A tropical seascape featuring vibrant turquoise and deep blue waters, with a white boat approaching a lush, green island. The shoreline is edged with rocks and trees, while fluffy white clouds drift across a bright blue sky, creating a serene and inviting coastal scene.

Caribbean Islands

Orient Express Sailing Yachts Caribbean Islands Cruises

12
voyages
18
upcoming departures

Orient Express Sailing Yachts runs 12 voyages in Caribbean Islands with 18 upcoming departures, from $19,315 to $57,945 per person, as of September 19, 2026. Every voyage below is bookable through Small Ship Travel, with a dedicated advisor from quote to sailing day.

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All Orient Express Sailing Yachts Caribbean Islands voyages

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