Leeward Islands yacht charter guide: A luxury Caribbean island hopping itinerary from St Martin to Antigua and beyond
Embark on a Leeward Islands yacht charter and travel through one of the Caribbean’s most desirable yachting regions, where elegance meets effortless escape. This luxury Caribbean island-hopping journey blends designer shopping, Michelin-level dining, private anchorages and sheltered passages into one refined Leeward Islands yacht charter itinerary through St Martin, Antigua and beyond.
The Leeward Islands: The Caribbean’s northern crown
Sprinkled throughout the northeastern Caribbean, the Leeward Islands are one of the most appealing cruising grounds in this utopian charter territory. With warm trade winds, turquoise shallows, short hops between ports, and sheltered harbours, the Leeward Islands offer ideal sailing conditions, while the region’s maritime heritage, which has been influenced by British, French and Dutch settlers, provides a venerable backdrop.
From the iconic superyacht hubs of St Barths and St Martin through the relatively quiet, untouched enclaves of Nevis and Anguilla, Leeward Islands yacht charters offer the perfect balance of cosmopolitan elegance and treasure-island escapism.
For an elevated sense of exclusivity and an itinerary that includes private anchorages, designer shopping and Michelin star-worthy dining paired with exemplary onboard service, book a Caribbean island hopping charter in the Leeward Islands with Edmiston.
Your Leeward Islands yacht charter itinerary: Discover the art of elevated Caribbean island hopping
Home to some of the Caribbean’s most coveted destinations, the Leeward Islands is a dream cruising ground, as renowned for the diversity of its offerings as it is for its stunning beaches.
Strung out across an area of some 150 miles from Anguilla in the north to Dominica in the south, the Leeward Islands have everything you need for a carefree charter holiday, from luxury resorts and fashionable clubs to castaway levels of serenity and beauty.
Experience St Barths’ sophisticated and distinctly French hospitality, relax into the barefoot luxury vibe of Anguilla, embrace the regal heritage of Antigua, and feel the soft sands of Barbuda’s unspoiled beaches between your toes. With Edmiston’s Leeward Islands yacht charter itinerary you can enjoy all this and more as part of one seamlessly curated journey.
St Martin: The cosmopolitan start to your Leeward Islands charter adventure
The launch pad for most Leeward Islands yacht charters, St. Martin is an island of two halves, both of which cater for charter guests extraordinarily well. In the northern part of the isle, St Martin wears its French character with pride and the many restaurants that line the beachfront in the small town of Grand Case have set it on course to become the gastronomic heart of the Caribbean.
Anchor off the town and head to Ocean 82 for stunning sea views as you feast on Rockefeller oysters or if your palate desires the most authentic French-infused Caribbean cooking on the isle, book a table at L’Auberge Gourmande.
There is an alternative anchorage at Anse Marcel – a fabulous spot for swimming and snorkelling – while on the Dutch-owned south of the isle, Simpson Bay is a great base for enjoying a glitzier, livelier side to the isle.
For a private beach escape, ask your captain to plot a course to Pinel Island later in the day, once the day-trippers have left for the afternoon, when you should have the place to yourselves.
St. Barths: Iconic glamour and unspoiled coves
It may be tiny but the island of St Barths has a big reputation for being the place to be and to be seen in the Leeward Islands thanks to its mix of upscale establishments and pristine, powdery white beaches.
St Barths has long been a glamorous meeting point on the sailing circuit and with its lively yacht scene, air of French refinement, designer boutiques, and romantic candlelit dining spots, it’s a must on any Leeward Islands yacht charter.
Anchor off Colombier Bay for quiet, blissful mornings exploring the waters of the protected marine reserve in peace, or dock in Gustavia Harbour for easy provisioning and tender drop offs.
Long, sun-soaked days unfold easily on St Barths, whether flopping on one of its gorgeous beaches, sharpening your game at the newly opened Le Domaine padel club, browsing the high-end boutiques of Gustavia, or pushing yourself on a coastal hike to Colombier, where your yacht can be waiting. Evenings, meanwhile, are reserved for soaking up the island’s inimitable energy at the legendary Eden Rock, where the Sand Bar’s DJ sets, fresh seafood and tropical-infused dishes perfectly capture the laid-back rhythm of the island.
Anguilla: Barefoot luxury and quiet wellbeing
Fringed by no fewer than 33 beaches, this little island, which is just 16 miles long by three miles wide, seems heaven sent for charter guests looking for short beach hops away from the crowds.
