Watch Sailing & Boating Adventures Around the World – Page 4 of 5

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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One Perfect Week in Florida (Before We Say Goodbye…) | SAILING SUNDAY Vlog: 298
Sailing Sunday

One Perfect Week in Florida (Before We Say Goodbye…) | SAILING SUNDAY Vlog: 298

We spent a full week soaking up Florida with friends (feat. Leading the Escapade): sunshine pontoon days, gym laughs, baby & dog living their best life and golden ICW sunsets on the hook. It’s our last move north before the next chapter, we talk honestly about selling the boat and what’s next f...
Bonaire to Cartagena! Our Caribbean Passage
Sailing Big Lost

Bonaire to Cartagena! Our Caribbean Passage

We’re a family sailing full-time, exploring the Caribbean and Central America aboard our sailing catamaran Big Lost. New episodes every Tuesday at 10:30 AM ET. After three incredible weeks in Bonaire, it’s time to say goodbye to this beautiful island—famous for its crystal-clear waters and vibrant ...
Our Baby’s First Emergency Visit After Sailing Back from the Bahamas | Sailing Sunday Vlog: 297
Sailing Sunday

Our Baby’s First Emergency Visit After Sailing Back from the Bahamas | Sailing Sunday Vlog: 297

We've crossed oceans...... Survived storms…... Robbed in Africa..... but nothing’s scarier than U.S. medical bills 😬 This week we sailed from the Bahamas back to the USA but this “routine crossing” turned as we arrived in USA. Between running from stormy tropical weather in the middle of hurri...
Путешествие в подарок! 🎁 Первая остановка — пещера Постойнска Яма в Словении 🌍
АванТуристи Малови

Путешествие в подарок! 🎁 Первая остановка — пещера Постойнска Яма в Словении 🌍

Начинаем новую серию видео о нашем необычном путешествии в честь дня рождения Натусли! 🎉 Первая остановка оказалась совершенно случайной, но именно такие моменты делают дорогу незабываемой. Мы посетили самую большую карстовую пещеру Европы — Постойнска Яма в Словении. Этот природный шедевр с подземн...
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 islands. Thank you for watching ...
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 the generator still needing parts and ...
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 trouble pulling up our anchor. We make it to ...
Our First BIG Crossing Back — Sailing USA to the Bahamas!| VLOG 288 0
Sailing Sunday

Our First BIG Crossing Back — Sailing USA to the Bahamas!| VLOG 288 0

This week’s episode is a big one — our first ocean crossing since moving back aboard, and Oakley’s very first offshore sail! We teamed up with friends for the crossing, forming a little convoy as we made the 12-hour run across the Gulf Stream and onto the Bahamas Banks. It was an early start, calm ...
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't know how much we appreciate it! To G...
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 piece of equipment! Thank you for watc...
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 fuel. The weather isn't doing us an...
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 making the right decision. Hopefully w...
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 #familyvlog #boatlife #familytravel...
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 different anchorages of Tonga with 5 or 6 ot...
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! Daniel and the boys also swim in the creepi...
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 journey across the Pacific Ocean. We skip ov...
Are We Really Doing A Reality TV Show? Episode 46
Sailing Banana Pancakes

Are We Really Doing A Reality TV Show? Episode 46

In this episode of Sailing Banana Pancakes, we wrap up our unforgettable time in Martinique, start major sailboat repairs, and head off on an epic sail toward Grenada—complete with a dolphin encounter that blew our minds! After spending weeks sailing through the Caribbean, Martinique gave us a chan...
St Lucia Adventure: Exploring the Majestic Pitons! Episode 45
Sailing Banana Pancakes

St Lucia Adventure: Exploring the Majestic Pitons! Episode 45

Sailing St. Lucia After the Storm | Anniversary, Chocolate & Mud Baths! | Ep. 45| Banana Pancakes We’re back with another unforgettable episode of our sailing adventure—and this one’s packed with tropical storms, wedding anniversaries, chocolate EVERYTHING, volcanic mud baths, and a wild ride t...
Rescued At Sea: Boat Adrift in Open Ocean. Episode 43
Sailing Banana Pancakes

Rescued At Sea: Boat Adrift in Open Ocean. Episode 43

From Chaos to Kindness | Sailing from Dominica to Martinique (ft. Engine Trouble, Mahi & a Rescue!) We left Dominica with over 20 knots of wind and immediately broke a cleat holding the Genoa—then the Genoa took out our light. Welcome to offshore sailing! Rough seas, tangled lines, and flying f...
Selling Our Boat: Survey Results & Repairs 🛠️
Sailing Big Lost

Selling Our Boat: Survey Results & Repairs 🛠️

✨Selling our boat comes with its challenges! In this video, we’re sharing the results of the buyer’s survey, the necessary repairs, and the negotiations we had to make. From unexpected fixes to finalizing the deal, this is a behind-the-scenes look at what it takes to sell a boat.⛵️ ⚓ Want to learn ...
A Baby, A Dog and Too Many Jobs! | Vlog 272
Sailing Sunday

A Baby, A Dog and Too Many Jobs! | Vlog 272

Our new family adventure begins! After years of sailing around the world on our boat, we’re now hitting the road in our newly renovated 5th wheel RV to get back to the boat. With a newborn baby, our 100lb dog and a mountain of tasks, the chaos is real as we prepare for an epic road trip across Ameri...
Epic Caribbean Adventure: Sailing to St. Kitts & Monserrat+Underwear Tuna Fishing in Big Seas! Ep.33
Sailing Banana Pancakes

Epic Caribbean Adventure: Sailing to St. Kitts & Monserrat+Underwear Tuna Fishing in Big Seas! Ep.33

Join us on an unforgettable adventure as we explore the lush beauty of St. Kitts, where monkeys roam free and history comes alive at an old sugar mill. Renting a car, we journey across the island, soaking in its vibrant culture and scenery. Then, we set sail for the volcanic island of Montserrat, b...
Sleeping in a Jungle Treehouse: The Ultimate Adventure! Episode 21
Sailing Banana Pancakes

Sleeping in a Jungle Treehouse: The Ultimate Adventure! Episode 21

“Boat Engine Fails, Jungle Adventures, and a Surf Crush? Dominican Republic Chaos!” Description Rewrite: In this episode, everything goes wrong—and then totally right! 🚤 Our sailboat engine overheats, the anchor won’t drop, and we’re forced to sail back to the marina. But the adventure doesn’t stop...
Sailing from BVI to Guatemala (FULL DOCUMENTARY)
Sailing Big Lost

Sailing from BVI to Guatemala (FULL DOCUMENTARY)

Join us on this thrilling ocean crossing as we embark on our 1st Passage from the British Virgin Islands to Guatemala. Experience the beauty of tropical sailing, the serenity of blue waters, and the adventurous boating lifestyle as we navigate through this incredible journey. Get a glimpse into the ...
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