Leeward Islands Yacht Charter

Luxury Yacht Charter Guide To The Leeward Islands

Known as one of the most laid-back collectives in the Caribbean, the Leeward Islands in the Lesser Antilles is a true tropical heaven perfect for luxury sailing vacations.

Home to the glamorous St Barts, the wilder side of St Kitts and Nevis, Anguilla's natural beauty, and the iconic honeymoon escapes of Antigua and Barbuda, the Leeward Islands offer a multilayered experience of the big blue.

Alongside the quintessential paradise islands, aquamarine waters, secluded beaches, and some of the best snorkeling and diving sites on the planet, the Leeward Islands boast a well-tailored boutique scene, buzzing nightlife, and tangled tales of history and culture.

Yachts in the Leeward Islands

Motor yachts
Sailing yachts

Book Your Yacht Charter Now

Please fill in this short form, and a member of our professional charter broker team will get in touch to arrange your exclusive yacht charter experience.


Beautiful Meads Bay is one of the most beautiful beaches in the Caribbean island of Anguilla
Dramatic orange sunrise over the Park Hyatt St Kitts, a luxury upscale hotel resort in Christopher Harbor, Saint Kitts
Shipwrecks lay in ruins on the shores of Sandy Ground Beach, on the island of Anguilla in the Caribbean

Reasons to Charter a Yacht in the Leeward Islands

Exclusive Pleasures

Against a lush backdrop of blue and gold and fragrant frangipani, the Leeward Islands may have her rum shacks and sleepy fishermen, but on islands like St Barts, you can find unbridled luxury in this lavish little yacht charter destination. St Barts is thoroughly thoroughbred – beautiful boutique hotels, white linen restaurants, and a well-heeled yacht crowd sipping rum cocktails at classy bars. Those looking for five-star pleasure in a Caribbean playground will adore this end of the Leeward Islands.

Sublime Sands

From Anguilla’s sweet little Sandy Island to endless stretches of silica white sand and murmuring blue that make up Barbuda’s secret beach scene – the Leeward Islands pulls out all the stops for sun-lounging on scenic strips. The best thing about taking a yacht charter around these parts is that you get to hop from shore to shore, seeking out jeweled coral shores and towering palms.

Historic Ports

The Leeward Islands echo with colonial whispers of the past. Etched across these yacht charter haunts, you will find crumbling plantation ruins, turning windmills, and historic dockyards. Antigua is home to the famous Nelson’s Dockyard and Falmouth Harbor, where 18th-centuryth century naval ships used to drop anchor in the safety of the colonial English harbor.

The Yacht Crowd

The tiny Leeward Island of St Barts throws quite a shindig come Christmas and New Year. For the well-versed yacht charter crowd – St Barts is the place to be when the countdown to midnight begins. A-Listers galore can be found on the shores of St Barts over the holiday period, so for those looking to rub shoulders with celebrities, moor your yacht charter at the Port de Plaisance and prepare to party.

Islands of the saints guadaloupe
Edge of Pool Overlooking Lagoon on Caribbean Island of St. Barts, French West Indies
South Friars Bay, Saint Kitts and Nevis

Where To Visit In The Leeward Islands

Choosing among Leeward Islands yacht charter routes is no easy task.

With so many charming islands and anchorages out there, picking just one island group or destination can be tricky.

Below, we list some of our favorite Leeward Islands yacht charter spots to suit every taste:

US Virgin Islands

Home to picturesque cays, white sand beaches, and Captain Morgan rum distillery, the US Virgin Islands is an excellent starting point for Leeward Islands yacht charters.

Pristine national parks, beautiful anchorages, and abundant marine life will charm adventure seekers and nature lovers, while the Islands' vibrant nightlife and colorful social scene, paired with fine dining experiences and a relaxed atmosphere, provide opportunities to soak up the local culture.


A dream luxury yacht destination, Anguilla boasts no less than 33 sandy beaches, secret islets, and crystalline waters ideal for exploring by a glass-bottomed kayak or with a snorkel mask in hand.

Known for its stunning rock formations, corals, and secluded coves, Anguilla is among the most beautiful of the Leewards Islands.

ATV and bicycle trails abound here for those looking for outdoor activities, Little Bay is a fantastic spot for sublime sunsets, and the Four Seasons hotel adds a touch of luxury and class to relax and unwind.

