How often are you able to take six weeks and travel somewhere you love without rules, requirements or rain?  What if you could live and sail on a 42 foot yacht in the Caribbean visiting several island nations, at your own speed, hiking and snorkeling whenever you choose, and have a shark try to bite your butt? 

Well, I just came back from completing all of these things and more, the Caribbean Walkabout, (to find out what it’s all about), was everything to be expected and much, much more.  Having made numerous one to two week sailing vacation trips to paradise over the years, this was my first opportunity to actually live the life of a sailing live-aboard since I was a full time charter captain and crew in 1979-1981.  For forty days and forty nights aboard what I called “Mark’s Ark”, me and various friends sailed to and explored just about every island from Anguilla to Dominica from May 26 to July 5, 2006.  Most amazingly, after 600 miles, we lived to tell about it! 

What follows is a five segment description full of lies and tall tales of that trip.  This is written to provide one captain’s view of how to most comfortably cruise this area at this time of year with plenty of tips and updates of the areas.  The segments roughly follow time frames that correspond to major crew changes.  Any one who has been or intends to sail the Caribbean will benefit and relate to the planning, adventure and cruising details provided.  Photos are included but you really must go see these places for yourself, and live the life of a live-aboard.   

{mosimage}I have always maintained that chartering and sailing in the Caribbean is best enjoyed during the shoulder seasons, from October 20 to December 1 and especially from May 1 to July 1.  The Caribbean winter season, while providing a welcome escape from the cold and hassles of northern living, also has the most risk and expense.  You pay the highest charter and air rates, with the lowest chances of availability, during the time of strongest, sometimes dangerous winds, to harbors that are often so full you must hurry to another less desirable spot at night, and most importantly, you have the least amount of privacy and security. 

Air and yacht savings often topping 30% with probably 75% fewer boats in winds traditionally a steady 12 to 18 knots and harbors where you are often the only visitor await the patient cruiser in late fall and early summer.  Acknowledging these facts, my search for true inner self and life’s great meanings had to occur in the early summer.  How could I meditate, (with a cold rum and ginger of course), while anchor dragging bare boats sporting their “Polish racing stripes” (fenders still attached to lifelines) slipped by? 

Many of us have often wondered if we would truly enjoy and thrive while boat camping for extended periods of time.  It’s easy to read books and plan trips and dream of months in paradise but will you get bored, lost, tired or just plain frustrated if you actually try it?  Living without daily luxuries like computers, TV, washers, freezers, ice and hot water might be acceptable but can you stand the cramped quarters, two hours per day of the motor running for the frig and hot muggy below decks?  Well, I had to find out.