Yes, take me there!
Charter yachts anchored in English Harbor, Antigua

Leeward Islands Yacht Charter Guide

Embraced by both the Atlantic and Caribbean seas, your laid-back and unplugged luxury yacht charter experience in the Leeward Islands offers tremendous variety.

Cultural imprints inherited from the islands’ British, French and Dutch colonial history, geological diversity, discoveries awaiting below the turquoise waters’ surface, and vacation activities to satisfy everyone’s interests, The Leeward Islands is a complete once-in-a-lifetime yachting destination.

While some islands are still part of the overseas territories of European nations, each island has its own local charm and traditions.

With multiple stops in one itinerary, the close distance between the islands allows for easy island-hopping and exploration.

10 reasons to plan a Leeward Islands yacht charter

Woman sunbathing on a Leeward Island
Remote Leeward Islands white sand beaches only accessible by yacht
  1. The variety of different cultures, geography and activities on this itinerary has something for everyone.
  2. Dreamy white sand beaches, sunshine and sparkling turquoise waters will instantly relax you.
  3. Try local Caribbean delicacies expertly prepared by your private chef on board.
  4. Swim among the tropical fish, sea turtles and colorful coral reefs.
  5. Sway to island rhythms with local live music.
  6. Decide if you prefer white, amber or gold rum (and which island makes the best cocktail).
  7. Traverse tropical forests as you hike dormant volcanoes.
  8. Party at the world’s prime beach clubs.
  9. Take in the colonial and plantation history lessons at UNESCO sites.
  10. Learn to love life from the locals. Don’t worry, be happy - Caribbean style.

1 week Leeward Islands yacht charter itinerary

Map of the Leeward Islands 7 days yacht charter itinerary
Suggested one week Leeward Islands luxury yacht route

Please Note: The dots indicate the approximate places where the yacht anchors for the night.

This proposed itinerary is meant to inspire you when organizing your trip along the Leeward Islands on a luxury yacht charter.

Remember that this is not a fixed itinerary and you can adapt the planning to your preferences.



Colorful seaside wooden buildings in Antigua, Caribbean
Antigua, a slice of paradise - Leeward Islands

Laid-back with a soulful vibe, Antigua sets the relaxed mood for your imminent Leeward Islands yachting experience.

As you board your ship in this premier world-class sailing destination, your yacht crew is waiting to fulfill your every desire for provisioning. Gourmet meals, water sports activities and private tour experiences await you. Prepared for the sophisticated traveller, Antigua will not disappoint you.

Ease into the cheerful ambience as you stroll among the typical wooden buildings with pastel-coloured shutters and smiling local residents.

In the port of St. John's, visit the Antigua Distillery to decide if you prefer the white, amber or gold rum variety. Rum will spice up your Caribbean-style cocktails on board your yacht this week.

Delve into how British colonial history made its mark. Visit Fort James' canons protecting a strategic point of the northern bay, once an important trading post for sugar. The centre of the island, Betty's Hope Historic Sugar Plantation, is worth a tour. The south boasts the island's UNESCO World Heritage site, Nelson's DockYard.

If you seek seclusion, the indented coastline of coves is a haven to be leisurely explored aboard your private yacht.

Along the western shores, the bright white calm sand beaches are what your imagination conjures up when dreaming of a Caribbean Sea holiday.

Featured activities

  • Scuba dive the Carlisle Bay Marine Park to explore shipwrecks.
  • Anchor near an idyllic uninhabited island like Prickly Pear.
  • Seek adventure with a hike in the rugged backcountry, trail blaze with a buggy or kayak in a mangrove.


The Gravenor Bay white sand beach in Barbuda, Leeward Islands
Gravenor Bay’s fine white sand beach - Barbuda

Antigua's twin island, Barbuda, invites you to dive with the tropical fish and sea turtles in the coral reefs below the turquoise water. Then, come onshore to the long stretch of white sand beach named after Princess Diana. This beach is tranquil, even in peak season and is perfect for a stroll and some exercise.

