Windward Islands Surf & Sunsets

One of the most sought-after yachting destinations in the Caribbean, the Windward Islands give you a glimpse of what the West Indies looked like in days of old. Technicolor travel posters come to life in its lush green mountains, shimmering blue waters, swaying palm trees and uncrowded beaches. Colorful fishing boats bob in the harbor next to private yachts, and resorts give way to charming boutique hotels and B&Bs.

Pastel Georgian buildings, crumbling forts, and rusting canons recall the days when pirates roamed the seas and Britain and France fought over who would rule these islands. And while each island has its unique charms, the pace of life is almost universally slow, with time to absorb the copious amounts of natural beauty and chat with people who are genuinely welcoming.

Sip a local Carib beer in the shade of sea grape trees. Dive off the Watersports Platform and snorkel above coral gardens entirely undisturbed by your passage. Stand on the ramparts of forts that have seen centuries come and go staring out at a view that never grows old. Discover islands that perfectly match your dreams.

An island’s windward side faces the trade winds, which come from across the Atlantic. On the leeward side, the Caribbean Sea is calmer. As a result, you’ll usually find the best beaches on the west side of each island.
Check out the nutmeg ice cream on Grenada, the Spice Island. It’s like a summer version of eggnog.
In tiny Bequia, an island of just 7 square miles, all beaches are public. They’re also clean and uncrowded, so take your pick.
The incredibly beautiful twin pitons on Saint Lucia are a UNESCO World Heritage Site. You can climb Gros Piton (with a guide), but it’s an exhausting climb and you’ll need good hiking shoes and plenty of water.
The people you meet in Les Saintes are descended from Breton corsairs (pirates), and they’re skilled sailors. Their distinctive shallow white hats are called salacos. If you would like to take a photo, be sure to ask first.