Watch Sailing & Boating Adventures Around the World tagged “Caribbean” – Page 3 of 157

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 49-72 of 3760 results
Massive LIGHTNING Storm Slams our Boat at Anchor! – The Lazy Geckos Ep. 333
Lazy Gecko Sailing & Adventures

Massive LIGHTNING Storm Slams our Boat at Anchor! – The Lazy Geckos Ep. 333

This week’s episode takes you from pure beach bliss to heart-pounding chaos at anchor. 🌴⚓ What starts as a gorgeous day ashore quickly turns into a race against the elements as a massive thunderstorm rolls in over the water. You’ll feel the tensi...
Sailing with Strength & Style – Lauryn on the Bowsprit
Sailing Doodles

Sailing with Strength & Style – Lauryn on the Bowsprit

We barely made it off the dock! 😳 Just as we were about to leave, the engine wouldn’t start — air in the fuel line. After priming and fixing the issue, we finally got the motor running smoothly and set out up the Chesapeake Bay toward the C&D Ca...
Lauryn Returns To The Crew For An Epic Boat Adventure!
Sailing Doodles

Lauryn Returns To The Crew For An Epic Boat Adventure!

This channel is funded by viewers like you. Please help us keep this channel creating great content by Joining the Sailing Doodles Navy https://sailingdoodles.podia.com/sailing-doodles-course-community or become a channel member https://www.youtube.com/c...
Ep. 77 Marlow Ropes comes on board as a major sponsor for the Elcano World Challenge
SAILING into FREEDOM

Ep. 77 Marlow Ropes comes on board as a major sponsor for the Elcano World Challenge

Marlow Ropes can be found at: https://www.marlowropes.com/ and https://www.marlowropes.com/us/ They’re supplying the Elcano World Challenge with BLUE OCEAN® Doublebraid, a line made from 75% recycled plastic bottles (rPET) that keeps the same handli...
SSL738 ~ Searching for KATRINA
Captain Rick Moore

SSL738 ~ Searching for KATRINA

Join our Patreon and join our Team SSL Crew! http://www.patreon.com/SailingSophisticatedLady Come and join us realtime at: http://www.facebook.com/groups/SSLBackstage http://www.instagram.com/SailingSophisticatedLady To all those contributing to our ne...
Final Sail in Greece! Chaotic Docking & Farewell to Miss Lone Star
Sailing Doodles

Final Sail in Greece! Chaotic Docking & Farewell to Miss Lone Star

It’s our last day in Greece aboard the charter catamaran, sailing from the beautiful island of Agistri back to Athens. As we entered the marina, a line of a couple dozen boats all tried to dock at once with the wind picking up—things got a little hecti...
SSL737 ~ It’s Time..
Captain Rick Moore

SSL737 ~ It’s Time..

Join our Patreon and join our Team SSL Crew! http://www.patreon.com/SailingSophisticatedLady Come and join us realtime at: http://www.facebook.com/groups/SSLBackstage http://www.instagram.com/SailingSophisticatedLady To all those contributing to our ne...
Fast Sailing to Poros & Finding a Private Paradise in Greece!
Sailing Doodles

Fast Sailing to Poros & Finding a Private Paradise in Greece!

On our next-to-last day sailing in Greece with Sailing Miss Lone Star, we had some of the best moments of the trip! 🌊⛵ We pushed the boat hard in brisk winds on the way to the beautiful Greek town of Poros, flying across the water under sail. The fol...
Toga Party in Greece! Sailing, BBQ, and Plate Breaking
Sailing Doodles

Toga Party in Greece! Sailing, BBQ, and Plate Breaking

Join us for a short but beautiful downwind sail from Aegina to Agistri, where things get interesting as I attempt a creative (and slightly unusual) mooring. After some relaxing beach time, we head to the Jamaica Yacht Club for an unforgettable Greek BBQ an...
Greek Island Adventure Ends in Trash Avalanche!
Sailing Doodles

Greek Island Adventure Ends in Trash Avalanche!

We continue our Greek island adventure with Sailing Miss Lone Star as we sail from Vathy to Aegina. Along the way we stumble across something unusual on the cliffsides… but the day finishes in true Mediterranean style — with a dip in crystal-clear wate...
EP 76 Vietnam War Museum
SAILING into FREEDOM

EP 76 Vietnam War Museum

Give it a thumbs up if you liked this episode! Get your Sailing Into Freedom Crew T-shirt: https://teespring.com/stores/sailing-into-freedom Want more? Became our patron and get access to exclusive content. https://www.patreon.com/sailingintofreedom If ...
Anchor Drops & Bikini Tops – Life with Brittany! – The Lazy Geckos Ep. 332
Lazy Gecko Sailing & Adventures

Anchor Drops & Bikini Tops – Life with Brittany! – The Lazy Geckos Ep. 332

We're island hopping, I finally get some time to enjoy my MS Bikinis! We've had it rough lately but this was the ah-ha moment!! Come enjoy it with us! If you enjoy our videos, please SUBSCRIBE! Check out our webpage at www.thelazygeckos.com Other Links:...
Clothing Optional Sailing in Greece! | 25+ Knot Winds on a Lagoon 38
Sailing Doodles

