The ultimate guide to exploring the Leeward Islands by superyacht
The ultimate guide to exploring the Leeward Islands by superyacht
Published 08 June 2026
Scattered over 150 miles from Anguilla to Dominica, this group of Caribbean islands is fascinatingly diverse. St Martin/Sint Maarten (part French, part Dutch) offers golden beaches, good nightlife and restaurants, casinos and luxury shopping. Laid back Anguilla has the whitest beaches and translucent water. St Barth is the ‘it’ island with red-tiled roofs, French cuisine and high-end boutiques, while Antigua is famous for its 365 beaches and the prettiest and most historic harbour in all of the Caribbean.
Sailing the Leeward Islands is the perfect way to discover some of the Caribbean’s most notable islands, beaches and adventures.
The best islands to visit on board a yacht on the Leeward Islands
From the iconic superyacht hub of St Barth to the peaceful Anguilla, a Leeward Islands yacht charter offers the perfect balance of cosmopolitan elegance and treasure-island escapism. With close proximity between the islands, it’s the perfect Caribbean island hopping adventure.
St Barth
St Barth is the epitome of Caribbean French chic – and never more so than when enjoyed from the deck of a superyacht. The island’s capital Gustavia is one of the prettiest in the West Indies archipelago, while its beaches are the stuff of Caribbean dreams. On a St Barth yacht charter, you’ll have Michelin starred restaurants, beaches and high-end shopping at your fingertips – you simply have to decide which beach to grace, where to snorkel, and which desirable restaurant to book.
Dock in Gustavia’s harbour with its blend of Caribbean charm and French Riviera elegance. The recognisable horseshoe bay is lined with superyachts, with red-tiled roofs peppering the hillside and designer boutiques steps from the water. To experience the island at its most vibrant, coincide your St Barth yacht charter with the famous New Year’s Eve fireworks display, March’s St Barth’s Bucket Regatta, or Les Voiles de St Barth in April.
Antigua
With beaches galore and a seafaring history, the island of Antigua has pole position on the Caribbean cruising map located at the southern part of the Leeward chain. On an Antigua yacht charter, soak up this unpretentious, old-world island and explore their biggest claim to fame – a staggering 365 beaches. Many are deserted, fringed by untouched rainforest and accessible only by tender, while others are home to lively beach clubs and gourmet restaurants.
Save time for the island’s verdant interior, best discovered at pace on a nail-biting zip wire through the rainforest, before exploring the island’s rich maritime history. Home to the British fleet in the late 17th century, the colonial naval buildings of Nelson’s Dockyard remain as they were when Nelson made his headquarters here as the Admiral in command of the West Indies fleet.
St Maarten
The Dutch territory of St Maarten shares its island with better known French colony St Martin, having signed the Treaty of Concordia in 1648 to establish the framework of coexistence between the two nations. Today, the Friendly Island (as it’s affectionately referred to) is a serene island paradise offering year-round sunny days, lush green hills and mountains, and a beautiful shoreline.
While the French side feels distinctly European and laid back, the Dutch nation is more developed, with a superyacht marina, restaurants, and bars in abundance. On a St Maarten yacht charter, meander down the cobblestone streets of the capital Philipsburg, with its vibrant bursts of colourful colonial-style architecture. Then sample fine dining delights where European meets Caribbean. As part of the Leeward Islands, St Maarten is an important regional yachting hub and regular point from which to embark on a Caribbean yacht charter, located just a short distance from St Barth and St Kitts.
Anguilla
Quintessentially Caribbean, Anguilla is made up of a small main island surrounded by offshore islets. It’s ideal for casual island-hopping by boat, dropping anchor to explore secluded coves and stepping ashore for a private beach BBQ set-up. Shoal Bay Anguilla is the island’s most famous beach, ranking among the top beaches in the entire world. Beautiful, with a pinkish-hued white sand and intense turquoise water. Stretching two miles, lining the shores are restaurants, beach bars and hotels, with many peaceful spots for snorkelling and swimming along the way.
Elsewhere on an Anguilla yacht charter, prehistoric petroglyphs can be found at Big Spring Cave, while East End Pond is a wildlife conservation site ideal for twitchers. And don’t forget Dog Island. Located northwest of Anguilla and enveloped by three small sandy cays, it’s an ideal place to swim in the shallows, snorkel among coral and fish, and even spot the occasional sea turtle.
St Kitts and Nevis
St Kitts and its diminutive neighbour Nevis are growing in popularity as luxury yacht charter destinations, thanks to the alluring superyacht marina at Christophe Harbour. Here you will find a blend of authentic Kittitian culture and outstanding luxury facilities, including the superyacht harbour and marina village.
Further afield on a St Kitts yacht charter you can discover a wealth of nature, history and culture among the island’s mountainous landscapes from colonial sugar plantations and fortresses to pristine black-sand beaches and tropical forests nestled under the peak of the dormant volcano Mount Liamuiga which boasts an excellent hiking trail.
