Leeward Islands Yacht Charters

Explore the Leeward Islands on your luxury yacht charter in the Caribbean

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  • The Leeward Islands offer the perfect combination of luxury and adventure, making them the perfect destination for yacht charters. This enchanting Caribbean archipelago boasts perfect white-sand beaches with crooked palms, celestial blue waters and impeccable views.

    A Leeward Islands yacht charter offers a perfect escape to the Caribbean.

    After watching the sunrise over the horizon, dive into the depths of the sea to see the locale’s vibrant corals and colorful fish. When you come up for air, head further inland to explore its dense rainforests or hike its towering volcanic peaks. Dotted with the remains of old military forts and sugar plantations, the Leeward Islands are bursting at the seams with interesting history.

    Leeward Islands Highlights

    • Natural beauty
    • Varied cultural history
    • Exceptional diving and snorkeling
    • Luxury resorts and spas
    • Great party spots

    Best Time to Charter in the Leeward Islands

    When to go: mid-December through May

    December through May is considered high season in the Leeward islands, with Christmas and New Years being the most popular time for yacht charters. Most yachts charge a premium for Holiday charters because of high demand.
    Many yachts relocate to other charter areas after May (from the Bahamas to New England to the Mediterranean) so the selection of charter yachts is limited in the summer months.

    Why Charter a Yacht in The Leeward Islands?

    Antigua view of English Harbour

    • Natural Beauty of the Leeward Islands

    From the coastal beaches of Anguilla and St. Bart’s to the volcanoes of St. Kitts, the Leeward Islands feature lush tropical landscape and miles of sandy beaches. Lucky charter guests can explore this tropical paradise up close and personal.

    • Varied Cultural History

    Though different in nature, the Leeward Islands all share a reverence for other cultures – especially considering their diverse origins. Take St. Maarten, for example, which houses two cultures in one; one half of the island is French, while the other is Dutch.

    • Exceptional Diving

    With its vibrant corals and tropical fish, the Caribbean Sea is a prime spot for water sports enthusiasts; especially diving and snorkeling. With its translucent blue hues and mild temperatures, this revered body of water is the perfect place to spot the most surreal sea life – even those swimming miles and miles away.

    • Luxury Resorts and Spas

    While some of the Leeward Islands are simple in nature, others were seemingly designed to cater to the rich and famous. Head to St. Bart’s crystal coast for some of the world’s most desired haunts: like the Eden Roc, Nikki Beach and more.

    • Unspoiled Cruising

    Floating seemingly off the radar in the Caribbean Sea, the Leeward Islands offer perfect breezes for smooth cruising among islands.

    Leeward Islands Yacht Charter Itinerary

    Leeward Islands itinerary map

    DAY 1: St Martin

    St Maarten - Marigot
    Your luxury yacht charter will begin in the iconic Simpson Bay in St Martin. This dual-nation island comprises Sint Maarten, the Dutch side, as well as St. Martin, the French side. Spend the afternoon shopping in Sint Maarten’s capital Philipsburg. In the evening, find the most incredible French Fare in St. Martin.

    DAY 2: St Barth’s

    St Barths - Gustavia
    St. Barth’s may be thousands of miles from Paris, but the French cuisine, luxury shopping and lavish lifestyle all can be found on this tiny bit of paradise. Renowned as a winter haven for the elite, there are few better places to spend the day.

    Head to Nikki Beach for afternoon cocktails or find a picture-perfect spot on the sand at Anse de Grande Saline, one of St. Barts most-revered beaches. In the evening, enjoy a one-of-a-kind meal with a view at On the Rocks in the always impressive Eden Rock hotel.

    DAY 3 & 4: St Kitts

    St Kitts palm trees
    St. Kitts is an outdoor lover’s paradise. Boasting beautiful, tropical rainforests, hiking and diving, there are plenty of activities to keep you busy. Grab your scuba gear and head for Brimstone Shallows, where the crystalline waters offer perfect views of fish and the occasional reef shark. Land lovers will enjoy exploring Mount Liamuiga. This stratovolcano, with a peak reaching 3,792 feet, is one of the tallest in the

    Golf enthusiasts in your yacht charter group will be keen to play a round at the Royal St. Kitts Golf Club. This 18-hole championship course is one of the must-do activities on the island. For those who prefer a different means of relaxation, the Emerald Mist Spa is worth the visit. And the St. Kitts Marriott Resort has a casino for those interested in playing their luck.

    DAY 5: Nevis

    Nevis island
    The unspoiled island of Nevis is just a quick cruise from St. Kitts. Here, nature abounds — keep an eye out for the wild Green Vervet Monkeys — and you truly feel like you can get away from it all. Spend your day ocean-side playing with the yacht’s water toys, on the tender casting a line, or enjoying some quiet time on Lovers Beach. This lush island is the perfect place to hike, bike or horseback ride.

    DAY 6: St Eustatius (Statia)

    Caribbean snorkeling
    The tiny island of St. Eustatius, affectionately known as Statia, is a former Dutch province. Here, you will find incredible diving and snorkeling opportunities. Coral reefs and wrecks abound. Spend the day exploring below the waterline. If you’ve had your fill of the sea, an extinct volcano, known as the Quill, is the perfect place for an afternoon hike. Guides are available for this adventure.

    DAY 7: Anguilla

    Anguilla island sandy beach
    Enjoy a leisurely day in Anguilla and take advantage of the exemplary service of your crew and enjoy the surrounding beaches, beach combing, and beach bars. If there are golfers in your party, this is great opportunity to hit the greens. Dine ashore if you like, as there are some good restaurants on the island. Anchor in Rendezvous Bay for the night.

    DAY 8: St Maarten

    St Maarten airplane landing
    Stroll through downtown Marigot, enjoy the markets, hike up to the top of Fort Louis, overlooking Marigot Bay or take the Jet skis out for one last run before disembarking and ending your yacht charter. Prepare for departure.