailing cruise to North Western Vancouver Island in the Pacific North West. This is the start of our most wild adventure to date, with heavy weather, big seas and extremely remote and...
Beautiful girls, Beautiful islands, Clothing optional… (pt 2)
Sailing Zingaro

Beautiful girls, Beautiful islands, Clothing optional… (pt 2)

Come SAILING with Zingaro!!!! Go to This is the SEQUAL to the video beautiful girls, beautiful islands, clothing optional. Want to SAIL with us? Book a trip: www.sailingzingaro.com Escape the cold to a tropical paradise: San Blas, Panama. Merry Christmas!!! If you would like to donate to Nerea and...
Swimming with our Girl Friends and Sailing, Surfing, in Tofino British Columbia – Ep50S3
Breaking Waves

Swimming with our Girl Friends and Sailing, Surfing, in Tofino British Columbia – Ep50S3

Ben and Alie are finally in Tofino! They set out to find a slip to call home, take advantage of the nearby surf and have a close encounter on the boat with a rock. With Clayoquot sound as their backyard they start to explore all the inlets available to them and find a great swimming hole with some q...
I Met The Nicest People Ever Here | Random Acts Of Village Kindness | Winded Voyage 4 | Episode 72
Winded Voyage Sailing

I Met The Nicest People Ever Here | Random Acts Of Village Kindness | Winded Voyage 4 | Episode 72

We have found a paradise of goodness in the village of Ribiera de Barca. It's rare that sailors anchor in front of their village, and we are welcome like royalty. Kids swim out to say hello, fishermen come for coffee and girls come for a beer and curious to see what the inside of a yacht looks ...
Diving Deeper with Delos + BIG NEWS!!! (Drenched Sailing Ep. 47)
Expedition Drenched

Diving Deeper with Delos + BIG NEWS!!! (Drenched Sailing Ep. 47)

We have something super exciting to share with you guys! We can't believe it either!!!! Buy Drenched Merchandise: Check out Rick on YouTube: Check out Shascha on YouTube: Check out Delos on YouTube: Check us out on Instagram! Check out Aquanauts Grenada If you love scuba, sailin...
Meeting SV Delos Part 2: SAILING & SCUBA!! (DRENCHED Ep. 46)
Expedition Drenched

Meeting SV Delos Part 2: SAILING & SCUBA!! (DRENCHED Ep. 46)

See what it's like to fly on the bow of SV Delos while she is under sail! Join us for more diving, more sailing, and more shenanigans! You dig it? Give it a big thumbs up 👍 & Subscribe. Check out Rick and Sophisticated Lady on YouTube: Check out S.V. Delos on YouTube: Check us out on ...
Love At First Dive! Meeting SV Delos! (DRENCHED Sailing Ep. 45)
Expedition Drenched

Love At First Dive! Meeting SV Delos! (DRENCHED Sailing Ep. 45)

You dig it? Give it a big thumbs up 👍 & Subscribe. We meet up with the gang from SV Delos and have allllllll the fun! We have a reunion with our old Pals Rick and Shascha from Sophisticated Lady, explore jungle water falls, go sailing, scuba diving, and take our underwater metal detector for i...
All Smiles At Sea (Sailing Drenched Ep. 29)
Expedition Drenched

All Smiles At Sea (Sailing Drenched Ep. 29)

We go in search of the world's largest predator and then we dive underneath a tiny, uninhabited island. This is probably one of the riskiest and most unique dives we've attempted in the caribbean thus far! Check us out on Instagram! Want more Sailing Sophisticated Lady? Check out Ric...
Goodbye Blonde Squad! (Sailing Drenched Ep. 28)
Expedition Drenched

Goodbye Blonde Squad! (Sailing Drenched Ep. 28)

The Blonde Squad parts as ways as Megan and Kelly move on to their next adventures! We paddle up a creepy windy river where pirates of the Caribbean was filmed. We sail up the coast of Dominica where we do one of our favorite dives of our entire trip through the Caribbean. ENTER TO WIN FREE DIVIN...
Captain Underpants Sails South! ~Sailing Drenched Ep. 27~
Expedition Drenched

Captain Underpants Sails South! ~Sailing Drenched Ep. 27~

Ain't no party like an underpants party! Sophisticated Lady continues south as we leave the incredible island of Guadeloupe. We make a quick overnight stop over at Isles Des Saintes to fill up on water and do some scuba diving, then we journey south to Dominica, probably our favorite island in...
Life is GOOD on Guadeloupe (Sailing Drenched Ep. 26)
Expedition Drenched

Life is GOOD on Guadeloupe (Sailing Drenched Ep. 26)

We follow in the footsteps of Jacques Cousteau and dive the marine reserve named in his honor. After finding out that it was Guadeloupe's national holiday we decided to celebrate in style and we get a little silly courtesy of our endless supply of rum on board. Thanks for watching! Help keep...
What SAILOR GIRLS Do In PARADISE! (Sailing DRENCHED Ep. 25)
Expedition Drenched

What SAILOR GIRLS Do In PARADISE! (Sailing DRENCHED Ep. 25)

When it comes to sailing life, girls have the most fun! We check out a volcano, do some incredible scuba diving, and hike to one of the most beautiful waterfalls we've ever seen. We hope you enjoy and thanks for watching! Help keep the dream afloat, support us on Patreon!!!!: Want more Sai...
Wild Nights and Deserted Islands~Sailing DRENCHED Ep.24~
Expedition Drenched

