The Great Wander

One Family's Journey to a New Life

Where will you go?

Where will we go?

As we dare to dream and give voice to our visions, we get two big questions:

  1. Where are you going to go?
  2. How are you paying for this?

I clearly remember the excitement and awe I felt when I graduated from high school.  I was inspired to live big…   


Today is your day.

You’re off to Great Places!

You’re off and away!”

Dr. Seuss, Oh the Places You’ll Go

So, where are we going to go?

As we’ve done research on the cruising life, one thing we’ve learned is that insurance dictates just about everything related to where you go.  Big surprise, right!  Yeah, not really a surprise.  Boating insurance can actually be challenging to get.  With the increase in the number and severity of tropical storms each year, insurance companies are increasingly reluctant to provide insurance, even for seasoned sailors.  So, the reality is, much of our destinations will be driven by what our insurance company will allow. 

But back to the dream, here’s what we are thinking we would like to do.

August to September seems to be prime time for buying a boat.  This matches well with ending a school year and transitioning our kids to their next steps, which is a prime consideration for this drastic change in our lives.  So, we’ll most likely be making our purchase in late summer.  That’s smack dab in the middle of hurricane season.  Insurance companies identify a “Hurricane Box” and require you to be out of the box during hurricane season.  Once we purchase our home on water, we will likely need to get out of the box as quickly as possible to comply with insurance requirements.  Here’s a map of the “Hurricane Box”. 

When we look at this map, we see sailing north as our best option for several reasons.  One, it keeps us in US waters, which means we are only learning to navigate a boat; the language, currency, food, and culture is familiar to us.  Second, it takes a lot less time to sail north out of the box than it is going south, getting us to safety and keeping us insured.  We’ve talked about is going as far north as we can after we buy the boat.  This will afford us time to learn more about sailing and begin to get our sea legs.  When the timing is right with the seasons we will head back south.  We envision exploring our way down the US coast aiming to reach warmer climates for the winter.

Seasoned sailors and those who have gone before us all say the Caribbean is a great place to really get your sea legs under you.  There’s island after island after island.  Which really translates to shorter passages as you are learning. It means we will have more opportunity to learn, more places to stop if we are tired, more anchorages, and more marinas if needed.  It will be a good place to be.  How long do we stay there?  We don’t really know at that point.  Where do go after we’ve ‘tired’ of the Caribbean?  The world is a big place!  We could go through the Panama Canal and then sail up to Alaska, we could go through the Canal and sail to the Galapagos, then to Easter Island, then to Fiji.  Of course, some of the unknown there is part of the point.  We want to see new and different places, and this is a way to do it.  Dr. Seuss said it well,

“You have brains in your head.

You have feet in your shoes.

You can steer yourself any direction you choose.

 You’re on your own.

And you know what you know. And YOU are the one who’ll decide where to go…”

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

About Me

An English diarist and naval administrator. I served as administrator of the Royal Navy and Member of Parliament. I had no maritime experience, but I rose to be the Chief Secretary to the Admiralty under both King Charles II and King James II through patronage, diligence, and my talent for administration.


%d bloggers like this: