The Windjammer Way

The Windjammer Way is a boutique tall ship cruise line redefining Caribbean travel through heritage, adventure, and sustainability. Our mission is to breathe new life into classic sailing experiences while empowering Caribbean communities and preserving maritime culture. We are currently restoring our flagship vessel, the legendary S/V Mandalay, a storied schooner with decades of sailing history in the region. Once complete, Mandalay will set sail on immersive voyages to off-the-beaten-path Caribbean destinations, offering guests a slower, more intentional way to experience the islands—powered by wind, tradition, and local hospitality. At the heart of our operations is a commitment to employing, training, and investing in Caribbean people. Our team, from ship crew to shoreside operations, is made up of passionate individuals from across the region. By committing to the Caribbean, we aim to stimulate local economies, support small island communities, and deliver authentic, unforgettable experiences to our guests. The Windjammer Way isn’t just a cruise — it’s a movement toward conscious, connected, and community-driven travel. Tall Ships. True Caribbean. The Windjammer Way.