Sail the Caribbean

Charter Sailing in the Caribbean

The Caribbean's numerous islands give you so many fabulous places to explore, so many diverse 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 can be the best time to charter a yacht. In the Carribean that's from April to July. 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 sailing holiday.

Regional Map of the Main Charter Sailing Areas

A One-way Cruise: Martinique to Grenada

There are quite simply countless itinerary options for sailing the Caribbean. For many charterers a downwind cruise offers the crew conditions for maximum enjoyment. So here's a sample north to south course plan that gives you the prevailing breeze abaft. 

Waterfront at Fort de France, Martinique's largest town

Sailing from Martinique to Grenanda 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 a snorkel, 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.

Wildlife viewing at its finest in the Tobago Cays

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.

Happy charterers enjoying their time ashore in the Grenadines

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.

Once you have experienced all the pleasures of sailing the Caribbean, chances are you'll be back one day for more.

Can I do a one-way charter in the Caribbean?

Yes, one-way charters are particularly popular in the Caribbean, where they open up possibilities a round trip of the same duration may not. Continue reading...

Which Caribbean destinations are best for yacht charters?

The Caribbean offers a wide range of charter environments, each with its own character: Continue reading...

What’s the best time of year to charter a yacht in the Caribbean?

The Caribbean enjoys reliable trade winds and a warm climate year-round, making it one of the most consistent sailing destinations on the planet. Continue reading...

Do I need a sailing qualifications to bareboat charter in the Caribbean?

In most of the Caribbean, you do not need a formal sailing qualification such as an ICC (International Certificate of Competence) or RYA certificate in order to take a bareboat charter. What you do need is to demonstrate sufficient sailing experience and practical knowledge to the charter operator Continue reading...

What sailing qualifications are required to bareboat charter in the Caribbean?

Unlike some other regions, most Caribbean destinations do not require a formal sailing licence to charter a bareboat. However, you must demonstrate sufficient experience and competence to safely operate the vessel. Continue reading...

When should I book a charter boat in the Caribbean and Bahamas?

The best time to charter in the Caribbean and Bahamas is from December through July, with peak season running mid-December to March. That’s when you’ll find the most settled weather and lively island atmospheres that are perfect for escaping southern hemisphere winters or northern chills. Continue reading...

What do you recommend about boat chartering in the Caribbean?

Chartering a boat in the Caribbean - including The Bahamas - is one of the most rewarding sailing experiences you can have. We recommend the region for its warm climate, steady trade winds, short sailing distances, and abundance of beautiful anchorages. Continue reading...