Anchor off Shoal Bay or Rendezvous Bay for easy tender access to some of the island’s cool beach clubs and day resorts where you can drift off while indulging in tranquil treatments, or enjoy a sunset dinner at one of its excellent shoreside restaurants. More active guests may prefer to take a horseback ride across the sand, or to snorkel amid some of the island’s shallow turquoise bays.
With friendly locals and a slow-pace of life imbued with infectious Calypso rhythms – some say the music here is better than on any other island – Anguilla is the kind of place you can’t help but be seduced by.
Antigua and Barbuda: Classic Caribbean charm and endless beaches
These dual isles are part of yachting lore. Steeped in maritime history, a visit here is a chance to immerse yourself in the vibrant island culture of yesteryear. Antigua’s restored Nelson’s Dockyard, named for the British Admiral who used it as a base in the 1780s, is an enlightening shore excursion and can only be improved with a long lunch in one of the English Harbour’s fine-dining restaurants.
The next day can be spent relaxing on Barbuda’s pink beaches or snorkelling in the calm waters of Green Island, a private island off Antigua’s east coast where you can swim in the company of turtles and shoals of colourful fish that thrive in these coral protected waters.
With plenty of deep-water anchorages and smooth cruising passages, there’s an ease about things here that mirrors the carefree atmosphere of life on board and is utterly irresistible.
St. Kitts and Nevis: Heritage, serenity, and tropical landscapes
While many stop-offs on Leeward Island charters have been gradually developed to meet the needs of yachting visitors, this dual-island nation has taken its own sweet Caribbean time about things and has been much quieter because of it.
Now, thanks to the accessibility of Christophe Harbour, more Leeward Islands superyacht charter guests are making their way here and there is a sprinkling of luxury golf courses and revamped plantation estates to prove it.
However, the real appeal here is that things have largely been left very much as nature intended. You can spend endless beach days undisturbed and take private hikes through lush island scenery without meeting another soul, making it still feel very much below radar.
Crafting your Leeward Islands yacht charter itinerary with Edmiston
As specialists in curating bespoke Leeward Islands yacht charters, Edmiston has the expertise to create fully tailored voyages for our guests. From private island bookings to exclusive beach access and helicopter transfers, our specialist charter teams can take care of all the arrangements to ensure an effortless charter experience for all.
We can also book tables at the best restaurants in the Caribbean region, arrange curated wellness charter days (both onboard and spa days ashore) and organise behind-the-scenes access and personalised cultural tours whether you are looking to enjoy luxury Caribbean events, or prefer the best hiking, incredible scuba diving, or just want to enjoy some of the most quiet islands in the Caribbean – we ensure each route is designed entirely around the tastes and interests of your charter party.
For more Caribbean yacht charter inspirations exploring the varied Caribbean island regions, see our other articles in this series: Windward Islands Yacht Charter Guide and 10 Things to do in the British Virgin Islands on a yacht charter.
Contact your Edmiston broker today and start planning your bespoke Leeward Islands yacht charter itinerary.
Explore our MOST POPULAR YACHTS for CHARTER.
Lady S
From €1,600,000 EUR p/week
93m (305’1”)
12 Guests
7 Cabins
Feadship
2019 / 2025
Arbema
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72m (236’3”)
12 Guests
8 Cabins
CRN
2010 / 2023
Sophia
From €1,700,000 EUR p/week
96.6m (316’11”)
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2017 / 2022
Soundwave
From $550,000 USD p/week
63m (206’8”)
12 Guests
6 Cabins
Benetti
2015 / 2025
Ventum Maris
Please enquire about charter rates
65.7m (215’7”)
12 Guests
7 Cabins
Amels
2011 / 2025
Sunrays
From €1,150,000 EUR p/week
85.5m (280’6”)
12 Guests
8 Cabins
Oceanco
2010 / 2025
Lady Britt
From $465,000 USD p/week
63m (206’8”)
12 Guests
7 Cabins
Feadship
2011 / 2022
Life Saga
From $635,000 USD p/week
65.23m (214’)
12 Guests
6 Cabins
Admiral
2019 / 2025
Arrow
From $900,000 USD p/week
75m (246’1”)
12 Guests
6 Cabins
Feadship
2020
Silver Angel
Please enquire about charter rates
64.5m (211’7”)
12 Guests
7 Cabins
Benetti
2009 / 2015
Acta
From $182,000 USD p/week
51.21m (168’)
10 Guests
5 Cabins
Feadship
2007 / 2020
Grace
From $255,000 USD p/week
52.3m (171’7”)
12 Guests
6 Cabins
Amels
2009 / 2024
Para Bellvm
Please enquire about charter rates
47m (154’2”)
11 Guests
6 Cabins
Sanlorenzo
2023