By Caribbean Compass
The terms Windward Islands and Leeward Islands are as embedded in Caribbean parlance as trade winds and rum punch. Yet ask a room of seasoned sailors—or even Caribbean locals—exactly where one ends and the other begins, and you’ll likely get a range of answers.
The truth is, the distinction is both geographical and nautical, shaped by history, prevailing winds, and colonial administration. Here’s your definitive guide to understanding what makes an island “Windward” or “Leeward”—and why the distinction matters.
Sailing Origins: Where the Terms Come From
The words “windward” and “leeward” are deeply rooted in nautical tradition.
Windward refers to the direction from which the wind is blowing—upwind.
Leeward refers to the direction the wind is blowing toward—downwind.
In the Caribbean, where the prevailing trade winds blow from the east-northeast, European ships arriving from the Atlantic would first encounter the easternmost islands—which they considered “windward.”
Thus, from a colonial sailing standpoint:
The Windward Islands are those facing into the wind—generally the southeastern arc of the Lesser Antilles.
The Leeward Islands are those downwind or northwest of the Windwards.
So Where’s the Divide?
This can get confusing because different maps and colonial powers defined the boundary differently. But today, the division is most commonly recognized as:
Leeward Islands (Northwest arc of the Lesser Antilles):
U.S. Virgin Islands
British Virgin Islands
Anguilla
Saint Martin / Sint Maarten
Saint-Barthélemy
Saba
Sint Eustatius
Saint Kitts and Nevis
Antigua and Barbuda
Montserrat
Guadeloupe (sometimes a dividing line)
Windward Islands (Southeastern arc of the Lesser Antilles):
Dominica (sometimes considered Leeward in older British definitions)
Martinique
Saint Lucia
Saint Vincent and the Grenadines
Grenada
Note: The French consider Guadeloupe and Martinique both part of the “Îles du Vent” (Windward Islands). The British historically placed Dominica in the Leewards, though most modern references include it in the Windwards due to its geography.
Colonial History Played a Role
European colonial powers didn’t just fight for land—they organized it.
The British Empire split its colonies administratively:
The British Leeward Islands Colony (1871–1958) included Antigua, Montserrat, Saint Kitts, Nevis, Anguilla, and at times Dominica.
The British Windward Islands Colony (1833–1958) governed Saint Lucia, Grenada, Saint Vincent, Barbados, and Dominica (after 1940).
The French maintained separate classifications. In their system:
Îles du Vent = Windward Islands (Martinique, Guadeloupe, etc.)
Îles Sous-le-Vent = Leeward Islands (like Saint Barthélemy, Saint Martin)
These designations were administrative, not always geographic.
Why This Matters to Sailors
For mariners, the Leeward/Windward divide still carries practical implications:
Windward Islands often have more wind exposure, higher rainfall, and steeper volcanic terrain—great for hiking, waterfalls, and lush anchorages.
Leeward Islands are drier, with calmer anchorages on the western sides, and are often preferred for easier line-of-sight sailing, hopping from island to island.
The entire Lesser Antilles arc—Windward and Leeward combined—is a sailor’s paradise. But understanding which is which helps with route planning, customs logistics, and seasonal weather considerations.
Geology and Geography
The Windward Islands are younger and more volcanic, with active peaks like La Soufrière in Saint Vincent or Mount Pelée in Martinique.
The Leeward Islands include more sedimentary or coral-based islands (e.g., Barbuda), with shallower reefs and flatter terrain.
Interesting Facts You Might Not Know
The term “Windward Islands” is used in multiple parts of the world, including the Windward Islands of French Polynesia—confusing? Yes. But rooted in sailing language.
Barbados, though further east than Saint Vincent, is not considered part of the Windward Islands. That’s because it’s an outlier to the east, separated from the main arc and geologically distinct.
Dominica’s identity has long been split—French sailors considered it Windward, while British colonial maps often placed it with the Leewards.
“Leeward Islands” is also the name of a cricket team, representing several of the northern islands in West Indies cricket.
The distinction between Windward and Leeward isn’t just about compass points—it’s about centuries of sailing tradition, imperial history, and the shaping of island identities.
