Yacht Charter Leeward Islands

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If you crave a Caribbean idyll with white-sand beaches, lush rainforests, and relaxed charm, the Leeward Islands, which have all your essentials in abundance, are definitely the yacht charter destination for you.

Spanning some 120 miles from Anguilla in the north to Dominica in the south, the islands link together in an enticing chain. From the sophisticated French island of St. Barths, which exudes a South-of-France feel with a tropical backdrop, to the old-world charm of Antigua, where you can visit forts and plantations from antiquity, both ashore and on the water, you’ll find an exotic concoction of modern chic and laidback Caribbean attitude.

Leeward Islands Yacht Charters

The Leeward Islands have long been a haven for seafarers, and today’s yachtsmen consider the sheltered waters to be some of the finest bluewater cruising grounds in the Caribbean sea. Step ashore during your yacht charter to discover a colorful mosaic of culture, cuisine, and natural beauty. You will find that every island has its own unique character and charm, inspiring you to discover the next as you cruise from Antigua to St. Martin during luxury Leeward Island yacht charters.

An Introduction to the Leeward Islands Yacht Charter


Spend a few days discovering Antigua’s 365 beaches before embarking on your yacht in English Harbor. The sandy beaches are the island’s primary attractions, but its appeal also lies in its maritime history – combined, they have placed the island in pole position on the Caribbean map.

St. Barts

With a distinctly French flavor, you’ll find a certain je ne sais quoi in St. Barths, the Leeward chain’s most exclusive and elegant island. The Caribbean’s take on the Côte d’Azur, this is your place to go for pristine beaches and gourmet restaurants. Its capital, Gustavia, is one of the prettiest in this part of the world, and the port is the perfect place to berth while you step ashore and browse the designer boutiques.

St. Kitts and Nevis

The rolling sugarcane fields, plantation ruins, and merchant houses on St. Kitts offer you insight into a colonial past. It’s worth spending a few nights ashore, either staying at one of the boutique hotel properties housed in the former plantation houses or one of the few luxury resorts that can be found on the island. There is also the opportunity to berth in the fully serviced Christophe Harbour, perfectly positioned to the south of the island for access to the capital Basse Terre and all the abundance of historical sites – remnants of the island’s colonial days when both the British and French were based on St. Kitts. Just two miles across the strait lies the lesser-developed island of Nevis, with its Robert Trent Jones II golf course and Pinney’s Beach — both of which are worth stepping ashore for.


Further north, the tiny island of Anguilla radiates an unspoiled innocence. Known for its magnificent beaches and crystal-clear waters, if you want to get away from it all, this is the place.

St. Maarten

Most itineraries finish in St. Martin (or Antigua) as both have international airports. The smallest island in the world to be split into two nations, St. Martin/St. Maarten is a wonderful mix of cultures. Known by many as the gourmet capital of the Caribbean, you will have your choice of Michelin-star restaurants and eclectic nightlife here. Whether you wish to discover the deserted cays or fashionable harbors, or a little bit of both, your Northrop & Johnson charter expert will provide ample opportunities to discover the cream of the Caribbean.

Get in touch with a yacht broker in the Leeward Islands

Northrop & Johnson is a leading international yacht brokerage with access to the best and most luxurious yachts for charter, including in the Leeward Islands. With offices in the heart of Miami, our yacht charter brokers boast unparalleled Leeward Islands expertise and market intelligence. We take pride in listening to our client’s needs and crafting exceptional charter itineraries in and around the Leeward Islands. Rent a superyacht in the Leeward Islands and enjoy the ultimate vacation on the water. Contact our yacht brokers in Miami today if you want to charter a luxury yacht in the Leeward Islands. We will be thrilled to assist you on your yachting journey, showing you the sample itinerary before creating a unique experience for you.

