Watch Sailing & Boating Adventures Around the World – Page 343 of 347

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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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...
16 – Exploring Dominica
Out Chasing Stars

16 – Exploring Dominica

Our next stop in the Caribbean was Dominica, where we anchored in Portsmouth and proceeded to explore the island by boat and by car. The natural beauty of the island was stunning and was topped off with a trip to the Emerald Pool and waterfall. While in Dominica we used the local market to re-prov...
How to choose a catamaran – Catamaran sailing techniques
Yachting World

How to choose a catamaran – Catamaran sailing techniques

Top multihull designer Nigel Irens guides us through the process of choosing a catamaran. We also speak to Lloyd Thornburg, owner and skipper of record-breaking Phaedo 3 and ask his opinion on what to look for
Gone With The Wynns 2.0
Gone with the Wynns

Gone With The Wynns 2.0

It's been over 4 years since we created a new "about us" or "Adventure" video. To say the task is daunting would be a complete understatement. But to go back through 6 years of videos is an epic adventure of it's own. It's like the video editing equivalent of cl...
SHE CRASHED IT!!! Sailing the Virgin Islands – Chase the Story 23
Chase the Story

SHE CRASHED IT!!! Sailing the Virgin Islands – Chase the Story 23

SHE CRASHED IT!!! Sailing the Virgin Islands - Chase the Story 23 We sailed Cheeky Monkey into St. John in the US Virgin Islands with a mission to run the 8 Tuff Miles road race and also to finally get our Swellpro Splash Drone off the ground and flying! The drone was a bit of a disaster but the r...
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&...
Sailing Tangaroa ep. 4 – Sailing the southwest of Western Australia
Sailing Tangaroa

Sailing Tangaroa ep. 4 – Sailing the southwest of Western Australia

As we continue our sailing journey along the stunning southwest of Western Australia, we catch tuna, see amazing sunsets, drive 4,600 km across the Nullarbor plain and back for a weekend of fun, do the historical parts of Albany, see huge whale skeletons and get caught in 50 knot winds and bare pole...
SAILING THE SPANISH VIRGIN ISLANDS!! – Chase the Story 22
Chase the Story

SAILING THE SPANISH VIRGIN ISLANDS!! – Chase the Story 22

Sailing the Spanish Virgin Islands (Puerto Rico): In this story Ryan and Tasha return from a brief trip to New York to collect two new members of crew and head out on a sailing adventure from the US Virgin Islands to the amazing Culebra Island, which is part of the Spanish Virgin Islands, which are ...
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 ...
Trailer: Sailing Around the World (Chase the Story)
Chase the Story

Trailer: Sailing Around the World (Chase the Story)

Sailing Around the World - Chase the Story Channel Trailer Turf to Surf sailing blog link: Sailing across the Atlantic was a success! We've had a blast putting together all 21 episodes taking us from La Rochelle, France to the Mediterranean and to the Caribbean. And now it's time for ...
A Glimpse of the Sweet Life – Sailing Our Dream Boat
Gone with the Wynns

A Glimpse of the Sweet Life – Sailing Our Dream Boat

Get all the new boat details and dealings on our site here: We made an offer on a catamaran! Wooo Hooo! Luckily the current owner likes us and has invited us on board to learn and sail with him from Vero Beach to Ft. Lauderdale so we can do the survey, haul-out and sea trial. Needless to say...
Crewing a Catamaran – Success is Failure Inside Out
Gone with the Wynns

Crewing a Catamaran – Success is Failure Inside Out

More lessons learned and our thoughts on this crazy sail: Today we're helping a friend sail south in his new-to-him Lagoon 410 S2 catamaran. We're going as crew to help ease the burden of the three day sail. It was supposed to be an easy sail from St. Augustine to Ft. Lauderdale. &...
15 – The Island of Beautiful Waters
Out Chasing Stars

