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How Did We Get Here?

Our plan to sail away with our kids and travel has become all consuming.

So much so, that it's easy to forget that this wasn't always the plan.

In fact, a few short years ago we didn't even have plans to own a boat.

Neither of us had ever sailed.

Travel had become one of those distant memories of a life pre-kids.

It felt incredibly far away and unattainable.

So, how did we get here?

Let's rewind.

Prior to the birth of our first child, travel had been a huge part of my life. Not to say I traveled extensively- but it was important enough to me that I would happily live off PBJ's- if it meant I could scrape together enough pennies for a trip to Europe or elsewhere.

Right before we found out we were having our eldest, we had just come back from a trip to Spain and Morocco.

We were excitedly planning our next trip- Machu Picchu, Lake Titicaca, and the Galapagos Islands. Even after having our first baby, we still planned on this trip.

Then baby number two came.

Then baby number three arrived.

Travel- rather suddenly seemed like an insurmountable mountain.

Then, one day Steve said, "why don't we live on a sailboat and circumnavigate?"

Y'all, I'm pretty sure I thought he'd lost his mind at that point.

The kids had done him in.

Okay, so the idea didn't really appear completely out of thin air, although it certainly seemed that way to me at the time.

Looking back I realize that it slowly built up to the idea of being full time liveaboards, and we rather quickly learned that the idea of an actual circumnavigation was a pretty lofty goal. Would we love to actually circumnavigate?


But- baby steps.

Back to our slow metamorphosis of a long term, early retirement, travel full time, with our circus full of children plan.

A few years ago we lived full time on Long Island, and we had bought property in upstate NY, not too far from Lake Ontario. One summer while renting a speedboat with Steve's family on Lake George, Steve said wouldn't it be cool to have a boat? Maybe we could even bring it back and forth from Long Island to our land upstate and use it on the Great Lakes. And I said, sure! But I also, didn't give it much thought. At the time it seemed like one of those random "wouldn't it be nice?" moments, that you never talk about again.

Some time shortly after that, we went to our first boat show, which consisted almost entirely of speedboats. At this point, the idea of a boat still wasn't really on my radar.

I'm not sure when Steve first came across information about the Great Loop. He was probably researching how possible it was to get a boat from Long Island to Lake Ontario. He came across information about the Erie Canal and learned that it was just a tiny segment of something called the Great Loop, and well- that's when the plan really began to take shape.

For those that don't know- the Great Loop is a loop of waterways that takes you from the Atlantic Ocean, into the Hudson River, and through the Erie Canal and the Great Lakes during the summer months, then through Chicago and down the Mississippi River and some of it's branches during the fall, and into the Gulf of Mexico at the end of hurricane season. Great Loopers will typically spend the winter months around Florida or the Bahamas, and then start working their way north up the east coast of Florida in the spring. You usually stay inside the ICW (Intracoastal Waterway) as far north as you can and make your way all the way back up to NY, thus completing your "loop". I should note that theoretically, you can begin and end your loop anywhere. We would just obviously be beginning in NY.

When we first learned about the Great Loop, we thought that maybe when we eventually retired we could do the Great Loop. We hoped to have a home in Florida by then (where my family is from), and we could spend summers in NY and winters in Florida. We thought we could offset our costs by renting out our homes when we weren't staying in them. During this same time period we realized that going by sailboat would save significantly in terms of fuel costs etc, and we began to transition to the idea of having a sailboat instead of a motorboat. It was a good plan, except it was an "in 20 years plan".

It was inconceivable to us that we could do something like this with children.

What about school?

How could we afford it?

What about work?

This is where pure burn out from the constant NYC/suburban rat race comes in.

We had 3 kids (soon to be 4, although we didn't know it yet). I stayed home with them while Steve commuted into Manhattan every day to work. We lived comfortably, but not extravagantly, and somehow managed to spend just about every penny he brought in. Looking back I honestly have no idea where all that money went, because we didn't do anything lavish, but there was never much in our savings accounts.

