Leeward Islands Yacht Charter Guide for 2026-2027
Discover the secrets of St. Martin, St. Barths, Anguilla, and Antigua as you vacation on your luxury yacht charter in the Leeward Islands in 2026 and 2027
Leeward Islands Crewed Motor Yachts | Leeward Islands Crewed Catamarans
Leeward Islands Destinations | Map
St. Barths Luxury Crewed Motor Yacht Itinerary | St. Martin Luxury Crewed Catamaran Itinerary
The Leeward Islands are an eclectic collection of volcanic island formations that lie to the east of Puerto Rico and the Virgin Islands. Part of the Lesser Antilles and arguably one of the most beautiful destinations in the world, the Leeward Islands are a perfect choice for your next yacht charter on a luxury crewed catamaran or crewed motor yacht. As you explore each of these distinct locales, expect to find unspoiled private beaches, chic shops, superb restaurants, and stunning coastlines.
With everything from secluded island paradises to lively towns with thriving nightlives, discover the perfect 7-day crewed motor yacht escape on board your Leeward Islands charter holiday. There is no better way for you and your family or friends to experience these waters.
Leeward Islands Yacht Charter Guides and Itineraries
Leeward Islands Crewed Motor Yachts
A luxury crewed motor yacht is the most exclusive way to see the Leeward Islands. With private cabins, spacious sundecks, and an attentive crew tailoring every detail of your trip, the week promises to be the perfect balance of luxury and adventure. For Christmas and New Year's there is no better place to be than St. Barths, viewing the fireworks from the deck with a glass of celebratory champagne. During your week long charter you will hop between famous beach clubs, waterfront restaurants, and glassy bays fit for water toys. Whenever you are ready to escape the crowds, simply head back to your private yacht and enjoy the views!
St. Barths Crewed Motor Yachts St. Martin Crewed Motor Yachts
Leeward Islands Crewed Catamarans
Cruise effortless between the Leeward Islands on a luxury crewed catamaran. With twin hulls, you benefit from extra stability, private cabins, and expansive deck space for leisure. As you make your way toward Anguilla, take advantage of the foredeck trampolines. There is nothing quite like the feeling of the wind at your back and an occasional sea spray, as you look onward toward endless views of turquoise waters. During your weekly charter, a professional and dedicated crew will take care of your every need.
St. Barths Crewed Catamarans St. Martin Crewed Catamarans
Leeward Islands Destinations
St. Martin | St. Barths | Anguilla | Antigua
Stretching across the northeastern Caribbean, the Leeward Islands combine vibrant culture, stunning coastlines, and exceptional cruising conditions. Sail between the glamour of St. Barths, the lively atmosphere of St. Martin, the pristine beaches of Anguilla, and the secluded bays of Antigua, discovering a different side of the Caribbean at every stop.
Map of the Leeward Islands
St. Martin
As the center of yachting and yacht racing in the Caribbean, St. Martin is the ideal destination to embark upon your Leeward Islands yacht charter. The island has a rich history and currently boasts dual French and Dutch nationality. In fact, the island is divided almost in half between the countries, and as a result, there is a fantastic mixing of cultures, with everything from French boulangeries to enticing Dutch beach clubs; there is something for everyone here.
You can fly into Princess Juliana International Airport and make a simple transfer to the waters of Simpson Bay, the Caribbean's largest lagoon. It is the perfect place to embark and set out upon your bespoke charter vacation. With nightclubs and fine dining available on the Dutch side and classical Caribbean towns like Marigot on the French, there is so much to discover here.
Anywhere you venture on this island, you will find beautiful beach resorts and have the opportunity to get a taste of the Caribbean lifestyle. For more information about the island, check out our St. Martin Yacht Charter Guide or reach out to one of our Charter Experts to start planning your perfect getaway.
St. Barths
St. Barths is a small yet highly desirable luxury charter destination with delicious food and wine, and an unmistakable sense of style and fashion. The island brings a new flavor of sophistication to the relaxed atmosphere of the Bahamas, making this paradise like a taste of the Mediterranean. This chic island is home to gorgeous, unpopulated beaches, fine restaurants, and fashionable shopping, and with Gustavia Harbor docking up to sixty yachts (200’ maximum) in the inner harbor and another 100+ anchorages in the outer harbor, there is no better time to charter a yacht in St. Barths.
For more than forty years, the island has hosted the annual St. Barths Music Festival, showcasing the best musicians, singers, and composers from renowned orchestras. Charter a yacht and live in unrivaled comfort as you listen to the finest music in the world. This island will give you a taste of pure luxury, whether on board a modern motor yacht, a sailing yacht, or a catamaran. With secluded beaches and some of the best restaurants in the Caribbean all over for you to discover, your visit to St. Barth's will be unforgettable. Find out more about chartering a crewed yacht from St. Barths or including it in your bareboat itinerary by visiting our St. Barths Yacht Charter Guide.
Anguilla
With its plethora of secluded beaches, Anguilla was one of the Caribbean’s best-kept secrets, but it is slowly becoming one of the most exclusive and sought-after destinations in the region. This British island will have you driving on the left side of the road and enjoying the palpable friendliness of the locals as you explore its hidden corners and relax on the beaches. Known as the culinary capital of the Caribbean, you are certain to find delectable cuisine and unmatched comfort in any of the restaurants on the island.
Charter clients can fly into the Anguilla airport directly now that the airport has been expanded for private jets or Anguilla is just six miles and twenty minutes by boat to the north of St. Martin and Princess Juliana International Airport. Once you are there, head to West End Bay for stunning sunsets, and cliff-top hikes, or while away the hours swimming the shallow waters of Forest Bay. With miles of empty beaches, even in the height of the season, you will feel truly relaxed and at one with nature exploring the shores of this beautiful island.
For more information on charters available from Anguilla visit our Anguilla Yacht Charter Guide or reach out to one of our Charter Experts.
Antigua
Antigua is home to 365 beaches and an exciting colonial history with the island's main harbor featured in the famous book Nelson's Navy. This must-see destination is surrounded by colorful coral reefs, and thriving schools of fish, offering an intimate view of its vibrant underwater world. Whether you want to snorkel or dive, many of our crewed charters include equipment for exciting expeditions! Visit the bustling town of St. Johns for fabulous shopping and some of the best dining experiences in the Caribbean.
On your charter, venture over to the nearby uninhabited island of Barbuda and experience its vibrant tropical wildlife and stunningly secluded beaches where you can disconnect from the outside world. Find your own piece of paradise here and watch one of the most beautiful sunsets in the world from the beach or your yacht. If you want to find out more about chartering a yacht from Antigua, visit our Antigua Yacht Charter Guide to start planning your dream vacation.
Our Caribbean Destinations: The Windward Islands | Antigua | British Virgin Islands | Grenada | Guadeloupe | Martinique | Spanish Virgin Islands | St Barths | Anguilla | St Martin/Maarten | St Lucia | St Vincent and the Grenadines | US Virgin Islands - St Thomas, St John, St Croix
