Orient Express Sailing Yachts

Explore the Caribbean this Winter

From October 2026 to March 2027, Orient Express Sailing Yachts will chart a new course through the Caribbean: short itineraries, intimate by design, from three nights to eight.

Crystalline waters, lush landscapes, secret coves, and sun-drenched shores. From Saint Barth to the British Virgin Islands, uncover a world of wonder, elegance, and island allure abord the world’s largest sailing yacht.

Our Selection of Caribbean Voyages
Designed for slow sailing, each itinerary unveils the Caribbean’s most breathtaking destinations, from the glamour of Saint Barth to the secluded beauty of the British Virgin Islands, with the idyllic Grenadines along the way.
ANTILLES ESCAPE
3 nights
October 26th to 29th 2026
From € 15,900 inc. taxes per suite
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VIRGIN GORDA & SAINT-BARTH FROM MARIGOT
4 nights
November 10th to 14th 2026
From € 21,200 inc. taxes per suite
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LEEWARD ISLANDS JOURNEY
4 nights
December 1st to 5th 2026
From € 21,200 inc. taxes per suite
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BARBADOS, THE GRENADINES & BEQUIA
4 nights
January 4th to 8th 2027
From € 21,200 inc. taxes per suite
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Caribbean Islands Odyssey
7 nights
February 3rd to 10th 2027
From € 37,100 inc. taxes per suite
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Barbados, THE Grenadines & Leeward Isles
8 nights
March 5th to 13th 2027
From € 44,720 inc. taxes per suite
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DISCOVER ALL CARIBBEAN VOYAGES?

An All-Inclusive Journey
Every journey is thoughtfully curated, with legendary Orient Express service, exceptional gastronomy, restorative wellness, exclusive destination experiences, arrival and departure services, all seamlessly included.
ALL-SUITE Ocean Views
Butler & laundry service • Bespoke amenities
dining
2 restaurants • 8 bars
• In-suite dining

WellnesS
Outdoor pools • hammam & sauna • fitness studio with expert-led coaching
entertainment
Marina & water toys
• Cinema • Theater • Music studio