Windward Islands Yacht Charters

The Windward Islands are a chain of volcanic islands in the southern Lesser Antilles, stretching from Martinique south to Grenada. They are known for lush rainforests, dramatic volcanic peaks, authentic Caribbean culture, secluded anchorages and some of the world's finest sailing grounds.

Unlike the Virgin Islands, which are famous for short island hops and protected waters, the Windward Islands offer longer passages, more varied scenery and a greater sense of exploration. This region rewards sailors looking for quieter anchorages, diverse cultures and spectacular natural beauty.

The Windward Islands also include the world-famous Grenadine Islands, one of the Caribbean's premier yacht charter cruising grounds.

Islands Covered

This regional guide includes:

• Martinique
• Saint Lucia
• Saint Vincent
• Bequia
• Mustique
• Canouan
• Mayreau
• Union Island
• Tobago Cays
• Petit St. Vincent
• Palm Island
• Petit Tabac
• Grenada
• Carriacou
• Petite Martinique

As Yacht Charter Agents expands, some destinations within this region may also receive their own dedicated destination guides.

• The famous Tobago Cays Marine Park
• Longer offshore sailing passages
• Luxury private islands such as Mustique
• Authentic Caribbean culture
• Volcanic landscapes
• Rainforests and waterfalls
• Excellent diving and snorkelling
• Boutique beach bars and restaurants
• Beautiful white-sand anchorages
• Outstanding kiteboarding around Union Island and Canouan

The Windward Islands & Grenadines could be the perfect destination if you:
✓ Love sailing between beautiful islands.
✓ Enjoy dramatic tropical scenery.
✓ Appreciate authentic Caribbean culture.
✓ Want exceptional snorkeling and swimming.
✓ Prefer relaxed anchorages over busy marinas.
✓ Enjoy discovering smaller island communities.
✓ Want a balance between adventure and luxury.

The Windward Islands may be less suitable if you:
• Prefer short cruising distances every day.
• Want a destination centred on shopping or nightlife.
• Are looking primarily for luxury resorts.
• Prefer staying close to one main island.

Those guests may also enjoy the Leeward Islands, U.S. Virgin Islands or the British Virgin Islands depending on the style of charter they're seeking.

The Windward Islands enjoy a warm tropical climate throughout much of the year and offer excellent sailing conditions during the main Caribbean charter season.

The best time to visit depends on whether your priorities are sailing conditions, quieter anchorages or enjoying the vibrant atmosphere of the Caribbean's busiest months.

December – April
Ideal For: Sailing enthusiasts • First-time visitors • Couples • Families
This is the most popular charter season.
Comfortable temperatures, reliable trade winds and excellent sailing conditions make it an outstanding time to explore the Windward Islands.
Premium yachts and holiday periods often book well in advance.

May – June
Ideal For: Returning charter guests • Relaxed cruising • Couples • Nature lovers
Late spring offers warm weather with a quieter atmosphere.
Many guests enjoy the opportunity to experience the islands with fewer visitors while still benefiting from rewarding sailing conditions.

July – November
Ideal For: Flexible travellers • Returning visitors
This period overlaps with the Caribbean hurricane season.
Charters continue to operate, but itineraries require greater flexibility and are always adapted to local weather conditions.

Seasonal Considerations
Unlike destinations where the emphasis is mainly on beaches, the Windward Islands are chosen by many guests because of the sailing itself.
Trade winds, sea conditions and visibility all contribute to the experience, making seasonal planning an important part of creating the right itinerary.

The Windward Islands are renowned for their rewarding sailing conditions, warm tropical climate and spectacular island scenery.

Steady trade winds, open-water passages and protected anchorages combine to create an experience that appeals to both experienced sailors and guests enjoying their very first crewed yacht charter.

Because you're travelling with a professional captain, you don't need to worry about interpreting weather forecasts or planning routes. Your crew continuously monitors local conditions, adjusting the itinerary where necessary to maximise both comfort and enjoyment.