The island is a natural paradise to spot a wide variety of Caribbean birds: gulls, herons, wading birds, hawks, osprey, hummingbirds, mockingbirds, grackles, The Tropic Bird - and the coveted endangered West Indian Whistling Duck.

Ask your Captain where the pink sand beach might be located on the island. The currents shift, so sometimes, Pink Sand Beach is not pink, and the pink sand can be found further north.

Featured activities

  • Savor locally caught lobster cooked to perfection by your yacht’s chef.
  • Hike to Darby’s cave with an enchanting interior ecosystem of palmetto palms, bats, birds and frogs deep within.
  • Sail to The Caves of Two Foot Bay to take a hike and see the views.


Sunset behind palm trees with a view to Nevis Island, Leeward Islands
View of Nevis Island

While sunbathing on the deck of your private yacht, Nevis Peak, a 3,232 dormant volcano, comes into view against a backdrop of lush greenery and the sea.

If you dare to touch the clouds above the peak, a professional guide is needed to ascend the steep and slippery path. The tropical rainforest adventure is perfect for the physically fit and energetic young guests at your party. Or, they can stay at sea level to kayak, windsurf or snorkel.

Meanwhile, for those needing a more relaxing activity, take a tour of Charlestown’s Museum of Nevis History. The building is the birthplace of Alexander Hamilton, a founding father of the United States.

Whatever you decide, your yacht crew will be looking forward to pampering you with refreshments upon your return for the sunset.

Featured activities

  • Try some of the 44 different types of mangos available only on Nevis Island.
  • Challenge your golf game with the narrow fairways of the Four Season’s resort
  • Nevis invites you to try some gourmet local specialties like conch gratin, johnny cakes and Creole-spiced scallops.

St. Kitts

Jacuzzi on yacht deck in the Caribbean
Luxuriate on board your Leeward Islands charter yacht

As you sail north toward St. Kitts on the Caribbean side, the Unesco Historical Site, Brimstone Hill Fortress, proudly displays its citadels, barracks and ramparts built by the British in the 17th century. From the sumptuousness of your private yacht, imagine how the old canons guarded the coast against French enemy warships.

Nearby, below the sea surface, privileged scuba divers swim through coral formations, spot sea turtles and colorful reef fish at The Sandy Point National Marine Park.

The white sand beaches on the southern end of Saint Kitts understandably are the most well known, but another option is to escape north to Dieppe Bay. Here it will feel like your own exclusive beach. The dark volcanic sand and offshore reefs offer a protected, tranquil tourist-free respite. Authentic, simple cafes with sea views give you a chance to try local dishes like Pelau or lobster.

Featured activities

  • Watch a demonstration of locally handmade Batik textiles at Romney Manor.
  • Visit, Wingfield Estate, the oldest intact distillery in the Caribbean.
  • Drive a 4x4 through rugged tropical island terrain.


A view of a mountain peak from Saba’s tropical forest, Leeward Islands
Saba’s tropical forest

Mountainous and lush from rich volcanic soil, this Dutch island’s charming architecture is forever memorable. Perched on mountain faces, each quaint wooden structure is white with a red rooftop, gingerbread trim and dark green and white shutters.

Meet a local neighbor that runs the tiny Dutch Museum Saba with loving care. You will learn fascinating details about the history of the tiles, textiles and books in the collection here and have a pleasant chat. Some items are for sale, so if you are an antique enthusiast, you might find a treasure to take home with you.

Featured activities

  • Hike the strenuous Sandy Cruz Trail to see incredible views of this unique island.
  • Have a quiet seafood salad lunch at the Queens Gardens Resort in an outdoor rainforest setting.
  • Reserve a private art class at Jobean Glass Art Studio.

St. Barts

A private onshore dining experience in St. Barts for two with candles
A romantic private onshore dining experience in St. Barts

Undoubtedly the Caribbean’s premier island St. Barts is distinctively French. The upscale, stylish ambience attracts the world’s jet set, which means the island must live up to its claim, “The Art of Being an Island.”

It is true that you can find peace and pristine white sand beaches lining the turquoise waters on St. Barts. However, superb dining, shopping and nightlife are a welcome contrast to the sleepy islands earlier in the itinerary.

