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We Didn’t Know If We’d Ever Sail Again
Finding Our Isla Sailing

We Didn’t Know If We’d Ever Sail Again

After our first year of sailing the Caribbean as a family, we sailed our Lagoon 450 south to Grenada to haul her out for hurricane season. But as we prepared to leave our floating home behind, we honestly didn’t know if we’d ever come back. Our final sail takes us from Martinique past the incredibl...
Eastern Caribbean Was NOT What We Expected
Finding Our Isla Sailing

Eastern Caribbean Was NOT What We Expected

This was NOT the Caribbean we expected. Sailing south through the Eastern Caribbean brought us to Guadeloupe—and what we found completely surprised us. After leaving St. Kitts and Nevis and making a quick stop in Montserrat, we sailed Isla into Deshaies, Guadeloupe, ready to get off the boat and e...
We Made an Offer on This HUGE Catamaran | Sailing Sunday Vlog 320
Sailing Sunday

We Made an Offer on This HUGE Catamaran | Sailing Sunday Vlog 320

We just sailed four days to reach this huge catamaran in search of our new floating home! We had previously put an offer in to buy this boat, sight unseen and only now are we discovering what we may have agreed to buy… Once the survey is complete, we continue our journey delivering our old boat wit...
New episode is up on our channel! ⛵️ #sailing #sailingadventures  #funny
Sailing Banana Pancakes

New episode is up on our channel! ⛵️ #sailing #sailingadventures #funny

One of the questions we get all the time: where do you put all your food?! A little look inside our galley, how we organize food, and where we manage to fit everything when your kitchen also has to survive life at sea.
The Greatest Gift My Parents Gave Us Wasn’t a Thing
Finding Our Isla Sailing

The Greatest Gift My Parents Gave Us Wasn’t a Thing

Sometimes the greatest gifts aren't things—they're the lessons and memories that stay with you forever. ❤️ This week aboard Isla, Nana and Gogo join our family to celebrate my 40th birthday, and what started as a family visit became one of our favorite weeks of boat life. We waste no tim...
We Needed to Leave… But the Weather Had Other Plans
Sailing Big Lost

We Needed to Leave… But the Weather Had Other Plans

We needed to get Big Lost to Tahiti. After dealing with alternator problems off and on since Saint Martin, there’s an alternator specialist in Tahiti who can finally help us figure out what’s going on. But sometimes the smartest decision you can make while cruising is deciding not to go. With 25–3...
Our Family Sailing Adventure Wasn’t Supposed to End Like This
The Cruising Kiwis

Our Family Sailing Adventure Wasn’t Supposed to End Like This

Family Sailing Adventure Wasn't Supposed To End Like This After safely sailing our damaged catamaran south from Antigua to Guadeloupe, we make one final stop in the breathtaking archipelago of Les Saintes, home to one of the Caribbean's most beautiful natural harbours and the best baguett...
We Came for Paradise    We Found Something Better
Sailing Big Lost

We Came for Paradise We Found Something Better

We crossed an ocean chasing paradise. What we found was something even more valuable. For months, our family had been working toward this moment. Crossing the Pacific meant weather windows, long passages, constant planning, and the relentless pursuit of the next destination. Every mile brought us ...
We Thought Success Looked Like This    We Were Wrong
Sailing Big Lost

We Thought Success Looked Like This We Were Wrong

We crossed an ocean dreaming about places like Fakarava. World-famous dives, crystal-clear lagoons, black pearls, and remote islands were everything we had imagined. But somewhere along the way, we realized this journey was changing more than our location. It was quietly changing the way we measured...
Our First Overnight Sail as a Family
Finding Our Isla Sailing

Our First Overnight Sail as a Family

Our first overnight sailing passage took us from St. Martin to the U.S. Virgin Islands aboard our Lagoon 450 catamaran—and honestly, it wasn't what we expected. As a family of six living aboard full-time, sailing through the night with our kids was one of the biggest milestones of our journey....
This Isn’t How We Imagined Starting Our Next Adventure | VLOG 313
Sailing Sunday

This Isn’t How We Imagined Starting Our Next Adventure | VLOG 313

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Life In the Tuamotus Isn’t As Easy As It Looks
Sailing Big Lost

Life In the Tuamotus Isn’t As Easy As It Looks

The Tuamotus are some of the most beautiful islands we've ever visited—but living this far from everything comes with challenges most people never see. In this episode, we explore life in the remote atolls of French Polynesia. From provisioning and planning an overnight passage, difficult ancho...
This Is Why We Crossed The Pacific
Sailing Big Lost

