The Sail Plan


We are a couple who have fallen in love with sailing. The wind and the water combine to a perfect cocktail to move these massive capable sailing boats across the seas! It’s magical.

Mike and I quit our jobs November 2017 after selling our house and many of our possessions of 20 + years. We now sail our 2005 Caliber 40 LRC in the Caribbean from December until June. This is our dream come true! We have come a long way from the winter months sitting by a fire when the wind was howling and temps below zero preparing for this , our new winter life.

We spent months reading all the Bluewater Sailing and Sailing magazine articles, Jimmy Cornell’s World Cruising Routes, Nicola Rodriguez, Sail Away, Bruce Van Sant’s  Gentleman’s Guide to Passages South, countless other publications, internet sites to educate ourselves in this planning stage. We went to the Chicago Sailboat Show and listened to the experts and experiences on the subjects of weather, managing electrical systems in a boat, anchoring, safety at sea…etc.

We initially became interested in just sailing the British Virgin Islands during the coldest part of Wisconsin’s winter, but this has morphed into a greater life plan.

So our first ocean crossing to the Bahamas was our shakedown cruise. And now that we travelled 2500 miles to Grenada in one season, we feel only a little experienced!

We feel it went well. We had a few issues come up and we were able to solve them or configure a workaround. We have some confidence now.

Every season our to do list seems to grow and change and we find that one task actually leads to 3 or 20 others to complete that task. The list includes:

  • Mapping our route. Which requires decisions on timing, crossings, and anchorages. This is a huge piece and it requires both of us to look at the various options and decide how long we think we need to spend in one location and how that will effect the overall progress to our final destination.
  • Gathering information on customs and immigration information for some 20 different islands. This can be done via internet or dozens of guide books which we have started collecting. A recent post by Cynical Sailor and His Salty Sidekick on keeping and saving books on board depicts the situation. Very funny , but very true reading. There is so much to learn from others…I presently have to learn to manage the information some how. I did start a computer file with downloads and links to important websites, but it is easy to get off-track and read for pure pleasure.
  • Safety equipment. This includes not only checking outdates on life jackets, fire extinguishers and flares, but also making sure our life raft is re-certified. (Which means taking the 100# beast off the boat and down the highway to a person with special skills to activate it, check the safety contents, inspect every inch of the raft to make sure there are no splitting seams and then repack and seal. While we hope this never , never has to be used it is what could save our lives. I digress…..Just finished reading Fastnet Force 10 by John Rousmaniere about the 1979 Fastnet sailboat race  from Isle of Wight on the southeast coast of England to Fastnet Rock off the Ireland coast where 300 yachts in a 600 mile race faced a terrible storm taking boats and lives with it. They discuss the value of a life raft, but also the most important issue of staying with the boat as long as it floats, it is the best chance for living.)
  • Creating our master provisions list (making sure that we have enough food and staples that we prefer/need/enjoy). Making a plan for where we will easily provision and find food and water most likely in places we will refuel.
  • Making arrangements for banking and billing while were gone.  #1 so that we can get to funds wherever we need them. #2 so that the recurring bills get paid.
  • Making certain we have repair parts for many different boat systems. Something always fails or breaks. Running a boat in the ocean is rough on the rigging and marine systems and when something breaks, especially if it is a vital piece of equipment.
  • Perfecting our communications  We need a way to effectively stay in touch with family, receive and manage mail, and most important receiving weather information.
  • Docking or Mooring Arrangements for where we will moor or leave the boat either in the Caribbean for the next season or in the states.

To each of these few items there are at least 7-10 further steps!

It is terribly easy to get caught up in doing so much research that we get bogged down and don’t get planning completed. There just comes the time to JUST DO IT!

Wait for the wind, loose the lines, and sail off!