Typical Conditions

Air Temperature
Warm tropical temperatures throughout the main charter season.

Sea Temperature
Comfortable year-round for swimming, snorkeling and water sports.

Water Clarity
Excellent throughout much of the region, particularly around reefs, bays and marine parks.

Cruising Style
The Windward Islands feature longer scenic passages than many Caribbean destinations, balanced by beautiful anchorages and rewarding stops along the way. The sailing itself becomes an important part of the holiday rather than simply the time between destinations.

What Happens if the Weather Changes?
Flexibility is one of the greatest advantages of chartering a private yacht.
If conditions make one anchorage or island less suitable, your captain can recommend an alternative route while preserving the spirit of your itinerary.
Many guests discover that these unexpected changes lead to some of the week's most memorable experiences.

The Windward Islands combine some of the Caribbean's most spectacular scenery with world-famous cruising grounds.

Each island offers its own unique character, from lush volcanic peaks and rainforest-covered hillsides to quiet anchorages, colourful waterfront villages and protected marine parks.

Rather than trying to visit every island, we recommend choosing an itinerary that allows you to appreciate the distinctive personality of each destination.

St. Lucia
Best For: First-time visitors • Dramatic scenery • Hiking • Photography
St. Lucia is one of the Caribbean's most recognisable islands, famous for the towering Pitons, lush rainforests and beautiful bays.
Its dramatic landscapes provide a spectacular backdrop for a yacht charter, while charming waterfront communities and secluded anchorages encourage guests to slow down and explore.
For many visitors, St. Lucia is the perfect introduction to the Windward Islands.

Bequia
Best For: Authentic Caribbean charm • Couples • Sailing enthusiasts • Relaxation
Bequia has long been one of the Caribbean's favourite yachting destinations.
Known for its friendly atmosphere, colourful harbour and relaxed pace of life, it offers an authentic island experience that has remained remarkably unchanged.
Many charter guests consider Bequia one of the highlights of the Grenadines.

Mustique
Best For: Luxury travellers • Couples • Privacy • Beautiful beaches
Mustique is renowned for understated luxury, beautiful villas and pristine beaches.
Arriving by yacht offers a unique opportunity to appreciate the island's spectacular coastline while enjoying the privacy and flexibility that only a yacht can provide.
Its exclusive reputation is balanced by a relaxed Caribbean atmosphere.

Tobago Cays
Best For: Snorkeling • Swimming • Marine life • Families
The Tobago Cays are widely regarded as one of the Caribbean's premier yacht charter destinations.
Protected by a horseshoe-shaped reef, these islands offer exceptional snorkeling, crystal-clear water and unforgettable opportunities to swim alongside marine life in a breathtaking natural setting.
For many guests, visiting the Tobago Cays becomes the defining moment of their charter.

Canouan
Best For: Couples • Luxury • Golf • Relaxation
Canouan combines luxury resorts with beautiful beaches and sheltered anchorages.
Guests can enjoy a relaxed pace while appreciating the island's natural beauty and premium facilities.
It provides an appealing contrast to the quieter islands nearby.

Which Islands Are Right for You?
If spectacular scenery is your priority, St. Lucia offers one of the Caribbean's most iconic landscapes.
Guests seeking authentic island life often fall in love with Bequia, while those looking for exceptional snorkeling and protected anchorages rarely forget the Tobago Cays.
Luxury travellers may be drawn to Mustique or Canouan, while longer charters can combine several islands into one unforgettable itinerary.
The best route depends on your interests, travel dates and the style of holiday you're hoping to create.

The Windward Islands offer some of the Caribbean's most spectacular beaches, where dramatic volcanic scenery, crystal-clear water and secluded anchorages combine to create unforgettable settings.

Many of these beaches are best experienced from the sea. Arriving aboard a yacht allows you to enjoy peaceful mornings before day visitors arrive, anchor close to the shoreline and combine swimming, snorkeling and paddleboarding into the same relaxed afternoon.

Rather than offering one style of beach, the Windward Islands provide remarkable variety throughout your charter.

