As these words are written, we are securely anchored in St. Maarten’s Simpson Bay Lagoon heeling 20 degrees to starboard from the latest 30-knot gust of wind that is pummeling our 38 foot sailing vessel “Aspen”.  We have seen 35 knots on the wind instruments so far today and even more wind is in the forecast.  These conditions are fairly normal for a winter cruising season in the Eastern Caribbean! 

What’s that?  No one has mentioned these conditions in any of the articles you have seen in Cruising World or Latitudes & Attitudes magazines?  None of the Annapolis Boat Show speakers portrayed the Eastern Caribbean as a true test of all the sailing skills you need to possess in order to safely survive down here?  That is exactly the reason we have written this Handbook for Caribbean Cruising!  The Eastern Caribbean is the ultimate test of your sailing expertise, onboard system knowledge and boat handling skills.  This is the “Big Time” as they say.

Prepare yourself and you will have a safe and enjoyable sailing adventure in the Eastern Caribbean.  If you fail to prepare yourself mentally and physically for your adventure, you will find yourself back in Chicken Harbor before the sun crosses the equator and heads north.  This guide will help prepare you for your sailing adventure by providing essential knowledge for your future down here.  This guide is not a substitute for the five standard cruising guides to the Eastern Caribbean (see below).  Instead this cruiser’s guide is an honest portrayal of what you can expect when sailing in the Eastern Caribbean.

What you expect

Nirvana, paradise, the ultimate cruising ground, heaven on Earth, a garden of Eden for sailors, the pinnacle of cruising!  These terms and many more have been used to describe the Caribbean as a destination for sailors throughout modern and probably ancient history.  Simply puruse any sailing magazine at your favorite bookstore and you will hear superlatives describing sailing in the Caribbean – that island-strewn sea of little latitudes south and east of Florida.

The rock-steady trade winds gently caress your sails as your sailing vessel plies the turquoise Caribbean waters toward a calm, peaceful and protected anchorage in the lee of a lush green island in the sun. It simply could not get any better than this, or so it seems.  However, what is the reality of sailing in the Caribbean?  Can we rely on the latest cruising guides, glossy magazine articles, SSCA articles and tales from previous visitors to these islands in the sun?  What can we expect when we take our journey of a lifetime to these islands? 

As we stated above, this guide is written to supplement the five good cruising guides that cover this area:

Chris Doyle’s Leeward Cruising Guide and Windward Cruising Guide

Donald Street’s timeless cruising guides to the Caribbean

Scott’s Cruising Guide to the US and British Virgin Islands

Passages South by Bruce Van Sant

Pavlidis’s Cruising Guides

While these five authors give you detailed information on each specific island in the Eastern Caribbean, we felt that they all lacked the honesty and clarity necessary to assist a cruiser on their journey among the islands.

You will find that there are many other so-called cruising guides to the Caribbean but none can compare with these five guides and it is best to save your money for buying sundowners in the anchorages of the Caribbean.


Yes, you are about to become a cruiser.  The definition of a cruiser is one who lives aboard and uses their own sailing vessel to seek out adventure and fun among the islands in the sun.  If you sail to the Caribbean, this defines you.  You are not a charterer, or a vagabound or a Mega Yacht owner or a yachtie.  You are a cruiser. 

The cruising community has undergone tremendous change in the last 20 years.  Today a cruiser is more likely to be retired from the working world, rather than on a short 2-year sabbatical.  The age group for cruisers has also risen steadily in that today we see more people in their 60’s and 70’s out on the sea.  Sure, there are still the young retired couples or families who happened to get lucky during one of the tech booms or real estate market swings but the older cruisers outnumber them.  There are also the younger group who still try to work their way through the cruising season but again, these people are rare.

A cruiser represents a new retirement option for people in their 60’s.  No longer is it necessary to pack up all your belongings and head for Florida, move into an assisted living community and wait for the end.  Today people are more active and lead healthier lives.  This change in lifestyle has led to the increase in age for a typical cruiser.  Yet the cruising lifestyle is very physical and requires a tremendous amount of work in order for a cruiser to be successful and safe in the Caribbean.  Power winches, anchor windlasses, GPS, and even contact with the world via cell phones has provided the opportunity for an older generation of cruisers to enjoy the Caribbean. 

Twenty years ago it was uncommon for people to sail for 6 months, leave their boat somewhere relatively safe in the Eastern Caribbean and fly back to their own country to live for 6 months.  Today that is commonplace.  The sailing community is full of commuters.  We can count on 1 hand the number of people who cruise full time that we know.  A 6-month break is now expected by cruising sailors.  The requirements to be a Seven Seas Cruising Association (SSCA) commodore include living on one’s boat full time.  However, more and more commodores do not really qualify to fly the commodore flag because they no longer live full time on their vessel.  These commodores may not have a shore side home but many have second homes on land and simply call their boat their primary home for the purpose of remaining a commodore with the SSCA.  This is simply the life of a cruiser in the 21st century.

Be Honest with Yourself

However, the cruising way of life is not for everyone by any stretch of the imagination.  Many new cruisers have forgotten that the sea remains the same.  The sea is unforgiving and can be extremely hostile to those unprepared.  15-foot seas and 25 knots of wind create dangerous situations for most sailors, including those physically unprepared or unable to handle these conditions.  An honest evaluation of your physical strengths and weaknesses must be included in any decision to retire to the sea or to sail away for an extended length of time.

Handbook for Caribbean Cruising

Volume 1: Eastern Caribbean