Watch Sailing & Boating Adventures Around the World – Page 18 of 18

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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In the Moment – Sailing, Service & Fear
Gone with the Wynns

In the Moment – Sailing, Service & Fear

I know sometimes our videos seem like everything is all fun and peachy, and generally we're happy people, but our life can be crazy! I think the video explains it better than we can in writing. Join the Crew and get more access on Patreon: & Read our post for more: Subscribe on YouTube:...
Sailing Schooled Ep. 1 – Miami, The Crew & Scarface
Gone with the Wynns

Sailing Schooled Ep. 1 – Miami, The Crew & Scarface

Sailing School Begins! Join us as we document the week of adventure and learning. Today it's an easy sail to Miami before we really dive into the hands-on schooling. Subscribe here: Read the full post, see our photos & get the details here: Join the Crew on Patreon What's cool...
Sailboat Life – Finding Our Groove & Getting Burned
Gone with the Wynns

Sailboat Life – Finding Our Groove & Getting Burned

We go into a lot more detail on our website: After spending a small fortune at the Harbor Towne Marina we decide to anchor out at Lake Sylvia near downtown Ft. Lauderdale for almost a week while we wait for our service appointment. We're surrounded by beautiful homes, there's a nice br...
Stripping the RV & Our Overloaded Sailboat
Gone with the Wynns

Stripping the RV & Our Overloaded Sailboat

This story is incomplete! Get the full scoop on our site here: It's embarrassing to share this video, we don't want to look like the Clampetts, but in the interest of bearing it all (and sharing the realities of moving) we're hitting the publish button on this horribly unorganized...
Day 2 as Sailboat Owners – A Broken Block, Lost Fish & Refugees
Gone with the Wynns

Day 2 as Sailboat Owners – A Broken Block, Lost Fish & Refugees

The video isn't the entire story, read more on our website: Our Second day on the water as new sailboat owners turns out to be quite the adventure. We pull up the anchor, get out of the ICW, head "outside" and turn south towards Ft. Lauderdale. Enjoy our vids? Want to give us a ...
OUR MAIDEN VOYAGE!
Gone with the Wynns

OUR MAIDEN VOYAGE!

There's details missing from this video so read our post: We're bringing a sailor with know how aboard, sailing our new boat from Vero to Ft. Lauderdale and taking the cats on their first boat trip. Definitely an action packed day for the whole family. Enjoy our vids? Want to give us...
From RV to Sailboat – Moving Day & Our Last Road Trip
Gone with the Wynns

From RV to Sailboat – Moving Day & Our Last Road Trip

Read the Details of what's happening to the RV and our Move-In thoughts here: We're moving into our new home on the water! Lot's of logistics here in moving the RV from West Palm Beach, to endless trips from the RV down the docks and into our Catamaran at Vero Beach. Crazy doesn&...
Buying a Sailboat – Survey, Haul-Out & Sea Trial
Gone with the Wynns

Buying a Sailboat – Survey, Haul-Out & Sea Trial

Find more details and info in the article on our site here: Our offer has been accepted on a Leopard 43 Catamaran and the next step in the process is a Survey, Haul-Out and Sea Trial. We've hired a guy named Brian Stetler out of Jupiter, Florida for the survey and it's his job to find ...
Sailboat Shopping & the Almost Perfect Catamaran
Gone with the Wynns

Sailboat Shopping & the Almost Perfect Catamaran

Get the full scoop on our site here: Today we set off to view what seems like the perfect cruising catamaran for our needs, but there is a GIANT "but". After the searching everywhere for the past month we've narrowed our search down to an Owners Version and we're on the hunt...
Sailboat Shopping – Searching for a Cruising Catamaran
Gone with the Wynns

Sailboat Shopping – Searching for a Cruising Catamaran

More of our Cruising Catamaran Sailboat shopping thoughts can be found here: Our Sailboat shopping experience begins. Today we're meeting with our boat broker for the first time at his office in Ft. Lauderdale then checking out a few Cats from 36 - 43 feet. It's an eye opening experien...
Sailing Virgins – Our Thoughts, Expectations & Uncertainties
Gone with the Wynns

Sailing Virgins – Our Thoughts, Expectations & Uncertainties

Get the entire scoop on our website here: We are blazing through the miles on our way from TX to FL to begin our sailboat search. Sitting for all these hours watching the mile markers pass by, we've had a ton of time to think about the adventures ahead. We decide to stretch our legs (and th...
ICAP LEOPARD 09 JP Morgan Round the Island Race (Uncut)
World On Water

ICAP LEOPARD 09 JP Morgan Round the Island Race (Uncut)

Maxi ICAP Leopard in the JP Morgan Asset Management Round the Island Race. This is the fun race of the seasn as thousands of boats and many thousands of sailors gather for this fantastic annual event. Uncut onboard "action" is seen here. For a complete report
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