Watch Sailing & Boating Adventures Around the World tagged “Paradise”

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 1-24 of 642 results
From SEA to SUMMIT – Sailing Family ROAD TRIPPING through the South Island of New Zealand Ep. 80
Sailing Machete

From SEA to SUMMIT – Sailing Family ROAD TRIPPING through the South Island of New Zealand Ep. 80

This week Daniel's parents are traveling with us as we road trip around the BEAUTIFUL South Island of New Zealand. Daniel has an entire itinerary planned to see the highlights of this part of New Zealand. I'm hoping everything is smooth cruising as we now ...
SAILS and TRAILS – EPIC Family REUNION in NEW ZEALAND – BUCKETLIST TRIP –  Episode 79
Sailing Machete

SAILS and TRAILS – EPIC Family REUNION in NEW ZEALAND – BUCKETLIST TRIP – Episode 79

This week Daniel's family makes it to NEW ZEALAND. We've got adventures planned from the moment their plane touches the grounds. We explore some of our favorite spots the North Island has to offer. Then we make it back to the boat to check out the bay of...
From Dreamy Anchorage to Pirate Drama | Sailing Sitka Ep 180
Sailing Sitka

From Dreamy Anchorage to Pirate Drama | Sailing Sitka Ep 180

Jay and Kenna were about a week into a postcard-worthy anchorage—spending their days lounging on the beach, sipping cocktails, surrounded by friends and fellow sailors, soaking up the beauty of the sailing lifestyle. But with all that beauty comes a bit ...
Anchored in Paradise: Discovering Nissos Peristera and Prasso, Greece
Dylan Magaster

Anchored in Paradise: Discovering Nissos Peristera and Prasso, Greece

Support your skin and support the channel with the best skin salve: https://www.captainssalve.com In today’s adventure, we set sail to the stunning, uninhabited island of Nissos Prasso, one of Greece’s most remote and beautiful locations. With no perma...
We haven’t stepped foot on land in a week! (and heres why) | Sailing Sitka Ep 178
Sailing Sitka

We haven’t stepped foot on land in a week! (and heres why) | Sailing Sitka Ep 178

Jay and Kenna have been off the grid, not setting foot on land for over a week while sailing through the San Blas Islands. While anchored at Green Island, they took it slow to ride out some intense winds. With no working outboard and a less-than-reliable p...
SAILING, REPAIRS, and FAMILY ON THE WAY | Boat Life Chaos in NEW ZEALAND (78)
Sailing Machete

SAILING, REPAIRS, and FAMILY ON THE WAY | Boat Life Chaos in NEW ZEALAND (78)

This week our family is moving up the coast of New Zealand trying to make it back to the Opua/Pahia area. The countdown is on for Daniel's parents to arrive and our generator is not working! We get the boat prepped and take off to the airport only to have...
A Week Living, Sailing, and Pregnant in Remote Fiji  – Episode 154
Sailing One Life

A Week Living, Sailing, and Pregnant in Remote Fiji – Episode 154

Want to help support our video productions and get real time updates? 🌍➡️Join our One Life Crew here: https://www.patreon.com/SailingOneLife 💦Grab a Sailing One Life Epic Water Filters Bottle! Use discount code EPICONELIFE here: https://www.epi...
Sailing the ISLANDS of New Zealand | An EPIC Kiwi CHRISTMAS (77)
Sailing Machete

Sailing the ISLANDS of New Zealand | An EPIC Kiwi CHRISTMAS (77)

This week our family is getting ready for Christmas! We hang out a bit more at Great Barrier Island then move on to Auckland. We see the Sky Tower, provision and make it to a passport appointment for John and Juju. When leaving Auckland, we have some t...
Sailing the Wild Coast of New Zealand | Hole in the Rock & Great Barrier Island (76)
Sailing Machete

Sailing the Wild Coast of New Zealand | Hole in the Rock & Great Barrier Island (76)

This week our family is getting ready for Thanksgiving and sailing down the coast of New Zealand. We check out the hole in the rock, hop our way down to Whangarei and make our way to Great Barrier Island. Thank you for watching and subscribing. You don'...
Sailing back to Paradise | Sailing Sitka Ep 172
Sailing Sitka

Sailing back to Paradise | Sailing Sitka Ep 172

Despite recent engine troubles, Jay and Kenna felt the pull to keep moving. With their sights set on the tropical paradise of San Blas, they set sail from Linton Bay—upwind and into the chop. Will they make it? Hit subscribe to follow the journey.
The DINGHY DILEMMA – Our NEW ZEALAND ADVENTURE is off to a ROCKY START (75)
Sailing Machete

The DINGHY DILEMMA – Our NEW ZEALAND ADVENTURE is off to a ROCKY START (75)

This week our family is sailing in the bay of islands of New Zealand. There is everything we could ever need here, including so many boat friends! Our dinghy has a major leak and it is in need of replacing. We won't get very far without that important ...
Our WORST PASSAGE Yet – 1100NM to NEW ZEALAND (74)
Sailing Machete

Our WORST PASSAGE Yet – 1100NM to NEW ZEALAND (74)

This week our family is sailing from Tonga to New Zealand. This passage is known to be a difficult one and it's living up to its reputation. We are starting out the passage worrying about boat damage from the whale collision and we are low on food AND fu...
FACING FURY – Surviving the STORM in TONGA  (73)
Sailing Machete

