Charter Destination The Windward Islands

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Sprinkled across the southern Lesser Antilles, stretching from Martinique to Grenada, the picture-perfect Windward Islands blaze a trail of powder-white beaches and crystalline waters.

Lying in the south eastern Caribbean in the path of the northeast trade winds, Barbados, Trinidad & Tobago, Martinique, St Lucia, St Vincent & The Grenadines and Grenada are known for their tropical scenery, stunning beaches, remote anchorages and hidden coves: all the ingredients for a perfect yacht charter.

Volcanic and rugged, adorned with lush scenery and surrounded by whimsical reefs and cays, this intoxicating yachting destination benefits from the close proximity the islands. Those seeking secluded anchorages, incredible dive sites and sublime island beauty will not be disappointed with this little slice of paradise.

Experience chic French Martinique, where the capital Fort-de-France has excellent restaurants paired with luxurious shopping. For nature enthusiasts, Dominica is one of the prime destinations in the region. A UNESCO World Heritage site, its lush rainforest and soaring peaks are great for outdoor pursuits including diving, whale and bird-watching, hiking and snorkelling. Barbados is a bustling and sophisticated island and a great entry point from which to explore the more remote Windward Islands.

Why Visit?

  • Beautiful beaches
  • Big game fishing
  • Great surf spots
  • Stunning views
  • World class restaurants
  • Wreck diving

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The Best of The Windward Islands

  • Visit the Pitons, the most impressive towering peaks in St. Lucia.
  • Head to Grenada: the best of both worlds, with its pristine beaches, chic city and bountiful, lush interior.
  • Take a slow boat up the mangrove-lined Indian River on Dominica.
When is the best time to charter a yacht in the Windward Islands?

The Windward Islands enjoy excellent cruising conditions from November to April, when the trade winds are steady, the seas are calm and the weather is warm and dry. This period is ideal for exploring the islands by sea, with consistent sailing conditions and clear visibility.

What makes the Windward Islands ideal for a yacht charter?

A Windward Islands yacht charter offers a truly authentic Caribbean experience, with lush volcanic landscapes, uncrowded anchorages and a strong sense of local culture. Travelling between the islands by yacht allows you to explore remote beaches, vibrant reef systems and historic harbours at your own pace, far from the busier cruising routes.

Which islands are included in a Windward Islands yacht charter?

The Windward Islands are rich in natural beauty and diversity. Popular destinations include:

St Vincent: dramatic volcanic scenery, waterfalls and traditional Caribbean charm

Bequia: relaxed island life, excellent anchorages and a welcoming sailing community

Mustique: exclusive villas, pristine beaches and refined island elegance

Canouan: luxury resorts, crystal-clear waters and world-class snorkelling

Union Island: vibrant culture and a gateway to the southern Grenadines

A yacht charter is one of the most rewarding ways to experience St Vincent and the Grenadines by sea, with each island offering its own distinct character.

Should I choose a sailing yacht or a motor yacht in the Windward Islands?

Both options offer exceptional ways to explore the region:

Sailing yachts are ideal for guests who enjoy steady trade winds and longer passages between islands, making the most of classic Caribbean sailing conditions.

Motor yachts are perfect for covering greater distances comfortably, with generous deck space and the ability to explore multiple islands with ease.

Your broker will advise on the best yacht based on your itinerary, group and preferred cruising style.

How much does a luxury yacht charter in the Windward Islands cost?

The cost of a luxury yacht charter in the Windward Islands depends on the yacht type, season and itinerary. From elegant sailing yachts to fully crewed motor yachts, your broker will provide personalised recommendations and a transparent overview of all costs involved.

Do I need a licence to charter a yacht in the Windward Islands?

A licence is only required if you plan to operate the yacht yourself. Most guests opt for a fully crewed charter, allowing them to relax while an experienced captain and crew manage navigation, island clearances and local regulations.

What is included when I charter a yacht in the Windward Islands?

Each yacht offers its own set of inclusions, typically covering the crew, accommodation, onboard amenities and water toys. Additional expenses such as fuel, provisioning, port fees and local taxes vary depending on the itinerary. Your broker will clearly outline all details before confirming your charter.

How far in advance should I book a Windward Islands yacht charter?

The Windward Islands are particularly popular during the winter charter season. To secure the best selection of yachts, especially for peak travel periods, we recommend booking 6–12 months in advance.

Need help or advice?

The yachting journey can be complex with many decisions to be made. Get in touch with Ocean Independence, and one of our specialist consultants will help you make the right choices.

As a truly global company with 15 offices worldwide, we’re available 24/7 to help with any enquiries.

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