Four Winds

Perched high on the ridge between Cane Garden Bay and Brewers Bay, Four Winds Villa is one of Tortola’s oldest and most character-rich homes, offering a rare blend of historic Caribbean charm and thoughtful modern upgrades. Set within a peaceful residential area, the villa enjoys cooling trade winds, sweeping views, and convenient access to Road Town, two of the island’s most beloved beaches, and nearby National Parks, an ideal base for swimming, hiking, and island exploration. Originally built in the late 1800s, Four Winds has been lovingly refreshed by its current owners, preserving the soul of traditional West Indian architecture while introducing modern comforts for today’s traveler. The property is made up of multiple charming structures connected by stone pathways, wooden decks, and lush tropical gardens, creating a sense of stepping back in time while still enjoying relaxed island living. Upon arrival, guests are welcomed into a sunken, garden-wrapped courtyard, a private, open-air living space shaded by mature trees. This tranquil spot is perfect for morning yoga, afternoon tea, or a West Indian–style BBQ prepared by your pre-arranged local chef, and serves as the heart of the villa. The main house is anchored by an expansive shaded wooden deck overlooking Cane Garden Bay, perfectly positioned for golden sunsets and evening breezes. This deck flows seamlessly into both the living room and the master suite, allowing for effortless indoor-outdoor living. Inside, warm wo