We were stressed and tired all the time.

We both felt that there had to be a better way.

A more fulfilling way.

This was about the time that Steve came to me with his circumnavigation idea. He had stumbled across the blog of another family that had left approximately 10 years prior and they were still out there living on their boat. Their boat name is Totem, and I'm linking them here because reading their blogs was instrumental in inspiring us. Looking back, I realize that reading about their experience was what made me understand that this was a real possibility for us.

My response at the time that he broached the idea though- was knee jerk.

Spend 3 weeks crossing the Pacific Ocean with a bunch of kids?

He was nuts.


I didn't know the first thing about homeschooling, and I felt grossly underprepared for such an undertaking.

What about friends and socialization for the kids?

What about our families?

How on earth could we possibly afford to do such a thing?

But then, other ideas began to take root.

Imagine the places we could see by traveling by boat. The island nations that we would probably never be able to visit in any other way.

Imagine the self sufficiency we would learn and teach our children.

Imagine living in a greener, more environmentally friendly way. Relying on solar and wind power.

Imagine the cultures that we would get to experience as a family.

Imagine the opportunities for learning by immersing ourselves in nature and other people's way of life.


We began to read other sailor's blogs and watch vlogs.

While there isn't a huge community of people doing this- they are out there.

Cruising different parts of the world with their children. Going out of their way to meet up so that their kids have the opportunity to play with and socialize with other kids.

For some families, it's a sabbatical. A few years off to travel, and then returning to work.

For others, it's an alternative lifestyle and they've figured out ways to financially stay afloat to continue traveling.

It's not a constant vacation, if that's what you're thinking at this point.

There's probably a misconception that anyone that can afford to live on a yacht and travel full time is incredibly wealthy, but this actually couldn't be further from the truth. Of course this is the case for some people, but it certainly doesn't apply to us, or most other sailing families.

While these boats are technically considered yachts, they are truly a tiny and minimalistic way of living.

Most families traveling the world this way are living on shoestring budgets.

They are still working in some way to bring in some form of income.

They're still schooling their children.

They're repairing every little bit they can on their boat themselves, because if they pay someone else to do it, it eats into their ability to continue traveling.

They are essentially, bringing their home with them everywhere they go.

In spite of all the challenges- suddenly, this became what we were going to do.

Could we save enough to leave in 10 years instead of 20 years?

Retire early?

So we would be younger, fitter, and more physically able to live this lifestyle?

Could we do this grand plan even sooner than that?

Could we leave in 5 years?

Yes, we could.

We didn't know how yet, but somehow, we were going to make it happen.

Then we found out we were pregnant.

Baby number 4 was on her way, but this wasn't going to stop us.

Maybe we would need a bigger boat.

Maybe we would give ourselves an extra year to save money.

Maybe we would give her an extra year so that she could go to formal school for kindergarten.

But we were still going.

So here we are, less than 4 years left before we make our grand escape.

What have we accomplished so far?

Well, little Emmeline (baby number 4) just turned 2 years old!

We've officially learned to sail.

We took our first certification class.

We've been logging as many hours as we possibly can sailing, to gain real experience.

We took our first boating safety class.

We've slashed our living budget to make room for saving, and we're actually seeing that measly little savings account grow.

We've bought our first sailboat to gain experience. A 30+ year old Catalina 30 that we're taking out on the Sound at every opportunity.

We've devoured books, blogs and vlogs.

We've created a plan for what we hope to accomplish in the next year in terms of furthering our education and experience and in terms of saving.

Are we ready?

Not even close, although the desire to set sail and start living this life NOW is huge.

Patience has never been my strong suit, haha.

I'm happy with what we've accomplished so far though, and I feel that we're on the right track.

We'll see what the next year brings!

Are you dreaming of making an escape?

What are you doing to make it real?

Have you already left?

What was the single most instrumental thing you did to prepare?

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