St Martin

Divided between two nations, France (St Martin) and the Netherlands (St Maarten), this unique island is a curious blend of the sophisticated European chich and the laidback Caribbean vibes.

One of the more glamorous destinations in the region, St Martin is famous for its boutiques, casinos, duty-free shopping, and fusion cuisine as well as upscale resorts and beaches.

St Barts

One of the wealthiest spots in the Leeward Islands and the whole of the Caribbean, St Barts is a favored haunt of the rich and the famous. Yacht charters cruising into these turquoise blue waters will find more than a dollop of joie de vivre waiting.

The French touch brings a new height of sophistication. Here, yacht charter guests will find fabulous French restaurants like La Guerite and La Plage. Eden Rock is a must-visit retreat for those looking to step ashore and mingle with the superstar crowd.

While visiting the island, duck into the art galleries of red-roofed Gustavia, sip cocktails at chic Nikki Beach in St Jeans, and go diving down on the nature reserve of St Barthelemy.

St Kitts And Nevis

St Kitts and neighboring Nevis are a couple of the most exciting yacht charter stops in the Leeward Islands. From zip lines to hiking through lush rainforests, climbing volcanoes, and chugging along on the Sugar Train, there are plenty of options to keep active yachters entertained.

The Sugar Train is a must for those who want to ride one of the last and the most scenic railway lines in the West Indies. History lovers will enjoy the UNESCO 17th-century citadel that crowns the Brimstone Hill Fortress National Park. Over on Nevis, there's the pinprick colonial capital of Charlestown, buttery-soft beaches, and the enigmatic shadow of the volcano.

Antigua and Barbuda

One of the most beloved sailing destinations in the region, Antigua and Barbuda has deep yachting traditions and is known for its world-class regattas and sailing events.

Pink sand beaches, secluded coves, coral reef magic, and abundant marine life make Antigua and Barbuda a perfect destination for those seeking nature, tranquility, and a dream vacation in a tropical paradise.

History and culture aficionados will enjoy Antigua's capital St John with its colonial heritage and a pretty English harbor where candy-colored buildings stand like macaroons against the iridescent shades of blue.

Other Yacht Charter Destinations in the Leeward Islands

For those looking to explore every corner of the Leeward Islands region, Montserrat and Guadeloupe are two hidden gems worthy of a visit.

Tiny yet spectacular Montserrat is famous for its rainforest-covered mountains, black sand beaches, and coral reefs. The neighboring Guadeloupe belonging to France, is home to an active volcano, rum distilleries, palm-fringed beaches, and vibrant Creole and French culture.

When To Charter A Yacht In The Leeward Islands

The Leeward Islands is a year-round destination, but the best of the sailing season is between January and May.

The high season is from December to April, and the rainy season typically lasts between June and November.

The Cost of a Yacht Charter in the Leeward Islands

The cost of yacht charters in the region can vary between $20,000 - $70,000 per week for a motor yacht and around $16,000 - $30,000 for a sailing yacht or a catamaran.

Luxury crewed yachts can go for as much as $100,000 and upward per week depending on the boat's size, type, and onboard amenities available.

Book A Leeward Islands Yacht Charter Vacation Today

Leewards Islands is the perfect place for a dreamy cruise in the Caribbean Sea.

From stunning beaches, tropical forests, and the natural beauty of the sapphire waters and powdery white sand to luxury resorts, gourmet restaurants, and boutique hotels, Leeward Islands is the perfect place to combine smooth cruising in paradise with luxurious living.

Sailing yachts provide an unparalleled experience of complete freedom and traveling in style, dropping anchor whenever you please and exploring the islands on your own terms.

Explore your options for the Leeward Islands charter yachts today and get ready to sail away into that tropical horizon.

Leeward Islands FAQs

What is the difference between Leeward and Windward Islands?

Leeward and Windward Islands are two island groups in the Lesser Antilles, named after their geographical position in relation to prevailing winds. The Windward Islands include Barbados, St Lucia, Martinique, Grenada, and St. Vincent and the Grenadines.

The largest Leeward island is Guadeloupe, a department of France.

The cost of a yacht charter in the region can range from $15,000 - $30,000 per week on average. However, larger luxury yachts with unique features (personal chefs, onboard entertainment, water toys, and the like) can cost $50,000 - $100,000 or more per week.