Leeward Islands:
Caribbean Sailing & Yacht Charter Vacations
Set sail through the Leeward Islands Caribbean, a constellation of idyllic destinations where steady trade winds, turquoise bays, and vibrant cultures make for an unforgettable sailboat vacation. Stretching from the Virgin Islands to Guadeloupe, this island chain offers some of the top sailing destinations in the world — perfect for both seasoned sailors and first-time charter guests seeking sun, sea, and serenity.
Why Choose the Leeward Islands for Your Next Sailing Adventure?
Unmatched Variety
From glamorous French isles to unspoiled volcanic peaks, the Leeward Islands offer unmatched diversity within short sailing distances. Discover white-sand beaches, hidden anchorages, and lively harbors — all within a day’s sail.
World-Class Sailing Grounds
Calm seas, predictable breezes, and well-charted routes make sailing the Leeward Islands ideal for every skill level. This region’s mix of open passages and sheltered bays ensures adventure and relaxation in equal measure.
A Rich Blend of Cultures
Dutch, British, French, and Creole influences weave through the islands’ food, music, and architecture. From a morning croissant in St. Martin to steel drums at sunset in Antigua, each stop reveals a new rhythm of island life.
Highlights of the Leeward Islands: An Island-Hopping Guide
The Virgin Islands (BVI & USVI) – The Sailor’s Playground
A haven for leeward island charters, the Virgin Islands boast easy line-of-sight navigation, lively beach bars, and world-famous anchorages like The Baths, White Bay, and Cane Garden Bay.
The Chic Isles (St. Martin, St. Barts & Anguilla) – Glamour and Gastronomy
The northern Leeward Islands shimmer with style — St. Martin’s dual-nation charm, St. Barts’ luxury boutiques, and Anguilla’s powdery beaches create a sophisticated sailing circuit.
The Historic & Volcanic Isles - St. Kitts & Nevis, Montserrat, Saba & Sint Eustatius – History and Hiking
Sail among green peaks and colonial forts. Explore rainforests, dormant volcanoes, and the warmth of island hospitality often missed by large cruise ships.
The Sailing Capitals (Antigua & Barbuda, Guadeloupe) – Beaches and Blue Water
Home to 365 beaches and world-class regattas, Antigua is a sailor’s dream. Neighboring Guadeloupe adds French flair with natural reserves, waterfalls, and Creole cuisine.
How to Get to the Leeward Islands
The main hubs
The Leeward Islands location makes them easily accessible from the U.S. and Europe. Key international gateways include:
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St. Maarten (SXM)
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Antigua (ANU)
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St. Thomas (STT)
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Guadeloupe (PTP)
Inter-Island Travel
Island-hopping is simple with regional airlines like LIAT, Winair, and Air Caraïbes, as well as inter-island ferries connecting smaller ports. Many travelers combine short flights with scenic sea passages for a seamless sailing journey.
Best Time to Visit the Leeward Islands
Peak Sailing Season
December–April:
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Air Temperature: 77–82°F (25–28°C)
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Water Temperature: 78–81°F (26–27°C)
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Wind: 15–22 knots, steady easterly trade winds — ideal for sailing
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Waves: 2–5 ft, calm inside bays and anchorages
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Precipitation: Low (1.5–3 in/month)
Dry, breezy, and buzzing with regattas — this is the best time for consistent winds and festive island life. Clear skies and low humidity make it perfect for both cruising and land excursions.
Shoulder Season
May, June & November:
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Air Temperature: 80–86°F (27–30°C)
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Water Temperature: 81–84°F (27–29°C)
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Wind: 10–18 knots, slightly lighter than winter
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Waves: 2–4 ft, calm to moderate
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Precipitation: Moderate (3–5 in/month)
Enjoy quieter marinas, calm seas, and excellent value. The sea remains warm, and occasional showers refresh the landscape — ideal for photographers and relaxed sailors.
Off Season
July–October:
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Air Temperature: 82–89°F (28–32°C)
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Water Temperature: 83–86°F (28–30°C)
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Wind: 8–15 knots, variable at times
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Waves: 2–6 ft, depending on weather systems
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Precipitation: Higher (5–7 in/month, with brief tropical downpours)
These months bring lush green hills and vibrant local festivals. While it’s hurricane season, most systems pass north, and careful planning allows for safe and rewarding adventures.