FACING FURY – Surviving the STORM in TONGA (73)

The week our family is in the Ha'apai island group of Tonga. It was all smooth sailing with friends until the weather forecast changed. Everyone left and we decided to stay behind and ride out the storm. It left us questioning our sanity and if we were ...
CAUGHT ON CAMERA – COLLISION with WHALE in TONGA – the Damage, the Drama, and the Aftermath (72)
Sailing Machete

CAUGHT ON CAMERA – COLLISION with WHALE in TONGA – the Damage, the Drama, and the Aftermath (72)

The week our family is moving to the Ha'apai island group of Tonga. It was all smooth sailing until Machete collided with a whale. Thank you for watching and subscribing. You don't know how much we appreciate it! To God be the glory! #sailingfamily #...
Getting delivered boat parts to the edge of civilization (FAIL)  | Sailing Sitka Ep 167
Sailing Sitka

Getting delivered boat parts to the edge of civilization (FAIL) | Sailing Sitka Ep 167

While cruising through the San Blas Islands, Jay and Kenna unfortunately broke the propeller on their outboard motor. Given the remote nature of the islands, where services like Amazon Prime are unavailable, obtaining replacement parts can be challenging. ...
A Not “Normal” Life – Raising a Family at Sea – Kids, Homeschool, Repairs in TONGA (Ep. 71)
Sailing Machete

A Not “Normal” Life – Raising a Family at Sea – Kids, Homeschool, Repairs in TONGA (Ep. 71)

The week our family is exploring Tonga! We sail to Tonga and catch a tuna on the way. We raft up to another boat at the customs dock and wait to officially check into Tonga. Jack finds the Tonga flag and marks this country on our map! We hop around the ...
Sometimes cruising doesn’t always go according to plan… | Sailing Sitka Ep 166
Sailing Sitka

Sometimes cruising doesn’t always go according to plan… | Sailing Sitka Ep 166

Jay and Kenna navigate the harsh realities of cruising. There are both challenges and benefits to sailing and both can rock your world. From fixing broken systems, to installing new ones and reaching for the medical kits with no healthcare facilities in si...
What Happens When You Sail 50 Miles and Discover a Hidden GEM?
Sailing Paradise Falls

What Happens When You Sail 50 Miles and Discover a Hidden GEM?

Sailing 50 Miles and Discovering a HIDDEN GEM We are FINALLY back out sailing on the ocean after 5 long months. Our family sails to Great Barrier Island on our catamaran and hike to find a swing bridge with a tree house and STUNNING views. A low pressure...
Found the CLEAREST Water In The World – Sailing Niue (Ep. 70)
Sailing Machete

Found the CLEAREST Water In The World – Sailing Niue (Ep. 70)

The week our family is exploring and LOVING Niue! We see it all - caves, chasms, and cliffs! And quite a few whale sightings, more than we have seen anywhere else. We also get to swim in some of the clearest water in the world! It's so beautiful! Dani...
Family, Fishing, & Sailing the Pacific – 1000 mile journey to an island we’ve NEVER heard of (69)
Sailing Machete

Family, Fishing, & Sailing the Pacific – 1000 mile journey to an island we’ve NEVER heard of (69)

Our family of six lives on a sailboat and this week it's time for us to leave French Polynesia because our visas are running out. We do a final hike up to the World War II cannons and check out of Bora Bora. We raise the sails and start our 1000 nm journe...
Sailing Off-Grid in One of the World’s Last Untouched Paradises | Sailing Sitka Ep 164
Sailing Sitka

Sailing Off-Grid in One of the World’s Last Untouched Paradises | Sailing Sitka Ep 164

In this episode, Jay and Kenna welcome aboard their friends from Canada and give them the full tropical, sailing experience by island hopping and cruising through the San Blas islands. We are sailing off-grid between sand spit islands in search for adventu...
The MOST Beautiful ISLANDS We’ve Ever Sailed- EPIC Family REUNION Sailing FRENCH POLYNESIA (68)
Sailing Machete

The MOST Beautiful ISLANDS We’ve Ever Sailed- EPIC Family REUNION Sailing FRENCH POLYNESIA (68)

This week we are in vacation mode making our way through the Society Islands of French Polynesia. Daniel's parents are staying on board and we are truly living our best life. We island hop from Moorea all the way to Bora Bora before Daniel's parents have...
San Blas at Last: A Sailors Dream Years in the Making | Sailing Sitka Ep 163
Sailing Sitka

San Blas at Last: A Sailors Dream Years in the Making | Sailing Sitka Ep 163

Jay and Kenna depart from Shelter Bay marina after a week straight of boat work and diagnosing problems. Finally, after stopping in Linton bay for one night, they sail to the desolate and world renowned San Blas islands. A dream come true. They've worked h...
TERROR in TAHITI – BOAT DRAGS through CROWDED ANCHORAGE – FAMILY SAILING AROUND THE WORLD (EP. 67)
Sailing Machete

TERROR in TAHITI – BOAT DRAGS through CROWDED ANCHORAGE – FAMILY SAILING AROUND THE WORLD (EP. 67)

We are in beautiful Tahiti prepping for Daniel's parents coming to visit. We move to the airport anchorage and visit Papeete. We find a thimble for Jessa's collection, boat parts, provisions and see the closing parade for the Olympics. We finally get th...
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