This Is Why We Crossed The Pacific

After crossing the Pacific Ocean and spending weeks in the Marquesas, we finally arrived at one of the places we've dreamed about for years: the Tuamotus. In this episode, we leave Nuku Hiva behind and make the 500 nautical mile passage to Raroia Atoll. After carefully timing our arrival throu...
SAYING GOODBYE – Sailing the Caribbean
The Cruising Kiwis

SAYING GOODBYE – Sailing the Caribbean

SAYING GOODBYE - Sailing the Caribbean Sooner or later, every voyage reaches it's destination, and this week is all about goodbyes. While I farewell my beautiful brother Angus, Rob, the boys and our patron Diane continue sailing south through the Caribbean Leeward Islands, Making their way fr...
What a Normal Week Looks Like Living on a Sailboat in the Bahamas | VLOG 310
Sailing Sunday

What a Normal Week Looks Like Living on a Sailboat in the Bahamas | VLOG 310

This week we're sharing our life living on a sailboat in the Bahamas! We're enjoying beach days with the family and Jackson our dog, celebrating a beautiful wedding with our friends, spotting dolphins and sharing another week of life aboard our sailboat. Thanks for coming along for the adv...
Guess How Much We Spent On Our Catamaran!
Finding Our Isla Sailing

Guess How Much We Spent On Our Catamaran!

After weeks of battling Christmas winds, rough anchorages, and learning how to sail our Lagoon 450, we finally arrived in Saint Martin — the cruiser "Promised Land." And then we spent $12,870.66. 😳 In this episode, we're transforming Isla from a bare-bones boat into a true home for ...
Life After Landfall | Exploring the Marquesas Following Our Pacific Crossing
Sailing Big Lost

Life After Landfall | Exploring the Marquesas Following Our Pacific Crossing

After crossing more than 3,000 miles of Pacific Ocean, we finally had a chance to slow down and enjoy life in the Marquesas Islands. But life after landfall isn't just tropical anchorages and waterfalls. There were still boat projects to finish, new places to explore, and old friends to reunite...
I was Fine…till I Wasn’t!! Tough times Sailing the Caribbean
The Cruising Kiwis

I was Fine…till I Wasn’t!! Tough times Sailing the Caribbean

I Was Fine... Till I Wasn't - Sailing the Caribbean Welcome back aboard for another Caribbean sailing adventure. This week our patrons our patrons Greg and Gideon experience their very first offshore sailing passage, on our live aboard catamaran, departing Saint Martin for Saint Barts. Its a...
Eventually, Life in the Pacific Felt Normal
Sailing Big Lost

Eventually, Life in the Pacific Felt Normal

Eventually, life in the Pacific started to feel normal. After more than a week at sea crossing the Pacific Ocean, the routines of offshore life slowly began to settle in. Night watches, sail changes, repairs, fishing, cooking, exhaustion, and family life all became part of our everyday rhythm somew...
We Left Everything Behind… Was It Worth It?
Sailing Big Lost

We Left Everything Behind… Was It Worth It?

We left everything behind to cross the Pacific Ocean with our kids. After weeks of waiting in Panama, we finally set sail — but the reality of life offshore hit fast. From losing wind and navigating shifting conditions, to gear failures and constant decision-making, this passage tested us in ways we...
We Questioned Everything… Was Boat Life a Mistake?
Sailing Holly Blue

We Questioned Everything… Was Boat Life a Mistake?

We’ve been living this life for 7 years now… Sailing, travelling, exploring — it looks like a dream. But behind the scenes, there are parts no one really talks about. In this episode, we open up about one of the hardest challenges we’ve faced as a family — something that made us stop and question ev...
We Finally Made it the San Blas “Swimming Pool”
Sailing Big Lost

We Finally Made it the San Blas “Swimming Pool”

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. In this episode aboard Sailing Big Lost, we finally trade the noseeums of Snug Harbor for sunshine, clear water, and one of the most iconic...
SOLO SAILING THE BRAZIL COAST
The Cruising Kiwis

SOLO SAILING THE BRAZIL COAST

SOLO SAILING THE BRAZIL COAST Welcome back aboard our floating home. After an unforgettable family reunion in Lucerne, Switzerland, where Finn and and Ben brought home silver for New Zealand at the rowing World Cup, Rob returns to Brazil for a solo sailing mission aboard our boat in the stunning m...
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...
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