How to Choose the Caribbean Sailing Holiday That's Right for You; Part 1 - Why & When

About Sailing Holidays in the Caribbean

The Caribbean is one of the world’s most famous and idyllic cruising grounds, with 26 island nations and over 7,000 islands in 2,500 square miles of sparkling blue sea the possibilities for a sailing holiday are countless.  If you’re looking for sophistication, great restaurants and nightlife then St Barth’s, Anguilla and St Maarten should be high on your wish list, in contrast with the rugged, rain-forest covered mountains of Dominica which offer a true escape from the 21st century….each island has it’s own unique atmosphere and charm.  The beauty of a sailing holiday is the ability to hop from one island to the other and to have several different vacation experiences in one trip.

When to Go

The high season in Caribbean runs from December to April when prices are highest and demand is greatest.  Weather conditions for sailing are perfect during these months with steady trade winds of around 20 to 25 knots, blue skies and a turquoise ocean.  The weather is also good in November, May and June but the demand tends to be lower so prices are more flexible.

Keen sailors will be watching the Caribbean Regatta Diary and timing their vacation so they can participate in the racing.  With acclaimed regattas such as Antigua Sailing Week and the St Maarten Heineken Regatta, there is always a vibrant social side to the racing which makes for a unique holiday experience, and even if you don’t sail, the evening events create an island-wide buzz with high profile bands often playing at the beach party venues.

Hurricane Season’s also Good!

The hurricane season runs from July to October; during these months the winds are lightest and there is a greater chance of rain, however most of the time the weather is good and all islanders keep a good watch on the weather forecasts for approaching hurricanes.  The chance of hurricanes is lowest in the southern-most islands and for this reason, if you're thinking about a sailing holiday in the low season, it’s better to focus on Grenada, Tobago, Trinidad, Venezuela or the Netherlands Antilles which are all, of themselves, fantastic places to sail and well off the beaten track.

What is Yacht Charter?

Yacht charter is simply the rental of a boat – motor or sail – for a period of time.  Each charter is subject to rental terms and these vary from charter company to charter company; terms also tend to vary according to the type of yacht charter as indicated in the sections to follow.

The alternatives to chartering a yacht include sailing flotillas and sailing holidays / vacations.  These types of holiday are geared towards smaller groups such as singles or couples, and offer a better price model if there's only one or two of you and/or you'd like the additional security of sailing with a group if you have less sailing experience.

If you want to learn to sail or improve your sailing skills, Sailing Schools offer you the chance to gain a certificate whilst you play in the sun.  You should bear in mind, however, that in order to complete a syllabus within the allotted time slot, Sailing School holidays offer a more structured vacation experience which some might find restrictive.

Compliance with Safety Standards

Boats offered for charters, sailing holidays or sailing courses must comply with safety standards set by their flag (country of registration) and are issued with a licence accordingly once they’ve passed an inspection.  This licence dictates the number of guests a boat can carry and the distance it’s approved to travel from a safe port on terra firma.

Booking a Yacht Charter

It’s possible to charter a boat directly from the owner, however depending on the type of boat your looking for it may not be possible to easily find a contact number for the owner’s representative or the yacht’s captain.  Many charter boat owners, particularly at the luxury end of the market, prefer to channel their charter enquiries through one or more agents, who receive in the region of 20% of the charter fee for managing the booking process.

Other, larger yacht charter companies manage and maintain a number of yachts on behalf of their own company and/or on behalf of owners.  This is particularly true of bareboat charter companies such as Sunsail or The Moorings.

Who is Yacht Charter For?

Yacht charter is particularly suitable for small groups of people or families who might otherwise hire a villa together but who like the additional freedom, exploration and escape offered by a yacht travelling around more than one island.  Like a rental villa, boats for charter come in all sizes and price brackets, with or without staff (crew).  Depending on the needs and experience of your group and the size of boat involved you might choose a fully crewed boat, Skippered charter or bareboat.  These options are explained in more detail in the sections to follow.

Sailing Holidays or Flotilla Vacations for Single Sailors

Operators offering sailing holidays and flotillas have chosen to cater to singles or couples without the resources to rent a bigger or more expensive boat to themselves.  Sailing singles and solo travellers are likely to prefer the option of booking just a berth (bunk or bed) or a cabin on a boat rather than paying to rent the whole boat!  Besides, sailing is very much a participatory sport where teamwork is much more fun than single handing so this often a great choice.  Most private charter yachts don’t offer the option of booking a single berth.

In Part 2, we take a closer look at the options for a sailing vacation in the Caribbean to help you home in on the right choice for you.

Yacht Ibis offers adventure sailing holidays with relaxed tuition for singles, couples or groups & families of up to 5 people.  You can book a single berth or the whole boat and your Captain, Samantha Bartlett can teach the RYA syllabus to Day Skipper Level or ASA to Basic Coastal Cruising standards.