Other yacht charter destinations closest to the Leeward Islands

Charter Highlights Leeward Islands

  • Explore the UNESCO World Heritage Site Nelson's Dockyard in Antigua – the only working Georgian dockyard in the world
  • Play a round at the Four Seasons Resort Nevis 18-hole golf course
  • Hike St. Eustatius' extinct volcano, known as the Quill
  • Dine at the François Plantation, Villa Marie Saint-Barth
  • The southern tip of St. Kitts offers spectacular diving
  • Explore Anguilla and appreciate the relaxed atmosphere the island offers
  • Visit this tropical paradise and stunning beaches, make reality the dream vacation for nature lovers
  • Reach the ideal destination in the Lesser Antilles to observe the natural beauty of the tropical islands' sunsets from a beautiful beach or onboard your sailing yacht
  • Look for quiet anchorages for your motor yacht in Barbuda, one of the most unscathed islands
  • Find your favourite coral reef between Kitts and Nevis, and St Maarten
  • Be part of the many sailing yachts that every year visit the English Harbour in Antigua, famous due to the annual regattas
  • Spend a night in St Tomas, famous for its vibrant nightlife
  • Smooth cruising by night between two islands, such as Antigua and Barbuda, will make you feel like you are in a movie: calm sea, shiny stars and untouched natural beauty

Leeward Islands Yacht Charter Itinerary

For a full list of all available itineraries & excursions, or to chart your own course please inquire.

Best Yachts for Charter in the Leeward Islands

Motor Yachts for Charter in the Leeward Islands

Sailing Yachts for Charter in the Leeward Islands

Leeward Islands Yacht Charter FAQ

Why charter a yacht in the Leeward Islands?

There are so many reasons why you should charter a sailing or motor yacht in this tropical paradise: they are known for their picturesque cruising grounds, spectacular diving with vibrant coral reefs and marine life, lush interiors, and spectacular cuisine, including gourmet restaurants. Each of these islands boasts its own unique culture and varied selection of experiences, ensuring there is always something new to discover. And, with hundreds of islands and islets to explore, you’re always going to find a Leeward Islands yacht rental experience that is unique to you. If you want to book crewed yacht charters, Northrop & Johnson can assist. We boast a superb charter yacht fleet, including motor yachts, sailing boats, and catamarans. Contact our team today; we look forward to helping you.

What sets the Leeward Islands apart from other Caribbean yacht charter destinations?

The Leeward Islands’ rich history and culture, scenic beauty, and diverse islands set these islands apart. Whether you are seeking to enjoy your days at the most exclusive beach clubs or relax on a secluded beach all to yourself, the Leeward Islands offer experiences that match your desired Caribbean getaway. Northrop & Johnson offers the best selection of rental yachts in the Leeward Islands and provides tailored itineraries for an incredible vacation on the water. Contact our team today and let us arrange your Leeward Islands yacht rental.

What are the must-visit destinations in the Leeward Islands?

The Leeward Islands offers a wonderful range of things to see and do for everyone, from culture enthusiasts to thrill seekers. Some of the best must-visit destinations in the Leeward Islands include:

  • Shop designer boutiques in Gustavia, St. Barts
  • Soak up the sun at Nikki Beach, one of the most exclusive beach clubs in St. Barts
  • Hike the Mount Liamuiga Volcano and the surrounding tropical forests on the beautiful island of St. Kitts and be rewarded with spectacular panoramic views
  • Experience the thrill of the world’s steepest zip line in St. Maarten, boasting 2,800 ft of cable that drops more than 1,000 ft.
  • Visit the Baths on Virgin Gorda in the British Virgin Islands, a beach that boasts huge slabs of granite caused by volcanic activity.
  • Sip on a Painkiller cocktail at the iconic Soggy Dollar Bar on Jost Van Dyke, British Virgin Islands.
  • Explore the beautiful, secluded beaches of the US Virgin Islands and the stunning coral reefs below the waves.
  • Swim with stingrays at Stingray City, Antigua.

