Handbook for Caribbean Cruising

Volume 1: Eastern Caribbean



The immediate response from all your friends and relatives when you announce your decision to go sailing in the Caribbean is something like, ‘where can we meet you?’

It is imperative that you explain that they will come to your boat – you will not bring your boat to them.  This means that once you arrive on a new island you will then advise them of your location and stay on the island to meet them.  You should under no circumstances agree to meet them on an island where you are not currently located.  The reason for this is that, in most cases, you will not be able to meet your friends because you have not yet arrived there for one reason or another (usually weather related or a mechanical breakdown).

Ok, so your friends or relatives decide to visit you for a week and will fly where you are anchored.  When they arrive you will need to adjust your lifestyle for the length of their stay.  Remember they are on vacation and need to be kept busy nearly 24 hours a day.  They can rest when they return home.

A successful cruise with friends or relatives involves planning.  Think of yourself as a charter boat (well, don’t act that badly) and plan accordingly.  Start the day early with a morning swim followed by a short sail to another anchorage and lunch in the cockpit.  The afternoon is used for snorkeling around the anchorage (looking at your anchor would be nice) or hiking or simply sunning on the beach – you did anchor where there is a beach right?  In the evening a BBQ onboard using your grill or a dinner ashore with lots of liquor is required.  Whatever your choice don’t forget to have everyone enjoy the stars before you hit the sack.  Sometime during the trip it will be necessary to provide a shopping excursion or two or three.  Your visitors need to purchase t-shirts, local handmade goods and liquor to take home with them. 

Some cruisers like to take their guests on a longer passage for their sailing adventure.  Perhaps you are anchored in Antigua and would like your guests to experience a glorious sail to St. Maarten, stopping at Nevis, St. Kitts and St. Barths along the way.  This is a great itinerary but a very risky venture.  The weather rarely cooperates and you will most likely make your friends very sick or injuring your well-maintained sailing vessel by beating her to death in order to make landfall on St. Maarten by the required date of their departure.  It is best to sail in one specific area instead of passagemaking.

The easiest places to have friends or family meet your vessel and have a great sailing adventure are:

St. Thomas – The flights to St. Thomas are easy and reasonably priced from anywhere.  Provisioning is great in St. Thomas so you can be ready for your guests.  Make sure to get a slip reservation at Crown Bay Marina the day before your guests arrive to insure the boat is all bright and shiny. From Crown Bay Marina the USVI’s and the BVI’s are an easy and a perfect cruising ground.  Even though this is the charter boat capital of the universe your guests will feel safe because anchoring is almost non-existent.  You are essentially required to pick up a mooring and this means ALL of the charter boats will be hanging off a mooring instead of running into you! If you tire of the USVI’s and BVI’s spectacular areas you can always hop over to the Spanish Virgins for a visit.  However, remember that the sail from the Spanish Virgins back to St. Thomas is hard on the wind and not easily accomplished during the winter months.

Antigua – This one island provides a tremendous variety of sailing, exploration and nightlife opportunities.  A circumnavigation of Antigua will provide deserted anchorages, great snorkeling, excellent beaches, a great Sunday night party at Shirley Heights and most of all the sailing is steeped in tradition from the days of Admiral Nelson.  Antigua is an easy flight destination from North America too.

St. Maarten/St. Martin – This dual nation island is world renown for its’ nightlife, fantastic beaches and is easily accessed with many flights from North America.  St. Maarten/St.Martin also provides an excellent gateway to a more lively cruising area – the islands of Anguilla, St. Barths, Saba, Statia, St. Kitts and even Nevis are a relatively short sail away.  The cultural diversity of these neighboring islands is something to experience!

The Grenadines – This area is further afield and more expensive to get to from North America.  The main base here is at Cannounan, or if your guests cannot afford that flight have them fly into St. Vincent.  This area is truly in the heart of the Caribbean you will find more untouched places to visit than further north.  While the Grenadines are more unspoiled than the previously mentioned destinations, the sailing here is also more serious so make sure your guests are avid sailors before inviting them here.  We have always found the boat boys very helpful and enjoyable but the charter boats can be unbearable most of the time.  There are also flights into Grenada but sailing into and out of Grenada is usually uncomfortable due to wind, sea and the lack of good anchorages so Grenada is not a recommended meeting place.