Caribbean Yacht Charter Guide

Resident Down Under? The Caribbean has never been closer. Air New Zealand now flies direct Auckland to Houston, Texas five days a week.
Simply the perfect place to take a bareboat or skippered sailing holiday. Such a diverse collection of islands dotting the clear blue sea, each with its own unique appeal. Local cultures that fascinate and entertain, offering a welcome that keeps charterers returning to these waters year after year. With its 7,000 Islands and 28 Island nations, reliable trade winds and long sailing season, the Caribbean is a region that offers an endless amount of holiday enjoyment.

Charter Regions within the Caribbean

Sailing in the Caribbean

In the Caribbean there are so many islands, so many different places to go and cultures to experience that the permutations for planning a sailing charter are simply too numerous to list. The sailing distances between territories can be very short, and there are countless yacht charter bases scattered across the region. That opens the door to all manner of opportunities – from a seven-day sail around one distinct island nation to a multi-week one-way charter that takes in a wide variety of cultures and geographical features.

The Caribbean yacht charter season is busy from November through July. The peak season is mid-December to March, when winter escapees from North America and Europe arrive in their greatest numbers.

The hurricane season arrives late July and can last until early October, although storms here are rare and tend to deflect northwards towards the USA rather than hit the Caribbean. These months have their advantages in that they are the least costly for chartering, particularly in the British Virgin Islands. At that time of year it is in fact more likely to encounter light winds than it is storms.  As with many yacht charter locations the shoulder season, in the Carribean from April to July, can be the best time to charter a yacht. There are less shore-based visitors then, yet you can expect settled and sunny weather, with warm, steady breezes prevailing.

We have access to over 30 charter bases in the region, from where you can take a sailboat vacation like no other. We select from the best boats available and guide you into the ideal sailing adventure that matches your interests and level of experience. The sailing options here are just about endless. Hopefully these pages will help you on your way to your much-anticipated Caribbean sailboat charter.

Sample charter sailboat holiday: one-way cruise from Martinique to Grenada

We hope these pages are helpful in your decision to embark on what can and should be the sailing adventure of a lifetime. There are quite simply countless itinerary options for sailing the Caribbean, and for many skippers, a downwind cruise offers the crew conditions for maximum enjoyment. So here's a sample plan, on a generally north to south course with the prevailing breeze abaft.  

You can expect winds primarily from the northeast, especially around peak season either side of Christmas. Sailing this course involves short stretches of open water, with a stiff and steady breeze on your aft quarter. That makes  for quick passages with most enjoyable sailing to a choice of Islands, whether it be for a lunch stop and  asnorkel, or an overnight stay.

The eastern Caribbean islands that form a distinctive arc on the map are collectively the Lesser Antilles, a mixture of  soverign states and territories governed by various powers. A trip along some of this chain exposes the voyager to a wide variety of cultures and customs in places that all sit in the idyllic picture-postcard surroundings of the movies and travel brochures. 

Starting in Martinique and sailing south, you are exploring the Windward Island group of the Antilles. Like most of this group, Martinique was orginally colonised by France, and French flair is still in evidence there today. Martinique offers excellent on-shore facilities for the visitor, and is a popular base for boat charters. The island is mountainous, but with plenty of white sandy beaches to enjoy, especially in the south.

The next island is St Lucia. It's some 30 nautical miles to Rodney Bay on St Lucia's northwest, so to get there requires an early start. There are several top spots to visit down the island's sheltered western coast. Take time out to investigate Les Deux Pitons.

Another long but relaxing sail to St Vincent and the Grenadines, so-named because of their joint French and British colonial history. St Vincent has its Blue Lagoon that you'll probably overnight in, while the Grenadines island group, some of which confusingly belong to Grenada, provide numerous anchoring options. The Grenadines stretch all the way to Grenada, your final port of call, making this part of the voyage very convenient for a leisurely sail. Call in at one of the uninhabited Tobago cays for a real taste of desert island living, if only for a few hours.

Once offshore Carriacou you are in Grenadan territory. Grenada, like St Lucia & St Vincent and the Grenadines, is now an independent member of the British Commonwealth, but with historical French influence. This is the 'Island of Spice' where nutmeg and mace production are important to the economy. As is tourism, and there is plenty to entertain you before concluding your vacation and departing these fabulous sailing waters. Chances are you'll be back one day for more.

Our Services

We work with all the best charter operators in the Caribbean. Let us sort through all the available boats and recommend the best options to suit your vacation plans. Some of the companies we work with offer extra services that are unique to their destinations. We will personalize your proposal and give you the benefit of our knowledge and contacts, for a most-enjoyable sailing holiday anywhere there's a boat to charter in the Caribbean. 

Enquire Now - Click Here   or view our bareboats and crewed yachts.

The Sail Connections Guarantee

One contact - every option - advice you can trust.

  • Matching any competitive offer 
  • Sourcing boats with discounts available
  • Personalising our proposal just for you
  • Qualifying the operator as well as the boat
  • Advising without bias based on 25+ years of experience

We will match any discount website offer on charter boat price, and still provide our customary high level of service. We do more than just book yachts!

Read our free charter guide for all you need to know about planning your sailing holiday.

Yachts in the Caribbean

Dufour 460 Grande Large
Dufour 460 Grande Large - 46.5' (14.2m) 8 Guests
Bali 4.5 Open Space
Bali 4.5 Open Space - 44.6' (13.6m) 8 Guests
Saona 47
Saona 47 - 42.65' (13m) 10 Guests
Lucia 40
Lucia 40 - 38.5' (11.7m) 8 Guests
Maestro 37 Power Cat
Maestro 37 Power Cat - 33.1' (10.1m) 6 Guests

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