Activities: Beyond the Deck of Your Yacht
Beaches & Watersports
Swim, paddleboard, or kayak through protected lagoons. Highlights include Shoal Bay (Anguilla) and Half Moon Bay (Antigua).
Diving & Snorkeling
Explore coral gardens, turtle sanctuaries, and shipwrecks like RMS Rhone. The region’s marine biodiversity makes it a diver’s paradise.
Historical Exploration
Tour Brimstone Hill Fortress, Nelson’s Dockyard, or the preserved ruins of Montserrat — echoes of centuries-old maritime heritage.
Fine Dining & Nightlife
From barefoot beach bars to Michelin-rated dining in St. Barts, the Leeward Islands vacation blends island flair with cosmopolitan indulgence.
Leeward Islands Sailing & Yacht Charter Options
Bareboat Charters
Perfect for experienced sailors craving independence. The BVI and St. Martin offer excellent marinas and provisioning facilities.
Crewed & Luxury Yachts
Enjoy five-star comfort aboard a private vessel with a professional captain and chef — ideal for honeymoons or family celebrations.
Cabin Charters
Solo traveler? Join a leeward island charter by-the-cabin charter and share the journey with like-minded adventurers.
Scuba Diving Liveaboard Safaris
Dive by day, relax by night — a spectacular way to combine exploration and comfort beneath the Caribbean waves.
Why Choose Neptune’s Daughter for Your Leeward Islands Charter?
At Neptune’s Daughter, every voyage is tailored to you. From yacht selection to route planning and travel logistics, our experts craft seamless experiences across the Leeward Islands Caribbean. We vet every boat, crew, and partner — so you can sail with confidence and ease.
Start Planning Your Trip to the Leeward 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: Bareboat charters start around $4,000/week; crewed yachts from $12,000/week including meals and services.
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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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Which Leeward Island is best for beginners?
The British Virgin Islands offer the calmest conditions and best facilities for first-time sailors. Sailing around St. Martin, Anguilla and St. Barths is also highly recommended for beginner sailors.
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What country owns the Leeward Islands?
The Leeward Islands span several nations and territories: - British: Anguilla, the British Virgin Islands, and Montserrat - French: Guadeloupe and St. Barts (Saint-Barthélemy) - Dutch: Sint Maarten, Saba, and Sint Eustatius - Independent Nations: Antigua & Barbuda, St. Kitts & Nevis, and Dominica - U.S.: The U.S. Virgin Islands (St. Thomas, St. John, and St. Croix) This blend of British, French, Dutch, American, and independent cultures gives the Leeward Islands Caribbean its rich diversity and timeless sailing appeal.
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What are the names of the Leeward Islands?
The chain includes the Virgin Islands, Anguilla, St. Martin, St. Barts, Saba, Sint Eustatius, St. Kitts, Nevis, Montserrat, Antigua, Barbuda, and Guadeloupe.
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What are the Leeward Islands?
They are part of the northern Lesser Antilles, lying where the Caribbean Sea meets the Atlantic Ocean.
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Where are the Leeward Islands located?
The Leeward Islands location extends from the Virgin Islands in the north to Guadeloupe in the south, bordering the Windward Islands.
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Are the Leeward Islands good for year-round sailing?
Yes, though December–April offers the most reliable weather and calm seas.
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Can I combine a Leeward Islands charter with other destinations?
Absolutely — many itineraries link with the Windward Islands or the Dutch Antilles for extended Caribbean adventures.
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What makes sailing in the Leeward Islands unique?
The Leeward Islands combine gentle trade winds, short island-hopping distances, and world-class marinas — perfect for both new and experienced sailors. You can explore multiple countries within a single week, discovering diverse cultures, cuisines, and landscapes, all under steady Caribbean sunshine.
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Do I need a visa or special documents to sail in the Leeward Islands?
Most travelers from the U.S., Canada, and Europe do not need a visa for short visits, though each island follows its own entry rules. Passports are required, and some territories may request customs clearance when sailing between nations (for example, between the British Virgin Islands and St. Martin). Your Neptune’s Daughter travel concierge will guide you through all entry requirements and clearance procedures before your trip.