How Did This Start?

The project started in 2004 when I was on a business trip from Massachusetts to Wisconsin. I had picked up Hal Roth’s book, ‘How to Sail Around the World’ and on the flight home, I penciled out a 5 year plan which would take us from non-sailors to blue water cruisers – and early retirement.

Step One: Learn to sail!

In the fall of 2004 we bought our first boat – a 30ft ‘S2′. A small cruising boat with limited amenities but good sailing characteristics – whatever that means! We hired a captain who gave us 5 half day lessons on our own boat – plus an additional lesson for my wife Laurie, who was being somewhat dragged along on this ride…

We sailed late on into the New England season – when there were few potential targets to hit – and we commissioned her early in 2005 so that again there would be limited scope for doing damage to other’s boats!

The summer of 2005 saw us gaining experience through daily mistakes made – fortunately none with disastrous consequences – and we sailed further and further afield as confidence grew, culminating in a 10 day holiday to Martha’s Vineyard which gave us a sense of cruising in a boat. When we arrived back to home port of Bristol, RI and my wife Laurie had secured us to our mooring, we settled in for a celebratory toast – and Laurie announced that if we’re going to do this more, we need a bigger boat! Music to any man’s ears! That was the last time we sailed the S2!

Step Two: Purchase the Boat!

With our extensive sailing experience(!), coupled with my extensive reading about all aspects of sailing and cruising, we moved forward to purchase our cruising boat – and selected a Crealock 37 – a real blue water boat. We sailed her for the few remaining weeks of the season to get a feel and then through the winter planned our first voyage – to Maine.

Best laid plans often don’t work out – which was the case for us as we headed off for Maine. We had planned to learn how to use the Monitor windvane that I’d installed over the winter as we sailed up to Maine, but with some boisterous weather all I managed to accomplish was to get myself very seasick! We ended up wimping out completely and sailing into Martha’s Vineyard with tail betwixt legs to lick our wounds.

Closer inspection of the Monitor’s instructions illuminated the fact that I had the vane mounted backwards – an easy fix and the following day in clamer waters, we learned how to use the vane as we sailed on to Nantucket. We did make it to Maine – but had to motor for 38 hours of the 45 hour passage so I’m not sure it counts…

We gained a real appreciation for the cruising lifestyle in that short vacation – and learned many more valuable sailing lessons to boot. Our return trip was most pleasant and we were able to sail nearly the whole way.

Step Three: Sell the House!

While we were up in Maine, our realtor managed to secure a buyer for our house, putting into motion our plan to move aboard our boat and sail across the Atlantic to tour around the Med for a couple of years. We both quit our jobs, giving our respective bosses plenty of notice – fortunate since the buyers ended up backing out of the deal. A few days later the real estate market in the US collapsed! We were both fortunate that our bosses both gave us back our jobs!

The following year – our third full season of sailing saw us sail to Bermuda and back. This gave us a real insight into passage planning and managing life in close quarters. It highlighted some deficiencies in the boat too – providing some much needed winter projects for me for the following off season! It also provided some confidence that yes, we can do this – we can plan our life around getting out of the rat race and taking a leisurely sail around the world…

With the US housing market tanking, our high ideas were taking a bit of a beating – especially when we decided that we needed to move to a bigger boat that would allow us to live aboard while still working – to build the kitty into a treasure trove from which we could launch our early retirement. In the early Spring of 2011, we closed on our Outbound 44 and our maiden voyage with her was a 900mile passage from St. Augustine, FL to Rhode Island. The Outbound is a very different kettle of fish to the Crealock, which was a small 37footer – this boat is a luxury yacht in comparison – and a speed merchant to boot!

By 2012, my five year plan was now solidly into its seventh year – but finally we managed to unload the house at the bottom of the market in late 2012.

With daughter Abigail graduating from University on May 31st, our plan is to allow the celebratory hangover clear and then set sail for the Azores, the first step into our new life.

Boston Flores

One thought on “How Did This Start?

  1. Andy Woodward

    Hi, we met at Little Jost Van Dyke. Last week, we are from Kansas, I still sail an S2 30. here. We were on a 48ft catamaran I had chartered from the moorings. I will look forward to hearing more of your adventures and seeing your fun pics.
    Smiles, and good sailing. Andy Woodward.


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