Windward Islands
The Windwards provide steady trade winds, volcanic landscapes and a more adventurous feel for guests seeking authentic Caribbean sailing.
Overview
The Windward Islands form the southern arc of the Lesser Antilles, curving down from Martinique to Grenada. Known for their consistent tradewinds, dramatic volcanic landscapes, and unspoiled anchorages, this region is a sailor’s paradise. Compared to the Leewards (BVI, St. Martin, Antigua), the Windwards feel more raw, adventurous, and authentic—perfect for guests who want turquoise water and lush rainforests, markets, waterfalls, rum distilleries, and culturally rich island life.
Expect steady 15–25 knot breezes, long scenic passages, dreamy coves, palm-fringed beaches, and a diverse mix of French, English, and Creole cultures.
Martinique
A vibrant French Caribbean island with volcanic peaks, black-sand beaches, chic marinas, rum distilleries, and world-class provisioning.
Highlights: Fort-de-France, Les Anses-d’Arlet, Mount Pelée, snorkeling in St. Pierre.
St. Lucia
Dramatic and romantic—famous for the iconic Pitons rising out of the sea.
Highlights: Soufrière hot springs, Marigot Bay, Rodney Bay nightlife, luxury resorts and spas.
St. Vincent & the Grenadines
Raw, natural, cinematic Caribbean with over 30 pristine islands and cays.
Highlights:
- St. Vincent: waterfalls, volcanic hiking, black-sand beaches
- Bequia: laid-back charm, waterfront bars, whale-crafting heritage
- Mustique: ultra-exclusive, home to villas, celeb hideaways, and Basil’s Bar
- Canouan: white-sand perfection, luxury camps & resorts
- Tobago Cays: a protected marine park—the crown jewel—sea turtles, sandbars, reef snorkeling
Grenada
“The Spice Island,” lush and green with cocoa, nutmeg, waterfalls, and beautiful southern bays.
Highlights: St. George’s, Underwater Sculpture Park, Grand Anse Beach, rum distilleries, Grenada chocolate.
WHY CHARTER IN THE WINDWARD ISLANDS
- Reliable Tradewinds — excellent sailing conditions
- Short Hops or Longer Passages — perfect for adventurous sailors
- Unspoiled Anchorages — quiet beaches, reefs, and wildlife
- Cultural Variety — French, Creole, British influences
- Less Crowded Than the Leewards — more authenticity, fewer mega-marinas
- Ideal for Catamarans — wide bays, reefs, and steady winds
POPULAR 7–10 DAY ROUTES
- St. Lucia → St. Vincent → Bequia → Mustique → Canouan → Tobago Cays → Union → Grenada
- Grenada → Carriacou → Union → Tobago Cays → Mayreau → Canouan
- Martinique → St. Lucia → St. Vincent & Grenadines → back to Martinique
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Key Attractions & Highlights
The iconic Pitons of St. Lucia
Sail beneath the breathtaking Gros and Petit Pitons—St. Lucia’s most iconic landmarks rising dramatically from the sea. These volcanic spires create one of the most unforgettable backdrops on any Windward Islands yacht charter, offering exceptional photo opportunities, snorkeling coves, and sunset anchorage
Tobago Cays Marine Park, home to turtles & coral gardens
A highlight of every Grenadines catamaran charter, the Tobago Cays are a cluster of untouched islands surrounded by protected reefs. Swim with sea turtles, explore vibrant coral gardens, and anchor in crystal-clear turquoise lagoons that feel like your own private paradise.
The charming harbor of Bequia
Bequia’s Port Elizabeth is a favorite stop for yacht charter guests thanks to its colorful waterfront, boutique shops, and relaxed Caribbean charm. It’s the perfect place to dine ashore, explore local culture, and enjoy the friendly cruising vibe of a true sailor’s island.
Mustique, the private island of villas & celebrity retreats
Mustique offers an exclusive, ultra-luxury escape on your Windward Islands yacht charter. Known for its upscale villas, pristine beaches, and legendary Basil’s Bar, this private island attracts royalty, celebrities, and travelers seeking total privacy and sophistication.