What are the best restaurants on a Leeward Island yacht charter vacation?

The Leeward Islands boasts superb gastronomic dining. Some of the best restaurants to visit include:

  • L’Atelier de Joel Robuchon, St. Barts – enjoy exquisite French cuisine at this stunning waterfront restaurant in Gustavia, St. Barts. Enjoy a tasting menu of signature Joel Robuchon dishes in the open kitchen or in the dining room.
  • Spice Mill Restaurant, St. Kitts – dine at this elegant waterfront restaurant and enjoy an internationally inspired menu of dishes made with the best locally sourced produce, including from the restaurant’s own garden.
  • Sol e Luna, Orient Bay, St. Martin – feast on French classics fused with Caribbean flavors at this romantic restaurant that is reminiscent of a tropical garden. Sit on the wraparound porch and enjoy incredible views of the Orient Bay.
  • Brandywine Estate Restaurant, Tortola, British Virgin Islands – this fabulous restaurant offers a menu of Mediterranean bistro cuisine made with the finest ingredients, including locally sourced seafood. Enjoy delightful dishes coupled with magnificent views of the sea.
  • Savant, St. Croix, US Virgin Islands – St. Croix is considered the culinary capital of the US Virgin Islands and St. Croix doesn’t disappoint. Enjoy a menu full of locally sourced Caribbean classics alongside an excellent wine menu.
  • The Cove Restaurant, Blue Waters Resort & Spa, Antigua – This gourmet restaurant is considered one of the best fine-dining destinations in Antigua. Enjoy a selection of French and Caribbean-inspired dishes coupled with stunning cliff-top views of the Caribbean Sea.

When you book a Leeward yacht rental with Northrop & Johnson, our charter brokers can help secure reservations at the best and most exclusive restaurants.

Where should I start my yacht charter in the Leeward Islands?

St. Maarten or Antigua are often the best places to start Leeward Islands yacht charters. This is because both islands have international airports, providing easy connections to the US via commercial and private jets. When you book a crewed yacht charter with Northrop & Johnson, we will help you arrange travel to and from your yacht, providing a seamless door-to-deck service that is second to none. Contact our team today and let us help you realize your dream of chartering a luxury yacht in the Leeward Islands.

What is the best time of year for a yacht charter in the Leeward Islands?

The best time of year for yacht charters in the Leeward Islands is during the winter months when the days are sun-drenched, there is little chance of rain, and the weather is less humid. The Leeward Islands yacht season typically runs from November to April, with the high season being December and January. The low season is during the summer months, which also coincides with the Leeward Islands’ hurricane season. The weather is still wonderfully warm and sunny; however, if you do visit during the summer months, there is a higher chance of inclement weather, including hurricanes. If you book a luxury yacht rental with Northrop & Johnson, our charter brokers will keep a close eye on the weather, especially during the summer months.

Are there any environmental or conservation guidelines I should be aware of during my yacht charter in the Leeward Islands?

The Leeward Islands have several marine protected areas and national parks, including fishing, diving, and anchoring restrictions. If you plan on fishing, you should also follow local fishing regulations, which include restrictions on what you can catch at certain times of the year. Your private yacht’s crew will be up-to-date on environmental and conservation guidelines and ensure the yacht always remains compliant.

How much is a Leeward Island yacht rental?

The cost of a Leeward Islands yacht rental will depend on multiple factors, including the size of the vessel, its onboard amenities, the year of build, the shipbuilder, your cruising itinerary, and the length of your charter getaway. The entry point for a one-week Leeward Islands yacht rental starts at around US$50,000 for smaller-sized boats, with the world’s finest mega yachts chartering for US$ 1 million. Northrop & Johnson has access to a superb fleet of yachts for charter in the Leeward Islands, including luxury motor yachts, sailing yachts, and multi-hull vessels such as catamarans. Contact our team and let us connect you with your ideal Caribbean luxury yacht charter.

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