Salt Whistle Bay – Mayreau
Best For: First-time visitors • Swimming • Couples • Relaxation
Salt Whistle Bay is one of the Caribbean's most photographed anchorages, with its gently curving white-sand beach, swaying palms and calm turquoise water.
Approaching by yacht reveals why it has become one of the signature stops in the Grenadines.
Many guests spend an entire afternoon here enjoying the beach, swimming and simply appreciating the surroundings.

Princess Margaret Beach – Bequia
Best For: Families • Swimming • Beach walks
Located just beyond Port Elizabeth, Princess Margaret Beach offers soft sand, calm water and beautiful views across Admiralty Bay.
Its sheltered conditions make it a favourite stop for yacht charter guests looking for a relaxed beach day.

Macaroni Beach – Mustique
Best For: Couples • Photography • Scenic walks
Macaroni Beach showcases another side of the Grenadines, with a long stretch of pale sand backed by lush tropical vegetation.
Its natural beauty and peaceful atmosphere make it one of Mustique's most memorable coastal locations.

Anse des Pitons – St. Lucia
Best For: Scenic cruising • Snorkeling • Photography
Set beneath the dramatic Pitons, this coastline offers one of the Caribbean's most iconic yacht charter settings.
Swimming and snorkeling beneath these volcanic peaks creates an experience that is unmistakably St. Lucia and unlike anywhere else in the region.

Tobago Cays Beaches
Best For: Snorkeling • Marine life • Families • Paddleboarding
The small beaches scattered throughout the Tobago Cays Marine Park provide some of the Caribbean's most rewarding opportunities to enjoy both the beach and the surrounding reef.
Guests often combine snorkeling, swimming and relaxing ashore while surrounded by crystal-clear water in every direction.

Beach Days in the Windward Islands
One day may be spent beneath towering volcanic mountains.
The next could be anchored beside a tiny coral island with nothing but white sand and turquoise water surrounding your yacht.
This contrast is one of the defining characteristics of the Windward Islands and keeps every charter feeling fresh and rewarding.

Dining in the Windward Islands is as relaxed and authentic as the cruising itself.

Throughout the region you'll discover colourful waterfront restaurants, beach bars, locally owned cafés and welcoming island communities where fresh seafood and Caribbean flavours take centre stage. Meals are rarely rushed. Instead, dining becomes another opportunity to slow down, enjoy the scenery and experience the warmth of island hospitality.

A yacht charter gives you the freedom to enjoy exceptional meals prepared onboard while also stepping ashore to discover the local character of each island.

Fresh Caribbean Seafood
Best For: Seafood lovers • Couples • Families
Fresh fish, lobster, shrimp and seasonal seafood appear on menus throughout the Windward Islands.
Prepared with local herbs, tropical fruit and regional spices, many dishes reflect generations of Caribbean culinary tradition while celebrating the freshness of locally sourced ingredients.

Beach Bars & Waterfront Dining
Best For: Relaxed lunches • Sunset drinks • Friends and families
The Windward Islands are famous for relaxed beach bars and waterfront restaurants where sandy feet are perfectly acceptable.
Many guests enjoy arriving by tender, spending a leisurely afternoon ashore and returning to the yacht as the sun begins to set.
These informal experiences often become some of the most memorable moments of the charter.

Local Caribbean Flavours
Best For: Cultural experiences • Food lovers
Every island adds its own influence to the dining experience.
Creole cooking, tropical fruit, locally grown produce and freshly baked breads create a style of cuisine that feels authentic rather than manufactured for tourism.
Sampling local dishes is one of the simplest and most enjoyable ways to experience the character of each island.

Dining Onboard
Some of the finest meals during your charter may never involve going ashore.
Breakfast with the Pitons rising in the distance.
Lunch anchored beside the Tobago Cays.
Dinner beneath a sky filled with stars while gently swinging at anchor.
Dining aboard your yacht combines privacy, comfort and spectacular surroundings that few restaurants can match.