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Guide To The Leeward Islands
Where turquoise waters meet laid-back island charm
This enchanting chain of Caribbean islands is a dream for yacht lovers, offering crystal-clear seas, sun-drenched beaches, and lush tropical scenery. The Leeward Islands combine natural beauty with a relaxed pace of life, making them the perfect setting for a sailing holiday.
Nestled between Puerto Rico and Dominica, the islands are blessed with both the gentle Caribbean Sea and the wilder Atlantic Ocean, creating diverse landscapes and experiences. Each island has its own personality — from glamorous Saint Barthélemy to untouched Dominica, historic Antigua, and vibrant Saint Martin — offering something unique to every traveler.
Cruising here means slipping easily from one paradise to another. You can explore volcanic peaks and coral islets, enjoy snorkelling and diving among thriving reefs and dolphins, or simply relax on deck with breathtaking views all around. Ashore, sample fresh seafood, Creole flavors, and island hospitality in local taverns and restaurants.
The Leeward Islands are best enjoyed between November and July, when warm breezes and sunny skies make for ideal sailing conditions. Whether you’re after tranquil coves, lively culture, or a mix of both, this region offers endless opportunities for discovery and leisure.
A yacht charter here promises more than just a vacation — it’s an invitation to experience the Caribbean at its most authentic and unforgettable.
Featured Yachts
SOUTH
$ 295,000
180 ft 12 guests 14 crew
from p/week
BLACKSHEEP
$ 80,000
123 ft 8 guests 6 crew
from p/week
TWO OCEANS
$ 32,000
55 ft 8 guests 2 crew
from p/week
INFINITY
$ 19,000
46 ft 6 guests 2 crew
from p/week
NAMASTE
$ 105,000
121 ft 10 guests 7 crew
from p/week
DELANA MAE
$ 26,000
50 ft 8 guests 2 crew
from p/week
ALANDREA1
$ 80,000
108 ft 10 guests 5 crew
from p/week
BEYOND
$ 21,900
50 ft 6 guests 2 crew
from p/week
MAMMA MIA
$ 95,000
120 ft 10 guests 7 crew
from p/week
SAMPLE ITINERARY
Antigua to Saint Martin
8-Day Leeward Islands Yacht Itinerary
Sailing from Antigua to Saint Martin is the perfect way to experience the beauty and diversity of the Leeward Islands. This week-long charter blends powder-soft beaches, vibrant culture, and chic island life, offering the best of the Caribbean at a relaxed pace.
Day 1 – Antigua
Begin your journey in Antigua, famous for its rich maritime heritage and 365 stunning beaches. Visit historic Nelson’s Dockyard, then set sail toward Nonsuch Bay for swimming, water sports, and a taste of laid-back island life.
Day 2 – Barbuda
Discover Barbuda, a secluded paradise known for pink sand beaches and the Frigate Bird Sanctuary. Snorkel among colorful reefs, stroll driftwood-strewn Atlantic shores, or relax on the calm Caribbean side.
Day 3 – St. Kitts
Cruise to St. Kitts, where lush rainforests and colonial history await. Explore the UNESCO-listed Brimstone Hill Fortress, enjoy golf or hiking, then end the day at a local beach bar.
Day 4 – Nevis
Cross to Nevis for a taste of authentic Caribbean charm. Wander tropical gardens, walk rainforest trails, or relax at Pinney’s Beach. Choose between a glamorous evening at the Four Seasons or cocktails at the famous Sunshine’s bar.
Day 5 – St. Barts
Arrive in chic St. Barts, renowned for luxury shopping, fine dining, and flawless beaches. Anchor at Saint-Jean Bay, visit world-famous Nikki Beach, or browse Gustavia’s designer boutiques and lively markets.
Day 6 – Anguilla
Enjoy Anguilla’s 33 dazzling beaches, perfect for sunbathing and swimming. In the evening, explore stylish beach bars or dine at gourmet restaurants, mingling with celebrities and locals alike.
Day 7 – Saint Martin
Sail into cosmopolitan Saint Martin, where French and Dutch cultures meet. Anchor at Pinel Island or Marigot Bay, enjoy watersports, or ride horses along pristine sands before a starlit dinner prepared by your private chef.
Day 8 – Departure
Wake for a final morning swim before disembarking in Saint Martin with memories of an unforgettable Caribbean escape.