Clothing Optional Sailing in Greece! | 25+ Knot Winds on a Lagoon 38

We’re back sailing in Greece with Miss Lone Star aboard a Lagoon 38 catamaran! 🌊⛵️ With the wind blowing over 20 knots, we reefed down twice and still flew along at 8 knots on our way from Aegina to one of my favorite harbors in the Saronic Island...
Baby on Board! Sailing from Athens to Aegina with Miss Lone Star
Sailing Doodles

Baby on Board! Sailing from Athens to Aegina with Miss Lone Star

We’re in Greece! 🇬🇷 In this episode, I fly into Athens to meet up with fellow YouTuber Sailing Miss Lone Star! @SailingMissLoneStar our very first collaboration. We chartered a beautiful catamaran and set sail on our maiden voyage together. Joinin...
Hauling Out for Hurricane Season
Sailing Doodles

Hauling Out for Hurricane Season

After weeks of hard work keeping my boat in shape, I finally wrap up the last round of repairs and set sail for Maryland. Along the way, I enjoy the last miles of the trip before hauling the boat out of the water, where it will be stored safely for the sum...
Can I Sail 500 Miles Alone Around Cape Hatteras?
Sailing Doodles

Can I Sail 500 Miles Alone Around Cape Hatteras?

I set out from Charleston, South Carolina, on a solo sailing journey of nearly 500 miles—rounding the notorious Cape Hatteras and heading up into the Chesapeake Bay. Along the way, I face changing weather, long nights at the helm, and the beauty (and cha...
Ep. 74 The ROYPOW Energy Storage System. It is so easy to install!
SAILING into FREEDOM

Ep. 74 The ROYPOW Energy Storage System. It is so easy to install!

ROYPOW supports the Elcano World Challenge #ROYPOW Check out ROYPOW here : https://www.roypow.com/marine-ess/ Contact ROYPOW here : [email protected] I cannot believe how easy it is to install this ROYPOW battery system. Literally in about 2 hours you ...
We Dive into a Blue Hole…And the Captain has a Panic Attack!! – The Lazy Geckos Ep. 331
Lazy Gecko Sailing & Adventures

We Dive into a Blue Hole…And the Captain has a Panic Attack!! – The Lazy Geckos Ep. 331

In this one we'll navigate the challenges of boat maintenance and the stresses of living remotely. Then we'll hike to the Blue Hole and jump right in! If you enjoy our videos, please SUBSCRIBE! Check out our webpage at www.thelazygeckos.com Other Link...
Boat Maintenance Mayhem After 400 Miles at Sea
Sailing Doodles

Boat Maintenance Mayhem After 400 Miles at Sea

After sailing more than 400 miles from the Bahamas to Charleston, SC, it’s time to tackle all the boat work I’ve been putting off. In the Bahamas, it’s nearly impossible to get the parts and materials you need—but now that I’m stateside, it’s f...
Sailing 400 Miles with No Rules? | Bahamas to USA Adventure
Sailing Doodles

Sailing 400 Miles with No Rules? | Bahamas to USA Adventure

We sail more than 400 nautical miles across open ocean, leaving the Bahamas behind and heading back to the U.S. coast — destination: Charleston, South Carolina. The weather throws us some surprises, the seas don’t make it easy, and morale is tested. Bu...
Ep. 73 VIETNAM WAR ZONE CHU CHI: The nightmare of battle in underground tunnels
SAILING into FREEDOM

Ep. 73 VIETNAM WAR ZONE CHU CHI: The nightmare of battle in underground tunnels

Give it a thumbs up if you liked this episode! Get your Sailing Into Freedom Crew T-shirt: https://teespring.com/stores/sailing-into-freedom Want more? Became our patron and get access to exclusive content. https://www.patreon.com/sailingintofreedom If ...
We Got Soaked… But the Watermaker Works! 🛠️🦈 Shark Alley Bound! – The Lazy Geckos Ep. 330
Lazy Gecko Sailing & Adventures

We Got Soaked… But the Watermaker Works! 🛠️🦈 Shark Alley Bound! – The Lazy Geckos Ep. 330

Experience a day filled with exciting water activities like snorkeling and exploring shark alley. We deal with ongoing issues with our water maker, showcasing frustrations and last ditch efforts to find solutions. If you enjoy our videos, please SUBSCRIB...
Our Last Bahamas Beach Day Was WILD! Jennifer is BACK!
Sailing Doodles

Our Last Bahamas Beach Day Was WILD! Jennifer is BACK!

Beautiful Jennifer rejoins the crew just in time for one last unforgettable beach day in the Bahamas! We sail up to stunning Spanish Cay, soaking in the final days of sunshine, clear blue water, and tropical vibes before setting our course back to the USA....
SSL736 ~ this Sh*t almost cost us our BOAT
Captain Rick Moore

SSL736 ~ this Sh*t almost cost us our BOAT

Join our Patreon and join our Team SSL Crew! http://www.patreon.com/SailingSophisticatedLady Come and join us realtime at: http://www.facebook.com/groups/SSLBackstage http://www.instagram.com/SailingSophisticatedLady To all those contributing to our ne...
Epic water experiences, one click away.

Something AWESOME is coming!
Be the FIRST to know⛵

Sign up for exclusive updates and be the first to hear when we go live!
Get sneak peeks, exciting announcement, and special content straight to your inbox!

We don’t spam! Read our privacy policy for more info.


WeBoating
Logo
Shopping cart