Watch Sailing & Boating Adventures Around the World – Page 2 of 4
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.
Showing 25-48 of 81 results
SSL 275 ~ Early Morning Rockstar..
Some of you will remember how I used to love posting videos about our 'backyard of the day', with amazing moments I enjoy sharing with you guys.. well this is one of those, and don't miss the special ending with our African Grey Parrot, 'TIKI', when you'll find out who ...
SSL 274 ~ Captain’s Log ~ Real Time Sunday!
We've been having a lot of fun recording some cool video content with our new 360 camera for you guys that will be coming up soon, if you want to check out the one we picked, have a look at the link below! Video by Brenden Moore, Intro by Captain Rick Happy Sunday Funday everyone, be sure an...
SSL 273 ~ Debauchery continues with SV DELOS and DRENCHED DIVING Crew!
The debauchery continues with SV DELOS crew, SSL, and DRENCHED DIVING! This day we go for a beautiful sail on the South coast of Grenada as we move to Secret Harbour in Mt Hartman Bay.. lots of fun along the way, and DELOS Crew learns what a Full Moon by daylight is! Lol John Wiles was our lates...
SSL 272 ~ Welcome SV DELOS crew aboard SOPHISTICATED LADY!
Part 2 of our SSL meet-up with SV DELOS series finds us welcoming Brian and Brady aboard SOPHISTICATED LADY to present them with the new Grenada flag we picked up for them to sport on DELOS... the original plan for the first day was to go diving, but timing didn't work out so everyone went for ...
SSL 271 ~ SSL meets SV DELOS ~ Day 1 – The Arrival! (Extended Version)
The one many of you have been waiting for, SSL meets SV DELOS! Yes the DELOS crew came up to meet SSL in Grenada this season, and we had so much fun hanging out with Brian, Brady, Karen, and Alex that somehow we ended up spending 6 weeks sailing around and showing them some of our favourite places...
SSL 269 ~ What happens in Grenada, STAYS in Grenada!
This episode edited by Shascha Z! Hope you guys enjoy, this is the 2nd of 3 weddings we did with Bill and Lori for their Valentine's wedding in Paradise aboard 'Sophisticated Lady'... Next episode you'll also meet some very special guests arriving that you may remember from past...
CaptainRick ~ I QUIT!!
Some of you may not 'get' this video, but for me it is a verbal stepping stone in setting my course to where I want to go next and leave behind things that aren't helping me move forward... I have a tendency to speak my mind, my thoughts, feelings etc... so while I don't expect a...
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...
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~
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~
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~
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~
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~
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~
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~
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~
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~
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...
SSL 91 ~ Time to go Sailing, ‘SOPHISTICATED LADY’ Style! (in 4K UltraHD)
Thanks so much to all our new supporters on Patreon! If you'd like to support our SSL Videos on Patreon, find us here! To view our new extended version SSL episodes AD-FREE with previously deleted scenes, full length interviews, dive scenes, drone aerials and more, visit our new Vimeo On Dema...
TRAVEL and DIVE the world! Our love story with the ocean!!!
Here's a little sneak peak at our new series DRENCHED! We are two scuba diving instructors, Nate and Jordan, on a mission to bring our beautiful blue world to all you viewers. Follow our adventure as we travel around the world by land, air, and sea, bringing you to dive destinations both ne...
SSL 80 ~ Tour of the NEW ARGYLE INTERNATIONAL AIRPORT in St Vincent, CARIBBEAN!
Thanks so much to all our new supporters on Patreon! If you'd like to support our SSL Videos on Patreon, find us here! To view our new extended version SSL episodes AD-FREE with previously deleted scenes, full length interviews, dive scenes, drone aerials and more, visit our new Vimeo On Dema...
SSL 11 ~ Boat Prep, Naked Beach, and Dinner Out!
Thanks so much to all our new supporters on Patreon! If you'd like to support our SSL Videos on Patreon, find us here! To view our new extended version SSL episodes AD-FREE with previously deleted scenes, full length interviews, dive scenes, drone aerials and more, visit our new Vimeo On Dema...
SSL 78 ~ Island Tour UNCLE WILLIE STYLE! In 4K ULTRA HD! :)
Thanks so much to all our new supporters on Patreon! If you'd like to support our SSL Videos on Patreon, find us here! To view our new extended version SSL episodes AD-FREE with previously deleted scenes, full length interviews, dive scenes, drone aerials and more, visit our new Vimeo On Dema...