Windward Islands:
Caribbean Sailing Vacations & Expeditions
Sail the Caribbean Windward Islands—a chain of lush, dramatic isles that rank among the Top Sailing Destinations on earth. From Dominica’s waterfalls to Martinique’s chic marinas, Saint Lucia’s Pitons, Saint Vincent and the Grenadines’ postcard anchorages, Carriacou’s traditional boatbuilding culture, and Grenada’s spice-scented shores, sailing the Windward Islands blends wild nature with French-Creole flair. Whether you’re dreaming of a small-ship Windward Islands cruise or bespoke windward islands boat charters, Neptune’s Daughter designs Chartered Sailing Vacations tailored to your style.
Why Cruise the Winward Islands?
Natural Diversity
ctive and dormant volcanoes, rainforest peaks, hot springs, black- and white-sand beaches, and thriving coral reefs create a spectacular playground for sailors and snorkelers.
Culture & Cuisine
Taste French-Creole markets in Martinique, nutmeg and cocoa in Grenada, and seaside barbecue in the Grenadines. Music festivals, yacht regattas, and village fêtes bring each island to life.
Small-ship Ease
Short hops mean effortless island-hopping. Smaller yachts and expedition ships slip into intimate coves the big ships miss—perfect for luxury small-ship Windward Islands cruise itineraries.
Highlights of the Windward Islands: An Island-by-Island Guide
Dominica - The Nature Isle
Boiling Lake hikes, Trafalgar Falls, emerald canyons, and world-class whale watching. Moor off Portsmouth and explore mangrove-lined Indian River by rowboat; dive pristine walls teeming with sponges and seahorses.
Martinique - The Isle of Flowers
French chic meets tropical soul: Le Marin’s modern marinas, rum distilleries, and black-sand Anse Noire. Sail north for soaring cliffs; linger south for sheltered coves, beach clubs, and refined bistros.
Saint Lucia - The Helen of the West
Anchor beneath the Pitons, soak in sulfur springs, zipline rainforests, and snorkel Anse Chastanet’s reef. Rodney Bay buzzes with nightlife; Marigot Bay offers serene, hurricane-hole calm.
Saint Vincent & the Grenadines - The Heart of the Grenadines
Short sails, big rewards: Bequia’s friendly waterfront, the sail-to-only Tobago Cays turtle sanctuary, chic Mustique, kitesurfing in Union Island, and sleepy Mayreau sunsets.
Grenada - the Spice Isle
Fragrant markets, cocoa estates, waterfalls, and the famed Underwater Sculpture Park. Sheltered anchorages ring the south coast, while true trade-wind passages await toward Carriacou and Petite Martinique.
How to Get to the Windward Islands
Main Gateways
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Saint Lucia: Hewanorra International Airport (UVF)
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Grenada: Maurice Bishop International Airport (GND)
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Saint Vincent: Argyle International Airport (SVD) (Additional regional access via Martinique’s Aimé Césaire International Airport (FDF).)
Inter-Island Travel
The windward Caribbean islands are built for easy movement: short sails between anchorages, reliable trade winds, and clear line-of-sight navigation. For fly-cruise combinations, frequent regional flights connect Saint Lucia, Saint Vincent, Grenada, and Martinique—seamlessly pairing air legs with Windward Islands boat charters.
Best Time to Visit the Windward Islands
Peak Sailing Season
December–May: Enjoy consistent trade winds (15–25 knots), sunny skies, and lower humidity. Daytime air temperatures average 80–85°F (27–29°C), with pleasant evening breezes dropping to around 75°F (24°C). The sea temperature hovers between 79–82°F (26–28°C)—perfect for long swims, snorkeling, and diving.
Shoulder Season
June & November: Still warm and inviting, with slightly higher humidity and brief tropical showers that refresh the landscape. Air temperatures stay around 83–88°F (28–31°C), and water temperatures remain steady at 81–84°F (27–29°C). Winds soften a bit, ideal for relaxed cruising.
Off Season
July-October: The warmest time of year, with lush scenery and fewer crowds. Expect air temperatures of 85–90°F (29–32°C) and sea temperatures of 82–86°F (28–30°C). It’s the Caribbean at its warmest and most tropical—plan with flexible itineraries and professional weather routing for optimal safety.
Activities: Immersing Yourself in Island Life
Snorkeling & Diving
Reef gardens in the Grenadines, Dominica’s walls, Grenada’s sculpture park, and turtle encounters in Tobago Cays.
