A picturesque bay filled with boats at sunset, surrounded by green hills under a cloudy sky.
YACHT CHARTER DESTINATION

Leeward Island Yacht Charter

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Island Hops Between Chic, Historic, and Wild

The Leeward Islands stretch roughly 120 miles from Anguilla to Dominica, and each island has its own personality. Short, easy hops connect rainforest hillsides, sandy coral cays, and volcanic craters, which makes this one of the most popular cruising grounds in the Caribbean.

St. Barths is the glamorous anchor, where designer boutiques line the harbor at Gustavia, lunch at Nikki Beach comes with rosé in a seaside cabana, and New Year's Eve fireworks light up a harbor full of superyachts. St. Martin offers a blend of French and Dutch culture, plenty of superyacht marinas, and easy international flights, making it a natural place to begin a charter. Farther south, Antigua pairs powder white beaches with the history of English Harbour and Nelson's Dockyard, once the base of the Leeward Islands fleet under Admiral Nelson, while St. Kitts and Nevis add volcanic scenery and a sundowner at SALT Plage in Christophe Harbour.

Glamour, history, and island calm sit side by side here, and no two days on the water feel the same.

Charter Itinerary

For a full itinerary, or to build your own experience, please inquire.

A Delta airplane flies low over a crowded turquoise beach with people looking up.

DAY 1

St. Maarten

The Leeward islands are a chain of serene islands encapsulated with silky white beaches and clear waters. They effortlessly combine the diverse history, culture and cuisine of the Caribbean. Your journey begins on this dual-national island that is actually two countries in one. Shared between the French and Dutch cultures, the sophisticated French St. Martin and the unique Dutch St. Maarten each offer their own exotic potion of modern chic and laid back Caribbean charm. Your big entrance to St. Maarten won’t go unnoticed as your final approach to landing is right over Maho beach, where the locals and tourists go to experience the thrill of having a plane fly just a short distance above their heads. The abundance of sunshine, fresh sea air and rich vegetation will get you in the mood to visit one of the incredible beaches or march you off in the direction of the numerous markets. There are also endless things to do at the lively casinos, restaurants, beach bars, cinemas and much more.

Aerial view of a tropical island with turquoise shallow waters meeting the deep blue ocean.

DAY 2

St. Martin

French St. Martin, with its exciting blend of European and Caribbean culture, will make you feel like you’re walking the streets of Paris with all the exquisite restaurants, French fashion boutiques and the smell of delicious pastries, guaranteeing you the authentic French experience outside of France. On the west coast of St. Martin lies the quaint Gallic town of Marigot. Overlooking the town is the castle of Fort Louis, built by King Louis XVI in 1789. Take a fort tour to visit the many historical buildings or take a stroll through history on Rue de la Republique. Join the local scene at the town’s colorful open-air market, indulge in French Caribbean cuisine at some of the village’s world-class restaurants and browse through the latest French fashion and art galleries as you explore the town.

Aerial view of a white boat speeding on clear blue water next to a lush green coastline.

DAY 3

Anguilla

The waters around this idyllic Caribbean sanctuary were declared a National Park due to its limestone foundation and numerous reefs, making this the perfect spot for snorkeling or scuba diving. There are also many beautiful and secluded beaches around Anguilla, so this is a great opportunity to relax and have a beach picnic or take a stroll from one beach to another. If you’re in the mood to do something exhilarating, there is an underwater cavern 6 miles northwest of the mainland, where nurse sharks and barracudas swim around the rock formations with several nearby sunken shipwrecks. Visit Johnno’s Bar on Sandy Ground beach, a typical Caribbean beach bar with a spectacular view, live music, delicious cocktails and electric atmosphere with people dancing the night away.

Tropical beach with turquoise water, boats, dense green vegetation, and a red salt pond.

DAY 4

Prickly Pear Cays

The Prickly Pear Cays are a small pair of uninhabited islands about six miles from Anguilla. The western cay is mainly rocky coral and scrub while the eastern cay is where you should be headed. As you arrive, you will go through a narrow passage between the two cays and get to a small island with a pristine white-sand beach, a tranquil bay of turquoise waters and a coral reef for swimming and snorkeling. There are no structures or residences on Prickly Pear other than Agatha’s restaurant and a small thatched Tiki Bar on the beach where you can get the best local beers and rum punches.