Hidden anchorages and secluded beaches in the Leeward Islands
Across the entire region, there are some incredibly secluded Caribbean beaches and bays for charterers looking for a crowd-free escape. From St Barth to Antigua, these remote paradises offer protection from trade winds and calm waters ideal for swimming.
Green Island Antigua
This idyllic, mostly uninhabited private island is located off Antigua’s eastern coast, just off Nonsuch Bay. Famed for its white sandy beaches, translucent waters, and vibrant fringing reefs, it’s one of the best spots in the Leeward Islands for snorkelling (keep an eye out for colourful fish, rays, and sea turtles).
Colombier beach
Found in the far northwest of St Barth, Colombier beach is accessible only by boat or hike, making it an exclusive secluded location for a stop on your Caribbean yacht charter. Because the beach is entirely undeveloped, it’s an incredibly peaceful escape.
Little Bay Anguilla
Anguilla has some beautifully secluded beaches, no more so than Little Bay. West-facing, this sublime sliver of sand can only be reached by boat is framed by beautifully layered limestone with varying shades of corals and greys.
A sample week-long Leeward Islands yacht charter itinerary
Exploring the Leeward Islands by yacht is an experience that blends culture, Caribbean island hopping, and secluded anchorages. Begin in St Maarten with its vibrant French culture, before a short sail to Anguilla where the legendary white sands of Shoal Bay await and opportunities for Caribbean snorkelling abound in the crystal clear waters. Next up, St Barth. Anchor in the chic port of Gustavia and spend the day browsing designer boutiques or lounging on Colombier beach for some solitude.
Cruising south, St Kitts is the next stop on your Caribbean yacht itinerary, where you can enjoy exceptional coral reef diving among colourful marine live before heading to neighbouring Nevis to hike the Nevis Peak rainforest trails. Conclude your charter on Antigua, exploring the historic Nelson’s Dockyard and savouring unforgettable Caribbean beach dining experiences on the island’s idyllic shores before departing.
Best time to rent a yacht in the Leeward Islands
The best time for a Caribbean yacht charter is during the dry season, from November to April. Escape for some winter sun and enjoy ideal sailing conditions with consistent trade winds and comfortable temperatures.
Why explore the Caribbean by yacht?
The Caribbean has an intoxicating allure for the superyachting crowd. A luxury Caribbean yacht charter offers big blue skies and cooling trade winds for a magnificent sailing and island-hopping adventure at any time of the year – whether you’re planning a summer vacation or taking in the winter sun. With some of the world’s best beaches, world-renowned St Barth beach clubs, and exotic wildlife, it’s a destination that stays with you long after you leave.
Ready to start your holiday in the Leeward Islands?
The Caribbean is a yachting playground like no other, and the Leeward Islands are a shining example offering a mix of nature, adventure, and relaxation. Whether you’re dreaming of a Burgess Caribbean charter exploring the wonders of Antigua, or a lively escape with friends in St Barth, our world-class services will ensure your Burgess yacht charter is an unforgettable experience. Ready to embark on your tropical escape? Contact us today to start planning the ultimate Caribbean getaway.
Speak to our Burgess Charter team and let us plan your perfect yacht vacation.
Frequently asked questions
Which islands are included in a Leeward Islands yacht charter?
The Leeward Islands are located in the north of the Caribbean Sea, with a yacht charter here visiting islands including St Maarten/St Martin, Anguilla, St Barth, Antigua, and St Kitts and Nevis. Because the region stretches over 150 miles, your charter broker will choreograph your charter into specific routes tailored exactly to you.
Are the Leeward Islands good for island hopping?
Yes, the Leeward Islands are widely considered one of the best island-hopping destinations in the world. With short sailing distances, consistent trade winds, and a diverse mix of European and Caribbean cultures, you can easily explore multiple unique islands in a single trip.
What makes the Leeward Islands different from the Windward Islands?
The Leeward and Windward Islands are both part of the Lesser Antilles, but they differ primarily in their geography, climate, and nautical history. The Windward Islands are located further south and east, facing the prevailing trade winds, which makes them wetter and more mountainous. The Leeward Islands are further north and west, making them drier and flatter.
Leeward Islands or The Bahamas?
It depends on your travel style. Choose The Bahamas for sandy beaches and a relaxed atmosphere with just a short travel distance from the US, while the Leeward Islands offer dramatic volcanic landscapes, diverse cultures, and excellent island hopping.
Leeward Islands or British Virgin Islands?
The British Virgin Islands (BVIs) are geographically part of the Leeward Islands, however they’re often categorised as their own distinct regional destination. For those looking for ideal sailing conditions and a laid-back vibe, make the BVIs your next charter destination. For a cultural diverse experience, varied terrain, and a bustling atmosphere, head to the broader Leeward Islands.
To find out more about Burgess’ yachts for sale and yachts for charter, please contact a Burgess broker. Alternatively, get in touch with one of our offices directly: London, Monaco, New York, Miami, Singapore or all other locations.
- Yachts, prices and availability are correct at the time of publication.
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