Wild Nights and Deserted Islands~Sailing DRENCHED Ep.24~

Goat stampedes, crabs, hot springs, and diving our very own private deserted island! This was probably one of the best 24 hours of our lives! After we meet a new friend Gonzi on the island of Nevis, we go on a whirlwind adventure of Pinney's (PENIS) beach, sunshine's beach bar, meet some ...
Scuba Diving At Booby Island! ~Sailing Drenched Ep. 23~
Expedition Drenched

Scuba Diving At Booby Island! ~Sailing Drenched Ep. 23~

Join us as we sail from Statia to St. Kitts, where we check out the local scene, enjoy fiesta friday, ride the most beautiful train in the world, then cruise over to Nevis for some diving at Booby Island. Life is good onboard Sophisticated Lady! Help keep the dream afloat, support us on Patreon!...
The First Day: Life is Golden At Sea~Sailing DRENCHED Ep. 22~
Expedition Drenched

The First Day: Life is Golden At Sea~Sailing DRENCHED Ep. 22~

The first day of life at sea! We had done some shorter day sails and weekend trips, but now we were on the big blue road FOR GOOD! Our first stop along the way did not disappoint. The island of St. Eustatius treated us to some amazing hiking, crazy shipwreck scuba diving at night, fresh coconuts, ...
Casting the lines: LET’S DO THIS!!! ~Sailing DRENCHED Ep. 21~
Expedition Drenched

Casting the lines: LET’S DO THIS!!! ~Sailing DRENCHED Ep. 21~

It's finally time to cast the lines and set sail on our biggest mission yet! Join us as we welcome our beautiful African Grey parrot Tiki, stock up on an ungodly amount of beer, and say goodbye to St. Martin for good! We have a gorgeous sail to the neighboring island of St. Eustatius and dive r...
Caribbean Life and the Blonde Squad! ~Sailing DRENCHED ep. 20~
Expedition Drenched

Caribbean Life and the Blonde Squad! ~Sailing DRENCHED ep. 20~

Join us for some island hopping and lion fish hunting, then we pick up our friends Megan and Kelly who are joining the crew for our sailing trip through the Caribbean. We do a little exploring around St. Martin, check out a really cool butterfly farm, visit the famous nude beach Orient Bay, and cre...
Flying A Drone While Sailing In Paradise! ~DRENCHED Ep. 19~
Expedition Drenched

Flying A Drone While Sailing In Paradise! ~DRENCHED Ep. 19~

We fly and sail through some of the most picture perfect islands in the world! After saying goodbye to our crew mate Jesse, we set sail from St Martin to the neighboring island of Anguilla where we do a little bit of island hopping and exploring, check out Little Bay Marine Preserve above and below...
HUGE Adventure On A TINY ISLAND w/ SAILING Sophisticated Lady ~DRENCHED Ep. 18~
Expedition Drenched

HUGE Adventure On A TINY ISLAND w/ SAILING Sophisticated Lady ~DRENCHED Ep. 18~

Bat caves, epic scuba diving, and standing on top of the Dutch Kingdom. Life doesn't get much better. Join us for our second episode on the stellar island of Saba! If you would like to be entered to win two days of Saba diving for 2 people, then visit our Patreon page here: Want more Sail...
How We Afford To Live On A SAILBOAT ~DRENCHED Ep. 17~
Expedition Drenched

How We Afford To Live On A SAILBOAT ~DRENCHED Ep. 17~

Ever wonder how we pay the bills while living on a sailboat? Come along with us on some work days as we film some commercials for a huge watersports company! Spoiler alert: It's a lot more play than work :) Want more Sailing Sophisticated Lady? Check out Rick's channel here: Help kee...
RESCUE MISSION with SSL!!! ~Sailing DRENCHED Ep. 16~
Expedition Drenched

RESCUE MISSION with SSL!!! ~Sailing DRENCHED Ep. 16~

Our sailing adventure begins after new crew gets deported and we travel to St. Kitts to rescue her! Mechanical problems, evil tarpon fish, and some of the most beautiful conditions we've ever seen make this rescue mission one to remember. Want more Sailing Sophisticated Lady? Check out Rick&#...
Goodbye Hawaii, HELLO SAILING! ~DRENCHED Ep. 15~
Expedition Drenched

Goodbye Hawaii, HELLO SAILING! ~DRENCHED Ep. 15~

We go out with a bang in our last days in Hawaii. First we go to one of Maui's funnest traditions, the Sunday drum circle at Little Beach where we watch some fire dancing, do some body painting, and enjoy a stellar sunset. Then we dive the famous Cathedrals of Lanaii before embarking on our n...
Meet the Maui MERMAID! ~DRENCHED Ep. 11~
Expedition Drenched

Meet the Maui MERMAID! ~DRENCHED Ep. 11~

Mermaids and Turtles! What a great first day in Maui! In this episode we leave Big Island (after a near death encounter with a centipede that has left me with nightmares) and head over to Maui. We take you along for a work day as we film a marketing video for Maui Spearfishing Academy and finish ...
Take the Plunge on Big Island Hawaii ~DRENCHED Ep. 9~
Expedition Drenched

Take the Plunge on Big Island Hawaii ~DRENCHED Ep. 9~

What more can we say, who doesn't love beer, scuba, and adventure! Support us on Patreon and become our dive buddy: In this episode we go on a tour of Kona Brewing Company and get a behind the scenes look at where our favorite beverages come from. The next morning we went on an awesome di...
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