The colorful market life of St. Vincent
St. Vincent delivers authentic Caribbean energy—from vibrant markets and local produce to black-sand beaches and volcanic scenery. Yacht charter guests love strolling through Kingstown’s markets, sampling island spices, and discovering the island’s cultural heartbeat.
Grenada’s waterfalls, spice farms, and underwater sculpture park
Grenada, the “Spice Island,” blends lush nature with world-class sailing. Explore cascading waterfalls, tour nutmeg and cocoa estates, and dive the famous Underwater Sculpture Park. It’s a diverse and exciting destination for both adventure-seeking and luxury-focused yacht charters.
Pristine beaches, reef-protected lagoons, and quiet anchorages
The Windward Islands are known for their powder-soft beaches, calm lagoons, and secluded anchorages—perfect for swimming, paddleboarding, and overnight stays. These serene locations allow crewed catamaran charters to enjoy peaceful evenings, turquoise water, and island-hopping at its finest
Best Time to Visit
The best time to charter the Windward Islands is December through June, when the tradewinds are steady, seas are calm, and weather is warm and dry.
Shoulder season (July–August) offers beautiful sailing but with a slightly higher chance of showers.
Hurricane season (Sept–Oct) has limited charters.
Local Information
Culture: A vibrant blend of French, English, Creole, and island traditions.
Currency:
Euro (€) in Martinique
Eastern Caribbean Dollar (XCD) in St. Lucia, St. Vincent, Grenadines & Grenada
Languages: English, French, and Creole variations.
Practical Tips:
Credit cards widely accepted
Anchorages are well-charted; marine parks may require permits
Island-hopping between short distances—ideal for families
Fresh seafood and local produce available island-to-island
Things to Do & See
Unforgettable Experiences
Snorkel with sea turtles in Tobago Cays
Hike the Gros Piton trail in St. Lucia
Explore the artisan shops & waterfront cafés of Bequia
Visit Basil’s Bar on Mustique
Dive shipwrecks off Grenada
Enjoy sunset beach BBQs on Mayreau
Swim in turquoise sandbars and reef-protected lagoons
Tour rum distilleries & cocoa plantations across the islands
Cuisine & Dining
Expect fresh seafood, island spices, Creole flavors, and French-Caribbean influences.
Signature dishes and experiences include:
Lobster BBQs in the Grenadines
Grilled mahi-mahi, snapper & tuna
Roti, curries, and Creole stews
French patisseries & cafés in Martinique
Rum tasting in St. Lucia & Grenada
Beach bars with local music and sunset cocktails
Getting There
Major airports with international access:
Martinique (FDF) – direct flights from Europe & connections via the Caribbean
St. Lucia (UVF) – direct flights from the U.S. & U.K.
Grenada (GND) – direct flights from U.S. & U.K.
Private jets frequently use Mustique (MQS), Canouan (CIW), and Union Island (UNI).
Most charters begin in St. Lucia, St. Vincent, Bequia, Canouan, or Grenada, depending on itinerary.
Photo Gallery
Related Itineraries
Adventure & Nature Expedition – Grenada to St. Vincent (10 Nights / 11 Days)
Grenada and St. Vincent offer an immersive nature expedition aboard a luxury catamaran, featuring rainforest hikes, coral diving, and island-hopping through the volcanic Grenadines.
The Superyacht Experience – St. Lucia, Bequia, Mustique and Tobago Cays
St. Lucia and the Grenadines offer a cinematic superyacht experience, blending high-end luxury and adventure across the exclusive islands of Bequia, Mustique, and the Tobago Cays.
Northeastern Caribbean – Nights that shimmer. Days that drift.
Experience the ultimate luxury yacht charter in the breathtaking Leeward Islands, blending adventure, relaxation, and world-class dining amidst stunning Caribbean landscapes.
Featured Charter Yachts
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