Leeward Islands Yacht Charter Guide

Ideal for island hopping from tiny deserted cays to fashionable harbors, the Leeward Islands offer the ultimate island lifestyle

If you crave a Caribbean idyll with white-sand beaches, lush rainforests and relaxed charm, then the Leeward Islands have all the essentials in abundance. Spanning some 120 miles from Anguilla in the north to Dominica in the south, the islands link together in an enticing chain. From the sophisticated French island of St. Barths to the old-world charm of Antigua, both ashore and on the water, they offer an exotic concoction of modern chic and laidback Caribbean attitude.

st. kitts

Panorama of beach in Martinique
Sample Itinerary

DAYS 1 & 2


Boasting warm and steady tradewinds, safe harbors and 365 beaches, Antigua is the winter destination of choice for many superyachts. Spend a few days cruising around the beautiful island, jumping in to discover some of the finest coral reefs in the Caribbean, before heading to the exclusive island of Nevis for a peaceful anchorage.



The island of Nevis is old Caribbean at its best – easy going and unspoiled by mass tourism, its few hotels are small and stylish and there are no glitzy clubs. Step ashore to explore the plantation houses and sugar cane hillsides that dot the landscape and spend the evening on the beach dancing to the reggae beats. Lift anchor to cruise across The Narrows to St. Kitts. Berth at Christophe Harbour and step ashore to Salt Plage for a cocktail with the yachting crowd.



Spend the day diving or snorkeling the underwater world around the tiny island of St. Eustatius, where coral reefs, exotic fish and wrecks abound. Step ashore to experience a laid-back Caribbean with a few places to eat and a little bit of history to contemplate.



Cruise towards the tiny island of Saba – as you approach the volcanic island seemingly rises out of the sea. Perfect for energetic hikers, explore the dramatic scenery inland. Saba doesn’t have any beaches but offers plenty of diving opportunities for the skilled scuba divers in the charter party. Spend a peaceful night anchored off the tranquil island.

DAYS 6 & 7


Cruise north to the quintessentially chic St. Barths. With a distinctly French flavor, St. Barths is the Leeward chain’s most exclusive and elegant island. The Caribbean’s take on St. Tropez, this is the place to go for pristine beaches, calm waters and gourmet restaurants. Take the tender to the bustling waterfront at Gustavia before anchoring off Shell Beach. Step ashore for cocktails and canapés at Do Brazil. St. Barths has so much to offer so dedicate at least two nights to the island, discovering the French island’s joie de vivre.

DAYS 8 & 9


Discover the low-lying coral island of Anguilla with its 12 miles of blinding white sand beaches and fabulous culinary scene. The most northerly of the Leewards, the island has excellent restaurants with wine lists to please a French sommelier. Spend the next few days in and around the reef-protected shallows of Shoal Bay East.

DAY 10


Cross over to St. Martin/St. Maarten and slowly acclimatize to a 21st century pace of life. The island enjoys a dual personality – part Dutch, part French – and has exuberant night spots, duty-free shops and exciting casinos promising an upbeat, cosmopolitan experience – the final link in your Leeward Islands chain.

Charter Experience

The Leeward Islands have long been a haven for seafarers and today’s yachtsmen consider the sheltered waters to be some of the finest bluewater cruising grounds in the Caribbean. With a colorful mosaic of culture, cuisine and natural beauty, every island has its own unique character and charm, inspiring you to discover the next as you cruise from Antigua to St. Martin during a luxury Leeward Islands yacht charter.


Spend a few days discovering Antigua’s 365 beaches before embarking on your luxury yacht in English Harbor. The beaches are the island’s primary attractions, but its appeal also lies in its maritime history – combined they have placed the island in pole position on the Caribbean map.  With a distinctly French flavor, St. Barths is the Leeward chain’s most exclusive and elegant island. The Caribbean’s take on the Côte d’Azur, this is the place to go for pristine beaches and gourmet restaurants. Its capital, Gustavia, is one of the prettiest in this part of the world and the port is the perfect place to berth while you step ashore and browse the designer boutiques.


The rolling sugarcane fields and ruins of plantation and merchant houses on St Kitts offer all those who step ashore insight into a colonial past. It is worth spending a few nights ashore, either staying at one of the boutique hotel properties housed in the former plantation houses or one of the few luxury resorts that can be found on the island. There is also the opportunity to berth in the fully serviced Christophe Harbour, perfectly positioned to the south of the island for access to the capital Basse Terre and all the abundance of historical sites – remnants of the island’s colonial days when both the British and French were based on St. Kitts. Just two miles across the strait lies the lesser-developed island of Nevis, with its Robert Trent Jones II golf course and Pinney’s Beach – both of which are worth stepping ashore for.


Further north the tiny island of Anguilla radiates an unspoiled innocence – the place to head if you want to get away from it all. Most itineraries finish in St. Martin (or Antigua) as both have international airports. The smallest island in the world to be split into two nations, St. Martin/St. Maarten is a wonderful mix of cultures. Known by many as the gourmet capital of the Caribbean, the island boasts a number of Michelin-star restaurants and offers an eclectic nightlife. Whether you wish to discover the deserted cays or fashionable harbors, or a little bit of both, your Northrop & Johnson charter expert will provide ample opportunities to discover the cream of the Caribbean.

Location Highlights

  • Step ashore to the uber-luxe Jumby Bay, Antigua
  • Explore the UNESCO World Heritage Site Nelson’s Dockyard – the only working Georgian dockyard in the world
  • Basse Terre on St. Kitts is home to reggae bars where you can ‘lime’ with the locals
  • Play a round at the Four Seasons Resort Nevis 18-hole golf course
  • Hike St. Eustatius’ extinct volcano, known as the Quill
  • Savor a Passionista rum cocktail at Bagatelle, St. Barths
  • Dine at the François Plantation, Villa Marie Saint-Barth
  • The southwest coast of St. Kitts offers spectacular diving
  • For sushi and live music head to Bête a Z’Ailes, St. Barths
  • Snorkel with angelfish in the shallow waters of North Sound, Great Bird Island
  • Step ashore to the beach club (modeled on Club 55) at Le Toiny, St. Barths

Expert Advice

Each of the fifteen Leeward Islands has something different to offer a yacht charter guest and with so many isles to explore, a luxury yacht charter is an ideal way to explore the islands’ unique cultures and cuisines.

Leeward Islands Yachts for Charter