15 – The Island of Beautiful Waters

Our adventures with family continues as Amy's cousins join us to explore Guadeloupe, known as the "Island of Beautiful Waters". We made landfall in Deshaies and explored the best botanical garden in the Caribbean, did some rock climbing on a river hike and visited Basse Terre. To to...
Sailing Tangaroa. ep. 3 – Sailing the Great Australian Bight
Sailing Tangaroa

Sailing Tangaroa. ep. 3 – Sailing the Great Australian Bight

We sailed across the Great Australian Bight on our 37 ft James Wharram catamaran! A young couple from South Australia, adventuring via the Western Australian coast line. We love positive vibes, much love fellow soul gypsy's and pirates, if you've got a dream, chase it! ARGGGGHHHHHHHHHHHH! ...
Atlantic Crossing: WE MADE IT!! – Chase the Story 21
Chase the Story

Atlantic Crossing: WE MADE IT!! – Chase the Story 21

We made it! Sailing across the Atlantic Ocean after 20 days at sea, sailing vessel Cheeky Monkey finally arrives to the Caribbean to the beautiful island of Antigua. It was a test of time for our six crew on board - did we make it with empty diesel tanks? Did we make it before Christmas? Did we make...
ATLANTIC CROSSING: STUCK IN A WIND HOLE! – Chase the Story 20
Chase the Story

ATLANTIC CROSSING: STUCK IN A WIND HOLE! – Chase the Story 20

Atlantic Crossing: Stuck in a Wind Hole! (Story 20) Sailing across the Atlantic Ocean comes with the challenge of tracking the weather and plotting a course that will take us across to the Caribbean with maximum wind and minimum motoring. When a storm on the north Atlantic sucks all the wind out o...
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...
14 – A Family Christmas in Antigua
Out Chasing Stars

14 – A Family Christmas in Antigua

The fun-to-suck ratio swings back to positive as we make a quick resupply stop in St. Martin and then continue on to Antigua. There, Amy's parents and uncle joined us for a tropical Christmas, some great sailing and even a day of zip-lining! To follow along with our cruising adventures, pleas...
Key West – Cheap Beer, Cool Cats & Heavenly Food
Gone with the Wynns

Key West – Cheap Beer, Cool Cats & Heavenly Food

Get the entire Key West scoop on our website here: Join us for a ride down the Florida Keys towards mile marker 0 in Key West. We share a few of our favorite stops along the famous Overseas Highway 1 and we end up in Key West. A little exploration, a little history, art and plenty of drinking, e...
SAILING THE ATLANTIC: SHE WENT OVERBOARD!! – Chase the Story 19
Chase the Story

SAILING THE ATLANTIC: SHE WENT OVERBOARD!! – Chase the Story 19

Sailing the Atlantic with Cheeky Monkey is finally here! Our first sailing video of Cheeky Monkey racing against the clock across the Atlantic Ocean to the Caribbean. ***WANT MORE?? SUBSCRIBE TO OUR CHANNEL!*** The time for preparing is over! We slip lines from the Canary Islands to adventure i...
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...
13 – Pizza, Friends, and Hard Lessons
Out Chasing Stars

13 – Pizza, Friends, and Hard Lessons

Our next stop in the Caribbean is the USVI's, where we enjoyed lots of pizza from Pizza Pi in Christmas Cove, hanging out with friends and learned a few hard lessons about boat maintenance! To follow along with our cruising adventures, please subscribe to our YouTube channel and check out our ...
WE COULDN’T FIND THE TURKEY – Chase the Story 16
Chase the Story

WE COULDN’T FIND THE TURKEY – Chase the Story 16

We set out in across the Atlantic and our first meal at sea is prepared by the Americans on board. ***SUBSCRIBE TO OUR YOUTUBE CHANNEL FOR UPDATES!!!*** Turf to Surf Blog Link: On November 26, 2015, the six crew of sailing vessel Cheeky Monkey set out with two missions - 1) show our French crew m...
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