Rue de la République, Rue du Général de Gaule, and la rue du Roi Oscar II in Gustavía titillate those who love shopping for fashion and jewelry in designer boutiques and delightful high-end shops that stay true to the charming local architecture.

Reserve at the Nikki Beach Club to lounge, listen to renowned DJs, and party with champagne from 11am to 7pm. You will likely see other superyacht neighbors taking full advantage of a day at the VIP section of the club too.

Featured activities

  • Dress up, dine and people watch at the many glamorous upbeat restaurants.
  • Dance on tables, drink champagne and let loose.
  • Choose the perfect chill-out space on your private yacht to recover from a night out in St Barts.


Paradise beach in Anguilla, Leeward Islands
Turquoise Caribbean waters and white sand beaches - Anguilla

Compared to its more lavish neighboring island, the casual elegance of Anguilla is perfect for recuperating your mind and spirit.

Extensive fine white soft sand beaches and crystal clear waters gently lap the shore. Drift from cove to cove on your luxury yacht to wherever the island breeze takes you.

A flat island with British influence, it is calm, unassuming with some of the world’s top 10 beaches like Shoal Bay East.

Celebrities come to Anguilla to disappear, and nobody will make a fuss over them. The locals are warm and genuine to everyone equally.

Clouds are much less common than on the more mountainous Caribbean Islands here. So take in the warm sun, listen to music or read a book while your crew finds the ideal place to set the anchor.

Choose the water sport in the sparkling blue water, sunbathe on the pristine beach or take the zodiac to a beach club for a meal. Eventually, you will delight in wiggling your toes in the soothing white sand.

Featured activities

  • Choose from a variety of easy going live music venues for reggae and live music near the shore.
  • Book a massage on the beach.
  • Discover off-island cays and hidden beaches that are accessible only by boat.

St. Marteen

Aerial view of a yacht moored in turquoise waters off a St. Martin beach
Turquoise waters beach - St. Martin (Leeward Islands)

Enjoy an unrushed cooked-to-order breakfast on the deck of your yacht near the uninhabited island of Tintamarre. There you can take a swim or hire a local conservationist to explain the marine life that surrounds you.

The promise of variety on your private luxury charter in the Leeward Islands would not be complete without a visit to the island of Saint Martin. The island is just 34 square miles and is the only place on earth where France and the Netherlands share a border. The mixture of cultures comes alive in festivals, cuisine, music, and dancing.

By now, the Caribbean sunshine has imbued you with happiness and a low-key vibe. You will surely take this cheerful, warm energy home with you.

Featured activities

  • Strap in, bend your legs, stick your feet up and zipline over the jungle canopy.
  • Hire a private local guide to explore hidden places not usually explored by tourists.
  • Drive around the circumference of the island and discover the differences between the French and Dutch sides for yourself.

Private yacht cruise on the Leeward Islands: Useful information

Duration: 1 week (8 days / 7 nights).
Boarding/Embarkation: Antigua
Disembarkation: St. Marteen
Closest Airport: Arrival at C.V Bird International Airport (Antigua) / Departure from Princesa Juliana International Airport (St. Marteen)
Marina Arrival: The marina is located on Antigua Island, 20km (25min approx) from the airport. Private transfer service, cab or public transport is available.
Best time to charter a yacht in the Leeward Islands: This is primarily a winter destination. The best time to enjoy a yacht charter holiday in the Leeward Islands is between November and July, when the climate is perfect, with temperatures in the upper 20s C to low 30s C, calm crystal waters, and consistent winds.
The Caribbean's primary high season is from mid-December to March when people around the world visit the Islands looking for a tropical winter tan. The hurricane season is from August to early October.
Best time to reserve a yacht in the Leeward Islands: Early booking is recommended, from August to December, where the availability of charter boats on the Leeward Islands is ample.

Let´s start planning your yacht cruise now

Get in contact and let our charter brokers help you find the perfect yacht for your next cruising holidays in the Leeward Islands.


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