Shore Excursions & Hiking
Piton climbs, Boiling Lake treks, waterfall dips, cocoa and rum estate tours, and canopy ziplines.
Cultural Experiences
Market mornings, steel-pan nights, sailing regattas, and village fêtes; savor boudin créole, bake-and-shark, and nutmeg-infused treats.
Onboard Relaxation
Swim-off transoms, paddleboards at sunrise, star-gazing from a quiet mooring, chef-prepared dinners on deck.
Windward Islands Sailing & Yacht Charter Options
Bareboat Charters
For experienced skippers craving independence. We match hulls, sail plans, and electronics to your route—ideal for hands-on Windward Islands passages and exploring hidden anchorages at your own pace.
Crewed Yachts
A private yacht with professional captain and chef: fully catered, expert routing, and boutique service—perfect for special occasions or ultra-relaxed Chartered Sailing Vacations where every detail is handled for you.
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Cabin Charters
Join a small group by the cabin—great value for solo travelers or couples seeking a hosted Windward Islands cruise with built-in camaraderie. Sail with like-minded adventurers, enjoy set itineraries, and let the crew handle the rest.
Scuba Diving Liveaboard Safaris
For divers and ocean lovers, liveaboard safaris offer the ultimate undersea adventure across the Caribbean Windward Islands. Wake up to new dive sites each morning—from Grenada’s famous Bianca C wreck and Underwater Sculpture Park to the pristine reefs of Carriacou and Saint Vincent. Expert dive guides, compressor-equipped vessels, and curated itineraries blend sailing and diving expeditions into one unforgettable journey.
Choose Neptune’s Daughter for Your Windward Islands Expedition
You bring the dream; we bring the blueprint. Our planners know the nuances of islands in the Windward Islands—from customs formalities to hidden hurricane-holes, from kid-friendly beaches to advanced dive spots. Expect vetted boats, trustworthy skippers, curated shore excursions, and 24/7 support—so your Caribbean Windward Islands escape is seamless from first inquiry to final landfall.
Start Planning Your Trip to the Windward Islands
Schedule your free 30-minute consultation and we’ll design a bespoke plan: route, yacht selection, provisioning, excursions, and travel logistics.
Pro Tips: Cost, booking window & insurance:
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Typical ranges: Cabin charters from budget-friendly options to premium small-ship suites; private monohulls/cats scale with size, season, and crew. Prices range from $2000 per person to $25,000 for a fully crewed boat charter for up to 12 guests.
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When to book: Peak season fills 6–12 months out; holiday weeks even earlier.
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Insurance & Protection: We recommend comprehensive travel insurance (medical, evacuation, trip interruption) and optional refundable terms where available. Visit our Travel Insurance page to browse plans and purchase a plan.
Frequently Asked Questions
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What should I pack for a Windward Islands sailing trip?
Light, quick-dry layers; sun protection (reef-safe sunscreen, hat, rash guard); boat shoes/sandals; a light rain jacket; compact daypack; and any personal snorkel gear you prefer. Soft-sided luggage only.
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How much does a sailing vacation in the Windward Islands cost?
Cabin charters start from value options and scale by season and ship; private bareboats and crewed yachts vary by size, age, and inclusions. We’ll quote transparent totals (yacht, provisioning, fuel, moorings, crew gratuities) before you book.
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Are the Windward Islands safe for tourists?
Yes—these islands are popular with sailors. Use normal travel common sense (lock dinghies, mind valuables, follow captain guidance), and rely on our vetted partners and local briefings.
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Where are the Windward Islands?
The Windward Islands form the southeastern arc of the Lesser Antilles in the Caribbean, generally including Dominica, Martinique, Saint Lucia, Saint Vincent and the Grenadines, and Grenada.
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Is the Windward Islands route suitable for solo travelers/families?
Absolutely. Cabin charters are great for solos; family-friendly crewed yachts offer flexible cabins, safe swim stops, and paced sailing days.
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What are the 4 main islands of the Windward Islands?
Many travelers refer to Martinique, Saint Lucia, Saint Vincent, and Grenada as the primary hubs, with Dominica also commonly included in the Windward group.
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What country owns the Windward Islands?
They’re a mix of sovereign nations and one French department: Dominica, Saint Lucia, Saint Vincent and the Grenadines, Grenada (independent states), and Martinique (an overseas department of France).
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Where are the Windward Islands located?
In the southeastern Caribbean Sea, north of Trinidad & Tobago and south of Barbados, forming the lower curve of the Lesser Antilles—often referred to as the windward Caribbean islands due to their position facing the trade winds.