The first decision in planning a Caribbean yacht charter is a choice between two distinct worlds. The Lesser Antilles are split, defined by the trade winds that have shaped their geography and character for centuries. To the north and west lie the Leeward Islands, a chain known for its vibrant social scene and polished glamour. To the south and east, the Windward Islands offer dramatic volcanic landscapes and a deeper sense of exploration.
The Social Stage: The Leeward Islands
The Leewards are the Caribbean’s playground. The islands are generally flatter, drier, and set closer together, making for effortless island hopping. This is where French sophistication meets a lively yachting scene, particularly in St Barth. Days here are spent moving between designer boutiques, romantic waterfront restaurants, and world-famous beach clubs.
Nearby, St Martin and St Maarten offer a dual experience on a single island. The Dutch side is known for its nightlife, casinos, and shopping, while the French side provides a quieter atmosphere with gourmet dining and exclusive resorts. The circuit is completed by Antigua, where historic English Harbour becomes a global hub for sailors and superyachts during its famous regatta season. For first-time charter guests seeking a cosmopolitan and sociable trip, the Leewards are often the starting point.
The Wild Interior: The Windward Islands
The Windward Islands present a more adventurous side of the Caribbean. Facing the prevailing trade winds, these islands are more mountainous, receive more rainfall, and are covered in lush rainforests. The experience here is less about the social scene and more about a connection with the landscape. The chain stretches from Martinique and St Lucia down to St Vincent and the Grenadines and Grenada.
In St Lucia, the iconic Pitons rise directly from the sea. Grenada’s interior is a network of rainforest trails that lead to waterfalls and spice plantations. Further south, the Tobago Cays in St Vincent and the Grenadines are a protected marine park, offering some of the region’s most pristine snorkeling among pristine coral reefs and resident sea turtles. The turquoise waters of Salt Whistle Bay in Mayreau and the quiet anchorages of Bequia showcase the region’s unspoilt beauty.