How did we arrange our lives to live on a sailboat? The hard way. 

What we didn't know when we instituted our 5-year plan to go cruising is that we were on a collision course with history, about to run smack into an economic crisis that would rock the world and turn our plans into a tedious waiting game.

In July 2008 I started a hopeful blog about the process of leaving called ploddingTOparadise.blogspot.com. In retrospect, I should not have used the word 'plodding' but rather 'running full speed' or 'racing.' Perhaps that was my first lesson in moving at a sailor's pace.

The blog started with a very short TO DO list:

1. Sell the wine shop
2. Sell the house 
3. Sell the current boat
4. Buy our cruising boat.

How long could it take to do four things?

Following is our story told in a timeline with links to the blog posts written at the time. It was a very long journey to the water but well worth the trip.

MAY 2005 
Chip and Tammy begin their five-year plan to go cruising.
27th Opened wine shop
We opened Chip's Wine & Beer Market as the first step in our five-year plan to cruise. We knew that to finance a life afloat, we needed a nest egg. Our way to create one was to build and then sell a wine shop on the strength of Chip's 25 years in the wine business and our familiarity with the local market in North Carolina's Outer Banks.

From the day we opened, our business blossomed. We underestimated both how quickly the business would grow.

Accelerate our 5-year plan into a 4-year plan and sell everything in the fall of 2008.

We thought since the business was doing so well and our kids would be off at college, we would just turn the whole plan back by one year. Cruising a year sooner!

18th Plodding to Paradise, our first blog begins
Feeling a burst of excitement, naively believing that we were a few months from sailing away, I exuberantly started logging our progress. Hope and naivety spring eternal.
Started preparation to get house and business ready to sell

When our kids left for college, we asked them to leave empty rooms. They did, empty if not clean. The rest of the house was our responsibility. It's amazing how much stuff a family of four can accumulate, almost none of it applicable to life onboard. It was a grueling and maddening process to rid ourselves of a 4-bedroom house full of stuff. Sometimes it progressed forward, and other times seemed to roll back on top of me.

We used every method we could think of to dispose of our belongings: gifting to friends, a garage sale, another garage sale (followed by a trip to Goodwill), eBay, Craigslist and finally Tammy's Shopping Channel on Facebook.

September 2008 dawned all bright and happy. We had made amazing progress toward selling everything. We were upbeat, hopeful, sometimes nostalgic, but incredibly excited that in our most generous dreams, we would be on the water in less than a year.

And then...

15th Lehmann Brothers files for bankruptcy, BankofAmerica buys Merrill Lynch, Dramatic drop in global stock markets
16th AIG suffers liquidity crisis
17th Chip and Tammy list business with broker << LOOK AT THAT!

I can't say it any better than I did back then, Timing is Everything. I wrote that we would look back some day and laugh, "Remember the week we put our business and house on the market, and the entire economy went to hell? Ha ha ha." Well, I'm still not there yet. It was just unbelievable. 

17th Markets continue dramatic decline, Dow drops 446.92
25th Federal regulators seize Washington Mutual, largest bank failure in U.S. history
26th Chip and Tammy put their house on market << CAN YOU BELIEVE THIS???

29th House rejects bailout; Dow suffers greatest loss in history of index, -777.68
Car sales in September plummet 27%
284,000 jobs lost

Now whose idea was it to start a year early?


1st Senate approves revised $700B bailout bill
2nd Dow drops 348.22
3rd House approves $700B bailout
6th Dow drops below 10,000 for first time in four years, global markets plummet
6th Iceland passes emergency legislation to seize and regulate their banks
8th Global markets experience huge drop
8th Federal Reserve loans AIG $37.8 billion

We were in the midst of doing the hard work of liquidating our belongings while at the same time keeping the house immaculate -- just in case a stupid person thought they might buy a house while the economic foundation of the planet was disintegrating. The wine shop was taking as much time as we would let it. We were tired. In some ways, it's good we did not know that it would be two whole years before we left the dock.

We were running our wine shop and on top of that, planning Pig Stein, our second annual beer festival -- outdoors, and the weather was not working in our favor.

9th Dow hits 5-year low
10th Stock markets crash across Europe and Asia
10th Dow lost 697 points in first 5 minutes
10th Dow closes 40% down from its record high on October 9, 2007
13th Dow soars 936 points, largest one-day advance ever
15th Dow plunges 733 points
16th Dow falls 400 but rallies to close up 401
22nd Dow drops 514
24th Markets plummet after Alan Greenspan calls the crisis "a once-in-a-century credit tsunami."
25th PIG STEIN Beer & BBQ Festival sponsored by Chip's Wine & Beer Market and High Cotton BBQ

It rained. The festival was successful anyway. We were exhausted, and all we really wanted was to go sailing.

28th Stocks rise dramatically in anticipated of rate cuts by central banks, Dow +889
240,000 jobs lost
Consumer confidence
and ours hits all-time low

November dawned 100% gloomy. We were on the eve of a major presidential election with no incumbent, and the economic crisis was taking center stage.

GM sales drop 45%
4th Obama wins Presidential Election
6th Dow has biggest two-day percentage drop since 1987
7th Unemployment rises to 6.5% in October
13th Dow has erratic ups and downs ending with a 550 point gain
13th October numbers show foreclosures up 25%
18th CEOs of three automakers plead for assistance from Congress
18th National Assoc of Realtors report median home price down 9% from last year
19th We reduce the price of the house $10K
19th October housing starts a lowest level since 1959
20th Dow loses 445 points
533,000 jobs lost

We watched and waited and somehow, somehow stayed hopeful. In a world where everything is quantified, we had no way to measure how long we would have to wait. Everything became a sign that maybe, just maybe there was progress.

1st Dow drops 680
2nd Automakers report huge declines from 31-47%
4th November retails numbers released showing drops of 12-15%
11th Number of people filing for unemployment hits 26-year high
11th Bernard Madoff arrested and charged with running $50B Ponzi scheme
681,000 jobs lost

December was dreadful. Our TO DO list looked very similar to the way it did when we created it:

1. Sell the wine shop 
2. Sell the house 
3. Sell the current boat 
4. Buy our cruising boat.

What would 2009 bring? Could 2009 be the year we would go sailing? Keep reading.


  1. I literally guffawed when I saw the 'diagram' explaining how you transitioned from land to water, brilliant!

    I have been building an online library of marina maps and slip diagrams to help boaters when they are coming into an unfamiliar marina (http://themarinersguide.blogspot.com/p/marina-map.html). If you have gathered any marina maps on your journey's I would love to add them to the site. If you'd like to contribute a diagram or map you could email me directly at Dale@TheMarinersGuide.com or you could send me a link. Much thanks and keep sailing!

  2. WOW! Great summary...I recall those days very well, and you really nail it down...and put your situation in excellent perspective for the reader...

    1. Thanks for reading, Pawblo! Tell us your story...