Tropical bay with turquoise water, anchored boats, lush green hills, and a sandy beach.

DAY 5

Seal Island Reef

Next up is Seal Island, a small island located about 1NM east of Prickly Pear Cays. The area is popular for snorkeling and scuba diving due to the extremely vibrant colored living reefs. In the evening, it’s the perfect place for a barbecue on the beach or dinner at anchor.

Sunset view of a vibrant coastal town harbor filled with boats and lush hills.

DAY 6

St. Barths

Today you’ll be in the lovely French island of St. Barts where you can anchor at Gustavia Harbor, a quaint town with Swedish links. Snorkel the wreck of the sunken motor yacht ‘Nonstop’ or go ashore and rent a Mini Moke car to tour the isolated beaches and admire the fabulous homes carved out of the hillsides. Go to a barefoot bar and drink beer, or dress up and go gourmet, the choice is yours. There are many world famous restaurants and with a variety of cusines to try, you’ll see all your options as you wonder the town, passing an abundance of chic boutiques, galleries and markets on your way. In the evening you may want to enjoy the buzzing night life of St. Barts, with all the live bands, cognac and lively Caribbean dancing.

Lush green volcanic island with rugged cliffs surrounded by deep blue ocean under a clear sky.

DAY 7

Saba

Saba rises majestically from its crystal clear waters, stretching her summit to caress the clouds. An exquisite natural beauty both above and below the water, it’s like no other Caribbean destination. Hike up the steep Mt. Scenery’s 3,084 feet trail and see the breath-taking view from the top or take a taxi up the zigzagging roads that pass by the banana plantations, oleander bushes and stunning ocean views. The road is full of hairpin turns so the drive by itself is an adventure. You can visit the many little shops in the village surrounded by clover and lemon grass. Keep your eyes peeled for Saba Lace, historically one of the island’s prized industries. For such a small place it certainly punches above its weight class, there are around 25 highly recommended dive sites, which include underwater hot springs and lava flows that are home to over 150 species of fish, turtles, sharks and coral.

Day 8

St. Maarten

Begin the last day of your charter with a final stroll on the beach or along the streets of Philipsburg. Enjoy an alfresco breakfast at one of the historic building restaurants that line the town’s white sandy shore. Your footprints in the sand may disappear, but your memories will last forever!

Yachts for Charter in the Leeward Islands

VOYAGE 590e

VOYAGE 590e

59’ VOYAGE yacht|2022

12 Guests 6 Staterooms

Caribbean Virgin Islands (US/BVI)

Ready to start your charter adventure?

Get in touch with us and one of our dedicated charter specialists will be at your service to answer all of your questions.

Frequently Asked Questions

Where do most Leeward Islands yacht charters begin?

St. Martin is a popular starting point, with numerous superyacht marinas and inbound international flights, though Antigua and St. Kitts are also common embarkation ports.

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

December through April is the best time for a Leeward Islands yacht charter, offering dry weather, steady trade winds, and the busiest social calendar of the season.

Is St. Barths worth visiting on a Leeward Islands yacht charter?

Yes, St. Barths is a charter mainstay, known for its upscale shopping and dining in Gustavia, beach clubs like Nikki Beach, and its lively yachting scene. It is especially popular as it hosts one of the best New Year's Eve celebrations in the world, though quayside spots in Gustavia should be reserved well in advance.

What makes the Tobago Cays different from other marine parks in the Caribbean?

The Tobago Cays National Marine Park is protected across five uninhabited islets and a horseshoe reef, offering a rare combination of turtle populated waters, coral gardens, and undeveloped anchorages within a single protected marine area.

How far in advance should you book a Leeward Islands charter for New Year's Eve or the Bucket regatta?

Early booking is strongly advised, since quayside berths in Gustavia during New Year's Eve and the March Bucket regatta are among the most sought-after in the Caribbean.

Is hurricane season a concern for a Leeward Islands yacht charter?

Yes, the Atlantic hurricane season runs from June through November, which is why most charters focus on the dry winter and spring months when weather is more settled.